73
Pathway
Histidine Metabolism
Histidine, an amino acid, plays an important role in the creation of proteins. It is unique as an amino acid as it is needed for nucleotide formation. The biosynthesis of histidine in adults begins with the condensation of ATP and PRPP (phosphoribosyl pyrophosphate) to form n-5-phosphoribosyl 1-pyrophosphate (phosphoribosyl-ATP). It is also worth noting that PRPP is the beginning compound for purine and pyrimidine creation. Subsequent histidine biosynthetic steps (from phosphoribosyl-ATP onwards) are likely to occur in the intestinal microflora. Elimination of the phosphate and the opening of the ring in phosphoribosyl-ATP forms phosphoribosyl-forminino-5-aminoimidazole-4-carboxamide ribonucleotide(phosphoribosyl-forminino-AICAR-phosphate). This is subsequently converted to 5-phosphoribulosyl-forminino-5-aminoimidazole-4-carboxamide ribonucleotide. Cleavage of this compound creates imidazole glycerol phosphate and AICAR (aminoimidazolecarboxamide ribonucleotide) with glutamine being involved as an amino group donor. AICAR is used again through the purine pathway while the imidazole glycerol phosphate is converted to imidazole acetal phosphate. Transamination yields histidinol phosphate which is then turned into histidinol, and then, finally, to histidine. L-histidine is catalyzed by histidine ammonia-lyase into urocanic acid. This acid is then converted to 4-imidazolone-5-propionic acid by urocanate hydratase. 4-imidazolone-5-propionic acid is then converted to formiminoglutamic acid, using the enzyme probable imidazolonepropionase. One last reaction occurs to allow for glutamate metabolism, as formiminoglutamic acid is converted to l-glutamic acid through the use of formimidoyltransferase-cyclodeaminase. Histidine is also a precursor for carnosine biosynthesis(via carnosine synthase), with beta-alanine being the rate limiting precursor. Anserine can be synthesized either from carnosine via carnosine N-methyltransferase or from 1-methylhistidine via carnosine synthase. Inversely, cytosolic non-specific dipeptidase catalyzes the synthesis of 1-methylhistidine from anserine.
Histidine is found in meat, seeds, nuts and whole grains. It is a very important amino acid in keeping a pH of 7 in the body, as it acts as a shuttle for protons to maintain a balance of acids and bases in the blood and different tissues.
Metabolic
PW000043
Center
PathwayVisualizationContext43
3050
2750
#000099
PathwayVisualization53
73
Histidine Metabolism
Histidine, an amino acid, plays an important role in the creation of proteins. It is unique as an amino acid as it is needed for nucleotide formation. The biosynthesis of histidine in adults begins with the condensation of ATP and PRPP (phosphoribosyl pyrophosphate) to form n-5-phosphoribosyl 1-pyrophosphate (phosphoribosyl-ATP). It is also worth noting that PRPP is the beginning compound for purine and pyrimidine creation. Subsequent histidine biosynthetic steps (from phosphoribosyl-ATP onwards) are likely to occur in the intestinal microflora. Elimination of the phosphate and the opening of the ring in phosphoribosyl-ATP forms phosphoribosyl-forminino-5-aminoimidazole-4-carboxamide ribonucleotide(phosphoribosyl-forminino-AICAR-phosphate). This is subsequently converted to 5-phosphoribulosyl-forminino-5-aminoimidazole-4-carboxamide ribonucleotide. Cleavage of this compound creates imidazole glycerol phosphate and AICAR (aminoimidazolecarboxamide ribonucleotide) with glutamine being involved as an amino group donor. AICAR is used again through the purine pathway while the imidazole glycerol phosphate is converted to imidazole acetal phosphate. Transamination yields histidinol phosphate which is then turned into histidinol, and then, finally, to histidine. L-histidine is catalyzed by histidine ammonia-lyase into urocanic acid. This acid is then converted to 4-imidazolone-5-propionic acid by urocanate hydratase. 4-imidazolone-5-propionic acid is then converted to formiminoglutamic acid, using the enzyme probable imidazolonepropionase. One last reaction occurs to allow for glutamate metabolism, as formiminoglutamic acid is converted to l-glutamic acid through the use of formimidoyltransferase-cyclodeaminase. Histidine is also a precursor for carnosine biosynthesis(via carnosine synthase), with beta-alanine being the rate limiting precursor. Anserine can be synthesized either from carnosine via carnosine N-methyltransferase or from 1-methylhistidine via carnosine synthase. Inversely, cytosolic non-specific dipeptidase catalyzes the synthesis of 1-methylhistidine from anserine.
Histidine is found in meat, seeds, nuts and whole grains. It is a very important amino acid in keeping a pH of 7 in the body, as it acts as a shuttle for protons to maintain a balance of acids and bases in the blood and different tissues.
Metabolic
1
845
7
SubPathway
1367
95
Compound
8
103
Lehninger, A.L. Lehninger principles of biochemistry (4th ed.) (2005). New York: W.H Freeman.
73
Pathway
104
Salway, J.G. Metabolism at a glance (3rd ed.) (2004). Alden, Mass.: Blackwell Pub.
73
Pathway
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
6
Myocyte
CL:0000187
2
Platelet
CL:0000233
8
Beta cell
CL:0000639
12
Astrocyte
CL:0000127
34
Mast Cell
CL:0000097
1
Homo sapiens
9606
Eukaryote
Human
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
2
Bacteria
2
Prokaryote
Bacteria
3
Escherichia coli
562
Prokaryote
19
Schizosaccharomyces pombe
4896
Eukaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
Eukaryote
African clawed frog
25
Escherichia coli (strain K12)
83333
Prokaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
23
Pseudomonas aeruginosa
287
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
51
Picea sitchensis
3332
Eukaryote
Sitka spruce
202
Spathaspora passalidarum
340170
Eukaryote
Spathaspora passalidarum
127
kjhkjh
0989088
Eukaryote
301
Gallus Gallus
1758
Prokaryote
230
Ambystoma mexicanum
8296
Eukaryote
axolotl
11
Extracellular Space
GO:0005615
5
Cytoplasm
GO:0005737
6
Lysosome
GO:0005764
4
Peroxisome
GO:0005777
3
Mitochondrial Matrix
GO:0005759
2
Mitochondrion
GO:0005739
10
Cell Membrane
GO:0005886
16
Lysosomal Lumen
GO:0043202
7
Endoplasmic Reticulum Membrane
GO:0005789
1
Cytosol
GO:0005829
18
Melanosome Membrane
GO:0033162
13
Endoplasmic Reticulum
GO:0005783
25
Golgi Apparatus
GO:0005794
14
Mitochondrial Outer Membrane
GO:0005741
12
Mitochondrial Inner Membrane
GO:0005743
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
15
Nucleus
GO:0005634
31
Periplasmic Space
GO:0005620
35
Chloroplast
GO:0009507
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
40
Periplasm
GO:0042597
27
Peroxisome Membrane
GO:0005778
32
Inner Membrane
GO:0070258
19
Sarcoplasmic Reticulum
GO:0016529
17
Nucleoplasm
GO:0005654
39
Mitochondrial membrane
GO:0031966
24
Mitochondrial Intermembrane Space
GO:0005758
1
Liver
BTO:0000759
72
9
4
Adrenal Medulla
BTO:0000049
71
8
25
Intestine
BTO:0000648
28
Stomach
BTO:0001307
155
26
7
Nervous System
BTO:0001484
8
Blood Vessel
BTO:0001102
74
11
11
Heart
BTO:0000562
73
10
6
Kidney
BTO:0000671
71
8
9
Muscle
BTO:0000887
141
18
2
Endothelium
BTO:0000393
18
Pancreas
BTO:0000988
3
Sympathetic Nervous System
BTO:0001832
24
Brain
BTO:0000142
89
16
5
cardiocyte
BTO:0001539
15
11
1
PW_BS000015
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31
4
PW_BS000024
220
1
4
PW_BS000024
312
5
23
1
PW_BS000024
320
11
23
PW_BS000024
310
31
2
PW_BS000024
882
31
202
PW_BS000552
883
1
202
1
PW_BS000552
167
31
1
PW_BS000167
788
24
11
1
3
PW_BS000524
597
24
1
12
PW_BS000336
141
1
7
19
1
PW_BS000141
71
11
1
3
PW_BS000071
84
24
11
1
PW_BS000084
288
14
4
1
PW_BS000024
372
10
2
PW_BS000028
189
32
18
PW_BS000024
317
32
23
PW_BS000024
21
5
1
1
4
PW_BS000021
74
1
3
PW_BS000074
41
8
1
1
PW_BS000041
879
24
1
127
3
PW_BS000552
1292
5
301
1
PW_BS000588
1293
1
301
1
PW_BS000588
1487
24
1
1
34
PW_BS000644
789
24
1
1
3
PW_BS000524
912
24
1
3
PW_BS000558
787
24
10
1
3
PW_BS000524
1070
24
14
1
3
PW_BS000578
1143
1
14
1
5
PW_BS000583
1546
24
1
17
3
PW_BS000656
1678
24
14
17
3
PW_BS000706
956
11
2
1
1
PW_BS000563
979
13
230
1
PW_BS000569
1294
2
301
1
PW_BS000588
23
Carnosine
HMDB0000033
Carnosine (beta-alanyl-L-histidine) is found exclusively in animal tissues. It is a dipeptide of the amino acids beta-alanine and histidine. Carnosine has the potential to suppress many of the biochemical changes that accompany ageing (e.g. protein oxidation, glycation, AGE formation, and cross-linking) and associated pathologies (PMID: 16804013). It is highly concentrated in muscle and brain tissues. Some autistic patients take it as a dietary supplement and attribute an improvement in their condition to it. Supplemental carnosine may increase corticosterone levels. This may explain the "hyperactivity" seen in autistic subjects at higher doses. Carnosine also exhibits some antioxidant effects. The antioxidant mechanism of carnosine is attributed to its chelating effect against metal ions, superoxide dismutase (SOD)-like activity, and ROS and free radicals scavenging ability (PMID: 16406688). Carnosine is a biomarker for the consumption of meat. Carnosine is found to be associated with carnosinuria, which is an inborn error of metabolism.
305-84-0
C00386
439224
15727
CARNOSINE
388363
NCCC(=O)N[C@@H](CC1=CN=CN1)C(O)=O
C9H14N4O3
InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1
CQOVPNPJLQNMDC-ZETCQYMHSA-N
226.2325
226.106590334
FDB000511
Carnosine;Ignotine;Karnozin;Karnozzn;L-carnosine;N-(3-aminopropanoyl)histidine;N-(b-alanyl)-l-histidine;N-b-alanyl-l-histidine;N-beta-alanyl-l-histidine;Sevitin;B-alanyl-l-histidine;B-alanylhistidine;Beta-alanyl-l-histidine;Beta-alanylhistidine;Nalpha-(beta-alanyl)-l-histidine;Nalpha-(b-alanyl)-l-histidine;Nalpha-(β-alanyl)-l-histidine;(2s)-2-(3-aminopropanoylamino)-3-(1h-imidazol-5-yl)propanoate
PW_C000023
Carnosi
531
15
1305
8
77582
114
78127
111
120443
409
121021
122
123077
137
123586
135
125687
483
127182
208
1420
Water
HMDB0002111
Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71% of Earth's surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the body's solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the sun's energy to split off water's hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the sun's energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia).
7732-18-5
C00001
962
15377
937
O
H2O
InChI=1S/H2O/h1H2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
18.0153
18.010564686
FDB013390
Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;Wasser
PW_C001420
H2O
55
8
94
9
109
5
139
4
151
3
162
14
481
13
526
15
624
28
652
10
691
20
770
33
823
18
838
2
1094
31
1377
49
1465
54
1590
43
2018
24
2532
22
2678
60
2727
46
2778
17
2805
29
3143
70
3164
72
3634
61
4598
36
4727
37
4941
93
5030
27
5156
7
5195
97
5214
100
5227
94
5236
103
5297
105
5319
111
5343
113
5355
112
5402
110
5470
123
5483
125
5492
126
5507
127
5534
130
5537
114
5541
129
5591
135
5608
118
5622
108
5691
6
5759
140
5778
101
5841
143
5853
146
5877
107
5890
95
5910
147
5940
151
6032
155
6059
157
6087
161
6123
163
6133
159
6215
1
6218
166
6477
178
6507
180
6600
152
6713
117
6840
188
6888
160
7162
205
7181
207
7193
206
7211
211
7228
213
7238
214
7243
215
7295
198
7350
216
7388
210
7401
212
7467
222
7492
224
7500
190
7588
170
8201
225
8237
226
8414
162
9265
26
11850
277
11922
164
12011
281
12213
285
12250
286
12264
287
12327
249
12520
227
12632
65
12693
290
12705
291
12715
292
13007
298
13019
300
13025
301
13037
302
13261
223
13327
294
15340
308
42327
315
42695
318
43691
322
76914
293
77019
253
77102
132
77131
133
77215
134
77378
331
77397
332
77471
333
77516
115
77536
334
77628
336
77722
337
77759
341
77816
343
77982
347
78071
329
78235
352
78242
353
78270
356
79113
360
80014
368
80039
370
80591
228
80656
119
93830
383
94794
384
110557
390
110639
391
115844
398
119879
232
119915
122
119963
406
120008
407
120046
408
120113
124
120365
412
120430
405
120438
409
120606
415
120794
414
121158
425
121240
429
121351
121
121381
419
121607
434
122118
382
122384
436
122753
120
122797
374
122804
443
123012
446
123064
376
123072
137
123131
447
123142
136
123162
448
123231
451
123384
450
123730
460
123810
464
123940
455
124165
469
124670
399
124938
471
124945
472
125305
297
125353
479
125386
481
125424
482
125480
299
125682
483
125707
478
125745
487
126054
490
126238
495
126273
484
126764
480
126896
501
126963
502
127017
388
127177
208
127199
209
127227
504
127506
507
127576
515
127836
389
128082
395
128176
513
140674
790
140675
834
140755
185
40
β-Alanine
HMDB0000056
beta-Alanine is the only naturally occurring beta-amino acid - an amino acid in which the amino group is at the beta-position from the carboxylate group. It is formed in vivo by the degradation of dihydrouracil and carnosine. It is a component of the naturally occurring peptides carnosine and anserine and also of pantothenic acid (vitamin B-5), which itself is a component of coenzyme A. Under normal conditions, beta-alanine is metabolized into acetic acid. beta-Alanine can undergo a transanimation reaction with pyruvate to form malonate-semialdehyde and L-alanine. The malonate semialdehyde can then be converted into malonate via malonate-semialdehyde dehydrogenase. Malonate is then converted into malonyl-CoA and enter fatty acid biosynthesis. Since neuronal uptake and neuronal receptor sensitivity to beta-alanine have been demonstrated, beta-alanine may act as a false transmitter replacing gamma-aminobutyric acid. When present in sufficiently high levels, beta-alanine can act as a neurotoxin, a mitochondrial toxin, and a metabotoxin. A neurotoxin is a compound that damages the brain or nerve tissue. A mitochondrial toxin is a compound that damages mitochondria and reduces cellular respiration as well as oxidative phosphorylation. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of beta-alanine are associated with at least three inborn errors of metabolism, including GABA-transaminase deficiency, hyper-beta-alaninemia, and methylmalonate semialdehyde dehydrogenase deficiency. beta-Alanine is a central nervous system (CNS) depressant and is an inhibitor of GABA transaminase. The associated inhibition of GABA transaminase and displacement of GABA from CNS binding sites can also lead to GABAuria (high levels of GABA in the urine) and convulsions. In addition to its neurotoxicity, beta-alanine reduces cellular levels of taurine, which are required for normal respiratory chain function. Cellular taurine depletion is known to reduce respiratory function and elevate mitochondrial superoxide generation, which damages mitochondria and increases oxidative stress (PMID: 27023909). Individuals suffering from mitochondrial defects or mitochondrial toxicity typically develop neurotoxicity, hypotonia, respiratory distress, and cardiac failure. beta-Alanine is a biomarker for the consumption of meat, especially red meat.
107-95-9
C00099
239
16958
B-ALANINE
234
DB03107
NCCC(O)=O
C3H7NO2
InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)
UCMIRNVEIXFBKS-UHFFFAOYSA-N
89.0932
89.047678473
FDB002253
2-carboxyethylamine;3-amino-propanoate;3-amino-propanoic acid;3-aminopropanoate;3-aminopropanoic acid;3-aminopropionate;3-aminopropionic acid;Abufene;B-alanine;Omega-aminopropionate;Omega-aminopropionic acid;B-aminopropanoate;B-aminopropanoic acid;B-aminopropionate;B-aminopropionic acid;Beta alanine;Beta-alanine;Beta-aminopropanoate;Beta-aminopropanoic acid;Beta-aminopropionate;Beta-aminopropionic acid;β-alanine
PW_C000040
b-Ala
41
3
49
8
527
15
2320
4
2747
2
5794
108
7071
188
12680
289
12687
290
42645
315
77522
112
77527
111
77578
114
78159
132
78633
133
120083
407
120439
409
120445
122
121056
124
122260
406
122830
119
123073
137
123079
135
123620
118
124813
120
125454
481
125683
483
125689
297
126389
299
126424
479
126992
206
127178
208
127184
205
127950
388
127992
501
116
L-Histidine
HMDB0000177
Histidine is an alpha-amino acid with an imidazole functional group. It is one of the 22 proteinogenic amino acids. Histidine was first isolated by German physician Albrecht Kossel in 1896. Histidine is an essential amino acid in humans and other mammals. It was initially thought that it was only essential for infants, but longer-term studies established that it is also essential for adults. Infants four to six months old require 33 mg/kg of histidine. It is not clear how adults make small amounts of histidine, and dietary sources probably account for most of the histidine in the body. Histidine is a precursor for histamine and carnosine biosynthesis. Inborn errors of histidine metabolism exist and are marked by increased histidine levels in the blood. Elevated blood histidine is accompanied by a wide range of symptoms, from mental and physical retardation to poor intellectual functioning, emotional instability, tremor, ataxia and psychosis. Histidine and other imidazole compounds have anti-oxidant, anti-inflammatory and anti-secretory properties (PMID: 9605177). The efficacy of L-histidine in protecting inflamed tissue is attributed to the capacity of the imidazole ring to scavenge reactive oxygen species (ROS) generated by cells during acute inflammatory response (PMID: 9605177). Histidine, when administered in therapeutic quantities is able to inhibit cytokines and growth factors involved in cell and tissue damage (US patent 6150392). Histidine in medical therapies has its most promising trials in rheumatoid arthritis where up to 4.5 g daily have been used effectively in severely affected patients. Arthritis patients have been found to have low serum histidine levels, apparently because of very rapid removal of histidine from their blood (PMID: 1079527). Other patients besides arthritis patients that have been found to be low in serum histidine are those with chronic renal failure. Urinary levels of histidine are reduced in pediatric patients with pneumonia. (PMID: 2084459). Asthma patients exhibit increased serum levels of histidine over normal controls (PMID: 23517038). Serum histidine levels are lower and are negatively associated with inflammation and oxidative stress in obese women (PMID: 23361591). Histidine supplementation has been shown to reduce insulin resistance, reduce BMI and fat mass and suppress inflammation and oxidative stress in obese women with metabolic syndrome. Histidine appears to suppress pro-inflammatory cytokine expression, possibly via the NF-?B pathway, in adipocytes (PMID: 23361591). Low plasma concentrations of histidine are associated with protein-energy wasting, inflammation, oxidative stress, and greater mortality in chronic kidney disease patients (PMID: 18541578). Histidine may have many other possible functions because it is the precursor of the ubiquitous neurohormone-neurotransmitter histamine. Histidine increases histamine in the blood and probably in the brain. Low blood histamine with low serum histidine occurs in rheumatoid arthritis patients. Low blood histamine also occurs in some manic, schizophrenic, high copper and hyperactive groups of psychiatric patients. Histidine is a useful therapy in all patients with low histamine levels. (http://www.dcnutrition.com ).
71-00-1
C00135
6274
15971
HIS
6038
DB00117
N[C@@H](CC1=CN=CN1)C(O)=O
C6H9N3O2
InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1
HNDVDQJCIGZPNO-YFKPBYRVSA-N
155.1546
155.069476547
FDB011856
(s)-1h-imidazole-4-alanine;(s)-2-amino-3-(4-imidazolyl)propionsaeure;(s)-4-(2-amino-2-carboxyethyl)imidazole;(s)-histidine;(s)-a-amino-1h-imidazole-4-propanoate;(s)-a-amino-1h-imidazole-4-propanoic acid;(s)-alpha-amino-1h-imidazole-4-propanoate;(s)-alpha-amino-1h-imidazole-4-propanoic acid;(s)-alpha-amino-1h-imidazole-4-propionate;(s)-alpha-amino-1h-imidazole-4-propionic acid;(s)1h-imidazole-4-alanine;3-(1h-imidazol-4-yl)-l-alanine;Amino-1h-imidazole-4-propanoate;Amino-1h-imidazole-4-propanoic acid;Amino-4-imidazoleproprionate;Amino-4-imidazoleproprionic acid;Glyoxaline-5-alanine;His;Histidine;L-(-)-histidine;H;L-histidin;(s)-α-amino-1h-imidazole-4-propanoate;(s)-α-amino-1h-imidazole-4-propanoic acid;(s)-a-amino-1h-imidazole-4-propionate;(s)-a-amino-1h-imidazole-4-propionic acid;(s)-α-amino-1h-imidazole-4-propionate;(s)-α-amino-1h-imidazole-4-propionic acid
PW_C000116
His
433
8
532
15
5024
50
5673
107
5674
108
42547
315
42563
318
77326
111
77583
114
78336
346
120339
122
120444
409
122990
135
123078
137
125661
297
125688
483
127155
205
127183
208
1005
Zinc (II) ion
HMDB0001303
Zinc is an essential element, necessary for sustaining all life.Physiologically, it exists as an ion in the body. It is estimated that 3000 of the hundreds of thousands of proteins in the human body contain zinc prosthetic groups. In addition, there are over a dozen types of cells in the human body that secrete zinc ions, and the roles of these secreted zinc signals in medicine and health are now being actively studied. Intriguingly, brain cells in the mammalian forebrain are one type of cell that secretes zinc, along with its other neuronal messenger substances. Cells in the salivary gland, prostate, immune system and intestine are other types that secrete zinc. Obtaining a sufficient zinc intake during pregnancy and in young children is a problem, especially among those who cannot afford a good and varied diet. Brain development is stunted by zinc deficiency in utero and in youth. Zinc is an activator of certain enzymes, such as carbonic anhydrase. Carbonic anhydrase is important in the transport of carbon dioxide in vertebrate blood. Even though zinc is an essential requirement for a healthy body, too much zinc can be harmful. Excessive absorption of zinc can also suppress copper and iron absorption. The free zinc ion in solution is highly toxic to plants, invertebrates, and even vertebrate fish. The Free Ion Activity Model (FIAM) is well-established in the literature, and shows that just micromolar amounts of the free ion kills some organisms.
23713-49-7
C00038
32051
29105
ZN%2b2
29723
DB01593
[Zn++]
Zn
InChI=1S/Zn/q+2
PTFCDOFLOPIGGS-UHFFFAOYSA-N
65.409
63.929146578
FDB003729
Zinc;Zinc ion;Dietary zinc;Zinc cation;Zinc, ion (zn2+);Zn(ii);Zn(2+);Zn2+
PW_C001005
Zinc
13
2
38
4
118
8
271
16
529
15
2957
51
3044
68
3120
29
3147
70
5410
117
5425
103
5434
118
5459
120
5560
132
5585
133
5598
135
7449
166
11787
198
12466
226
12724
290
13321
151
76967
225
77401
111
77580
114
77929
336
80400
1
120020
124
120035
406
120060
122
120441
409
121257
429
123075
137
123827
464
125398
299
125413
479
125438
297
125685
483
126938
388
126953
501
126976
205
127180
208
414
Adenosine triphosphate
HMDB0000538
Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).
56-65-5
C00002
5957
15422
ATP
5742
DB00171
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H16N5O13P3
InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
ZKHQWZAMYRWXGA-KQYNXXCUSA-N
507.181
506.995745159
FDB021813
5'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acid
PW_C000414
ATP
9
2
21
4
60
8
266
16
414
22
478
13
733
32
799
5
934
39
976
3
2105
18
2112
10
2146
49
2156
14
2160
58
2405
59
2434
27
2726
46
2812
29
3029
66
3163
72
3616
61
3617
51
4399
23
4474
31
4768
91
4864
54
5032
89
5035
26
5155
7
5205
97
5215
100
5250
104
5291
101
5313
111
5346
112
5390
103
5406
117
5430
118
5443
120
5542
129
5556
132
5569
133
5603
135
5621
108
5846
143
5854
146
5876
107
5897
147
5924
151
6048
155
6109
161
6230
166
6493
178
6839
188
6870
160
6976
199
7157
205
7184
206
7209
210
7225
213
7229
211
7298
198
7302
216
7390
217
7408
218
7432
163
7481
222
7499
190
8186
225
11847
277
11903
170
12010
281
12039
164
12178
285
12578
226
12691
290
13264
223
15327
308
42326
315
42621
322
42694
318
77028
253
77218
134
77233
329
77468
333
77632
336
78037
332
78041
350
78168
128
78214
351
78240
353
78411
335
78494
115
78850
130
78865
331
78919
334
80028
368
80046
184
80674
119
85629
1
94826
124
113234
94
113282
388
116280
109
119914
122
119992
406
120154
407
120245
382
120362
412
121246
429
121392
123
121397
433
121471
408
121974
410
122065
125
122079
383
122083
405
122402
422
122444
435
122919
399
123009
446
123816
464
123951
447
123956
468
124029
374
124527
444
124616
136
124630
398
124634
376
124943
472
124972
375
125011
470
125304
297
125371
479
125392
299
125515
481
125595
484
126123
485
126220
300
126234
495
126240
478
126547
491
126596
499
126913
501
127123
389
127731
516
127781
395
127796
390
127801
209
128119
508
128167
517
140770
891
1034
Adenosine diphosphate
HMDB0001341
Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.
58-64-0
C00008
6022
16761
ADP
5800
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H15N5O10P2
InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
XTWYTFMLZFPYCI-KQYNXXCUSA-N
427.2011
427.029414749
FDB021817
Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acid
PW_C001034
ADP
23
4
134
8
415
22
482
13
801
5
963
15
978
3
1061
14
1518
2
1901
49
2104
18
2113
10
2161
58
2408
59
2435
27
2728
47
2736
46
2855
29
3165
72
3635
61
4400
23
4476
31
4770
91
5036
26
5157
7
5208
97
5217
100
5315
111
5349
112
5392
103
5446
120
5544
129
5572
133
5624
108
5741
117
5764
101
5849
143
5856
146
5878
107
5899
147
5926
151
6050
155
6111
161
6231
166
6495
178
6700
94
6841
188
6872
160
7159
205
7187
206
7208
210
7226
213
7231
211
7300
198
7303
216
7391
217
7410
218
7433
163
7483
222
8187
225
11851
277
11905
170
12013
281
12180
285
13262
223
15329
308
42328
315
42398
313
42622
322
42696
318
77029
253
77087
132
77216
134
77306
329
77472
333
77663
336
78039
332
78043
350
78170
128
78215
351
78244
353
78414
335
78495
115
78705
331
78849
130
78920
334
80030
368
80622
118
80651
135
80676
119
94827
124
113283
388
116204
109
119944
122
119994
406
120156
407
120318
382
120366
412
121248
429
121394
123
121399
433
121472
408
121899
383
121976
410
122064
125
122085
405
122405
422
122445
435
122973
399
123013
446
123818
464
123953
447
123958
468
124030
374
124452
398
124529
444
124615
136
124636
376
124947
472
124975
375
125012
470
125334
297
125373
479
125492
299
125517
481
125645
484
126125
485
126219
300
126235
495
126242
478
126550
491
126597
499
126915
501
127733
516
127780
395
127797
390
127803
209
128122
508
128168
517
128313
389
1104
Phosphate
HMDB0001429
Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.
14265-44-2
C00009
1061
18367
CPD-8587
1032
OP(O)(O)=O
H3O4P
InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)
NBIIXXVUZAFLBC-UHFFFAOYSA-N
97.9952
97.976895096
DBMET00532
FDB022617
Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ion
PW_C001104
Pi
24
4
84
8
814
5
818
18
831
2
980
3
1763
14
1767
49
2500
10
2729
47
2737
46
3129
29
3166
72
3636
61
3851
23
4249
22
4475
31
5031
27
5158
7
5207
97
5216
100
5317
111
5351
112
5381
103
5447
120
5543
129
5573
133
5605
135
5625
108
5693
6
5848
143
5855
146
5911
147
5941
151
6040
155
6100
161
6294
107
6487
178
6691
101
6714
117
6842
188
6889
160
7161
205
7189
206
7212
211
7306
198
7389
210
7402
212
7436
163
7475
222
8196
225
8258
227
10118
241
10134
257
11748
132
11761
115
11773
213
11904
170
11927
164
12014
281
12728
290
13263
223
34819
17
42255
304
42350
315
42435
318
43692
322
77018
253
77194
293
77217
134
77940
336
77966
130
78048
332
78057
329
78245
353
78669
331
80022
368
89279
308
93831
383
94796
384
110558
390
110640
391
113235
94
115845
398
116206
109
119982
406
120069
122
120699
407
121057
124
121216
125
121268
429
121352
121
121409
123
121423
382
121852
405
123304
119
123621
118
123786
136
123838
464
123968
447
123981
399
124405
376
124948
472
125362
479
125446
297
125774
481
125954
299
126221
478
126594
300
126604
298
126723
484
126904
501
127413
388
127783
209
128166
395
128177
513
128315
389
1027
Manganese
HMDB0001333
Manganese is an essential trace nutrient in all forms of life. Physiologically, it. exists as an ion in the body. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver.
16397-91-4
C19610
27854
29035
MN%2b3
25916
[Mn++]
Mn
InChI=1S/Mn/q+2
WAEMQWOKJMHJLA-UHFFFAOYSA-N
54.938
54.938049636
FDB003636
Manganese;Manganese (ii) ion;Manganese(ii);Manganese, ion (mn2+);Manganous ion;Mn(2+);Mn2+
PW_C001027
Mn2+
27
4
473
8
1486
49
1553
43
2271
2
2394
3
2513
14
5394
103
5450
120
5576
133
6052
155
6113
161
6497
178
6926
160
7485
222
11880
198
11939
225
11958
164
12471
249
13360
151
15221
306
77050
294
77494
111
77832
132
77961
112
78267
356
78490
115
78524
331
79247
293
80032
368
119996
406
120401
122
121058
124
121211
407
121295
383
121378
419
122488
405
123044
135
123622
118
123781
119
123865
398
123937
455
125054
376
125375
479
125976
495
126051
490
126060
297
126158
299
126543
481
126642
478
126917
501
127429
390
127503
507
127512
205
127765
388
128116
206
128218
209
921
S-Adenosylmethionine
HMDB0001185
S-Adenosylmethionine (CAS: 29908-03-0), also known as SAM or AdoMet, is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in the treatment of chronic liver disease (From Merck, 11th ed). S-Adenosylmethionine is a natural substance present in the cells of the body. It plays a crucial biochemical role by donating a one-carbon methyl group in a process called transmethylation. S-Adenosylmethionine, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine, and other molecules.
485-80-3
C00019
24762165
15414
S-ADENOSYLMETHIONINE
31983
DB00118
C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
C15H23N6O5S
InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1
MEFKEPWMEQBLKI-AIRLBKTGSA-O
399.445
399.145063566
FDB022473
(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine;2-s-adenosyl-l-methionine;5'-deoxyadenosine-5'-l-methionine disulfate ditosylate;Active methionine;Ademetionine;Adenosylmethionine;Adomet;Donamet;L-s-adenosylmethionine;S-(5'-adenosyl)-l-methionine;S-(5'-deoxyadenosin-5'-yl)-l-methionine;S-adenosyl methionine;S-adenosyl-l-methionine disulfate tosylate;S-adenosyl-l-methionine;S-adenosyl-methionine;S-adenosylmethionine;5'-deoxyadenosine-5'-l-methionine disulphate ditosylate;S-adenosyl-l-methionine disulphate tosylate;(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner salt;[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl][(3s)-3-amino-3-carboxypropyl](methyl)sulfonium;Acylcarnitine;Sam;Same
PW_C000921
SAMe
519
8
633
30
704
20
1220
3
1880
27
2066
2
4681
10
5023
50
5604
135
7136
163
7540
210
7544
213
7632
160
8266
151
9235
195
11874
198
12031
222
12358
225
15293
249
15345
18
15363
309
76897
293
76899
164
76984
224
77488
111
77731
338
77772
341
78099
132
78303
351
78335
346
79155
112
79961
361
80861
22
94830
382
94833
386
113286
389
113288
397
115543
399
115546
401
120393
122
120537
413
120939
407
121052
124
122282
435
123171
449
123505
119
123616
118
124836
470
125859
297
125879
481
126304
299
126447
499
127321
205
127340
206
127595
388
128017
517
364
3-Methylhistidine
HMDB0000479
3-Methylhistidine is a product of peptide bond synthesis and methylation of actin and myosin. The measurement of 3-methylhistidine provides an index of the rate of muscle protein breakdown. 3-Methylhistidine is a biomarker for meat consumption, especially chicken. It is also a biomarker for the consumption of soy products.
368-16-1
C01152
64969
27596
58494
[H][C@](N)(CC1=CN=CN1C)C(O)=O
C7H11N3O2
InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
JDHILDINMRGULE-LURJTMIESA-N
169.1811
169.085126611
FDB021798
(2s)-2-amino-3-(1-methyl-1h-imidazol-5-yl)propanoate;(2s)-2-amino-3-(1-methyl-1h-imidazol-5-yl)propanoic acid;3-methyl-l-histidine;3-methylhistidine;3-n-methyl-l-histidine;L-3-methylhistidine;N(pai)-methyl-l-histidine;N(pi)-methyl-l-histidine;N(pros)-methyl-l-histidine;N3-methyl-l-histidine;Pi-methyl-l-histidine;Tau-methyl-l-histidine;Tau-methylhistidine;1-methylhistidine;N-pros-methyl-l-histidine
PW_C000364
3-Mhis
528
15
1308
8
5026
50
5027
51
5028
63
77579
114
78130
111
78332
346
78333
326
78334
342
120440
409
121024
122
123074
137
123589
135
125684
483
127179
208
749
S-Adenosylhomocysteine
HMDB0000939
S-Adenosyl-L-homocysteine (SAH) is formed by the demethylation of S-adenosyl-L-methionine. S-Adenosylhomocysteine (AdoHcy or SAH) is also the immediate precursor of all of the homocysteine produced in the body. The reaction is catalyzed by S-adenosylhomocysteine hydrolase and is reversible with the equilibrium favoring formation of SAH. In vivo, the reaction is driven in the direction of homocysteine formation by the action of the enzyme adenosine deaminase which converts the second product of the S-adenosylhomocysteine hydrolase reaction, adenosine, to inosine. Except for methyl transfer from betaine and from methylcobalamin in the methionine synthase reaction, SAH is the product of all methylation reactions that involve S-adenosylmethionine (SAM) as the methyl donor. Methylation is significant in epigenetic regulation of protein expression via DNA and histone methylation. The inhibition of these SAM-mediated processes by SAH is a proven mechanism for metabolic alteration. Because the conversion of SAH to homocysteine is reversible, with the equilibrium favoring the formation of SAH, increases in plasma homocysteine are accompanied by an elevation of SAH in most cases. Disturbances in the transmethylation pathway indicated by abnormal SAH, SAM, or their ratio have been reported in many neurodegenerative diseases, such as dementia, depression, and Parkinson's disease (PMID: 18065573, 17892439). Therefore, when present in sufficiently high levels, S-adenosylhomocysteine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of S-adenosylhomocysteine are associated with S-adenosylhomocysteine (SAH) hydrolase deficiency and adenosine deaminase deficiency. S-Adenosylhomocysteine forms when there are elevated levels of homocysteine and adenosine. S-Adenosyl-L-homocysteine is a potent inhibitor of S-adenosyl-L-methionine-dependent methylation reactions. It is toxic to immature lymphocytes and can lead to immunosuppression (PMID: 221926).
979-92-0
C00021
25246222
16680
ADENOSYL-HOMO-CYS
388301
N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=O
C14H20N6O5S
InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1
ZJUKTBDSGOFHSH-WFMPWKQPSA-N
384.411
384.12158847
DBMET00514
FDB022327
(s)-5'-(s)-(3-amino-3-carboxypropyl)-5'-thioadenosine;2-s-adenosyl-l-homocysteine;5'-deoxy-s-adenosyl-l-homocysteine;5'-s-(3-amino-3-carboxypropyl)-5'-thio-l-adenosine;Adenosyl-l-homocysteine;Adenosyl-homo-cys;Adenosylhomo-cys;Adenosylhomocysteine;Adohcy;Formycinylhomocysteine;L-5'-s-(3-amino-3-carboxypropyl)-5'-thior-adenosine;L-s-adenosyl-homocysteine;L-s-adenosylhomocysteine;S-(5'-adenosyl)-l-homocysteine;S-(5'-deoxyadenosin-5'-yl)-l-homocysteine;S-(5'-deoxyadenosine-5')-l-homocysteine;S-adenosyl-l-homocysteine;S-adenosyl-homocysteine;Sah;(2s)-2-amino-4-({[(2s,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid;S-[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl]-l-homocysteine;S-adenosylhomocysteine
PW_C000749
SAH
520
8
575
18
635
30
705
20
1221
3
1882
27
2067
2
4683
10
5025
50
5607
136
7137
163
7542
210
7546
213
7634
160
8268
151
9237
195
11875
198
12359
225
15294
249
15364
309
77489
111
77611
130
77733
338
77773
341
78098
132
78305
351
78337
346
79156
112
79962
361
80863
22
94831
382
94834
386
113287
389
113289
397
115544
399
115547
401
120394
122
120486
125
120539
413
120940
407
121053
124
122284
435
123037
135
123173
449
123506
119
123617
118
124838
470
125880
481
126303
299
126449
499
127341
206
127596
388
128019
517
693
Histamine
HMDB0000870
Histamine, also known as eramin or ceplene, belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group. Histamine exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Histamine has been found throughout most human tissues, and has also been detected in most biofluids, including feces, saliva, urine, and blood. Within the cell, histamine is primarily located in the myelin sheath. In humans, histamine is involved in the phenbenzamine H1-antihistamine action pathway, the omeprazole action pathway, the levocetirizine H1-antihistamine action pathway, and the propiomazine H1-antihistamine action pathway. Histamine is also involved in several metabolic disorders, some of which include the thiazinamium H1-antihistamine action pathway, the metiamide action pathway, the quetiapine H1-antihistamine action pathway, and the histidinemia pathway. Outside of the human body, histamine can be found in a number of food items such as daikon radish, jicama, caraway, and japanese walnut. This makes histamine a potential biomarker for the consumption of these food products. Histamine is an amine derived by enzymatic decarboxylation of histidine. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and also a centrally acting neurotransmitter.
51-45-6
C00388
774
18295
HISTAMINE
753
NCCC1=CNC=N1
C5H9N3
InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)
NTYJJOPFIAHURM-UHFFFAOYSA-N
111.1451
111.079647303
FDB012596
1h-imidazole-4-ethanamine;2-(1h-imidazol-4-yl)ethanamine;2-(1h-imidazol-4-yl)ethylamine;2-(1h-imidazol-5-yl)ethanamine;2-(1h-imidazol-5-yl)ethylamine;2-(4-imidazolyl)ethanamine;2-(4-imidazolyl)ethylamine;2-imidazol-4-yl-ethylamine;2-imidazol-4-ylethylamine;4-(2-aminoethyl)-1h-imidazole;4-(2-aminoethyl)imidazole;4-imidazoleethylamine;5-imidazoleethylamine;Eramin;Ergamine;Ergotidine;Free histamine;Hsm;Histamine;L-histamin base;L-histamine;Theramine;B-imidazolyl-4-ethylamine;Beta-aminoethylglyoxaline;Beta-aminoethylimidazole;Beta-aminothethylglyoxaline;Beta-imidazolyl-4-ethylamine
PW_C000693
Hsm
1310
8
3153
14
4151
15
4159
2
67311
1
70008
308
78132
111
121026
122
123591
135
1316
Carbon dioxide
HMDB0001967
Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially.
124-38-9
C00011
280
16526
274
O=C=O
CO2
InChI=1S/CO2/c2-1-3
CURLTUGMZLYLDI-UHFFFAOYSA-N
44.0095
43.989829244
DBMET00423
FDB014084
Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride;[co2];Co2;E 290;E-290;E290;R-744
PW_C001316
CO2
50
8
121
1
204
4
480
13
503
18
640
3
677
31
695
20
806
5
1133
43
1638
49
1745
2
2551
17
3144
70
5283
103
5320
111
5750
108
5771
101
5968
100
6026
155
6078
161
6471
178
6637
107
6922
190
7017
160
7035
163
7061
188
7163
205
7308
198
7333
213
7461
222
7530
210
8215
225
8223
151
9158
249
11849
277
11908
170
12464
226
12688
290
42626
315
43523
318
76994
293
77122
133
77170
132
77470
333
77739
112
77750
129
77763
341
78077
134
78405
356
78427
334
78941
331
79227
130
80008
368
80675
119
80717
135
94836
384
113291
391
115549
121
119954
406
120089
122
120155
407
120364
412
120556
414
120833
419
120922
124
120991
408
121284
125
121505
383
122744
120
123011
446
123190
450
123418
455
123489
118
123556
374
123855
136
124063
398
125344
479
125460
297
125516
481
125824
490
125870
299
125931
482
126280
480
126887
501
127052
206
127277
507
127331
388
127390
502
140798
185
1148
Pyridoxal 5'-phosphate
HMDB0001491
This is the active form of vitamin B6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (pyridoxamine). -- Pubchem; Pyridoxal-phosphate (PLP, pyridoxal-5'-phosphate) is a cofactor of many enzymatic reactions. It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. -- Wikipedia.
54-47-7
C00018
1051
18405
PYRIDOXAL_PHOSPHATE
1022
DB00114
CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O
C8H10NO6P
InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)
NGVDGCNFYWLIFO-UHFFFAOYSA-N
247.1419
247.024573569
FDB021820
Apolon b6;Biosechs;Codecarboxylase;Coenzyme b6;Hairoxal;Hexermin-p;Hi-pyridoxin;Hiadelon;Himitan;Pal-p;Plp;Phosphopyridoxal;Phosphopyridoxal coenzyme;Pidopidon;Piodel;Pydoxal;Pyridoxal 5'-phosphate;Pyridoxal 5-phosphate;Pyridoxal p;Pyridoxal phosphate;Pyridoxal-p;Pyridoxyl phosphate;Pyromijin;Sechvitan;Vitahexin-p;Vitazechs;3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde;3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate;Phosphoric acid mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester;Pyridoxal 5-monophosphoric acid ester;Pyridoxal 5'-(dihydrogen phosphate);Pyridoxal-5'-phosphate;Pyridoxal 5'-phosphoric acid;3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphoric acid;Phosphate mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester;Pyridoxal 5-monophosphate ester;Pyridoxal 5'-(dihydrogen phosphoric acid);Pyridoxal 5-phosphoric acid;Pyridoxal phosphoric acid;Pyridoxal-5'-phosphoric acid
PW_C001148
Pyr-5'P
18
2
32
4
45
3
51
8
122
1
401
19
696
20
1110
42
1450
50
1458
26
2120
10
2150
49
5325
111
5416
117
5421
103
5441
118
5455
120
5567
132
5581
133
6533
85
7018
160
7167
205
7216
212
7222
213
11858
161
12175
151
12623
31
12628
18
12684
289
12689
290
77017
253
77037
225
77041
293
77052
224
77526
112
77764
341
77973
346
77979
327
78292
345
78855
332
78862
331
80696
135
98630
7
119912
122
120024
124
120029
406
120087
407
120817
418
121149
423
121155
424
122069
123
122076
383
122834
119
123402
454
123721
458
123727
459
124620
447
124627
398
125302
297
125402
299
125407
479
125458
481
125803
489
126224
298
126231
495
126942
388
126947
501
126996
206
127258
506
127786
513
127793
390
717
1-Methylhistamine
HMDB0000898
1-Methylhistamine belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group. 1-Methylhistamine is slightly soluble (in water) and a very strong basic compound (based on its pKa). 1-Methylhistamine has been found in human bone marrow and brain tissues, and has also been detected in most biofluids, including saliva, cerebrospinal fluid, feces, and blood. Within the cell, 1-methylhistamine is primarily located in the cytoplasm. In humans, 1-methylhistamine is involved in the histidine metabolism pathway. 1-Methylhistamine is also involved in the metabolic disorder called the histidinemia pathway. 1-Methylhistamine is a histamine metabolite. It is a product of histamine 1-methyltransferase [EC 2.1.1.8] in the pathway histidine metabolism (KEGG).
501-75-7
C05127
3614
29009
N-METHYL-HISTAMINE
3488
CN1C=NC(CCN)=C1
C6H11N3
InChI=1S/C6H11N3/c1-9-4-6(2-3-7)8-5-9/h4-5H,2-3,7H2,1H3
FHQDWPCFSJMNCT-UHFFFAOYSA-N
125.1716
125.095297367
FDB022306
1-methyl-1h-imidazole-4-ethanamine;1-methyl-4-(2-aminoethyl)imidazole;1-methyl-4-(b-aminoethyl)imidazole;1-methyl-4-(beta-aminoethyl)imidazole;1-methyl-4-histamine;1-methylhistamine;2-(1-methyl-1h-imidazol-4-yl)ethanamine;2-(1-methyl-1h-imidazol-4-yl)ethylamine;4-(2-aminoethyl)-1-methyl-imidazole;4-(2-aminoethyl)-1-methylimidazole;H137;Methylhistamine;N( 1)-methylhistamine;N(t)-methylhistamine;N-methylhistamine;N-tele-methylhistamine;N-telle-methylhistamine;N1-methylhistamine;Nt-methylhistamine;Ntau-methylhistamine;Tele-methylhistamine;3-methylhistamine;4-(1-aminoethyl)-1-methyl-1h-imidazole;N(1)-methylhistamine
PW_C000717
1Mhis
1312
8
78134
111
121028
122
123592
135
1065
Oxygen
HMDB0001377
Oxygen is the third most abundant element in the universe after hydrogen and helium and the most abundant element by mass in the Earth's crust. Diatomic oxygen gas constitutes 20.9% of the volume of air. All major classes of structural molecules in living organisms, such as proteins, carbohydrates, and fats, contain oxygen, as do the major inorganic compounds that comprise animal shells, teeth, and bone. Oxygen in the form of O2 is produced from water by cyanobacteria, algae and plants during photosynthesis and is used in cellular respiration for all living organisms. Green algae and cyanobacteria in marine environments provide about 70% of the free oxygen produced on earth and the rest is produced by terrestrial plants. Oxygen is used in mitochondria to help generate adenosine triphosphate (ATP) during oxidative phosphorylation. For animals, a constant supply of oxygen is indispensable for cardiac viability and function. To meet this demand, an adult human, at rest, inhales 1.8 to 2.4 grams of oxygen per minute. This amounts to more than 6 billion tonnes of oxygen inhaled by humanity per year. At a resting pulse rate, the heart consumes approximately 8-15 ml O2/min/100 g tissue. This is significantly more than that consumed by the brain (approximately 3 ml O2/min/100 g tissue) and can increase to more than 70 ml O2/min/100 g myocardial tissue during vigorous exercise. As a general rule, mammalian heart muscle cannot produce enough energy under anaerobic conditions to maintain essential cellular processes; thus, a constant supply of oxygen is indispensable to sustain cardiac function and viability. However, the role of oxygen and oxygen-associated processes in living systems is complex, and they and can be either beneficial or contribute to cardiac dysfunction and death (through reactive oxygen species). Reactive oxygen species (ROS) are a family of oxygen-derived free radicals that are produced in mammalian cells under normal and pathologic conditions. Many ROS, such as the superoxide anion (O2-)and hydrogen peroxide (H2O2), act within blood vessels, altering mechanisms mediating mechanical signal transduction and autoregulation of cerebral blood flow. Reactive oxygen species are believed to be involved in cellular signaling in blood vessels in both normal and pathologic states. The major pathway for the production of ROS is by way of the one-electron reduction of molecular oxygen to form an oxygen radical, the superoxide anion (O2-). Within the vasculature there are several enzymatic sources of O2-, including xanthine oxidase, the mitochondrial electron transport chain, and nitric oxide (NO) synthases. Studies in recent years, however, suggest that the major contributor to O2- levels in vascular cells is the membrane-bound enzyme NADPH-oxidase. Produced O2- can react with other radicals, such as NO, or spontaneously dismutate to produce hydrogen peroxide (H2O2). In cells, the latter reaction is an important pathway for normal O2- breakdown and is usually catalyzed by the enzyme superoxide dismutase (SOD). Once formed, H2O2 can undergo various reactions, both enzymatic and nonenzymatic. The antioxidant enzymes catalase and glutathione peroxidase act to limit ROS accumulation within cells by breaking down H2O2 to H2O. Metabolism of H2O2 can also produce other, more damaging ROS. For example, the endogenous enzyme myeloperoxidase uses H2O2 as a substrate to form the highly reactive compound hypochlorous acid. Alternatively, H2O2 can undergo Fenton or Haber-Weiss chemistry, reacting with Fe2+/Fe3+ ions to form toxic hydroxyl radicals (-.OH). (PMID: 17027622, 15765131).
7782-44-7
C00007
977
15379
CPD-6641
952
O=O
O2
InChI=1S/O2/c1-2
MYMOFIZGZYHOMD-UHFFFAOYSA-N
31.9988
31.989829244
FDB022589
Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948
PW_C001065
O2
95
9
110
5
245
16
500
18
505
8
549
14
625
28
638
3
649
10
674
31
688
20
754
15
763
4
769
33
836
2
1375
49
2016
24
2531
22
2803
29
4260
42
4747
13
5467
123
5480
125
5493
126
5508
127
5809
108
5973
147
6129
159
7006
188
7032
163
7050
160
7319
213
7533
210
7560
212
8395
151
11816
216
11864
198
11883
215
11894
211
12057
225
12063
164
12247
286
12279
226
12325
249
12706
291
12716
292
13004
298
13016
300
13026
301
13038
302
13260
223
42276
17
42657
315
76910
293
77044
294
77214
134
77350
111
77363
130
77377
331
77395
332
77497
113
77512
115
77537
334
77626
336
77723
337
77736
112
77747
129
77756
341
77805
114
77812
133
78070
329
78151
132
78381
345
78805
343
79111
360
120047
408
120383
122
120426
405
120542
407
120553
414
120594
409
120601
406
120883
415
121045
124
121104
383
121605
434
121656
429
122117
382
122573
418
122689
384
122798
374
122822
443
123027
135
123060
376
123128
447
123139
136
123163
448
123176
119
123187
450
123219
137
123226
120
123459
451
123609
118
123669
398
124163
469
124214
464
124669
399
125145
454
125275
121
125425
482
125706
478
125731
483
125737
297
125740
479
125884
481
126100
299
126272
484
126522
495
126721
489
126825
480
126964
502
126986
207
127198
209
127214
208
127219
205
127222
501
127305
504
127345
206
127557
388
127574
515
127835
389
128081
395
128095
390
128312
506
128432
391
2083
Methylimidazole acetaldehyde
HMDB0004181
Methyimidazole acetaldehyde is a metabolite of histamine. The metabolites of ethanol and acetaldehyde can successfully compete with methylimidazole acetaldehyde, since the alcohol and histamine metabolic pathways in the body have two enzymes in common, aldehyde dehydrogenase and aldehyde oxidase. (PMID: 10344773).
19639-03-3
C05827
193545
28104
167957
CN1C=NC(CC=O)=C1
C6H8N2O
InChI=1S/C6H8N2O/c1-8-4-6(2-3-9)7-5-8/h3-5H,2H2,1H3
GCQHUBANENYTLB-UHFFFAOYSA-N
124.1405
124.063662888
FDB023327
1-methylimidazole-4-acetaldehyde;Methylimidazoleacetaldehyde;Methylimidazole acetaldehyde
PW_C002083
MetmAch
1314
8
78136
111
121030
122
123594
135
35
Ammonia
HMDB0000051
Ammonia is a colourless alkaline gas and is one of the most abundant nitrogen-containing compounds in the atmosphere. It is an irritant with a characteristic pungent odor that is widely used in industry. Inasmuch as ammonia is highly soluble in water and, upon inhalation, is deposited in the upper airways, occupational exposures to ammonia have commonly been associated with sinusitis, upper airway irritation, and eye irritation. Acute exposures to high levels of ammonia have also been associated with diseases of the lower airways and interstitial lung. Small amounts of ammonia are naturally formed in nearly all tissues and organs of the vertebrate organism. Ammonia is both a neurotoxin and a metabotoxin. In fact, it is the most common endogenous neurotoxin. A neurotoxin is a compound that causes damage to neural tissue and neural cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Ammonia is recognized to be central in the pathogenesis of a brain condition known as hepatic encephalopathy, which arises from various liver diseases and leads to a build up ammonia in the blood (hyperammonemia). More than 40% of people with cirrhosis develop hepatic encephalopathy. Part of the neurotoxicity of ammonia arises from the fact that it easily crosses the blood-brain barrier and is absorbed and metabolized by the astrocytes, a population of cells in the brain that constitutes 30% of the cerebral cortex. Astrocytes use ammonia when synthesizing glutamine from glutamate. The increased levels of glutamine lead to an increase in osmotic pressure in the astrocytes, which become swollen. There is increased activity of the inhibitory gamma-aminobutyric acid (GABA) system, and the energy supply to other brain cells is decreased. This can be thought of as an example of brain edema. The source of the ammonia leading to hepatic encephalopathy is not entirely clear. The gut produces ammonia, which is metabolized in the liver, and almost all organ systems are involved in ammonia metabolism. Colonic bacteria produce ammonia by splitting urea and other amino acids, however this does not fully explain hyperammonemia and hepatic encephalopathy. The alternative explanation is that hyperammonemia is the result of the intestinal breakdown of amino acids, especially glutamine. The intestines have significant glutaminase activity, predominantly located in the enterocytes. On the other hand, intestinal tissues only have a little glutamine synthetase activity, making it a major glutamine-consuming organ. In addition to the intestine, the kidney is an important source of blood ammonia in patients with liver disease. Ammonia is also taken up by the muscle and brain in hepatic coma, and there is confirmation that ammonia is metabolized in muscle. Excessive formation of ammonia in the brains of Alzheimer's disease patients has also been demonstrated, and it has been shown that some Alzheimer's disease patients exhibit elevated blood ammonia concentrations. Ammonia is the most important natural modulator of lysosomal protein processing. Indeed, there is strong evidence for the involvement of aberrant lysosomal processing of beta-amyloid precursor protein (beta-APP) in the formation of amyloid deposits. Inflammatory processes and activation of microglia are widely believed to be implicated in the pathology of Alzheimer's disease. Ammonia is able to affect the characteristic functions of microglia, such as endocytosis, and cytokine production. Based on these facts, an ammonia-based hypothesis for Alzheimer's disease has been suggested (PMID: 17006913, 16167195, 15377862, 15369278). Chronically high levels of ammonia in the blood are associated with nearly twenty different inborn errors of metabolism including: 3-hydroxy-3-methylglutaryl-CoA lyase deficiency, 3-methyl-crotonylglycinuria, argininemia, argininosuccinic aciduria, beta-ketothiolase deficiency, biotinidase deficiency, carbamoyl phosphate synthetase deficiency, carnitine-acylcarnitine translocase deficiency, citrullinemia type I, hyperinsulinism-hyperammonemia syndrome, hyperornithinemia-hyperammonemia-homocitrullinuria syndrome, isovaleric aciduria, lysinuric protein intolerance, malonic aciduria, methylmalonic aciduria, methylmalonic aciduria due to cobalamin-related disorders, propionic acidemia, pyruvate carboxylase deficiency, and short chain acyl CoA dehydrogenase deficiency (SCAD deficiency). Many of these inborn errors of metabolism are associated with urea cycle disorders or impairment of amino acid metabolism. High levels of ammonia in the blood (hyperammonemia) lead to the activation of NMDA receptors in the brain. This results in the depletion of brain ATP, which in turn leads to the release of glutamate. Ammonia also leads to the impairment of mitochondrial function and calcium homeostasis, thereby decreasing ATP synthesis. Excess ammonia also increases the formation of nitric oxide (NO), which in turn reduces the activity of glutamine synthetase, and thereby decreases the elimination of ammonia in the brain (PMID: 12020609). As a neurotoxin, ammonia predominantly affects astrocytes. Disturbed mitochondrial function and oxidative stress, factors implicated in the induction of the mitochondrial permeability transition, appear to be involved in the mechanism of ammonia neurotoxicity. Ammonia can also affect the glutamatergic and GABAergic neuronal systems, the two prevailing neuronal systems of the cortical structures. All of these effects can lead to irreversible brain damage, coma, and/or death. Infants with urea cycle disorders and hyperammonemia initially exhibit vomiting and increasing lethargy. If untreated, seizures, hypotonia (poor muscle tone, floppiness), respiratory distress (respiratory alkalosis), and coma can occur. Adults with urea cycle disorders and hyperammonemia will exhibit episodes of disorientation, confusion, slurred speech, unusual and extreme combativeness or agitation, stroke-like symptoms, lethargy, and delirium. Ammonia also has toxic effects when an individual is exposed to ammonia solutions. Acute exposure to high levels of ammonia in air may be irritating to skin, eyes, throat, and lungs and cause coughing and burns. Lung damage and death may occur after exposure to very high concentrations of ammonia. Swallowing concentrated solutions of ammonia can cause burns in the mouth, throat, and stomach. Splashing ammonia into eyes can cause burns and even blindness.
7664-41-7
C00014
222
16134
AMMONIA
217
N
H3N
InChI=1S/H3N/h1H3
QGZKDVFQNNGYKY-UHFFFAOYSA-N
17.0305
17.026549101
FDB003908
Ammonia anhydrous;Ammonia inhalant;Ammonia solution strong [usan];Ammonia water;Ammoniak;Liquid ammonia;Am-fol;Ammonia;Ammonia (conc 20% or greater);Ammonia gas;Ammonia solution;Ammonia solution strong (nf);Ammonia water (jp15);Ammoniac [french];Ammoniaca [italian];Ammoniacum gummi;Ammoniak [german];Ammoniak kconzentrierter;Ammoniakgas;Ammonium ion;Amoniak [polish];Anhydrous ammonia;Aromatic ammonia vaporole;Azane;Nh(3);Nh3;Nitro-sil;Primaeres amin;Sekundaeres amin;Spirit of hartshorn;Tertiaeres amin;[nh3];Ammoniac;Amoniaco;R-717;Ammonia solution strong
PW_C000035
NH3
97
9
112
5
133
8
142
4
438
2
479
13
550
14
1468
54
2533
22
2572
3
5338
111
6016
147
7022
160
7177
205
11786
198
11848
277
11885
215
12708
291
12718
292
76966
225
77046
294
77329
133
77343
132
77469
333
77499
113
77539
334
77597
115
77985
347
77993
112
78072
329
79244
293
80650
135
80657
119
116203
109
119921
122
120049
408
120053
126
120136
407
120343
406
120363
412
120462
405
121046
124
121161
425
122119
382
122800
374
122805
443
122993
120
123010
446
123096
376
123610
118
123733
460
124671
399
125311
297
125427
482
125431
301
125502
481
125663
479
125708
478
126102
299
126274
484
126966
502
126970
207
127039
206
127158
501
127200
209
127600
388
127837
389
1783
Hydrogen peroxide
HMDB0003125
Hydrogen peroxide (H2O2) is a very pale blue liquid which appears colourless in a dilute solution, slightly more viscous than water. It is a weak acid. It has strong oxidizing properties and is therefore a powerful bleaching agent that is mostly used for bleaching paper, but has also found use as a disinfectant and as an oxidizer. Hydrogen peroxide in the form of carbamide peroxide is widely used for tooth whitening (bleaching), both in professionally- and in self-administered products. Hydrogen peroxide (H2O2) is a well-documented component of living cells. It plays important roles in host defense and oxidative biosynthetic reactions. In addition there is growing evidence that at low levels, H2O2 also functions as a signaling agent, particularly in higher organisms. H2O2 has increasingly been viewed as an important cellular signaling agent in its own right, capable of modulating both contractile and growth-promoting pathways with more far-reaching effects. Due to the accumulation of hydrogen peroxide in the skin of patients with the depigmentation disorder vitiligo, the human epidermis cannot have the normal capacity for autocrine synthesis, transport and degradation of acetylcholine as well as the muscarinic (m1-m5) and nicotinic signal transduction in keratinocytes and melanocytes. Accumulating evidence suggests that hydrogen peroxide (H(2)O(2)) plays an important role in cancer development. Experimental data have shown that cancer cells produce high amounts of H(2)O(2). An increase in the cellular levels of H(2)O(2) has been linked to several key alterations in cancer, including DNA alterations, cell proliferation, apoptosis resistance, metastasis, angiogenesis and hypoxia-inducible factor 1 (HIF-1) activation. (PMID: 17150302, 17335854, 16677071, 16607324, 16514169).
7722-84-1
C00027
784
16240
HYDROGEN-PEROXIDE
763
OO
H2O2
InChI=1S/H2O2/c1-2/h1-2H
MHAJPDPJQMAIIY-UHFFFAOYSA-N
34.0147
34.005479308
FDB014562
Adeka super el;Albone;Albone 35;Albone ds;Anti-keim 50;Asepticper;Baquashock;Cix;Clarigel gold;Crestal whitestrips;Crystacide;Dentasept;Deslime lp;Hioxyl;Hipox;Hybrite;Hydrogen dioxide;Hydrogen peroxide;Inhibine;Lase peroxide;Lensan a;Magic bleaching;Metrokur;Mirasept;Nite white excel 2;Odosat d;Opalescence xtra;Oxigenal;Oxydol;Oxyfull;Oxysept;Oxysept i;Pegasyl;Perhydrol;Perone;Peroxaan;Peroxclean;Quasar brite;Select bleach;Superoxol;T-stuff;Whiteness hp;Whitespeed;Xtra white;[oh(oh)];Dihydrogen dioxide;H2o2;Hooh
PW_C001783
H2O2
98
9
113
5
188
8
551
14
627
28
755
15
1243
3
1691
2
1749
51
2534
22
3818
10
4749
13
4752
31
5495
126
5502
123
5510
127
5810
108
6005
147
7038
163
8396
151
11817
216
11886
215
12461
226
12709
291
12719
292
13028
301
13035
298
13040
302
13405
222
42658
315
77022
225
77047
294
77079
293
77500
113
77540
334
77598
115
77720
332
77725
337
77806
114
77810
111
77819
326
78073
329
78152
132
78598
112
120050
408
120102
122
120463
405
120595
409
120609
416
120954
407
121047
124
122120
382
122801
374
122814
443
122839
135
123097
376
123157
447
123165
448
123220
137
123234
452
123520
119
123611
118
124672
399
125428
482
125469
297
125709
478
125732
483
125748
488
125895
481
126103
299
126275
484
126967
502
126978
207
127006
205
127201
209
127215
208
127230
505
127356
206
127601
388
127838
389
964
FAD
HMDB0001248
FAD, also known as flavitan or adeflavin, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is slightly soluble (in water) and a moderately acidic compound (based on its pKa). FAD has been found in human liver and muscle tissues, and has also been detected in multiple biofluids, such as feces and blood. Within the cell, FAD is primarily located in the cytoplasm, mitochondria, endoplasmic reticulum and peroxisome. FAD exists in all living organisms, ranging from bacteria to humans. In humans, FAD is involved in the risedronate action pathway, the ibandronate action pathway, the valine, leucine and isoleucine degradation pathway, and the pyrimidine metabolism pathway. FAD is also involved in several metabolic disorders, some of which include the oncogenic action OF L-2-hydroxyglutarate in hydroxygluaricaciduria pathway, gaba-transaminase deficiency, 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, and the saccharopinuria/hyperlysinemia II pathway. FAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).
146-14-5
C00016
643975
16238
FAD
559059
DB03147
CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2
C27H33N9O15P2
InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1
VWWQXMAJTJZDQX-UYBVJOGSSA-N
785.5497
785.157134455
FDB022511
1h-purin-6-amine flavin dinucleotide;1h-purin-6-amine flavine dinucleotide;Adenine-flavin dinucleotide;Adenine-flavine dinucleotide;Adenine-riboflavin dinuceotide;Adenine-riboflavin dinucleotide;Adenine-riboflavine dinucleotide;Fad;Flamitajin b;Flanin f;Flavin adenine dinucleotide;Flavin adenine dinucleotide oxidized;Flavin-adenine dinucleotide;Flavine adenosine diphosphate;Flavine-adenine dinucleotide;Flavitan;Flaziren;Isoalloxazine-adenine dinucleotide;Riboflavin 5'-adenosine diphosphate;Riboflavin-adenine dinucleotide;Riboflavine-adenine dinucleotide;Adeflavin
PW_C000964
FAD
99
9
114
5
186
8
192
3
216
4
253
17
628
28
825
18
840
2
1188
14
1489
42
1612
29
1622
49
2133
58
2536
22
3723
26
4602
36
4688
31
4741
13
4758
10
4881
6
5268
103
5285
102
5335
111
5496
126
5511
127
5613
118
6030
155
6054
156
6082
161
6116
162
6390
1
6475
178
6499
179
6666
107
7039
163
7175
205
7321
213
7465
222
7487
223
9076
224
11818
216
11887
215
11899
211
12296
225
12328
249
12443
151
12519
227
12595
226
12710
291
12720
292
13029
301
13041
302
43623
318
77080
293
77126
133
77152
134
77501
113
77507
112
77518
115
77541
334
77615
132
77726
337
78054
329
78375
345
78930
331
79222
336
79272
358
80012
368
80034
369
80714
119
119958
406
119999
384
120051
408
120107
407
120432
405
120453
122
120490
124
121278
429
121298
418
121417
382
121489
383
122748
120
122776
121
122802
374
122823
443
123066
376
123087
135
123166
448
123849
464
123868
454
123976
399
124047
398
125348
479
125378
480
125429
482
125474
481
125697
297
125979
489
126107
299
126277
484
126891
501
126920
391
126968
502
126987
207
127011
206
127310
209
127432
506
127602
388
127840
389
140790
185
140799
186
143
NADP
HMDB0000217
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).
53-59-8
C00006
5886
18009
NAD(P)
5675
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H28N7O17P3
InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
XJLXINKUBYWONI-NNYOXOHSSA-N
743.405
743.075452041
FDB021908
Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acid
PW_C000143
NADP
183
8
191
3
768
5
780
10
824
18
839
2
1611
29
1617
49
4685
31
4796
14
4801
14
5308
111
5790
108
6017
147
6132
159
6273
35
6778
117
7069
188
7105
163
7152
205
7206
160
7317
213
7346
210
7562
212
7589
170
8197
225
8220
151
8419
224
11811
198
11897
211
12008
222
12152
164
12249
286
12597
226
12650
249
42344
315
43745
322
76913
293
77164
132
77384
331
77396
332
77461
130
77515
115
77624
336
77814
334
77870
112
80713
119
113165
94
120106
407
120429
405
120450
122
120604
408
120618
123
121142
125
121277
429
121401
124
121485
383
123063
376
123084
135
123229
374
123243
447
123713
136
123848
464
123960
118
124043
398
125473
481
125694
297
125743
482
126215
299
126528
495
127010
206
127225
502
127570
388
128100
390
140709
168
1712
Methylimidazoleacetic acid
HMDB0002820
Methylimidazoleacetic acid is the main metabolite of histamine. This end product of histamine catabolism is formed by N-methylation in the imidazole ring to methylhistamine by histamine methyltransferase (EC 2.1.1.8) and a subsequent oxidative deamination in the side chain by type B monoamine oxidase (EC 1.4.3.4). Based on studies, it is known that as much as 70 to 80 percent of the histamine metabolized in the body is excreted in the urine as methylimidazoleacetic acid. Thus, urinary methylimidazoleacetic acid being the major and specific histamine metabolite is a clear marker of any changes in histamine metabolism in the body. The urinary excretion of methylimidazoleacetic acid is considered a reliable indicator of histamine turnover rate in the body. The excretion of methylimidazoleacetic acid is higher in men than in women. However, this gender difference is abolished when corrected for creatinine excretion. A possible explanation is that basal histamine turnover is related to body size. There is no significant difference in methylimidazoleacetic acid excretion between smokers and non-smokers when analyzing absolute values (mg/24 h). When using methylimidazoleacetic acid values corrected for creatinine excretion female smokers have significantly higher methylimidazoleacetic acid excretion compared to nonsmokers (PMID: 11411609, 7130180, 10350179, 10202992).
2625-49-2
C05828
75810
1606
68319
CN1C=NC(CC(O)=O)=C1
C6H8N2O2
InChI=1S/C6H8N2O2/c1-8-3-5(7-4-8)2-6(9)10/h3-4H,2H2,1H3,(H,9,10)
ZHCKPJGJQOPTLB-UHFFFAOYSA-N
140.1399
140.05857751
FDB023069
1,4-methyl-imidazoleacetic acid;1,4-methylimidazoleacetate;1-methyl-1h-imidazole-4-acetate;1-methyl-1h-imidazole-4-acetic acid;1-methyl-4-imidazoleacetate;1-methyl-4-imidazoleacetic acid;1-methylimidazole-4-acetate;Miaa;Methylimidazole acetate;Methylimidazoleacetate;Methylimidazoleacetic acid;N tau-methylimidazoleacetic acid;Tele-methylimidazoleacetate;Tele-methylimidazoleacetic acid;1,4-methyl-imidazoleacetate;2-(1-methylimidazol-4-yl)acetate;1-methylimidazole-4-acetic acid
PW_C001712
Mldzaa
1316
8
78138
111
121032
122
123596
135
146
NADPH
HMDB0000221
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).
53-57-6
C00005
22833512
16474
NADPH
17215925
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H30N7O17P3
InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
ACFIXJIJDZMPPO-NNYOXOHSSA-N
745.4209
745.091102105
FDB021909
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reduced
PW_C000146
NADPH
185
8
190
3
778
10
796
5
821
18
837
2
1609
29
1615
49
4687
31
4793
14
4797
14
5310
111
5789
108
5972
147
6128
159
6271
35
6779
117
7068
188
7103
163
7154
205
7205
160
7315
213
7345
210
7559
212
7591
170
8194
225
8219
151
8421
224
11812
198
11893
211
12006
222
12150
164
12245
286
12596
226
12648
249
42343
315
43746
322
76911
293
77166
132
77385
331
77394
332
77460
130
77504
112
77511
115
77623
336
80712
119
113164
94
120105
407
120425
405
120452
122
120616
123
121141
125
121275
429
121402
124
121483
383
123059
376
123086
135
123241
447
123712
136
123846
464
123961
118
124041
398
125472
481
125696
297
126214
299
126529
495
127009
206
127572
388
128101
390
140706
168
40034
Hydrogen Ion
HMDB0059597
Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])
C00080
1038
15378
1010
[H+]
H
InChI=1S/p+1
GPRLSGONYQIRFK-UHFFFAOYSA-N
1.0079
1.007825032
H+;H(+);Hydrogen cation;Hydron;Proton
PW_C040034
H+
215
4
670
8
753
15
788
31
848
3
1116
2
1463
26
1464
54
2231
49
2780
17
4250
22
4254
42
4547
10
4576
18
4694
70
5241
103
5327
111
5353
112
5626
108
5639
107
5699
100
5720
105
5742
117
5963
147
6037
155
6070
157
6093
161
6130
159
6232
166
6483
178
6601
152
6692
101
6843
188
6910
187
7100
163
7168
205
7191
206
7453
219
7454
220
7472
222
7525
213
7532
210
7558
212
7572
160
7590
170
8195
225
8218
151
8243
226
8413
162
8420
224
9139
195
9155
249
11915
164
12015
281
12181
285
12246
286
12266
287
12521
227
13257
223
13325
294
15330
308
42329
315
42354
318
42401
322
42405
312
42454
320
76912
293
77136
133
77210
134
77372
331
77804
114
77955
132
77990
327
77991
347
78379
345
79929
130
80019
368
80387
310
80388
304
80722
119
93823
124
94823
383
110550
388
112855
94
113280
390
115537
398
115539
118
115856
336
116205
109
119973
406
120193
407
120549
122
120593
409
121170
424
121171
425
122569
418
122615
384
122687
125
122758
120
123183
135
123218
137
123742
459
123743
460
125141
454
125188
121
125273
136
125359
479
125550
481
125730
483
125736
297
125809
299
126517
495
126717
489
126766
480
126823
300
126902
501
127213
208
128308
506
128361
391
128430
395
140692
882
140693
883
140699
167
140707
168
140715
14
140742
788
140743
597
140760
185
1992
Imidazole-4-acetaldehyde
HMDB0003905
Imidazole-4-acetaldehyde is a naturally occurring aldehyde metabolite of histamine formed by the action of histaminase (E.C. 1.4.3.6), and can be synthesized by oxidation of histidine. Aldehyde dehydrogenase (EC 1.2.1.3) is the only enzyme in the human liver capable of catalyzing dehydrogenation of aldehydes arising via monoamine, diamine, and plasma amine oxidases. NAD-linked dehydrogenation of short chain aliphatic aldehydes has been found in virtually every organ of the mammalian body. Imidazole-4-acetaldehyde is a good substrate for all aldehyde dehydrogenase isozymes. Experimentally, the prebiotic formation of histidine has been accomplished by the reaction of erythrose with formamidine followed by a Strecker synthesis. Imidazole-4-acetaldehyde could have been converted to histidine on the primitive earth by a Strecker synthesis, and several prebiotic reactions could convert imidazole-4-glycol and imidazole-4-ethanol to imidazole-4-acetaldehyde. (PMID: 2071588, 2957640, 11536478).
645-14-7
C05130
150841
27398
132948
O=CCC1=CN=CN1
C5H6N2O
InChI=1S/C5H6N2O/c8-2-1-5-3-6-4-7-5/h2-4H,1H2,(H,6,7)
MQSRGWNVEZRLDK-UHFFFAOYSA-N
110.1139
110.048012824
FDB023247
1h-imidazole-4-acetaldehyde;1h-imidazole-5-acetaldehyde;4-imidazolylacetaldehyde;Imidazole acetaldehyde;Imidazole-4(or 5)-acetaldehyde
PW_C001992
Imd4aca
1318
8
78140
111
121034
122
123598
135
721
NAD
HMDB0000902
NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).
53-84-9
C00003
5893
15846
NAD
5682
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H27N7O14P2
InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BAWFJGJZGIEFAR-NNYOXOHSSA-N
663.4251
663.109121631
FDB022309
3-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nad
PW_C000721
NAD
140
4
150
3
353
8
651
10
1114
2
1134
43
1273
5
1466
54
2229
49
2779
17
2835
29
3107
9
4807
18
4813
18
4819
28
4902
6
4960
31
5167
95
5238
103
5334
111
5360
112
5469
123
5482
125
5590
135
5610
118
5696
100
5738
108
5827
141
5912
147
5942
151
6024
155
6072
157
6076
161
6385
1
6469
178
6772
117
6890
160
7012
188
7097
163
7174
205
7197
206
7405
198
7459
222
8241
226
8359
225
9085
224
11819
216
12322
249
13006
298
13018
300
13256
223
42404
322
42619
315
77104
132
77120
133
77209
134
77370
331
77650
336
77667
334
77702
332
77709
130
77915
113
77983
347
78406
356
80006
368
80690
119
93825
124
110552
388
112750
166
112853
94
119929
122
119952
406
120171
407
120834
419
120984
408
121159
425
121242
126
121259
429
121817
383
122614
384
122742
120
123130
447
123141
136
123419
455
123549
374
123731
460
123812
443
123829
464
124370
398
125187
121
125319
297
125342
479
125530
481
125806
299
125825
490
125924
482
126515
495
126765
480
126885
501
127278
507
127383
502
128089
390
128360
391
128428
395
140757
185
1357
Imidazoleacetic acid
HMDB0002024
Imidazoleacetic acid, also known as 4(5)-imidazoleacetate or imac, belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. Imidazoleacetic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Imidazoleacetic acid has been primarily detected in feces, urine, blood, and cerebrospinal fluid. Within the cell, imidazoleacetic acid is primarily located in the cytoplasm and mitochondria. In humans, imidazoleacetic acid is involved in the histidine metabolism pathway. Imidazoleacetic acid is also involved in the metabolic disorder called the histidinemia pathway. Outside of the human body, imidazoleacetic acid can be found in a number of food items such as pepper (c. frutescens), black-eyed pea, rambutan, and common hazelnut. This makes imidazoleacetic acid a potential biomarker for the consumption of these food products. Imidazoleacetic acid is a metabolite product of Histamine metabolism. It is present in normal urine and increased in histidinemic patients. (PMID 6530403).
645-65-8
C02835
28305488
16974
4-IMIDAZOLEACETATE
86856
OC(=O)CC1=CN=CN1
C5H6N2O2
InChI=1S/C5H6N2O2/c8-5(9)1-4-2-6-3-7-4/h2-3H,1H2,(H,6,7)(H,8,9)
PRJKNHOMHKJCEJ-UHFFFAOYSA-N
126.1133
126.042927446
FDB012464
1h-imidazol-4-ylacetic acid;1h-imidazole-4-acetic acid;4(5)-imidazoleacetate;4-imidazoleacetate;4-imidazoleacetic acid;Iaa;Imac;Izc;Imidazol-4-ylacetic acid;Imidazole acetate;Imidazole-4-acetate;Imidazole-4-acetic acid;Imidazolyl-4-acetic acid;Lopac-i-0375;Imidazoleacetic acid;1h-imidazole-4-acetate;Imidazol-4-ylacetate;4(5)-imidazoleacetic acid;Imidazoleacetate
PW_C001357
Imaa
1320
8
78141
111
121035
122
123599
135
1144
NADH
HMDB0001487
NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).
58-68-4
C00004
439153
16908
NADH
388299
DB00157
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O14P2
InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BOPGDPNILDQYTO-NNYOXOHSSA-N
665.441
665.124771695
FDB022649
1,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotide
PW_C001144
NADH
143
4
153
3
490
8
648
10
1115
2
1275
5
1469
54
2230
49
2781
17
2836
29
3109
9
4806
18
4812
18
4821
28
4904
6
4959
31
5169
95
5240
103
5332
111
5358
112
5466
123
5479
125
5593
135
5698
100
5737
108
5829
141
5915
147
5945
151
6027
155
6079
161
6387
1
6472
178
6771
117
6893
160
7011
188
7099
163
7172
205
7195
206
7462
222
8244
226
8360
225
9086
224
11809
198
11821
216
12320
249
13003
298
13015
300
13255
223
42403
322
42618
315
77107
132
77123
133
77208
134
77371
331
77651
336
77668
334
77700
332
77707
130
77917
113
77986
347
80009
368
80691
119
93822
124
110549
388
112854
94
115838
118
119955
406
120172
407
120378
122
120986
408
121162
425
121244
126
121693
429
121818
383
122616
384
122745
120
123127
447
123138
136
123551
374
123734
460
123814
443
124242
464
124371
398
125189
121
125345
479
125531
481
125762
297
125808
299
125926
482
126516
495
126767
480
126888
501
127385
502
128090
390
128362
391
128429
395
140759
185
205
Urocanic acid
HMDB0000301
Urocanic acid is a breakdown (deamination) product of histidine. In the liver, urocanic acid is an intermediate in the conversion of histidine to glutamic acid, whereas in the epidermis, it accumulates and may be both a UV protectant and an immunoregulator. Urocanic acid (UA) exists as a trans isomer (t-UA, approximately 30 mg/cm2) in the uppermost layer of the skin (stratum corneum). t-UA is formed as the cells of the second layer of skin become metabolically inactive. During this process, proteins and membranes degrade, histidine is released, and histidase (histidine ammonia lyase) catalyzes the deamination of histidine to form t-UA. t-UA accumulates in the epidermis until removal by either the monthly skin renewal cycle or sweat. Upon absorption of UV light, the naturally occurring t-UA isomerizes to its cis form, c-UA. Because DNA lesions (e.g., pyrimidine dimers) in the lower epidermis can result from UV-B absorption, initial research proposed that t-UA acted as a natural sunscreen absorbing UV-B in the stratum corneum before the damaging rays could penetrate into lower epidermal zones. Researchers have found that c-UA also suppresses contact hypersensitivity and delayed hypersensitivity, reduces the Langerhans cell count in the epidermis, prolongs skin-graft survival time, and affects natural killer cell activity.
104-98-3
C00785
736715
30817
UROCANATE
643824
DB01971
OC(=O)\C=C\C1=CNC=N1
C6H6N2O2
InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+
LOIYMIARKYCTBW-OWOJBTEDSA-N
138.124
138.042927446
FDB000921
3-(1h-imidazol-4-yl)-2-propenoate;3-(1h-imidazol-4-yl)-2-propenoic acid;3-(1h-imidazol-4-yl)acrylate;3-(1h-imidazol-4-yl)acrylic acid;3-(4-imidazolyl)acrylate;3-(4-imidazolyl)acrylic acid;5-imidazoleacrylate;5-imidazoleacrylic acid;Imidazole-4-acrylate;Imidazole-4-acrylic acid;Imidazoleacrylic acid;Urocanate;Urocanic acid
PW_C000205
Urocana
434
8
77327
111
120340
122
122991
135
125662
297
127156
205
802
4-Imidazolone-5-propionic acid
HMDB0001014
4-Imidazolone-5-propanoate is a metabolite of histidine metabolism. It is produced from urocanic acid by the enzyme urocanate hydratase [EC:4.2.1.49]. 4-Imidazolone-5-propionic acid can spontaneously decay to 4-oxoglutaramate or formylisoglutamine. It is also converted to N-forminimo-L-glutamate by the enzyme imidazolonepropionase [EC:3.5.2.7].
17340-16-8
C03680
128
27384
4-IMIDAZOLONE-5-PROPIONATE
125
OC(=O)CCC1N=CNC1=O
C6H8N2O3
InChI=1S/C6H8N2O3/c9-5(10)2-1-4-6(11)8-3-7-4/h3-4H,1-2H2,(H,9,10)(H,7,8,11)
HEXMLHKQVUFYME-UHFFFAOYSA-N
156.1393
156.053492132
FDB022371
(s)-3-(5-oxo-4,5-dihydro-3h-imidazol-4-yl)propanoate;(s)-3-(5-oxo-4,5-dihydro-3h-imidazol-4-yl)propanoic acid;3-(4-oxo-4,5-dihydro-1h-imidazol-5-yl)propanoate;3-(4-oxo-4,5-dihydro-1h-imidazol-5-yl)propanoic acid;3-(5-oxo-4,5-dihydro-3h-imidazol-4-yl)propanoate;3-(5-oxo-4,5-dihydro-3h-imidazol-4-yl)propanoic acid;4,5-dihydro-4-oxo-5-imidazolepropanoate;4,5-dihydro-4-oxo-5-imidazolepropanoic acid;4,5-dihydro-5-oxo-1h-imidazole-4-propanoate;4,5-dihydro-5-oxo-1h-imidazole-4-propanoic acid;4-imidazolone-5-propanoate;4-imidazolone-5-propanoic acid;4-imidazolone-5-propionate;4-imidazolone-5-propionic acid;Imidazol-4-one-5-propionate;Imidazol-4-one-5-propionic acid;Imidazolone propionate;Imidazolone propionic acid;Imidazolonepropanoate;Imidazolonepropanoic acid
PW_C000802
4Im-5pa
1322
8
78143
111
121037
122
123601
135
680
Formiminoglutamic acid
HMDB0000854
Formiminoglutamic acid, also known as N-formimino-L-glutamate or acid, formiminoglutamic, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Formiminoglutamic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Formiminoglutamic acid has been detected in multiple biofluids, such as feces and urine. Within the cell, formiminoglutamic acid is primarily located in the cytoplasm. In humans, formiminoglutamic acid is involved in the histidine metabolism pathway. Formiminoglutamic acid is also involved in the metabolic disorder called the histidinemia pathway. Measurement of this acid in the urine after oral administration of histidine provides the basis for the diagnostic test of folic acid deficiency and of megaloblastic anemia of pregnancy.
816-90-0
C00439
439233
7274
N-FORMIMINO-L-GLUTAMATE
388370
OC(=O)CC[C@H](NC=N)C(O)=O
C6H10N2O4
InChI=1S/C6H10N2O4/c7-3-8-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H2,7,8)(H,9,10)(H,11,12)/t4-/m0/s1
NRXIKWMTVXPVEF-BYPYZUCNSA-N
174.1546
174.064056818
FDB022280
Formimino-l-glutamate;Formimino-l-glutamic acid;Formimino-glu;Formiminoglutamate;N-(iminomethyl)-l-glutamic acid;N-formimidoyl-glutamic acid;N-formimidoyl-l-glutamate;N-formimidoyl-l-glutamic acid;N-formimino-l-glutamate;N-formimino-l-glutamic acid;N-formimino-glutamate
PW_C000680
FormGlu
1324
8
78145
111
121039
122
123603
135
1221
Tetrahydrofolic acid
HMDB0001846
Tetrahydrofolate is a soluble coenzyme (vitamin B9) that is synthesized de novo by plants and microorganisms, and absorbed from the diet by animals. It is composed of three distinct parts: a pterin ring, a p-ABA (p-aminobenzoic acid) and a polyglutamate chain with a number of residues varying between 1 and 8. Only the tetra-reduced form of the molecule serves as a coenzyme for C1 transfer reactions. In biological systems, the C1-units exist under various oxidation states and the different tetrahydrofolate derivatives constitute a family of related molecules named indistinctly under the generic term folate. (PMID 16042593). Folate is important for cells and tissues that rapidly divide. Cancer cells divide rapidly, and drugs that interfere with folate metabolism are used to treat cancer. Methotrexate is a drug often used to treat cancer because it inhibits the production of the active form, tetrahydrofolate. Unfortunately, methotrexate can be toxic, producing side effects such as inflammation in the digestive tract that make it difficult to eat normally. -- Wikipedia; Signs of folic acid deficiency are often subtle. Diarrhea, loss of appetite, and weight loss can occur. Additional signs are weakness, sore tongue, headaches, heart palpitations, irritability, and behavioral disorders. Women with folate deficiency who become pregnant are more likely to give birth to low birth weight and premature infants, and infants with neural tube defects. In adults, anemia is a sign of advanced folate deficiency. In infants and children, folate deficiency can slow growth rate. Some of these symptoms can also result from a variety of medical conditions other than folate deficiency. It is important to have a physician evaluate these symptoms so that appropriate medical care can be given. -- Wikipedia; Folinic acid is a form of folate that can help 'rescue' or reverse the toxic effects of methotrexate. Folinic acid is not the same as folic acid. Folic acid supplements have little established role in cancer chemotherapy. There have been cases of severe adverse effects of accidental substitution of folic acid for folinic acid in patients receiving methotrexate cancer chemotherapy. It is important for anyone receiving methotrexate to follow medical advice on the use of folic or folinic acid supplements. -- Wikipedia. Low concentrations of folate, vitamin B12, or vitamin B6 may increase the level of homocysteine, an amino acid normally found in blood. There is evidence that an elevated homocysteine level is an independent risk factor for heart disease and stroke. The evidence suggests that high levels of homocysteine may damage coronary arteries or make it easier for blood clotting cells called platelets to clump together and form a clot. However, there is currently no evidence available to suggest that lowering homocysteine with vitamins will reduce your risk of heart disease. Clinical intervention trials are needed to determine whether supplementation with folic acid, vitamin B12 or vitamin B6 can lower your risk of developing coronary heart disease. -- Wikipedia.
135-16-0
C00101
13781857
20506
THF
18714427
DB00116
NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)N2)N1
C19H23N7O6
InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11-,12?/m0/s1
MSTNYGQPCMXVAQ-PXYINDEMSA-N
445.4292
445.170981503
FDB022705
(6s)-tetrahydrofolate;(6s)-tetrahydrofolic acid;5,6,7,8-tetrahydrofolate;5,6,7,8-tetrahydrofolic acid;Tetra-h-folate;Tetrahydrafolate;Tetrahydrofolate;Tetrahydrofolic acid;Tetrahydropteroyl mono-l-glutamate;Tetrahydropteroylglutamate
PW_C001221
THFA
448
4
571
8
975
3
1809
2
5307
111
5347
112
5601
135
5786
108
6009
147
7066
188
7151
205
7185
206
7583
163
11797
198
42640
315
77336
133
78118
132
120352
406
120482
122
120696
407
122166
124
123001
120
123301
119
124718
118
125673
479
125749
297
125771
481
126324
299
127168
501
127886
388
1179
5-Formiminotetrahydrofolic acid
HMDB0001534
5-Formiminotetrahydrofolic acid belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. 5-Formiminotetrahydrofolic acid is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, 5-formiminotetrahydrofolic acid is primarily located in the cytoplasm. In humans, 5-formiminotetrahydrofolic acid is involved in the folate metabolism pathway, the folate malabsorption, hereditary pathway, the histidine metabolism pathway, and the methotrexate action pathway. 5-Formiminotetrahydrofolic acid is also involved in a couple of metabolic disorders, which include the histidinemia pathway and methylenetetrahydrofolate reductase deficiency (MTHFRD). 5-Formiminotetrahydrofolic acid is a substrate for Formimidoyltransferase-cyclodeaminase.
2311-81-1
C00664
530
15639
5-FORMIMINO-THF
11267158
NC1=NC2=C(N(C=N)C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)CN2)C(=O)N1
C20H24N8O6
InChI=1S/C20H24N8O6/c21-9-28-12(8-24-16-15(28)18(32)27-20(22)26-16)7-23-11-3-1-10(2-4-11)17(31)25-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,21,23H,5-8H2,(H,25,31)(H,29,30)(H,33,34)(H4,22,24,26,27,32)
YCWUVLPMLLBDCU-UHFFFAOYSA-N
472.4546
472.18188054
FDB022676
5-formimidoyltetrahydrofolate;5-formiminotetrahydrofolate;5-formimidoyltetrahydrofolic acid
PW_C001179
5-FTHA
958
8
5337
111
7176
205
120686
122
123295
135
125765
297
95
L-Glutamic acid
HMDB0000148
Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. (http://en.wikipedia.org/wiki/Glutamic_acid).
56-86-0
C00025
33032
16015
GLT
30572
DB00142
N[C@@H](CCC(O)=O)C(O)=O
C5H9NO4
InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
WHUUTDBJXJRKMK-VKHMYHEASA-N
147.1293
147.053157781
FDB012535
(2s)-2-aminopentanedioate;(2s)-2-aminopentanedioic acid;(s)-(+)-glutamate;(s)-(+)-glutamic acid;(s)-2-aminopentanedioate;(s)-2-aminopentanedioic acid;(s)-glutamate;(s)-glutamic acid;1-amino-propane-1,3-dicarboxylate;1-amino-propane-1,3-dicarboxylic acid;1-aminopropane-1,3-dicarboxylate;1-aminopropane-1,3-dicarboxylic acid;2-aminoglutarate;2-aminoglutaric acid;2-aminopentanedioate;2-aminopentanedioic acid;Aciglut;Aminoglutarate;Aminoglutaric acid;E;Glt;Glu;Glusate;Glut;Glutacid;Glutamicol;Glutamidex;Glutaminate;Glutaminic acid;Glutaminol;Glutaton;L-(+)-glutamate;L-(+)-glutamic acid;L-glu;L-glutamate;L-glutaminate;L-glutaminic acid;L-a-aminoglutarate;L-a-aminoglutaric acid;L-alpha-aminoglutarate;L-alpha-aminoglutaric acid;A-aminoglutarate;A-aminoglutaric acid;A-glutamate;A-glutamic acid;Alpha-aminoglutarate;Alpha-aminoglutaric acid;Alpha-glutamate;Alpha-glutamic acid;Acide glutamique;Acido glutamico;Acidum glutamicum;Glutamate;Glutamic acid;L-glutaminsaeure
PW_C000095
Glu
16
2
44
3
65
8
119
1
138
4
164
14
969
9
1105
42
1448
50
1456
26
1462
54
5323
111
5344
113
5415
117
5439
118
5565
132
5631
107
5632
108
5859
105
6006
147
6071
157
6191
94
6531
85
6838
187
6844
188
7092
72
7093
71
7165
205
7182
207
7514
224
7518
151
8208
225
8373
220
11792
198
11855
161
12004
222
12621
31
12683
289
12697
290
42348
315
42349
318
42845
320
77020
253
77332
133
77525
112
77971
346
77977
327
77981
347
78291
345
80649
135
120023
124
120040
122
120086
407
120347
406
120692
126
120816
418
121147
423
121153
424
121157
425
122833
119
122997
120
123299
443
123401
454
123719
458
123725
459
123729
460
125401
299
125418
297
125457
481
125667
479
125769
301
125802
489
126941
388
126995
206
127162
501
127257
506
140738
84
140739
597
32
Adenosine monophosphate
HMDB0000045
Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP can be produced during ATP synthesis by the enzyme adenylate kinase. AMP has recently been approved as a 'Bitter Blocker' additive to foodstuffs. When AMP is added to bitter foods or foods with a bitter aftertaste it makes them seem 'sweeter'. This potentially makes lower calorie food products more palatable.
61-19-8
C00020
6083
16027
AMP
5858
DB00131
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
C10H14N5O7P
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
UDMBCSSLTHHNCD-KQYNXXCUSA-N
347.2212
347.063084339
DBMET00485
FDB021806
5'-amp;5'-adenosine monophosphate;5'-adenylate;5'-adenylic acid;Amp;Adenosine 5'-monophosphate;Adenosine 5'-phosphate;Adenosine 5'-phosphorate;Adenosine 5'-phosphoric acid;Adenosine phosphate;Adenosine-5'-monophosphorate;Adenosine-5'-monophosphoric acid;Adenosine-5-monophosphorate;Adenosine-5-monophosphoric acid;Adenosine-monophosphate;Adenosine-phosphate;Adenovite;Adenylate;Adenylic acid;Cardiomone;Lycedan;Muscle adenylate;Muscle adenylic acid;My-b-den;My-beta-den;Phosaden;Phosphaden;Phosphentaside;5'-o-phosphonoadenosine;Adenosine 5'-(dihydrogen phosphate);Adenosine monophosphate;Adenosine-5'p;Adenosini phosphas;Ado5'p;Fosfato de adenosina;Pa;Pado;Phosphate d'adenosine;5'-adenosine monophosphoric acid;Adenosine phosphoric acid;Adenosine 5'-(dihydrogen phosphoric acid);Adenosine 5'-monophosphoric acid;Adenosine monophosphoric acid;Adenosine-5'-monophosphate;Phosphoric acid d'adenosine
PW_C000032
AMP
11
2
34
4
62
8
270
16
734
32
881
22
1189
14
4572
5
4867
54
5033
89
5251
104
5408
117
5423
103
5432
118
5457
120
5558
132
5583
133
5779
101
5795
108
6977
199
7072
188
11789
198
11868
161
11988
151
12003
222
12580
226
12636
31
12694
290
13331
225
42266
3
42646
315
77234
329
77325
111
78392
334
78809
115
79320
112
80399
1
80684
135
80900
7
119916
122
120016
124
120031
406
120246
382
120888
405
121954
408
122920
399
123464
376
124507
374
125306
297
125394
299
125409
479
125596
484
126853
205
126934
388
126949
501
127124
389
127311
209
127711
502
140771
891
170
Pyrophosphate
HMDB0000250
The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.
14000-31-8
C00013
644102
18361
PPI
559142
DB04160
OP(O)(=O)OP(O)(O)=O
H4O7P2
InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)
XPPKVPWEQAFLFU-UHFFFAOYSA-N
177.9751
177.943225506
FDB021918
(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ion
PW_C000170
Ppi
12
2
35
4
63
8
429
23
735
32
882
22
1217
3
1620
49
2410
59
2815
29
4175
14
4868
54
5034
89
5252
104
5294
101
5409
117
5424
103
5433
118
5458
120
5548
111
5559
132
5584
133
5606
135
5655
108
5879
107
6239
166
6978
199
7073
188
7134
163
7272
160
7312
198
7318
213
8275
151
8283
210
11869
161
12002
222
12041
164
12315
225
12323
249
12512
288
12579
226
12695
290
15219
306
15375
18
34760
17
42561
315
42697
318
77235
329
77317
128
77635
336
78416
335
78928
331
79153
112
79950
134
79958
130
80047
372
80417
170
85630
1
94786
384
94814
125
94819
382
98678
223
110634
391
113270
395
113275
389
115527
136
115532
399
119934
122
120017
124
120032
406
120330
410
120936
407
121261
429
121341
121
121486
383
122407
422
122985
444
123502
119
123831
464
124044
398
124977
375
125324
297
125395
299
125410
479
125597
484
125656
485
125876
481
126552
491
126869
205
126935
388
126950
501
127337
206
128124
508
140772
891
514
Copper
HMDB0000657
Copper is an essential nutrient to all higher plants and animals. Physiologically, it exists as an ion in the body. In animals, it is found primarily in the bloodstream, as a cofactor in various enzymes, and in copper-based pigments. In the body, copper shifts between the cuprous (Cu1+) and cupric (Cu2+) forms, though the majority of the body's copper is in the Cu2+ form. The ability of copper to easily accept and donate electrons explains its important role in oxidation-reduction (redox) reactions and in scavenging free radicals. Copper is a critical functional component of a number of essential enzymes known as cuproenzymes. For instance, the copper-dependent enzyme, cytochrome c oxidase, plays a critical role in cellular energy production. By catalyzing the reduction of molecular oxygen (O2) to water (H2O), cytochrome c oxidase generates an electrical gradient used by the mitochondria to create the vital energy-storing molecule, ATP. Another cuproenzyme, lysyl oxidase, is required for the cross-linking of collagen and elastin, which are essential for the formation of strong and flexible connective tissue. Another cuproeznyme, Monoamine oxidase (MAO), plays a role in the metabolism of the neurotransmitters norepinephrine, epinephrine, and dopamine. MAO also functions in the degradation of the neurotransmitter serotonin, which is the basis for the use of MAO inhibitors as antidepressants. One of the most important cuproenzymes is Superoxide dismutase (SOD). SOD functions as an antioxidant by catalyzing the conversion of superoxide radicals (free radicals or ROS) to hydrogen peroxide, which can subsequently be reduced to water by other antioxidant enzymes. Two forms of SOD contain copper: 1) copper/zinc SOD is found within most cells of the body, including red blood cells, and 2) extracellular SOD is a copper-containing enzyme found at high levels in the lungs and low levels in blood plasma. In sufficient amounts, copper can be poisonous or even fatal to organisms. Copper is normally bound to cuproenzymes (such as SOD, MOA) and is thus only toxic when unsequestered and unmediated. It is believed that zinc and copper compete for absorption in the digestive tract so that a diet that is excessive in one of these minerals may result in a deficiency in the other. An imbalance of zinc and copper status might be involved in human hypertension.
15158-11-9
C00070
27099
29036
CUCL2
25221
[Cu++]
Cu
InChI=1S/Cu/q+2
JPVYNHNXODAKFH-UHFFFAOYSA-N
63.546
62.929601079
FDB003582
Copper;Cu;Copper (ii) ion;Copper(ii) cation;Copper, ion (cu2+);Cu(ii);Cu2+;Cu(2+);Cupric ion
PW_C000514
Cu
408
19
552
14
702
20
756
15
761
8
771
33
2011
2
2019
24
6587
109
7009
189
42791
317
77049
294
77599
115
77770
341
77807
114
77811
111
77817
343
78153
132
79114
360
79246
293
120464
405
120596
409
120599
122
120607
415
121048
124
121608
434
123098
376
123221
137
123224
135
123232
451
123612
118
124166
469
125710
478
125733
483
125738
297
125746
487
127202
209
127216
208
127220
205
127228
504
127577
515
127588
388
353
Calcium
HMDB0000464
Calcium is essential for the normal growth and maintenance of bones and teeth, and calcium requirements must be met throughout life. Requirements are greatest during periods of growth, such as childhood, during pregnancy and when breast-feeding. Long-term calcium deficiency can lead to osteoporosis, in which the bone deteriorates and there is an increased risk of fractures. Adults need between 1,000 and 1,300 mg of calcium in their daily diet. Calcium is essential for living organisms, particularly in cell physiology, and is the most common metal in many animals. Physiologically, it exists as an ion in the body. Calcium combines with phosphorus to form calcium phosphate in the bones and teeth. It is essential for the normal functioning of nerves and muscles and plays a role in blood coagulation (as factor IV) and in many enzymatic processes. Calcium is an important component of a healthy diet. A deficit can affect bone and tooth formation, while overretention can cause kidney stones. Vitamin D is needed to absorb calcium. Dairy products, such as milk and cheese, are a well-known source of calcium. However, some individuals are allergic to dairy products and even more people, particularly those of non-European descent, are lactose-intolerant, leaving them unable to consume dairy products. Fortunately, many other good sources of calcium exist. These include: seaweeds such as kelp, wakame and hijiki; nuts and seeds (like almonds and sesame); beans; amaranth; collard greens; okra; rutabaga; broccoli; kale; and fortified products such as orange juice and soy milk. Calcium has also been found to assist in the production of lymphatic fluids.
14127-61-8
C00076
271
29108
CA%2b2
266
DB01373
[Ca++]
Ca
InChI=1S/Ca/q+2
BHPQYMZQTOCNFJ-UHFFFAOYSA-N
40.078
39.962591155
FDB003513
Ca;Calcium element;Ca(2+);Ca2+;Calcium ion;Calcium, doubly charged positive ion
PW_C000353
Ca2+
276
16
303
8
553
14
601
2
941
15
993
21
997
35
1046
3
1163
46
1164
47
1478
49
1491
42
1552
43
2116
58
2138
17
2796
18
2937
9
3159
71
3160
72
3942
29
4186
66
4782
10
4822
28
5340
111
5780
101
7179
205
7232
211
7258
160
7281
190
11774
213
11837
198
11842
210
12198
164
12215
285
15288
151
15350
308
69336
1
77389
331
77600
115
78154
132
78266
356
78526
345
78724
130
78908
114
80413
74
80589
228
81826
51
120220
122
120465
405
121049
124
121300
418
121377
419
121850
383
121923
125
122370
409
122895
135
123099
376
123613
118
123870
454
123936
455
124403
398
124476
136
124924
137
125571
297
125711
478
125981
489
126009
299
126050
490
126533
495
127203
209
127434
506
127460
388
127502
507
128105
390
140676
790
140677
834
140695
50
7226
Topaquinone
HMDB0011639
Topaquinone (TPQ), is the quinone of 2,4,5-trihydroxyphenylalanine. TPQ is the cofactor in most copper-containing amine oxidases. It is produced by post-translational modification of a strictly conserved active-site tyrosine residue with the participation of the copper ion at the active site. Once formed, TPQ acts as a switch between the heterolytic transformation of amine substrates to aldehydes, via a pyridoxal phosphate-like Schiff base complex, and one electron chemistry involving reduction of molecular oxygen (PMID: 12686122).
64192-68-3
123871
36076
TOPAQUINONE
110408
N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(O)=O
C9H9NO5
InChI=1S/C9H9NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11H,1,10H2,(H,14,15)/t5-/m0/s1
YWRFBISQAMHSIX-YFKPBYRVSA-N
211.1715
211.048072403
(s)-a-amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoate;(s)-a-amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoic acid;(s)-alpha-amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoate;(s)-alpha-amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoic acid;2,4,5-trihydroxyphenylalanine quinone;6-hydroxydopa quinone;6-hydroxydopaquinone;O-topaquinone;Tpq;Topa quinone;Topaquinone;A-amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoate;A-amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoic acid;Alpha-amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoate;Alpha-amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoic acid
PW_C007226
TopQne
554
14
4473
2
77048
294
77601
115
78155
132
79245
293
120466
405
121050
124
123100
376
123614
118
125712
478
127204
209
127620
388
126
Anserine
HMDB0000194
This dipeptide is normally absent from human tissues and body fluids, and its appearance there is an artifact of diet (Proc Soc Pediatr Res 134, 1967.) and serum carnosinase deficiency. (OMIM 212200) Anserine is present in the skeletal muscle of birds and certain species of mammals, notably the rabbit, rat, and whale, contains anserine. (Proc Soc Pediatr Res 134, 1967) The methyl group of anserine is added to carnosine by the enzyme S-adenosylmethionine: carnosine N-methyltransferase. (J Biol Chem 237:1207, 1962.).
584-85-0
C01262
112072
18323
100482
CN1C=NC=C1C[C@H](NC(=O)CCN)C(O)=O
C10H16N4O3
InChI=1S/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1
MYYIAHXIVFADCU-QMMMGPOBSA-N
240.259
240.122240398
FDB021903
Anserine;L-anserine;L-n-b-alanyl-3-methyl-histidine;L-n-beta-alanyl-3-methyl-histidine;N-b-alanyl-3-methyl-l-histidine;N-beta-alanyl-3-methyl-l-histidine;Beta-alanyl-n(pai)-methyl-l-histidine;Beta-alanyl-3-methyl-l-histidine;B-alanyl-3-methyl-l-histidine;β-alanyl-3-methyl-l-histidine;B-alanyl-n(pai)-methyl-l-histidine;β-alanyl-n(pai)-methyl-l-histidine
PW_C000126
Anserin
525
15
42262
2
77577
114
78157
132
120437
409
121054
124
123071
137
123618
118
125681
483
127176
208
1
1-Methylhistidine
HMDB0000001
One-methylhistidine (1-MHis) is derived mainly from the anserine of dietary flesh sources, especially poultry. The enzyme, carnosinase, splits anserine into b-alanine and 1-MHis. High levels of 1-MHis tend to inhibit the enzyme carnosinase and increase anserine levels. Conversely, genetic variants with deficient carnosinase activity in plasma show increased 1-MHis excretions when they consume a high meat diet. Reduced serum carnosinase activity is also found in patients with Parkinson's disease and multiple sclerosis and patients following a cerebrovascular accident. Vitamin E deficiency can lead to 1-methylhistidinuria from increased oxidative effects in skeletal muscle.
332-80-9
C01152
7020397
50599
CPD-1823
83153
DB04151
CN1C=NC(C[C@H](N)C(O)=O)=C1
C7H11N3O2
InChI=1S/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
BRMWTNUJHUMWMS-LURJTMIESA-N
169.1811
169.085126611
FDB012119
1 methylhistidine;1-mhis;1-methyl histidine;1-methyl-histidine;1-methyl-l-histidine;1-n-methyl-l-histidine;L-1-methylhistidine;N1-methyl-l-histidine;Pi-methylhistidine;(2s)-2-amino-3-(1-methyl-1h-imidazol-4-yl)propanoic acid;1-methylhistidine;(2s)-2-amino-3-(1-methyl-1h-imidazol-4-yl)propanoate
PW_C000001
1-Mhis
6660
1
6661
41
7367
152
7437
51
42263
2
78158
132
121055
124
123619
118
140688
879
23
tRNA(His)
RNA
PW_NA000023
29178
TRNAHIS
1326
8
42265
3
78147
111
121041
122
123605
135
144678
1292
24
L-Histidyl-tRNA(His)
RNA
PW_NA000024
29155
LHTH
1327
8
42267
3
78148
111
121042
122
123606
135
144679
1292
456
Beta-Ala-His dipeptidase
Q96KN2
Preferential hydrolysis of the beta-Ala-|-His dipeptide (carnosine), and also anserine, Xaa-|-His dipeptides and other dipeptides including homocarnosine
HMDBP00473
CNDP1
18q22.3
BC110295
1
3.4.13.20
530
15
1306
8
144662
1292
146029
32
4059
Carnosine synthase 1
A5YM72
Catalyzes the synthesis of carnosine, homocarnosine, and anserine. Carnosine is synthesized more efficiently than homocarnosine.
HMDBP08844
CARNS1
11q13.2
BC036557
1
6.3.2.11
1307
8
42264
2
144663
1292
144676
1293
457
Protein arginine N-methyltransferase 3
O60678
Methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues in some proteins
HMDBP00474
PRMT3
11p15.1
AC108005
1
2.1.1.-
1309
8
144664
1292
146058
50
828
Histidine decarboxylase
P19113
Catalyzes the biosynthesis of histamine from histidine.
HMDBP00885
HDC
15q21-q22
X54297
1
4.1.1.22
1311
8
144665
1292
146032
1487
146038
789
418
Histamine N-methyltransferase
P50135
Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
HMDBP00427
HNMT
2q22.1
AF523357
1
2.1.1.8
1313
8
144666
1292
164
Amine oxidase [flavin-containing] A
P21397
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
HMDBP00169
MAOA
Xp11.3
X60809
1
1.4.3.4
1315
8
2013
2
2537
22
3724
26
4742
13
142652
789
142654
912
142655
787
142963
1070
143184
39
143383
1143
144667
1292
145836
399
149687
1546
149697
1678
286
Aldehyde dehydrogenase, dimeric NADP-preferring
P30838
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
HMDBP00292
ALDH3A1
17p11.2
M77477
1
1.2.1.5
1317
8
2015
2
3402
7
3619
29
5002
31
142964
789
143384
26
144668
1292
289
Aldehyde dehydrogenase, mitochondrial
P05091
HMDBP00295
ALDH2
12q24.2
K03001
1
1.2.1.3
547
4
1321
8
1871
3
3009
2
135492
18
141577
956
142021
979
143475
54
144669
1292
145837
120
647
Histidine ammonia-lyase
P42357
HMDBP00683
HAL
12q22-q24.1
AK303544
1
4.3.1.3
435
8
144670
1292
857
Urocanate hydratase
Q96N76
HMDBP00914
UROC1
3q21.3
BC115406
1
4.2.1.49
1323
8
144671
1292
3890
Probable imidazolonepropionase
Q96NU7
HMDBP08674
AMDHD1
12q23.1
CH471054
1
3.5.2.7
1325
8
144672
1292
650
Formimidoyltransferase-cyclodeaminase
O95954
Folate-dependent enzyme, that displays both transferase and deaminase activity. Serves to channel one-carbon units from formiminoglutamate to the folate pool.
Binds and promotes bundling of vimentin filaments originating from the Golgi (By similarity).
HMDBP00686
FTCD
21q22.3
AF169017
1
2.1.2.5; 4.3.1.4
952
8
144673
1292
382
Amiloride-sensitive amine oxidase [copper-containing]
P19801
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
HMDBP00390
ABP1
7q36.1
BC014093
1
1.4.3.22
1319
8
2012
2
144119
3
144674
1294
11856
Carnosine N-methyltransferase
Q8N4J0
N-methyltransferase that mediates the formation of anserine (beta-alanyl-N(Pi)-methyl-L-histidine) from carnosine. Anserine, a methylated derivative of carnosine (beta-alanyl-L-histidine), is an abundant constituent of vertebrate skeletal muscles. Also methylates other L-histidine-containing di- and tripeptides such as Gly-Gly-His, Gly-His and homocarnosine (GABA-His).
CARNMT1
1
2.1.1.22
42259
2
144675
1293
146028
32
11858
cytosolic non-specific dipeptidase
Q96KP4
Hydrolyzes a variety of dipeptides including L-carnosine but has a strong preference for Cys-Gly (PubMed:19346245). Acts as a functional tumor suppressor in gastric cancer via activation of the mitogen-activated protein kinase (MAPK) pathway. An elevated level of CNDP2 activates the p38 and JNK MAPK pathways to induce cell apoptosis, and a lower level of CNDP2 activates the ERK MAPK pathway to promote cell proliferation (PubMed:24395568). Isoform 2 may play a role as tumor suppressor in hepatocellular carcinoma (HCC) cells (PubMed:17121880). Catalyzes the production of N-lactoyl-amino acids from lactate and amino acids by reverse proteolysis (PubMed:25964343).
CNDP2
1
3.4.13.18
42268
2
144677
1293
608
Probable histidine--tRNA ligase, mitochondrial
P49590
HMDBP00642
HARS2
5q31.3
U18936
1
6.1.1.21
1329
3
144680
1294
611
Histidine--tRNA ligase, cytoplasmic
P12081
HMDBP00645
HARS
5q31.3
U18936
1
6.1.1.21
1328
8
144681
1292
152
Beta-Ala-His dipeptidase
1
PW_P000152
170
456
2
66
1005
2
366
Carnosine synthase 1
1
PW_P000366
388
4059
4
169
1027
8
367
Protein arginine N-methyltransferase 3
1
PW_P000367
389
457
1
368
Histidine decarboxylase
1
PW_P000368
390
828
2
170
1148
1
369
Histamine N-methyltransferase
1
PW_P000369
391
418
1
370
Amine oxidase [flavin-containing] A
1
PW_P000370
392
164
1
171
964
1
371
Aldehyde dehydrogenase, dimeric NADP-preferring
1
PW_P000371
393
286
1
159
Aldehyde dehydrogenase, mitochondrial
1
PW_P000159
177
289
4
545
4
110
Histidine ammonia-lyase
1
PW_P000110
125
647
1
373
Urocanate hydratase
1
PW_P000373
395
857
1
174
721
1
374
Probable imidazolonepropionase
1
PW_P000374
396
3890
1
175
1005
1
266
Formimidoyltransferase-cyclodeaminase
1
PW_P000266
285
650
8
119
1148
1
372
Amiloride-sensitive amine oxidase [copper-containing]
1
PW_P000372
394
382
2
172
514
2
173
353
4
438
7226
1
5703
Carnosine N-methyltransferase
1
PW_P005703
13187
11856
42260
2
5704
cytosolic non-specific dipeptidase
1
PW_P005704
13188
11858
2
743
1027
4
42269
2
376
Probable histidine--tRNA ligase, mitochondrial
1
PW_P000376
398
608
2
133730
3
375
Histidine--tRNA ligase, cytoplasmic
1
PW_P000375
397
611
2
133731
8
664
false
PW_R000664
Right
2727
23
1
Compound
false
2728
1420
1
Compound
true
2729
40
1
Compound
false
2730
116
1
Compound
true
157
152
3.4.13.20
209
false
PW_R000209
Right
919
414
1
Compound
true
920
116
1
Compound
false
921
40
1
Compound
true
922
1034
1
Compound
true
923
1104
1
Compound
true
924
23
1
Compound
false
448
366
6.3.2.11
308
false
PW_R000308
Right
1298
116
1
Compound
false
1299
921
1
Compound
true
1300
364
1
Compound
false
1301
749
1
Compound
true
449
367
2.1.1.-
213
false
PW_R000213
Right
935
116
1
Compound
false
936
693
1
Compound
false
937
1316
1
Compound
true
450
368
4.1.1.22
314
false
PW_R000314
Right
1321
921
1
Compound
true
1322
693
1
Compound
false
1323
749
1
Compound
true
1324
717
1
Compound
false
451
369
2.1.1.8
157
false
PW_R000157
Right
701
717
1
Compound
false
702
1420
1
Compound
true
703
1065
1
Compound
true
704
2083
1
Compound
false
705
35
1
Compound
true
706
1783
1
Compound
true
452
370
1.4.3.4
125
false
PW_R000125
Right
520
2083
1
Compound
false
521
143
1
Compound
true
522
1420
1
Compound
true
523
1712
1
Compound
false
524
146
1
Compound
true
525
40034
1
Compound
true
453
371
1.2.1.5
132
false
PW_R000132
Right
562
1992
1
Compound
false
563
721
1
Compound
true
564
1420
1
Compound
true
565
1357
1
Compound
false
566
1144
1
Compound
true
567
40034
1
Compound
true
455
159
1.2.1.3
646
false
PW_R000646
Both
2670
116
1
Compound
false
2671
35
1
Compound
false
2672
205
1
Compound
false
131
110
4.3.1.3
868
false
PW_R000868
Both
3521
802
1
Compound
false
3522
205
1
Compound
false
3523
1420
1
Compound
true
456
373
4.2.1.49
321
false
PW_R000321
Right
1346
802
1
Compound
false
1347
1420
1
Compound
true
1348
680
1
Compound
false
457
374
3.5.2.7
869
false
PW_R000869
Both
3524
1221
1
Compound
true
3525
680
1
Compound
false
3526
1179
1
Compound
true
3527
95
1
Compound
false
458
266
83
false
PW_R000083
Right
323
693
1
Compound
false
324
1420
1
Compound
true
325
1065
1
Compound
true
326
1992
1
Compound
false
327
35
1
Compound
true
328
1783
1
Compound
true
454
372
1.4.3.22
72857
PW_R072857
Right
250358
921
1
Compound
true
250359
23
1
Compound
false
250360
749
1
Compound
true
250361
126
1
Compound
false
62986
5703
72858
PW_R072858
Right
250362
414
1
Compound
true
250363
1
1
Compound
false
250364
40
1
Compound
true
250365
1034
1
Compound
true
250366
1104
1
Compound
true
250367
126
1
Compound
false
62987
366
72859
PW_R072859
Right
250368
126
1
Compound
false
250369
1420
1
Compound
true
250370
40
1
Compound
true
250371
1
1
Compound
false
62988
5704
3.4.13.18
870
false
PW_R000870
Right
3528
414
1
Compound
true
3529
116
1
Compound
false
3530
23
1
NucleicAcid
true
3531
32
1
Compound
true
3532
170
1
Compound
true
3533
24
1
NucleicAcid
false
459
375
6.1.1.21
460
376
6.1.1.21
2137
23
8
81
false
1660
1590
10
regular
200
190
2138
1420
8
49
false
1555
1450
10
regular
78
78
2139
40
8
81
false
1450
1140
10
regular
200
190
2140
116
8
81
false
1658
982
10
regular
200
190
2141
1005
8
9
false
1650
1330
19
regular
100
25
2142
414
8
42
false
1870
1330
10
regular
50
30
2143
40
8
81
false
1925
1140
10
regular
200
190
2144
1034
8
43
false
1871
1505
10
regular
50
30
2145
1104
8
46
false
1934
1543
10
regular
44
43
2146
1027
8
9
false
1775
1392
19
regular
100
25
2147
921
8
81
false
1545
290
10
regular
200
190
2148
364
8
81
false
985
680
10
regular
200
190
2149
749
8
81
false
965
290
10
regular
200
190
2150
693
2
81
false
1030
978
10
regular
200
190
2151
1316
8
52
false
1241
939
10
regular
78
78
2152
1148
8
9
false
1370
1015
10
regular
100
35
2153
921
8
81
false
1235
1143
10
regular
200
190
2154
749
8
81
false
1235
1378
10
regular
200
190
2155
717
8
81
false
1030
1558
10
regular
200
190
2156
1420
8
49
false
982
1758
10
regular
78
78
2157
1065
8
65
false
1208
1759
10
regular
78
78
2158
2083
8
81
false
1035
2053
10
regular
200
190
2159
35
8
63
false
976
1944
10
regular
78
78
2160
1783
8
56
false
1224
1949
10
regular
78
78
2161
964
8
9
false
1082
1855
19
regular
100
25
2162
143
8
61
false
1005
2268
10
regular
50
30
2163
1420
8
49
false
1210
2253
10
regular
78
78
2164
1712
8
81
false
1033
2563
10
regular
200
190
2165
146
8
62
false
1003
2473
10
regular
50
30
2166
40034
8
55
false
1214
2434
10
regular
78
78
2169
1992
3
81
false
410
1563
10
regular
200
190
2174
721
8
59
false
580
1803
10
regular
50
30
2175
1420
8
49
false
375
1768
10
regular
78
78
2176
1357
8
81
false
413
2068
10
regular
200
190
2177
1144
8
60
false
578
2008
10
regular
50
30
2178
40034
8
55
false
364
1979
10
regular
78
78
2179
35
8
63
false
2126
934
10
regular
78
78
2180
205
8
81
false
2285
981
10
regular
200
190
2181
802
8
81
false
2285
1486
10
regular
200
200
2182
1420
8
49
false
2225
1191
10
regular
78
78
2183
721
8
9
false
2335
1298
19
regular
100
25
2184
1420
8
49
false
2190
1691
10
regular
78
78
2185
680
8
81
false
2285
1956
10
regular
200
190
2186
1005
8
9
false
2335
1791
19
regular
100
25
2187
1221
8
81
false
2040
2066
10
regular
200
190
2188
1179
8
81
false
2040
2316
10
regular
200
200
2189
95
8
81
false
2285
2471
10
regular
200
190
2190
1148
8
9
false
2340
2241
19
regular
100
35
2191
414
8
42
false
1998
427
10
regular
50
30
2192
32
8
44
false
2263
423
10
regular
50
30
2193
170
8
45
false
2266
623
10
regular
63
43
2194
414
8
42
false
1893
832
10
regular
50
30
2195
32
8
44
false
2343
832
10
regular
50
30
2196
170
8
45
false
2281
900
10
regular
63
43
10709
1420
3
49
false
472
1128
10
regular
78
78
10710
1065
3
65
false
348
1179
10
regular
78
78
10711
35
3
63
false
370
1474
10
regular
78
78
10712
1783
3
56
false
583
1484
10
regular
78
78
10713
514
3
9
false
467
1335
19
regular
100
25
10714
353
3
9
false
467
1315
19
regular
100
25
10715
7226
3
9
false
462
1415
19
regular
100
25
835897
921
2
81
false
1425
1685
10
regular
200
190
835898
749
2
81
false
1425
1950
10
regular
200
190
835899
126
2
81
false
1660
2050
10
regular
200
190
835900
414
2
42
false
1513
2460
10
regular
50
30
835901
1
2
81
false
1658
2625
10
regular
200
190
835902
40
2
81
false
1423
2500
10
regular
200
190
835903
1034
2
43
false
1511
2300
10
regular
50
30
835904
1104
2
46
false
1551
2228
10
regular
44
43
835905
1027
2
9
false
1650
2350
19
regular
100
25
835993
1420
2
49
false
1917
2306
10
regular
78
78
835994
40
2
81
false
1913
2530
10
regular
200
190
835995
1027
2
9
false
1775
2437
19
regular
100
25
34
23
96
8
false
1808
507
14
120
nucleic_acid
regular
120
115
35
24
96
8
false
2383
505
14
120
nucleic_acid
regular
120
115
36
23
96
8
false
1923
687
14
120
nucleic_acid
regular
120
115
807
456
8
6
false
1620
1330
8
subunit
regular
160
80
808
4059
8
8
false
1750
1397
8
subunit
regular
140
85
809
457
8
2
false
1295
560
8
subunit
regular
150
70
810
828
8
6
false
1345
1035
8
subunit
regular
160
80
811
418
8
2
false
1055
1323
8
subunit
regular
150
70
812
164
8
2
false
1057
1865
8
subunit
regular
150
70
813
286
8
6
false
1055
2343
8
subunit
regular
160
80
815
289
8
8
false
440
1870
8
subunit
regular
140
85
816
647
8
2
false
1970
1040
8
subunit
regular
150
70
817
857
8
2
false
2310
1308
8
subunit
regular
150
70
818
3890
8
2
false
2310
1801
8
subunit
regular
150
70
819
650
8
7
false
2290
2256
8
subunit
regular
190
85
5751
382
3
6
false
432
1340
8
subunit
regular
160
80
369110
11856
2
2
false
1685
1880
8
subunit
regular
150
70
369111
4059
2
8
false
1630
2365
8
subunit
regular
140
85
369141
11858
2
6
false
1745
2452
8
subunit
regular
160
80
915025
608
3
6
false
2073
494
8
subunit
regular
160
80
915026
611
8
6
false
2070
805
8
subunit
regular
160
80
755
152
53
8
800
807
329
2141
3103
Cofactor
756
366
53
8
801
808
330
2146
3110
Cofactor
757
367
53
8
802
809
758
368
53
8
803
810
331
2152
3118
Cofactor
759
369
53
8
804
811
760
370
53
8
805
812
332
2161
3129
Cofactor
761
371
53
8
806
813
763
159
53
8
808
815
764
110
53
8
809
816
765
373
53
8
810
817
335
2183
3156
Cofactor
766
374
53
8
811
818
336
2186
3160
Cofactor
767
266
53
8
812
819
337
2190
3165
Cofactor
4717
372
53
3
5722
5751
2209
10713
16828
Cofactor
2210
10714
16829
Cofactor
2211
10715
16830
Cofactor
261318
5703
53
2
368284
369110
261319
366
53
2
368285
369111
5302
835905
1186465
Cofactor
261350
5704
53
2
368315
369141
5314
835995
1186632
Cofactor
790354
376
53
3
911536
915025
790355
375
53
8
911537
915026
3099
M1699 1589 C1699 1559 1700 1440 1700 1410
5
false
18
3100
M1633 1489 C1671 1489 1700 1440 1700 1410
5
false
18
3101
M1650 1235 C1697 1235 1700 1300 1700 1330
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3102
M1697 1173 C1697 1203 1700 1300 1700 1330
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3103
M80 325 L80 375 L130 325 z
10
true
18
3104
M1870 1345 C1835 1345 1820 1367 1820 1397
5
false
18
3105
M1820 1171 C1820 1201 1820 1367 1820 1397
5
false
18
3106
M1925 1235 C1885 1235 1819 1274 1820 1397
5
false
18
3107
M1871 1520 C1844 1520 1820 1512 1820 1482
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3108
M1934 1564.5 C1856 1563.5 1820 1540 1820 1482
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3109
M1823 1587 C1823 1557 1820 1512 1820 1482
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3110
M100 150 L100 200 L150 150 z
10
true
18
3111
M1758 982 C1754 754 1608 590 1445 595
5
false
18
3112
M1645 480 C1645 536 1574 591 1445 595
5
false
18
3113
M1085 680 C1094 590 1265 595 1295 595
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3114
M1065 480 C1067 576 1204 595 1295 595
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3115
M1658 1077 C1628 1077 1535 1075 1505 1075
5
false
18
3116
M1230 1073 C1260 1073 1315 1075 1345 1075
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3117
M1280 1017 C1280 1050 1315 1075 1345 1075
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3118
M975 1180 L975 1230 L1025 1180 z
10
true
18
3119
M1235 1238 C1190 1238 1130 1266 1130 1323
5
false
18
3120
M1130 1168 C1130 1198 1130 1293 1130 1323
5
false
18
3121
M1235 1473 C1182 1472 1131 1448 1130 1393
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3122
M1130 1558 C1130 1528 1130 1423 1130 1393
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3123
M1130 1748 C1130 1778 1132 1835 1132 1865
5
false
18
3124
M1060 1797 C1089 1797 1132 1835 1132 1865
5
false
18
3125
M1208 1798 C1184 1798 1132 1835 1132 1865
5
false
18
3126
M1135 2053 C1135 2023 1132 1965 1132 1935
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3127
M1054 1983 C1079 1984 1132 1965 1132 1935
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3128
M1224 1988 C1199 1988 1132 1965 1132 1935
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3129
M100 150 L100 200 L150 150 z
10
true
18
3130
M1135 2243 C1135 2273 1135 2313 1135 2343
5
false
18
3131
M1055 2283 C1090 2283 1135 2313 1135 2343
5
false
18
3132
M1210 2292 C1185 2292 1135 2313 1135 2343
5
false
18
3133
M1133 2563 C1133 2533 1135 2453 1135 2423
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3134
M1053 2488 C1086 2488 1135 2453 1135 2423
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3135
M1214 2473 C1186 2473 1135 2453 1135 2423
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3144
M510 1753 C510 1783 510 1840 510 1870
5
false
18
3145
M580 1818 C553 1818 510 1840 510 1870
5
false
18
3146
M453 1807 C478 1807 510 1840 510 1870
5
false
18
3147
M513 2068 C513 2038 510 1985 510 1955
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3148
M578 2023 C554 2023 510 1985 510 1955
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3149
M442 2018 C469 2018 510 1985 510 1955
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3150
M1858 1077 C1888 1077 1940 1075 1970 1075
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3151
M2165 1012 C2165 1039 2150 1075 2120 1075
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3152
M2285 1076 C2255 1076 2150 1075 2120 1075
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3153
M2385 1486 C2385 1456 2385 1408 2385 1378
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3154
M2385 1171 C2385 1201 2385 1278 2385 1308
5
false
18
false
false
3155
M2303 1230 C2370 1232 2385 1278 2385 1308
5
false
18
false
false
3156
M100 150 L100 200 L150 150 z
10
true
18
3157
M2385 1686 C2385 1716 2385 1771 2385 1801
5
false
18
3158
M2268 1730 C2349 1733 2385 1771 2385 1801
5
false
18
3159
M2385 1956 C2385 1926 2385 1901 2385 1871
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3160
M100 150 L100 200 L150 150 z
10
true
18
3161
M2240 2161 C2365 2166 2385 2226 2385 2256
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3162
M2385 2146 C2385 2176 2385 2226 2385 2256
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3163
M2240 2416 C2288 2416 2386 2387 2385 2341
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3164
M2385 2471 C2385 2441 2385 2371 2385 2341
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3165
M100 150 L100 200 L150 150 z
10
true
18
16822
M1030 1073 C605 1067 511 1262 512 1340
5
false
18
16823
M511 1206 C511 1236 512 1310 512 1340
5
false
18
16824
M426 1218 C481 1218 515 1280 512 1340
5
false
18
16825
M510 1563 C510 1533 512 1450 512 1420
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
16826
M448 1513 C498 1522 512 1450 512 1420
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
16827
M583 1523 C511 1526 512 1450 512 1420
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
16828
M1062 1430.5 L1062 1480.5 L1112 1430.5 z
10
true
18
16829
M1062 1430.5 L1062 1480.5 L1112 1430.5 z
10
true
18
16830
M1062 1430.5 L1062 1480.5 L1112 1430.5 z
10
true
18
16831
M2385 2661 C2385 2691 2385 2716 2385 2746
5
false
18
true
M 2427.5 2733.0096189432334 L 2435 2746 L 2442.5 2733.0096189432334
false
true
M 2442.5 2673.9903810567666 L 2435 2661 L 2427.5 2673.9903810567666
false
1186455
M1625 1780 C1696 1780 1760 1850 1760 1880
5
false
18
1186456
M1760 1780 C1760 1810 1760 1850 1760 1880
5
false
18
1186457
M1625 2045 C1711 2047 1760 1980 1760 1950
5
false
18
true
M 1233.9468550441647 1493.261556296296 L 1219 1492 L 1225.380887721186 1505.5751343230784
false
1186458
M1760 2050 C1760 2020 1760 1980 1760 1950
5
false
18
true
M 1233.9468550441647 1493.261556296296 L 1219 1492 L 1225.380887721186 1505.5751343230784
false
1186459
M1563 2475 C1611 2475 1700 2480 1700 2450
5
false
18
1186460
M1700 2625 C1700 2595 1700 2480 1700 2450
5
false
18
1186461
M1623 2595 C1702 2595 1700 2537 1700 2450
5
false
18
1186462
M1561 2315 C1612 2312 1700 2335 1700 2365
5
false
18
true
M 1221.9468550441647 1926.261556296296 L 1207 1925 L 1213.380887721186 1938.5751343230784
false
1186463
M1595 2249.5 C1670 2249.5 1700 2335 1700 2365
5
false
18
true
M 1221.9468550441647 1926.261556296296 L 1207 1925 L 1213.380887721186 1938.5751343230784
false
1186464
M1698 2244 C1698 2274 1700 2335 1700 2365
5
false
18
true
M 1221.9468550441647 1926.261556296296 L 1207 1925 L 1213.380887721186 1938.5751343230784
false
1186465
M1570.5 2290 L1570.5 2340 L1620.5 2290 z
10
true
18
1186628
M1822 2243 C1822 2273 1825 2422 1825 2452
5
false
18
1186629
M1917 2345 C1855 2346 1825 2422 1825 2452
5
false
18
1186630
M1913 2625 C1857 2626 1825 2562 1825 2532
5
false
18
true
M 1123.9468550441647 2187.261556296296 L 1109 2186 L 1115.380887721186 2199.575134323078
false
1186631
M1824 2621 C1824 2591 1825 2562 1825 2532
5
false
18
true
M 1123.9468550441647 2187.261556296296 L 1109 2186 L 1115.380887721186 2199.575134323078
false
1186632
M1595.5 2327.5 L1595.5 2377.5 L1645.5 2327.5 z
10
true
18
3606512
M2023 457 C2022 492 2054 534 2073 534
5
false
18
3606513
M1758 982 C1756 772 1887 537 2073 534
5
false
18
3606514
M2288 453 C2288 488 2253 532 2233 534
5
false
18
true
M 1559.9468550441647 397.261556296296 L 1545 396 L 1551.380887721186 409.5751343230783
false
3606515
M2297.5 623 C2302.5 599 2263 534 2233 534
5
false
18
true
M 1559.9468550441647 397.261556296296 L 1545 396 L 1551.380887721186 409.5751343230783
false
3606516
M1923 537 C1953 537 2043 534 2073 534
5
false
18
3606517
M2388 535 C2358 535 2263 534 2233 534
5
false
18
true
M 1559.9468550441647 397.261556296296 L 1545 396 L 1551.380887721186 409.5751343230783
false
3606518
M1943 847 C1973 847 2040 845 2070 845
5
false
18
3606519
M1820 985 C1877 920 1952 851 2070 845
5
false
18
3606520
M2343 847 C2313 847 2260 845 2230 845
5
false
18
true
M 1622.9468550441647 529.261556296296 L 1608 528 L 1614.380887721186 541.5751343230784
false
3606521
M2312.5 900 C2310.5 858 2260 845 2230 845
5
false
18
true
M 1622.9468550441647 529.261556296296 L 1608 528 L 1614.380887721186 541.5751343230784
false
3606522
M1983 794 C1985 831 2040 845 2070 845
5
false
18
3606523
M2443 612 C2443 755 2302 849 2230 845
5
false
18
true
M 1622.9468550441647 529.261556296296 L 1608 528 L 1614.380887721186 541.5751343230784
false
626
53
664
8
2325
2137
3099
Left
2326
2138
3100
Left
2327
2139
3101
Right
2328
2140
3102
Right
597
157
755
627
53
209
8
2329
2142
3104
Left
2330
2140
3105
Left
2331
2143
3106
Left
2332
2144
3107
Right
2333
2145
3108
Right
2334
2137
3109
Right
598
448
756
628
53
308
8
2335
2140
3111
Left
2336
2147
3112
Left
2337
2148
3113
Right
2338
2149
3114
Right
599
449
757
629
53
213
8
2339
2140
3115
Left
2340
2150
3116
Right
2341
2151
3117
Right
600
450
758
630
53
314
8
2342
2153
3119
Left
2343
2150
3120
Left
2344
2154
3121
Right
2345
2155
3122
Right
601
451
759
631
53
157
8
2346
2155
3123
Left
2347
2156
3124
Left
2348
2157
3125
Left
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2158
3126
Right
2350
2159
3127
Right
2351
2160
3128
Right
602
452
760
632
53
125
8
2352
2158
3130
Left
2353
2162
3131
Left
2354
2163
3132
Left
2355
2164
3133
Right
2356
2165
3134
Right
2357
2166
3135
Right
603
453
761
634
53
132
8
2364
2169
3144
Left
2365
2174
3145
Left
2366
2175
3146
Left
2367
2176
3147
Right
2368
2177
3148
Right
2369
2178
3149
Right
605
455
763
635
53
646
8
2370
2140
3150
Left
2371
2179
3151
Right
2372
2180
3152
Right
606
131
764
636
53
868
8
2373
2181
3153
Left
2374
2180
3154
Right
2375
2182
3155
Right
607
456
765
637
53
321
8
2376
2181
3157
Left
2377
2184
3158
Left
2378
2185
3159
Right
608
457
766
638
53
869
8
2379
2187
3161
Left
2380
2185
3162
Left
2381
2188
3163
Right
2382
2189
3164
Right
609
458
767
3143
53
83
3
10176
2150
16822
Left
10177
10709
16823
Left
10178
10710
16824
Left
10179
2169
16825
Right
10180
10711
16826
Right
10181
10712
16827
Right
3252
454
4717
272844
53
72857
2
1064976
835897
1186455
Left
1064977
2137
1186456
Left
1064978
835898
1186457
Right
1064979
835899
1186458
Right
231911
62986
261318
272845
53
72858
2
1064980
835900
1186459
Left
1064981
835901
1186460
Left
1064982
835902
1186461
Left
1064983
835903
1186462
Right
1064984
835904
1186463
Right
1064985
835899
1186464
Right
231912
62987
261319
272876
53
72859
2
1065067
835899
1186628
Left
1065068
835993
1186629
Left
1065069
835994
1186630
Right
1065070
835901
1186631
Right
231943
62988
261350
788504
53
870
3
3192422
2191
3606512
Left
3192423
2140
3606513
Left
3192424
2192
3606514
Right
3192425
2193
3606515
Right
1216
34
3606516
Left
1217
35
3606517
Right
745202
460
790354
788505
53
870
8
3192426
2194
3606518
Left
3192427
2140
3606519
Left
3192428
2195
3606520
Right
3192429
2196
3606521
Right
1218
36
3606522
Left
1219
35
3606523
Right
745203
459
790355
937
845
53
14
false
2310
2746
16
regular
870
2189
16831
Left
100
13
305
1805
1.5
1.5
-90
2
1
490
240
101
13
1785
345
1.5
1.5
0
2
1
490
240
187177
251
252
1.9
1.9
0
3
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327
267
479744
755
415
1.9
1.9
55
2
3
280
360
140
M127 274 C127 224 177 174 227 174 C924 174 1829 174 2526 174 C2576 174 2626 224 2626 274 C2626 1047 2626 2053 2626 2826 C2626 2876 2576 2926 2526 2926 C1829 2926 924 2926 227 2926 C177 2926 127 2876 127 2826 C127 2053 127 1047 127 274
1
true
6
2499.0
2752.0
150
235
Intracellular Space
1190
220
20
1.6
1.6
200
15
151
235
Extracellular Space
490
65
20
1.3
1.3
200
15
890882
235
Mitochondria
345
1012
20
1.6
1.6
200
15
890883
235
Mitochondria
2030
310
20
1.3
1.3
200
15