367
Pathway
Intracellular Signalling Through PGD2 receptor and Prostaglandin D2
PGD is the major prostanoid released from human mast cells upon immunological challenge. Prostaglandin D2 (PGD2) can trigger asthmatic responses by acting as a cell-derived mediator in mice. The PGD receptor activates G(s) proteins which lead to the activation of adenylyl cyclase which produces the secondary messenger cAMP. cAMP activates PKA (protein kinase A) which phosphorylates downstream effectors that lead to a specific cellular response.
Signaling
PW000451
Top
PathwayVisualizationContext467
1500
3400
#000099
PathwayVisualization351
367
Intracellular Signalling Through PGD2 receptor and Prostaglandin D2
PGD is the major prostanoid released from human mast cells upon immunological challenge. Prostaglandin D2 (PGD2) can trigger asthmatic responses by acting as a cell-derived mediator in mice. The PGD receptor activates G(s) proteins which lead to the activation of adenylyl cyclase which produces the secondary messenger cAMP. cAMP activates PKA (protein kinase A) which phosphorylates downstream effectors that lead to a specific cellular response.
Signaling
1
731
Vasodilation
ActivatingSubPathway
1207
41
Compound
2
732
Asthmatic Response
ActivatingSubPathway
1208
41
Compound
2
1129
7642548
Boie Y, Sawyer N, Slipetz DM, Metters KM, Abramovitz M: Molecular cloning and characterization of the human prostanoid DP receptor. J Biol Chem. 1995 Aug 11;270(32):18910-6.
367
Pathway
1130
Krauss, G. Biochemistry of signal transduction and regulation. (3rd ed.) (2003) Weinheim; New York : Wiley-VCH
367
Pathway
1
Cell
CL:0000000
3
Neuron
CL:0000540
2
Platelet
CL:0000233
5
Hepatocyte
CL:0000182
4
Cardiomyocyte
CL:0000746
8
Beta cell
CL:0000639
7
Epithelial Cell
CL:0000066
14
Parietal Cell
CL:0000162
21
Theca Cell
CL:0000503
22
Granulosa Cell
CL:0000501
19
Sertoli Cell
CL:0000216
6
Myocyte
CL:0000187
20
Leydig Cell
CL:0000178
1
Homo sapiens
9606
Eukaryote
Human
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
3
Escherichia coli
562
Prokaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
Eukaryote
African clawed frog
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
2
Bacteria
2
Prokaryote
Bacteria
19
Schizosaccharomyces pombe
4896
Eukaryote
25
Escherichia coli (strain K12)
83333
Prokaryote
23
Pseudomonas aeruginosa
287
Prokaryote
51
Picea sitchensis
3332
Eukaryote
Sitka spruce
157
Acinetobacter baumannii
107673
Prokaryote
56
Andro
6666
Eukaryote
1
Cytosol
GO:0005829
13
Endoplasmic Reticulum
GO:0005783
11
Extracellular Space
GO:0005615
5
Cytoplasm
GO:0005737
3
Mitochondrial Matrix
GO:0005759
10
Cell Membrane
GO:0005886
4
Peroxisome
GO:0005777
14
Mitochondrial Outer Membrane
GO:0005741
2
Mitochondrion
GO:0005739
7
Endoplasmic Reticulum Membrane
GO:0005789
25
Golgi Apparatus
GO:0005794
27
Peroxisome Membrane
GO:0005778
15
Nucleus
GO:0005634
26
Golgi Apparatus Membrane
GO:0000139
35
Chloroplast
GO:0009507
12
Mitochondrial Inner Membrane
GO:0005743
31
Periplasmic Space
GO:0005620
32
Inner Membrane
GO:0070258
37
Basolateral cell membrane
GO:0016323
65
Presynaptic membrane
GO:0042734
24
Brain
BTO:0000142
89
16
2
Endothelium
BTO:0000393
1
Liver
BTO:0000759
72
9
7
Nervous System
BTO:0001484
5
cardiocyte
BTO:0001539
8
Blood Vessel
BTO:0001102
74
11
18
Pancreas
BTO:0000988
25
Intestine
BTO:0000648
28
Stomach
BTO:0001307
155
26
26
Lung
BTO:0000763
35
Ovary
BTO:0000975
38
Myenteric Plexus
BTO:0002436
32
Adrenal Cortex
BTO:0000045
34
Testis
BTO:0001363
6
Kidney
BTO:0000671
71
8
14
Eye
BTO:0000439
153
24
11
Heart
BTO:0000562
73
10
9
Muscle
BTO:0000887
141
18
4
Adrenal Medulla
BTO:0000049
71
8
2
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1
1
PW_BS000002
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PW_BS000170
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1084
Prostaglandin D2
HMDB0001403
Prostaglandin D2 (or PGD2) is a prostaglandin that is actively produced in various organs such as the brain, spleen, thymus, bone marrow, uterus, ovary, oviduct, testis, prostate and epididymis, and is involved in many physiological events. PGD2 binds to the prostaglandin D2 receptor (PTGDR) which is a G-protein-coupled receptor. Its activity is mainly mediated by G-S proteins that stimulate adenylate cyclase resulting in an elevation of intracellular cAMP and Ca2+. PGD2 promotes sleep; regulates body temperature, olfactory function, hormone release, and nociception in the central nervous system; prevents platelet aggregation; and induces vasodilation and bronchoconstriction. PGD2 is also released from mast cells as an allergic and inflammatory mediator. Prostaglandin H2 is an unstable intermediate formed from PGG2 by the action of cyclooxygenase (COX) in the arachidonate cascade. In mammalian systems, it is efficiently converted into more stable arachidonate metabolites, such as PGD2, PGE2, PGF2a by the action of three groups of enzymes, PGD synthases (PGDS), PGE synthases and PGF synthases, respectively. PGDS catalyzes the isomerization of PGH2 to PGD2. Two types of PGD2 synthase are known. Lipocalin-type PGD synthase is present in cerebrospinal fluid, seminal plasma and may play an important role in male reproduction. Another PGD synthase, hematopoietic PGD synthase is present in the spleen, fallopian tube, endometrial gland cells, extravillous trophoblasts and villous trophoblasts, and perhaps plays an important role in female reproduction. Recent studies demonstrate that PGD2 is probably involved in multiple aspects of inflammation through its dual receptor systems, DP and CRTH2. (PMID: 12148545)Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways.
41598-07-6
C00696
448457
15555
5Z13E-15S-9-ALPHA15-DIHYDROXY-11-O
395250
DB02056
[H][C@](O)(CCCCC)\C=C\[C@@]1([H])C(=O)C[C@]([H])(O)[C@]1([H])C\C=C/CCCC(O)=O
C20H32O5
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1
BHMBVRSPMRCCGG-OUTUXVNYSA-N
(5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid
352.4651
352.224974134
-3.61
3
prostaglandin D2
0
-1
FDB022602
(5z,13e)-(15s)-9,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e)-(15s)-9,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;(5z,13e)-(15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e)-(15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;(5z,13e)-(15s)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;(5z,13e)-(15s)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e,15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e,15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;(5z,13e,15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dien-1-oate;(5z,13e,15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dien-1-oic acid;(5z,9-alpha,13e,15s)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oate;(5z,9-alpha,13e,15s)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oic acid;(5z,9alpha,13e,15s)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oate;(5z,9alpha,13e,15s)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oic acid;(5z,13e)-(15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e)-(15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;11-dehydroprostaglandin f2-alpha;11-dehydroprostaglandin f2alpha;9s,15s-dihydroxy-11-oxo-5z,13e-prostadienoate;9s,15s-dihydroxy-11-oxo-5z,13e-prostadienoic acid;Pgd2;Prostaglandin d2;(5z,13e,15s)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e)-(15s)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e)-(15s)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;(5z,13e,15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e,15s)-9a,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;(5z,13e,15s)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acid;(5z,13e,15s)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoate;(5z,13e,15s)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoic acid
PW_C001084
ProglD2
617
2
1352
18
4165
15
77419
130
121083
125
123648
136
936
Guanosine diphosphate
HMDB0001201
Guanosine 5'-(trihydrogen diphosphate). A guanine nucleotide containing two phosphate groups esterified to the sugar moiety. It is an ester of pyrophosphoric acid with the nucleoside guanosine. GDP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase guanine. GDP is the product of GTP dephosphorylation by GTPases, e.g. the G-proteins that are involved in signal transduction.
146-91-8
C00035
8977
17552
GDP-4-DEHYDRO-6-DEOXY-D-MANNOSE
8630
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
C10H15N5O11P2
InChI=1S/C10H15N5O11P2/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(25-9)1-24-28(22,23)26-27(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
QGWNDRXFNXRZMB-UUOKFMHZSA-N
[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
443.2005
443.024329371
-2.00
7
{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
0
-3
FDB022487
5'-gdp;Gdp;Guanosine 5'-(trihydrogen pyrophosphate);Guanosine 5'-diphosphate;Guanosine 5'-pyrophosphate;Guanosine mono(trihydrogen diphosphate);Guanosine pyrophosphate;Guanosine-5'-diphosphate;Guanosine-diphosphate;Ppg;Guanosine diphosphate;Guanosine 5'-diphosphoric acid
PW_C000936
GDP
83
8
238
4
1762
14
2391
2
4154
73
5007
85
5382
103
6041
155
6101
161
6488
178
7476
222
11754
115
11771
211
11823
198
12727
290
13395
151
69322
1
77142
133
77546
111
77952
132
80023
368
80080
308
80122
164
89115
253
119983
406
120068
122
121205
124
121847
405
122766
120
122820
135
123775
118
124400
376
125363
479
125445
297
126905
501
126984
205
423
Magnesium
HMDB0000547
Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.
22537-22-0
C00305
888
18420
13-HYDROXY-MAGNESIUM-PROTOPORP
865
DB01378
[Mg++]
Mg
InChI=1S/Mg/q+2
JLVVSXFLKOJNIY-UHFFFAOYSA-N
magnesium(2+) ion
24.305
23.985041898
0
magnesium(2+) ion
2
2
FDB003518
Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+
PW_C000423
Mg2+
86
8
227
4
268
16
476
2
727
26
811
5
819
18
883
22
936
39
983
3
992
21
1167
46
1483
49
1529
43
1764
14
2124
10
2411
59
2942
23
3126
29
3373
7
4540
31
4774
91
4869
54
4974
56
5253
104
5329
111
5356
112
5376
103
5906
147
5934
151
6038
155
6094
161
6250
166
6484
178
6594
164
6881
160
6979
199
7170
205
7194
206
7227
213
7233
211
7250
214
7310
216
7313
198
7473
222
11763
132
11843
210
12312
225
12324
249
12513
288
12581
226
12729
290
15275
285
15337
308
77137
133
77236
329
77937
336
78393
334
78417
335
78489
115
78522
331
78536
356
78574
130
80020
368
80045
184
80048
372
80623
118
80654
135
80865
15
80965
253
81841
51
93832
383
94900
27
108596
223
110559
390
115687
398
119974
406
120070
122
120247
382
120702
407
120981
408
121181
124
121265
429
121319
419
121924
125
122086
405
122408
422
122759
120
122921
399
123307
119
123546
374
123835
464
123889
455
124477
136
124637
376
124978
375
125447
297
125598
484
125669
479
125777
481
125921
482
125947
299
125973
495
126000
490
126243
478
126553
491
126753
300
127125
389
127164
501
127380
502
127407
388
127451
507
127804
209
128125
508
128347
395
140773
891
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
({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
507.181
506.995745159
-2.05
7
adenosine triphosphate
0
-3
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
41
cAMP
HMDB0000058
cAMP or cyclic AMP is an adenine nucleotide containing one phosphate group which is esterified to both the 3'- and 5'-positions of the sugar moiety. It is a second messenger and a key intracellular regulator, functioning as a mediator of activity for a number of hormones, including epinephrine, glucagon, and ACTH. cAMP is synthesized from ATP by adenylate cyclase. Adenylate cyclase is located at the cell membranes. Adenylate cyclase is activated by the hormones glucagon and adrenaline and by G protein. Liver adenylate cyclase responds more strongly to glucagon, and muscle adenylate cyclase responds more strongly to adrenaline. cAMP decomposition into AMP is catalyzed by the enzyme phosphodiesterase.
60-92-4
C00575
6076
17489
CAMP
5851
DB02527
[H][C@@]12COP(O)(=O)O[C@@]1([H])[C@@H](O)[C@@H](O2)N1C=NC2=C1N=CN=C2N
C10H12N5O6P
InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
IVOMOUWHDPKRLL-KQYNXXCUSA-N
(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
329.2059
329.052519653
-1.96
3
(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2,7-dihydroxy-tetrahydro-4H-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
0
-1
FDB001497
Cyclic AMP;3'5'-cyclic amp;6-(6-amino-9h-purin-9-yl)tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide;Acrasin;Adenosine 3',5'-cyclic monophosphate;Adenosine 3',5'-cyclic phosphate;Adenosine 3',5'-cyclophosphate;Adenosine 3',5'-monophosphate;Adenosine 3,5'-cyclic monophosphorate;Adenosine 3,5'-cyclic monophosphoric acid;Adenosine cyclic monophosphate;Adenosine cyclic-monophosphate;Adenosine-cyclic-phosphate;Adenosine-cyclic-phosphoric-acid;Cyclic 3',5'-amp;Cyclic 3',5'-adenylate;Cyclic 3',5'-adenylic acid;Cyclic amp;Cyclic adenosine 3',5'-phosphate;Camp;Adenosine 3',5'-phosphate;Adenosine-3',5'-cyclic-monophosphate;Cyclic adenylic acid;Adenosine 3',5'-cyclic monophosphoric acid;Adenosine 3',5'-cyclic phosphoric acid;Adenosine 3',5'-phosphoric acid;Adenosine-3',5'-cyclic-monophosphoric acid;Cyclic adenylate
PW_C000041
cAMP
267
16
475
2
935
39
1000
21
1916
8
4174
14
11830
198
78709
111
80044
184
121904
122
124457
135
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
(phosphonooxy)phosphonic acid
177.9751
177.943225506
4
pyrophosphoric acid
0
-3
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
986
Guanosine triphosphate
HMDB0001273
Guanosine triphosphate (GTP) is a guanine nucleotide containing three phosphate groups esterified to the sugar moiety. GTP functions as a carrier of phosphates and pyrophosphates involved in channeling chemical energy into specific biosynthetic pathways. GTP activates the signal transducing G proteins which are involved in various cellular processes including proliferation, differentiation, and activation of several intracellular kinase cascades. Proliferation and apoptosis are regulated in part by the hydrolysis of GTP by small GTPases Ras and Rho. Another type of small GTPase, Rab, plays a role in the docking and fusion of vesicles and may also be involved in vesicle formation. In addition to its role in signal transduction, GTP also serves as an energy-rich precursor of mononucleotide units in the enzymatic biosynthesis of DNA and RNA.
86-01-1
C00044
6830
15996
GTP
6569
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
C10H16N5O14P3
InChI=1S/C10H16N5O14P3/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
XKMLYUALXHKNFT-UUOKFMHZSA-N
({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
523.1804
522.990659781
-1.70
8
triphosphate, guanosine
0
-3
FDB022527
5'-gtp;Gtg;Gtp;Guanosine 5'-(tetrahydrogen triphosphate);Guanosine 5'-triphosphate;Guanosine 5'-triphosphorate;Guanosine 5'-triphosphoric acid;Guanosine triphosphate;Guanosine mono(tetrahydrogen triphosphate) (ester);H4gtp;Guanosine-5'-triphosphate
PW_C000986
GTP
81
8
240
4
1939
2
4091
14
4153
73
5006
85
5384
103
6043
155
6103
161
6490
178
7478
222
11753
115
11769
198
11981
151
12725
290
69327
1
76962
225
77144
133
77544
111
77951
132
80025
368
80088
308
80121
164
89113
253
119985
406
120066
122
121204
124
122768
120
122818
135
123774
118
125365
479
125443
297
126480
299
126907
501
126982
205
128051
388
2084
Prostaglandin D2 receptor
Q13258
Receptor for prostaglandin D2 (PGD2). The activity of this receptor is mainly mediated by G(s) proteins that stimulate adenylate cyclase, resulting in an elevation of intracellular cAMP. A mobilization of calcium is also observed, but without formation of inositol 1,4,5-trisphosphate
HMDBP02759
PTGDR
14q22.1
DQ418808
1
4167
2
4986
14
864
Adenylate cyclase type 2
Q08462
This is a membrane-bound, calmodulin-insensitive adenylyl cyclase.
HMDBP00921
ADCY2
5p15.3
AB028983
1
4.6.1.1
3829
2
4173
14
136381
74
139735
777
139845
48
140537
789
140601
183
140899
898
141495
948
142983
1073
143085
787
144285
8
144338
1224
144356
1226
144367
1230
144378
1234
1601
Guanine nucleotide-binding protein G(s) subunit alpha isoforms short
P63092
Guanine nucleotide-binding proteins (G proteins) are involved as modulators or transducers in various transmembrane signaling systems. The G(s) protein is involved in hormonal regulation of adenylate cyclase:it activates the cyclase in response to beta-adrenergic stimuli
HMDBP01781
GNAS
20q13.3
M14631
1
3810
2
4139
14
4158
73
5011
85
5162
8
135588
599
139731
777
139935
43
139987
48
140363
658
140890
898
140893
899
141483
949
141487
946
143229
789
143306
1138
144176
72
144341
1224
144348
1226
144359
1230
144370
1234
1315
cAMP-dependent protein kinase catalytic subunit beta
P22694
Mediates cAMP-dependent signaling triggered by receptor binding to GPCRs. PKA activation regulates diverse cellular processes such as cell proliferation, the cell cycle, differentiation and regulation of microtubule dynamics, chromatin condensation and decondensation, nuclear envelope disassembly and reassembly, as well as regulation of intracellular transport mechanisms and ion flux
HMDBP01415
PRKACB
1p36.1
AY927366
1
2.7.11.11
3837
2
3853
23
4199
8
139720
792
139891
48
140973
3
141504
948
141521
949
141537
789
141556
947
141562
946
141642
26
141920
658
141940
67
141947
66
142200
834
142785
1050
142814
1011
142823
1014
144183
72
144339
1224
144351
1226
144362
1230
144373
1234
3625
Guanine nucleotide-binding protein G(I)/G(S)/G(O) subunit gamma-12
Q9UBI6
Guanine nucleotide-binding proteins (G proteins) are involved as a modulator or transducer in various transmembrane signaling systems. The beta and gamma chains are required for the GTPase activity, for replacement of GDP by GTP, and for G protein- effector interaction
HMDBP08405
GNG12
1p31.3
AF188181
1
3811
2
4137
14
4156
73
5009
85
139733
777
140361
658
140892
898
140895
899
141485
949
141489
946
144342
1224
144349
1226
144360
1230
144371
1234
3618
Gβ
P62873
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-1 is a guanine nucleotide-binding protein (G protein) are involved as a modulator or transducer in various transmembrane signaling systems. The beta and gamma chains are required for the GTPase activity, for replacement of GDP by GTP, and for G protein- effector interaction
HMDBP08398
GNB1
1p36.33
BC005888
1
3812
2
4138
14
4157
73
5010
85
5161
8
69324
1
70006
308
135590
599
136006
608
136181
66
136187
665
138502
560
139732
777
140362
658
140534
787
140891
898
140894
899
141375
50
141423
52
141484
949
141488
946
142503
74
142960
1033
143307
1138
144343
1224
144350
1226
144361
1230
144372
1234
3627
Guanine nucleotide-binding protein G(T) subunit gamma-T1
P63211
Guanine nucleotide-binding proteins (G proteins) are involved as a modulator or transducer in various transmembrane signaling systems. The beta and gamma chains are required for the GTPase activity, for replacement of GDP by GTP, and for G protein- effector interaction
HMDBP08407
GNGT1
7q21.3
BC029367
1
5160
8
135589
599
136222
14
139734
777
991
Prostaglandin D2 receptor
1
PW_P000991
1120
2084
1
4164
14
122
Adenylate cyclase type 2
1
PW_P000122
140
864
1
57
423
2
465
24
121
Guanine nucleotide-binding protein alpha
1
PW_P000121
139
1601
1
464
20
922
cAMP-dependent protein kinase catalytic subunit beta
1
PW_P000922
1047
1315
1
374
423
1
120
Guanine nucleotide-binding protein gamma-beta
1
PW_P000120
137
3627
1
138
3618
1
463
24
596
false
PW_R000596
Right
2516
414
1
Compound
false
2517
41
1
Compound
false
4200
170
1
Compound
true
80
122
4.6.1.1
1994
121
1970
false
PW_R001970
Right
7152
41
1
Compound
false
7153
41
1
Compound
false
7154
922
1
ProteinComplex
false
1816
922
2.7.11.11
2126
false
PW_R002126
Right
7557
121
1
ProteinComplex
false
7558
120
1
ProteinComplex
false
7564
991
1
ProteinComplex
false
9030
986
1
Compound
false
7562
120
1
ProteinComplex
false
7563
121
1
ProteinComplex
false
7565
991
1
ProteinComplex
false
9031
936
1
Compound
false
1958
PW_R001958
Right
7121
121
1
ProteinComplex
false
7122
122
1
ProteinComplex
false
7123
121
1
ProteinComplex
false
7124
122
1
ProteinComplex
false
209
PW_T000209
244
1084
1
Compound
15
2
Right
175
991
2013-09-16T14:05:00-06:00
2013-09-16T14:05:00-06:00
14
8438
1084
15
81
false
710
280
10
regular
200
190
8439
1084
2
3
true
645
350
10
regular
100
110
8626
936
53
false
655
560
10
regular
50
30
8636
423
14
9
false
2305
450
10
regular
100
25
8650
414
2
42
false
2065
590
10
regular
50
30
8651
41
2
81
false
2520
665
10
regular
200
190
8652
170
2
45
false
2465
585
10
regular
63
43
8653
986
2
9
true
1937
620
10
regular
100
35
8654
41
2
81
false
2765
1110
10
regular
200
190
8655
423
2
9
false
2365
1155
10
regular
100
25
8656
423
2
9
false
2637
960
10
regular
100
25
11527
986
14
54
false
640
710
10
regular
50
30
11528
936
14
53
false
1115
810
10
regular
50
30
11529
986
54
false
1405
735
10
regular
50
30
11530
1084
15
81
false
285
105
10
regular
200
190
11531
1084
2
3
true
50
100
10
regular
100
110
11532
936
53
false
240
560
10
regular
50
30
11533
423
14
9
false
1465
445
10
regular
100
25
11534
423
14
9
true
2065
320
10
regular
100
25
11535
986
54
false
2160
470
10
regular
50
30
4380
2084
14
80
false
695
445
7
subunit
regular
200
130
4652
864
14
99
false
2295
465
8
subunit
regular
150
70
4673
1601
2
2
true
1907
640
8
subunit
regular
150
70
4674
1315
2
6
false
2335
1160
8
subunit
regular
160
80
4675
1315
2
6
false
2542
965
8
subunit
regular
160
80
6080
1601
14
98
false
680
560
8
subunit
regular
150
70
6081
3625
14
2
false
745
620
8
subunit
regular
150
70
6082
3618
14
97
false
820
560
8
subunit
regular
150
70
6083
3625
14
2
false
115
1070
8
subunit
regular
150
70
6084
3618
14
97
false
110
1140
8
subunit
regular
150
70
6085
1601
14
98
false
1420
745
8
subunit
regular
150
70
6086
2084
14
80
false
1105
445
8
subunit
regular
200
130
6087
2084
14
80
false
280
440
8
subunit
regular
200
130
6088
1601
14
98
false
255
560
8
subunit
regular
150
70
6089
3618
97
false
390
560
8
subunit
regular
150
70
6090
3625
14
2
false
330
620
8
subunit
regular
150
70
6091
864
14
99
false
1440
460
8
subunit
regular
150
70
6092
1601
14
98
false
2165
470
8
subunit
regular
150
70
6093
864
14
2
true
2160
345
8
subunit
regular
150
70
3627
991
351
4357
4380
3839
122
351
14
4627
4652
1656
8636
13303
Cofactor
3857
121
351
2
4648
4673
1665
8653
13339
Cofactor
3858
922
351
2
4649
4674
1666
8655
13342
Cofactor
3859
922
351
2
4650
4675
1667
8656
13344
Cofactor
4977
121
351
14
6008
6080
4978
120
351
14
6009
6081
6010
6082
4979
120
351
14
6011
6083
6012
6084
4980
121
351
14
6013
6085
4981
991
351
14
6014
6086
4982
991
351
6015
6087
4983
122
351
14
6016
6091
2361
11533
17969
Cofactor
4984
121
351
14
6017
6092
4985
122
351
14
6018
6093
2362
11534
17972
Cofactor
12816
M512 651 C566 652 631 649 677 650
149
false
18
true
M 347.7612552253443 326.86224623128464 L 355 340 L 362.7582561250444 327.16218624927865
false
12817
M645 405 C615 405 925 515 895 515
149
true
18
13303
M1530 865 L1530 915 L1580 865 z
10
true
18
13336
M2090 590 C2091 535 2128 505 2165 505
5
false
18
false
false
13337
M2620 665 C2608 569 2500 503 2445 500
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
13338
M2496.5 585 C2495.5 551 2479 508 2445 500
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
13339
M377.5 355 L377.5 405 L427.5 355 z
10
true
18
13340
M2620 855 C2620 896 2620 931 2622 965
149
false
18
false
false
13341
M2765 1205 C2656 1170 2631 1094 2622 1045
149
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
13342
M2815 975 L2815 1025 L2865 975 z
10
true
18
13343
M2495 1200 C2569 1203 2620 1117 2622 1045
149
false
18
true
M 2375.6837856364605 910.4772766607826 L 2390 906 L 2378.9644574902213 895.8404330055425
false
13344
M2602.5 810 L2602.5 860 L2652.5 810 z
10
true
18
13481
M2720 760 C2863 766 2865 706 2970 705
149
false
18
true
M 2387.0096189432334 792.5 L 2400 785 L 2387.0096189432334 777.5
false
13482
M2720 760 C2867 759 2841 819 2970 820
149
false
18
true
M 2467.0096189432334 957.5 L 2480 950 L 2467.0096189432334 942.5
false
17958
M665 710 C695 710 710 657 680 590
5
false
18
true
M 642.1538449508291 498.79113490461873 L 630 490 L 628.4635763199186 504.9211059333846
false
17959
M1140 810 C1135 704 926 629 820 620
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
17960
M830 595 C860 595 896 183 920 200
5
true
18
17961
M970 595 C1000 595 896 183 920 200
5
true
18
17962
M895 515 C925 515 896 183 920 200
5
true
18
17963
M260 1175 C744 1135 1249 681 820 620
5
false
18
true
M 226.32851528422364 1066.4555450210873 L 214 1075 L 227.56397271534254 1081.404579937626
false
17964
M1420 780 C1280 781 1130 643 820 620
5
false
18
true
M 1247.0096189432334 657.5 L 1260 650 L 1247.0096189432334 642.5
false
17965
M1145 515 C1115 553 1001 591 895 515
5
false
18
true
M 1042.8372053132102 424.84325837351065 L 1045 410 L 1031.0639638302089 415.54859404482534
false
17966
M385 295 C387 330 384 431 385 465
149
false
18
true
M 328.3249233682022 356.567079544655 L 335 370 L 343.2957120454455 357.5027538369827
false
17967
M61 112 C84 128 124 155 148 172
5
true
18
17968
M1570 780 C1664 778 1680 667 1820 607
149
false
18
17969
M1520 745 L1520 795 L1570 745 z
10
true
18
17970
M1590 495 C1620 495 1649 619 1817 609
149
false
18
17971
M2165 505 C2135 505 1797 584 1821 601
5
true
18
17972
M1820 905 L1820 955 L1870 905 z
10
true
18
17973
M2240 470 C2011 365 1936 560 1819 608
149
false
18
true
M 2157.0096189432334 382.5 L 2170 375 L 2157.0096189432334 367.5
false
2587
351
596
2
8223
8650
13336
Left
8224
8651
13337
Right
8225
8652
13338
Right
2618
1808
3839
2619
1809
3857
2588
351
1970
2
8226
8651
13340
Left
8227
8654
13341
Right
558
3858
13343
Right
2620
1816
3859
3291
351
2126
14
10878
11527
17958
Left
10879
11528
17959
Right
767
4977
17960
Left
768
4978
17961
Left
769
3627
17962
Left
770
4979
17963
Right
771
4980
17964
Right
772
4981
17965
Right
3292
351
1958
14
773
4980
17968
Left
774
4983
17970
Left
775
4984
17971
Right
776
4985
17973
Right
326
209
351
735
8438
12816
Left
736
8439
12817
Right
211
3627
175
440
209
351
943
11530
17966
Left
944
11531
17967
Right
289
4982
175
812
731
351
217
false
2970
670
16
regular
768
8651
13481
Left
813
732
351
217
false
2970
785
16
regular
769
8651
13482
Left
42
8626
84
11529
85
11532
86
11535
66
6088
67
6089
68
6090
187439
1656
640
1.3
1.3
0
2
90
484
497
591
M127 604 C127 554 177 504 227 504 C1121 504 2284 504 3178 504 C3228 504 3278 554 3278 604 C3278 807 3278 1070 3278 1273 C3278 1323 3228 1373 3178 1373 C2284 1373 1121 1373 227 1373 C177 1373 127 1323 127 1273 C127 1070 127 807 127 604
1
true
6
3151.0
869.0
556
235
Activation
1685
565
20
1.0
1.0
200
15
557
235
Activation
280
345
20
1.0
1.0
200
15
573
235
Activation
2535
855
20
1.0
1.0
200
15
575
235
Regulatory subunits
2905
1080
20
1.0
1.0
200
15
576
235
Regulatory subunits
2405
930
20
1.0
1.0
200
15
622
235
Activation
2735
715
20
1.0
1.0
200
15
912
235
Extracellular Space
1100
210
20
1.3
1.3
200
15
913
235
Intracellular Space
555
760
20
1.3
1.3
200
15