Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:18 UTC
HMDB IDHMDB01314
Secondary Accession NumbersNone
Metabolite Identification
Common NameCyclic GMP
DescriptionGuanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed).
Structure
Thumb
Synonyms
  1. 3',5'-Cyclic GMP
  2. 3',5'-Guanosine
  3. 3',5'-Guanosine monophosphate
  4. cGMP
  5. Cyclic 3',5'-guanosine monophosphate
  6. Cyclic GMP
  7. Cyclic guanosine 3',5'-monophosphate
  8. Cyclic-GMP
  9. Guanosine 3',5'-cyclic phosphate
  10. Guanosine 3',5'-cyclic-monophosphate
  11. Guanosine 3',5'-monophosphate
  12. Guanosine cyclic-monophosphate
  13. Guanosine-cyclic-phosphoric-acid
Chemical FormulaC10H12N5O7P
Average Molecular Weight345.2053
Monoisotopic Molecular Weight345.047434275
IUPAC Name9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2$l^{5}-furo[3,2-d][1,3,2$l^{5}]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one
Traditional IUPAC Name3',5'-cyclic gmp
CAS Registry Number7665-99-8
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1
InChI Identifier
InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1
InChI KeyZOOGRGPOEVQQDX-UUOKFMHZSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleotides
Sub ClassPurine Ribonucleotides
Other Descriptors
  • 3',5'-Cyclic nuclcleotides(KEGG)
  • 3',5'-cyclic Purine Nucleotides
  • 3',5'-cyclic purine nucleotide(ChEBI)
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Hypoxanthine
  • Imidazole
  • Imidazopyrimidine
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Phosphoric Acid Ester
  • Purine
  • Purinone
  • Pyrimidine
  • Pyrimidone
  • Secondary Alcohol
Direct ParentPurine Ribonucleoside Monophosphates
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Purine metabolism
  • Second messenger
ApplicationNot Available
Cellular locations
  • Extracellular
  • Nucleus
  • Golgi apparatus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility3.79 g/LALOGPS
logP-2ALOGPS
logP-2.1ChemAxon
logS-2ALOGPS
pKa (strongest acidic)2.05ChemAxon
pKa (strongest basic)1.41ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count8ChemAxon
hydrogen donor count4ChemAxon
polar surface area170.52ChemAxon
rotatable bond count1ChemAxon
refractivity71.72ChemAxon
polarizability29.19ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Nucleus
  • Golgi apparatus
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Aorta
  • Blood Vessels
  • Kidney
  • Platelet
  • Smooth Muscle
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.0055 +/- 0.0003 uMAdult (>18 years old)MaleNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.0024 +/- 0.0005 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.0035 +/- 0.0003 uMAdult (>18 years old)BothSildenafil-induced headache
Associated Disorders and Diseases
Disease References
Headache
  • Kruuse C, Frandsen E, Schifter S, Thomsen LL, Birk S, Olesen J: Plasma levels of cAMP, cGMP and CGRP in sildenafil-induced headache. Cephalalgia. 2004 Jul;24(7):547-53. Pubmed: 15196297
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022549
KNApSAcK IDNot Available
Chemspider ID22734
KEGG Compound IDC00942
BioCyc IDCGMP
BiGG ID1485267
Wikipedia LinkCyclic GMP
NuGOwiki LinkHMDB01314
Metagene LinkHMDB01314
METLIN ID6152
PubChem Compound24316
PDB ID35G
ChEBI ID16356
References
Synthesis ReferenceSekhar, Konjeti R.; Grondin, Pascal; Francis, Sharron H.; Corbin, Jackie D. Design and synthesis of xanthines and cyclic GMP analogs as potent inhibitors of PDE5. Phosphodiesterase Inhibitors (1996), 135-146.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mashayekhi F, Aghahoseini F, Rezaie A, Zamani MJ, Khorasani R, Abdollahi M: Alteration of cyclic nucleotides levels and oxidative stress in saliva of human subjects with periodontitis. J Contemp Dent Pract. 2005 Nov 15;6(4):46-53. Pubmed: 16299606
  2. Rudman D, O'Brien MS, McKinney AS, Hoffman JC Jr, Patterson JH: Observations on the cyclic nucleotide concentrations in human cerebrospinal fluid. J Clin Endocrinol Metab. 1976 Jun;42(6):1088-97. Pubmed: 180045
  3. Martina V, Benso A, Gigliardi VR, Masha A, Origlia C, Granata R, Ghigo E: Short-term dehydroepiandrosterone treatment increases platelet cGMP production in elderly male subjects. Clin Endocrinol (Oxf). 2006 Mar;64(3):260-4. Pubmed: 16487434
  4. Kotikoski H, Moilanen E, Vapaatalo H, Aine E: Biochemical markers of the L-arginine-nitric oxide pathway in the aqueous humour in glaucoma patients. Acta Ophthalmol Scand. 2002 Apr;80(2):191-5. Pubmed: 11952488
  5. Young DV, Cochran ED, Dhawan V, Earl RA, Ellis JL, Garvey DS, Janero DR, Khanapure SP, Letts LG, Melim TL, Murty MG, Shumway MJ, Wey SJ, Zemtseva IS, Selig WM: A comparison of the cyclooxygenase inhibitor-NO donors (CINOD), NMI-1182 and AZD3582, using in vitro biochemical and pharmacological methods. Biochem Pharmacol. 2005 Nov 1;70(9):1343-51. Pubmed: 16168964
  6. Dobrzynski E, Montanari D, Agata J, Zhu J, Chao J, Chao L: Adrenomedullin improves cardiac function and prevents renal damage in streptozotocin-induced diabetic rats. Am J Physiol Endocrinol Metab. 2002 Dec;283(6):E1291-8. Pubmed: 12424108
  7. Willoughby SR, Stewart S, Chirkov YY, Kennedy JA, Holmes AS, Horowitz JD: Beneficial clinical effects of perhexiline in patients with stable angina pectoris and acute coronary syndromes are associated with potentiation of platelet responsiveness to nitric oxide. Eur Heart J. 2002 Dec;23(24):1946-54. Pubmed: 12473257
  8. Barani J, Gottsater A, Mattiasson I, Lindblad B: Platelet and leukocyte activation during aortoiliac angiography and angioplasty. Eur J Vasc Endovasc Surg. 2002 Mar;23(3):220-5. Pubmed: 11914008
  9. Schiessl B, Strasburger CJ, Bidlingmaier M, Spannagl M, Ugele B, Kainer F: Decreasing resistance in the maternal uterine and peripheral arterial system is apparently unrelated to plasma and urinary levels of nitrite/nitrate and cyclic-guanosinmonophosohate during the course of normal pregnancies. J Perinat Med. 2003;31(4):281-6. Pubmed: 12951882
  10. Bai X, Wang H, Li Z, Liu K: Correlation between blood cAMP, cGMP levels and traumatic severity in the patients with acute trauma and its clinical significance. J Huazhong Univ Sci Technolog Med Sci. 2004;24(1):68-70. Pubmed: 15165120
  11. Beltowski J, Jamroz A, Borkowska E: [Heme oxygenase and carbon monoxide in the physiology and pathology of the cardiovascular system] Postepy Hig Med Dosw (Online). 2004 Mar 3;58:83-99. Pubmed: 15069378
  12. Peracchi M, Lombardi L, Maiolo AT, Bamonti-Catena F, Toschi V, Chiorboli O, Mozzana R, Polli EE: Plasma and urine cyclic nucleotide levels in patients with acute and chronic leukemia. Blood. 1983 Mar;61(3):429-34. Pubmed: 6297636
  13. Ilecka J: Decreased cerebrospinal fluid cGMP levels in patients with amyotrophic lateral sclerosis. J Neural Transm. 2004 Feb;111(2):167-72. Epub 2003 Dec 12. Pubmed: 14767719
  14. Hunter KA, Singh GJ, Simpkins CO: Cyclic gmp is a measure of physiologic stress. J Natl Med Assoc. 2001 Jul-Aug;93(7-8):256-62. Pubmed: 11491275
  15. Zhang H, Zheng RL, Xu CY: [Relationships between lipid peroxidation or cyclic nucleotides and motility in human asthenozoosperm and normosperm] Shi Yan Sheng Wu Xue Bao. 1998 Dec;31(4):341-6. Pubmed: 12016956
  16. Engelhardt T, Galley HF, MacLennan FM, Webster NR: Saliva cyclic GMP increases during anaesthesia. Br J Anaesth. 2002 Oct;89(4):635-7. Pubmed: 12393367
  17. Galassi F, Renieri G, Sodi A, Ucci F, Vannozzi L, Masini E: Nitric oxide proxies and ocular perfusion pressure in primary open angle glaucoma. Br J Ophthalmol. 2004 Jun;88(6):757-60. Pubmed: 15148207
  18. Zhao L, Gray L, Leonardi-Bee J, Weaver CS, Heptinstall S, Bath PM: Effect of aspirin, clopidogrel and dipyridamole on soluble markers of vascular function in normal volunteers and patients with prior ischaemic stroke. Platelets. 2006 Mar;17(2):100-4. Pubmed: 16421011
  19. Martina V, Origlia C, Bruno GA, Messina M, Ferri M, Pescarmona GP: Serum DHEAS levels correlate with platelet cGMP in normal women. J Endocrinol Invest. 2001 Nov;24(10):RC28-30. Pubmed: 11765058
  20. St Pierre MV, Schlenker T, Dufour JF, Jefferson DM, Fitz JG, Arias IM: Stimulation of cyclic guanosine monophosphate production by natriuretic peptide in human biliary cells. Gastroenterology. 1998 Apr;114(4):782-90. Pubmed: 9516399

Enzymes

Gene Name:
PDE1A
Uniprot ID:
P54750
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE8A
Uniprot ID:
O60658
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE1B
Uniprot ID:
Q01064
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE3B
Uniprot ID:
Q13370
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE6C
Uniprot ID:
P51160
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE7A
Uniprot ID:
Q13946
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE3A
Uniprot ID:
Q14432
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE10A
Uniprot ID:
Q9Y233
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE1C
Uniprot ID:
Q14123
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE4B
Uniprot ID:
Q07343
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE7B
Uniprot ID:
Q9NP56
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE9A
Uniprot ID:
O76083
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE2A
Uniprot ID:
O00408
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE6A
Uniprot ID:
P16499
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE8B
Uniprot ID:
O95263
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE4C
Uniprot ID:
Q08493
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE6B
Uniprot ID:
P35913
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE4D
Uniprot ID:
Q08499
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE4A
Uniprot ID:
P27815
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE5A
Uniprot ID:
O76074
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
ADCY7
Uniprot ID:
P51828
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY4
Uniprot ID:
Q8NFM4
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY6
Uniprot ID:
O43306
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY5
Uniprot ID:
O95622
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY8
Uniprot ID:
P40145
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY9
Uniprot ID:
O60503
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY3
Uniprot ID:
O60266
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY1
Uniprot ID:
Q08828
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
ADCY2
Uniprot ID:
Q08462
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
NPR2
Uniprot ID:
P20594
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
GUCY1B3
Uniprot ID:
Q02153
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
GUCY2D
Uniprot ID:
Q02846
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
GUCY1A3
Uniprot ID:
Q02108
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
NPR1
Uniprot ID:
P16066
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
GUCY2C
Uniprot ID:
P25092
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
GUCY1A2
Uniprot ID:
P33402
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
GUCY2F
Uniprot ID:
P51841
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
GUCY1B2
Uniprot ID:
O75343
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
CNGA1
Uniprot ID:
P29973
Gene Name:
ADCY10
Uniprot ID:
Q96PN6
Reactions
Guanosine triphosphate unknown Cyclic GMP + Pyrophosphatedetails
Gene Name:
PDE11A
Uniprot ID:
Q9HCR9
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails