Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000570
Identification
Name: Cyclic GMP
Description:Guanosine 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.
Structure
Thumb
Synonyms:
  • 3',5'-Cyclic GMP
  • 3',5'-Guanosine
  • 3',5'-Guanosine monophosphate
  • 3',5'-Guanosine monophosphoric acid
  • CGMP
  • Cyclic 3',5'-guanosine monophosphate
  • Cyclic 3',5'-guanosine monophosphoric acid
  • Cyclic GMP
  • Cyclic guanosine 3',5'-monophosphate
  • Cyclic guanosine 3',5'-monophosphoric acid
  • Cyclic-GMP
  • Guanosine 3',5'-cyclic phosphate
  • Guanosine 3',5'-cyclic phosphoric acid
  • Guanosine 3',5'-cyclic-monophosphate
  • Guanosine 3',5'-cyclic-monophosphoric acid
  • Guanosine 3',5'-monophosphate
  • Guanosine 3',5'-monophosphoric acid
  • Guanosine cyclic-monophosphate
  • Guanosine cyclic-monophosphoric acid
  • Guanosine-cyclic-phosphoric-acid
Chemical Formula: C10H12N5O7P
Average Molecular Weight: 345.2053
Monoisotopic Molecular Weight: 345.047434275
InChI Key: ZOOGRGPOEVQQDX-UUOKFMHZSA-N
InChI: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
CAS number: 7665-99-8
IUPAC Name:9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2???furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one
Traditional IUPAC Name: cyclic-GMP
SMILES:NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine ribonucleotides
Direct Parent Purine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • 3',5'-cyclic purine ribonucleotide
  • Purinone
  • Hypoxanthine
  • 6-oxopurine
  • Purine
  • Imidazopyrimidine
  • Pyrimidone
  • Pyrimidine
  • Primary aromatic amine
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Lactam
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
LogP:-2.968PhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.79 mg/mLALOGPS
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 Area170.52 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.72 m3·mol-1ChemAxon
Polarizability29.19 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001i-2972000000-80320c485cef8d6d91adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0904000000-65ab088e129c01a9b140View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-fc45e23a1d622d9a6848View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-0900000000-d7d3bc38b1c32086753eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-1709000000-881760c573673e832db8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-f74b8ec55fbea3fdf8cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003u-9600000000-d7f00c8f8cec474c7304View in MoNA
References
References:
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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
  • 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
  • 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
  • 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
Synthesis Reference: Sekhar, 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) Download (PDF)
External Links:
ResourceLink
CHEBI ID16356
HMDB IDHMDB01314
Pubchem Compound ID24316
Kegg IDC00942
ChemSpider ID22734
WikipediaCyclic GMP
BioCyc IDCGMP
EcoCyc IDCGMP
Ligand ExpoPCG