Record Information
Version2.0
Creation Date2012-05-31 14:02:50 -0600
Update Date2015-09-13 12:56:13 -0600
Secondary Accession Numbers
  • ECMDB04034
Identification
Name:Cyclic 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.
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
Weight:Average: 345.2053
Monoisotopic: 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-2λ⁵-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
Description belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassCyclic purine nucleotides
Direct Parent3',5'-cyclic purine nucleotides
Alternative Parents
Substituents
  • 3',5'-cyclic purine ribonucleotide
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Vinylogous amide
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Primary amine
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 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 Area170.52 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.72 m³·mol⁻¹ChemAxon
Polarizability29.19 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001i-2972000000-80320c485cef8d6d91adView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-2972000000-80320c485cef8d6d91adView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f76-3901000000-c970aad6713a547b2d8fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4590100000-edbc82f84eca5a64f5a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uec-2904000000-85af5865e64af24e7691View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0904000000-e34bb3204af3b18ddf11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0908000000-35925bce602ee60e24eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0904000000-93fabfb961527e02671eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0907000000-60b56b2fcc437a04a7b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0908000000-16c413e42a41fa5e7262View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udl-3904000000-051a745d5db4f607a935View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0901000000-a2a6721a5a98c3d3e945View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udj-0907000000-ae3d3b4dfb6aefdd34c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udj-0904000000-fd635f17953dbbff039bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0902000000-36d8b1a240f9f6471886View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-4c75be42ba8dbd671bbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-06ee1dc93418cde4fe39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-db6612a4a4b92db51507View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-8455683aa1bc0141dd38View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-196c267f58b468d3a8f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-7637808812023bf3fb33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-34c09019debbbd2ef2a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-db049b28da12291887ceView 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

Enzymes

General function:
Involved in adenylate cyclase activity
Specific function:
ATP = 3',5'-cyclic AMP + diphosphate
Gene Name:
cyaA
Uniprot ID:
P00936
Molecular weight:
97585
Reactions
ATP = 3',5'-cyclic AMP + diphosphate.
General function:
Involved in phosphorus-oxygen lyase activity
Specific function:
In association with DosC is involved in the production and removal of the second messenger c-di-GMP in response to changing O(2) levels. Has phosphodiesterase (PDE) activity with c- di-GMP (PubMed:15995192), very poor activity on cAMP (PubMed:15995192) but not with cGMP, bis(p-nitrophenyl) phosphate or p-nitrophenyl phosphate (PubMed:11970957). Cyclic-di-GMP is a second messenger which controls cell surface-associated traits in bacteria
Gene Name:
dosP
Uniprot ID:
P76129
Molecular weight:
90260
Reactions
Cyclic di-3',5'-guanylate + H(2)O = 5'-phosphoguanylyl(3'->5')guanosine.