Cyclic GMP (CHEM035165)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:32:33 UTC
Update Date2016-11-09 01:21:15 UTC
Accession NumberCHEM035165
Identification
Common NameCyclic GMP
ClassSmall Molecule
DescriptionCyclic guanosine monophosphate is 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)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CGMPChEBI
Guanosine 3',5'-cyclic monophosphateChEBI
Guanosine 3',5'-cyclic phosphateChEBI
Guanosine cyclic monophosphateChEBI
Guanosine 3',5'-cyclic monophosphoric acidGenerator
Guanosine 3',5'-cyclic phosphoric acidGenerator
Guanosine cyclic monophosphoric acidGenerator
3',5'-Cyclic GMPHMDB
3',5'-GuanosineHMDB
3',5'-Guanosine monophosphateHMDB
Cyclic 3',5'-guanosine monophosphateHMDB
Cyclic guanosine 3',5'-monophosphateHMDB
Cyclic-GMPHMDB
Guanosine 3',5'-cyclic-monophosphateHMDB
Guanosine 3',5'-monophosphateHMDB
Guanosine cyclic-monophosphateHMDB
Guanosine-cyclic-phosphoric-acidHMDB
Cyclic 3',5'-monophosphate, guanosineHMDB
GMP, CyclicHMDB
Guanosine cyclic-3',5'-monophosphateHMDB
monoPhosphate, guanosine cyclicHMDB
3',5'-monoPhosphate, guanosine cyclicHMDB
Cyclic-3',5'-monophosphate, guanosineHMDB
Guanosine cyclic 3',5'-monophosphateHMDB
Guanosine cyclic 3,5 monophosphateHMDB
Cyclic monophosphate, guanosineHMDB
Guanosine cyclic 3',5' monophosphateHMDB
Chemical FormulaC10H12N5O7P
Average Molecular Mass345.205 g/mol
Monoisotopic Mass345.047 g/mol
CAS Registry Number7665-99-8
IUPAC Name9-[(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 Namecyclic-GMP
SMILESNC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1
InChI IdentifierInChI=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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 Area170.52 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.72 m³·mol⁻¹ChemAxon
Polarizability29.19 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001i-2972000000-80320c485cef8d6d91adSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-2972000000-80320c485cef8d6d91adSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f76-3901000000-c970aad6713a547b2d8fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4590100000-edbc82f84eca5a64f5a5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uec-2904000000-85af5865e64af24e7691Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0904000000-e34bb3204af3b18ddf11Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0908000000-35925bce602ee60e24eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0904000000-93fabfb961527e02671eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0907000000-60b56b2fcc437a04a7b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0908000000-16c413e42a41fa5e7262Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udl-3904000000-051a745d5db4f607a935Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0901000000-a2a6721a5a98c3d3e945Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udj-0907000000-ae3d3b4dfb6aefdd34c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udj-0904000000-fd635f17953dbbff039bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0902000000-36d8b1a240f9f6471886Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-4c75be42ba8dbd671bbfSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-06ee1dc93418cde4fe39Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-db6612a4a4b92db51507Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-8455683aa1bc0141dd38Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-196c267f58b468d3a8f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-7637808812023bf3fb33Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-34c09019debbbd2ef2a6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-db049b28da12291887ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0904000000-65ab088e129c01a9b140Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-fc45e23a1d622d9a6848Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-0900000000-d7d3bc38b1c32086753eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-1709000000-881760c573673e832db8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-f74b8ec55fbea3fdf8cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003u-9600000000-d7f00c8f8cec474c7304Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02315
HMDB IDHMDB0001314
FooDB IDFDB030764
Phenol Explorer IDNot Available
KNApSAcK IDC00019673
BiGG ID1485267
BioCyc IDNot Available
METLIN ID6152
PDB IDNot Available
Wikipedia LinkCyclic guanosine monophosphate
Chemspider ID22734
ChEBI ID16356
PubChem Compound ID24316
Kegg Compound IDC00942
YMDB IDYMDB00454
ECMDB IDECMDB04034
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. Ilecka J: Decreased cerebrospinal fluid cGMP levels in patients with amyotrophic lateral sclerosis. J Neural Transm (Vienna). 2004 Feb;111(2):167-72. Epub 2003 Dec 12.
13. 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.
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.
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.
16. 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.
17. Engelhardt T, Galley HF, MacLennan FM, Webster NR: Saliva cyclic GMP increases during anaesthesia. Br J Anaesth. 2002 Oct;89(4):635-7.
18. 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.
19. 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.
20. 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.
21. 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.
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=24591051
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=24705918