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Identification
YMDB IDYMDB00454
Name3',5'-cyclic GMP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCyclic GMP, also known as CGMP or 3',5'-cyclic GMP, 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. Cyclic GMP is a moderately basic compound (based on its pKa). Cyclic GMP exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • 3',5'-Cyclic GMP
  • 3',5'-guanosine
  • 3',5'-guanosine monophosphate
  • cGMP
  • cyclic 3',5'-guanosine monophosphate
  • cyclic gmp
  • cyclic guanosine 3',5'-monophosphate
  • cyclic-GMP
  • guanosine 3,5-cyclic monophosphate
  • guanosine 3,5-cyclic phosphate
  • Guanosine 3',5'-cyclic monophosphate
  • guanosine 3',5'-cyclic phosphate
  • guanosine 3',5'-cyclic-monophosphate
  • guanosine 3',5'-monophosphate
  • Guanosine cyclic 3',5'-(hydrogen phosphate)
  • Guanosine cyclic monophosphate
  • guanosine cyclic-monophosphate
  • guanosine-cyclic-phosphoric-acid
  • Guanosine 3',5'-cyclic monophosphoric acid
  • Guanosine 3',5'-cyclic phosphoric acid
  • Guanosine cyclic monophosphoric acid
  • Cyclic 3',5'-monophosphate, guanosine
  • GMP, Cyclic
  • Guanosine cyclic-3',5'-monophosphate
  • monoPhosphate, guanosine cyclic
  • 3',5'-monoPhosphate, guanosine cyclic
  • Cyclic-3',5'-monophosphate, guanosine
  • Guanosine cyclic 3',5'-monophosphate
  • Guanosine cyclic 3,5 monophosphate
  • Cyclic monophosphate, guanosine
  • Guanosine cyclic 3',5' monophosphate
CAS number7665-99-8
WeightAverage: 345.2053
Monoisotopic: 345.047434275
InChI KeyZOOGRGPOEVQQDX-UUOKFMHZSA-N
InChIInChI=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
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 IUPAC Namecyclic-GMP
Chemical FormulaC10H12N5O7P
SMILESNC1=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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB ReactionsNot Available
KEGG Reactions
water + 3',5'-cyclic GMPGuanosine monophosphate + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Eckstein, H., Flugge, B. (1999). "Guanosine 3':5'-cyclic monophosphate-dependent particulate protein kinase activity from yeast (Saccharomyces cerevisiae)." Z Naturforsch C 54:84-93.10097409
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.
External Links:
ResourceLink
CHEBI ID16356
HMDB IDHMDB01314
Pubchem Compound ID24316
Kegg IDC00942
ChemSpider ID22734
FOODB IDFDB022549
WikipediaCyclic_guanosine_monophosphate
BioCyc IDCGMP

Enzymes

General function:
Involved in catalytic activity
Specific function:
Controls the level of cAMP in yeast cells, together with the low-affinity cAMP phosphodiesterase (PDE1)
Gene Name:
PDE2
Uniprot ID:
P06776
Molecular weight:
60999.19922
Reactions
Adenosine 3',5'-cyclic phosphate + H(2)O → adenosine 5'-phosphate.