PCG

CYCLIC GUANOSINE MONOPHOSPHATE

Created: 1999-07-08
Last modified:  2024-09-27

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Chemical Details

Formal Charge0
Atom Count35
Chiral Atom Count5
Bond Count38
Aromatic Bond Count5
2D diagram of PCG

Chemical Component Summary

NameCYCLIC GUANOSINE MONOPHOSPHATE
Systematic Name (OpenEye OEToolkits)2-amino-9-[(4R,6S,7R,8R)-4,7-dihydroxy-4-oxo-3,5,9-trioxa-4$l^{5}-phosphabicyclo[4.3.0]nonan-8-yl]-1H-purin-6-one
FormulaC10 H12 N5 O7 P
Molecular Weight345.205
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C4NC(=Nc1c4ncn1C3OC2COP(=O)(OC2C3O)O)N
SMILESCACTVS3.341NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH]4CO[P](O)(=O)O[CH]4[CH]3O
SMILESOpenEye OEToolkits1.5.0c1nc2c(n1C3C(C4C(O3)COP(=O)(O4)O)O)N=C(NC2=O)N
Canonical SMILESCACTVS3.341 NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@@H]4CO[P@](O)(=O)O[C@H]4[C@H]3O
Canonical SMILESOpenEye OEToolkits1.5.0 c1nc2c(n1[C@H]3[C@@H]([C@H]4C(O3)CO[P@](=O)(O4)O)O)N=C(NC2=O)N
InChIInChI1.03 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
InChIKeyInChI1.03 ZOOGRGPOEVQQDX-UUOKFMHZSA-N

Drug Info: DrugBank

DrugBank IDDB02315 
NameCyclic GMP
Groups experimental
DescriptionCyclic guanosine monophosphate (Cyclic GMP) 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)
Synonyms
  • 3',5'-cyclic GMP
  • Guanosine 3',5'-cyclic phosphate
  • cGMP
  • Guanosine cyclic monophosphate
  • Guanosine 3',5'-cyclic monophosphate
Categories
  • Guanine Nucleotides
  • Heterocyclic Compounds, Fused-Ring
  • Nucleic Acids, Nucleotides, and Nucleosides
  • Nucleotides
  • Nucleotides, Cyclic
CAS number7665-99-8

Drug Targets

NameTarget SequencePharmacological ActionActions
cGMP-dependent 3',5'-cyclic phosphodiesteraseMGQACGHSILCRSQQYPAARPAEPRGQQVFLKPDEPPPPPQPCADSLQDA...unknown
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2MDARGGGGRPGESPGATPAPGPPPPPPPAPPQQQPPPPPPPAPPPGPGPA...unknown
cAMP-dependent protein kinase type I-alpha regulatory subunitMESGSTAASEEARSLRECELYVQKHNIQALLKDSIVQLCTARPERPMAFL...unknown
Solute carrier family 22 member 6MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...unknown
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 24316, 5280386, 135398570
ChEMBL CHEMBL395336
ChEBI CHEBI:16356