Showing metabocard for Guanosine 2',3'-cyclic phosphate (BMDB0011629)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:21:59 UTC
Update Date2020-05-21 16:28:54 UTC
BMDB IDBMDB0011629
Secondary Accession Numbers
  • BMDB11629
Metabolite Identification
Common NameGuanosine 2',3'-cyclic phosphate
DescriptionGuanosine 2',3'-cyclic phosphate, also known as cyclic guanosine 2',3'-monophosphate, belongs to the class of organic compounds known as 2',3'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C2 and C3 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group. Guanosine 2',3'-cyclic phosphate exists in all living organisms, ranging from bacteria to humans. Based on a literature review a significant number of articles have been published on Guanosine 2',3'-cyclic phosphate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Cyclic guanosine 2',3'-monophosphateChEBI
Guanosine 2',3'-cyclic monophosphateChEBI
Guanosine cyclic 2',3'-(hydrogen phosphate)ChEBI
Guanosine cyclic-2',3'-monophosphateChEBI
O(2'),O(3')-Hydroxyphosphoryl-guanosineChEBI
Cyclic guanosine 2',3'-monophosphoric acidGenerator
Guanosine 2',3'-cyclic monophosphoric acidGenerator
Guanosine cyclic 2',3'-(hydrogen phosphoric acid)Generator
Guanosine cyclic-2',3'-monophosphoric acidGenerator
Guanosine 2',3'-cyclic phosphoric acidGenerator
2',3'-Cyclic GMP, lithium saltMeSH, HMDB
2',3'-Cyclic GMP, monosodium saltMeSH, HMDB
Guanosine cyclic 2,3 monophosphateMeSH, HMDB
2',3'-Cyclic GMP, sodium saltMeSH, HMDB
Guanosine cyclic 2',3'-monophosphateMeSH, HMDB
Guanosine 2',3'-cyclic phosphateChEBI
2',3'-Cyclic GMPMeSH
Chemical FormulaC10H12N5O7P
Average Molecular Weight345.2053
Monoisotopic Molecular Weight345.047434275
IUPAC Name9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-2-amino-6,9-dihydro-3H-purin-6-one
Traditional Name9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-2-amino-3H-purin-6-one
CAS Registry Number15718-49-7
SMILES
NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12
InChI Identifier
InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-6-5(3(1-16)20-9)21-23(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 KeyUASRYODFRYWBRC-UUOKFMHZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2',3'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C2 and C3 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 Parent2',3'-cyclic purine nucleotides
Alternative Parents
Substituents
  • 2',3'-cyclic purine ribonucleotide
  • Ribonucleoside 3'-phosphate
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Organic phosphoric acid derivative
  • Azole
  • 1,3_dioxaphospholane
  • Heteroaromatic compound
  • Imidazole
  • Tetrahydrofuran
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.6ALOGPS
logP-2.4ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.7ChemAxon
pKa (Strongest Basic)2.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area170.52 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity71.28 m³·mol⁻¹ChemAxon
Polarizability29.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-01x1-3972000000-df2552fc3c7b33d5fbfbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-01x1-3972000000-df2552fc3c7b33d5fbfbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01c3-3933000000-4fe05159f55ac562ab6aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5962000000-2fa436cbb4e5959d639dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1904000000-8fb2afe37dd02a6d845eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-ca072c32c08d839446b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-2900000000-950846db10c3ea5bf17aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-0409000000-7560a795a4081c2a83aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-5678b133858684f7c137View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pc3-6900000000-860a8c5cf0d45d6b0444View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-361a2474138028086bb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0903000000-946cd7b17d2fe5f36ad6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1922000000-4f6eb6f377248f3ec6d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-9ebf2bf873fdea0ab0a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-0629000000-1f736274756361159764View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3900000000-fdd7fdc6c2d094787d5bView in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0011629
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028329
KNApSAcK IDNot Available
Chemspider ID83792
KEGG Compound IDC06194
BioCyc IDCPD-3709
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481125
PDB IDNot Available
ChEBI ID28181
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Guanylate cyclase soluble subunit beta-1
General function:
Signal transduction mechanisms
Specific function:
Mediates responses to nitric oxide (NO) by catalyzing the biosynthesis of the signaling molecule cGMP.
Gene Name:
GUCY1B1
Uniprot ID:
P16068
Molecular weight:
70502.0
Reactions
Guanosine triphosphate → Guanosine 2',3'-cyclic phosphate + Pyrophosphatedetails
Enzyme Details
2. cGMP-specific 3',5'-cyclic phosphodiesterase
General function:
Involved in 3',5'-cyclic-GMP phosphodiesterase activity
Specific function:
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:8530505). Specifically regulates nitric-oxide-generated cGMP (By similarity).
Gene Name:
PDE5A
Uniprot ID:
Q28156
Molecular weight:
98627.0
Reactions
Guanosine 2',3'-cyclic phosphate + Water → Guanosine monophosphatedetails
Enzyme Details
3. Guanylate cyclase soluble subunit alpha-1
General function:
Signal transduction mechanisms
Specific function:
Not Available
Gene Name:
GUCY1A1
Uniprot ID:
P19687
Molecular weight:
77533.0
Reactions
Guanosine triphosphate → Guanosine 2',3'-cyclic phosphate + Pyrophosphatedetails