Guanosine 2',3'-cyclic phosphate (CHEM040377)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 20:35:11 UTC
Update Date2016-11-09 01:22:14 UTC
Accession NumberCHEM040377
Identification
Common NameGuanosine 2',3'-cyclic phosphate
ClassSmall Molecule
DescriptionA 2',3'-cyclic purine nucleotide in which guanosine is used as the parent nucleoside.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass345.205 g/mol
Monoisotopic Mass345.047 g/mol
CAS Registry Number634-02-6
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
SMILESNC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12
InChI IdentifierInChI=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
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 Solubility3.53 g/LALOGPS
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
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)splash10-01x1-3972000000-df2552fc3c7b33d5fbfbSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-01x1-3972000000-df2552fc3c7b33d5fbfbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01c3-3933000000-4fe05159f55ac562ab6aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5962000000-2fa436cbb4e5959d639dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1904000000-8fb2afe37dd02a6d845eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-ca072c32c08d839446b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-2900000000-950846db10c3ea5bf17aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-0409000000-7560a795a4081c2a83aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-5678b133858684f7c137Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pc3-6900000000-860a8c5cf0d45d6b0444Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-361a2474138028086bb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0903000000-946cd7b17d2fe5f36ad6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1922000000-4f6eb6f377248f3ec6d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-9ebf2bf873fdea0ab0a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-0629000000-1f736274756361159764Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3900000000-fdd7fdc6c2d094787d5bSpectrum
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
1D NMR13C 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 IDNot Available
HMDB IDHMDB0011629
FooDB IDFDB028329
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-3709
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID83792
ChEBI ID28181
PubChem Compound ID53481125
Kegg Compound IDC06194
YMDB IDNot Available
ECMDB IDECMDB11629
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Genschik P, Billy E, Swianiewicz M, Filipowicz W: The human RNA 3'-terminal phosphate cyclase is a member of a new family of proteins conserved in Eucarya, Bacteria and Archaea. EMBO J. 1997 May 15;16(10):2955-67.
2. Filipowicz W, Billy E, Drabikowski K, Genschik P: Cyclases of the 3'-terminal phosphate in RNA: a new family of RNA processing enzymes conserved in eucarya, bacteria and archaea. Acta Biochim Pol. 1998;45(4):895-906.
3. Hamada K, Yokoro K: Blocking of DNA synthesis in vitro by a guanosine 2',3'-cyclic phosphate: a possible mechanism of chromosome aberrations induced by U5 snRNA. Mutat Res. 1995 Jan;326(1):71-82.
4. Diamantstein T, Ulmer A: Effect of cyclic nucleotides on DNA synthesis in mouse lymphoid cells. Immunol Commun. 1975;4(1):51-62.
5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.