guanosine 2',3'-cyclic monophosphate (PAMDB120487)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120487
Identification
Name: guanosine 2',3'-cyclic monophosphate
Description:A 2',3'-cyclic nucleotide(1−) which is obtained from 2',3'-cyclic GMP by removal of a proton from the cyclic phosphate group.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2',3'-cyclic GMP
  • cGMP(1−)
  • cyclic guanosine 2',3'-monophosphate(1−)
  • guanosine 2',3'-cyclic monophosphate(1−)
  • guanosine 2',3'-cyclic phosphate(1−)
  • guanosine cyclic-2',3'-monophosphate(1−)
  • O2',O3'-hydroxyphosphoryl-guanosine(1−)
Chemical Formula: C10H11N5O7P
Average Molecular Weight: 344.2
Monoisotopic Molecular Weight: 345.04742
InChI Key: UASRYODFRYWBRC-UUOKFMHZSA-M
InChI: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)/p-1/t3-,5-,6-,9-/m1/s1
CAS number: 15718-49-7
IUPAC Name:(3aR,4R,6R,6aR)-4-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-6-(hydroxymethyl)tetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-2-olate 2-oxide
Traditional IUPAC Name: 9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2???furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-2-amino-3H-purin-6-one
SMILES:C2(=NC1(C(=O)NC(N)=NC=1N2C4(OC(CO)C3(OP(=O)([O-])OC34))))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct Parent 2',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 Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.53 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity71.28 m3·mol-1ChemAxon
Polarizability29.11 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
guanosine 2',3'-cyclic monophosphate + Water → guanosine 3'-monophosphate + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-01x1-3972000000-df2552fc3c7b33d5fbfbView in MoNA
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
References
References:
  • 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. [9184239 ]
  • 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. [10397337 ]
  • 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. [7528887 ]
  • Diamantstein T, Ulmer A: Effect of cyclic nucleotides on DNA synthesis in mouse lymphoid cells. Immunol Commun. 1975;4(1):51-62. [163786 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
HMDBHMDB11629
BIGG47631
CHEMSPIDER10463758
CHEBI60837
PUBCHEM23421170
LIGAND-CPDC06194