Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB003624
Identification
Name: 8-oxo-dGMP
Description:8-Oxo-dGMP is a metabolite of 8-oxo-dGTP which is a potent mutagenic substrate for DNA synthesis. 8-Oxo-dGTP is rapidly degraded to 8-oxo-dGMP by cellular 8-oxo-dGTPase activity.
Structure
Thumb
Synonyms:
  • (2R,3S,5R)-5-(2-amino-6,8-dioxo-3,7-dihydropurin-9-yl)-3-hydroxyoxolan-2-ylmethyl dihydrogen phosphate
  • (2R,3S,5R)-5-(2-amino-6,8-dioxo-3,7-Dihydropurin-9-yl)-3-hydroxyoxolan-2-ylmethyl dihydrogen phosphoric acid
  • 2'-Deoxy-7,8-dihydro-8-oxo-5'-guanylate
  • 2'-deoxy-7,8-dihydro-8-oxo-5'-guanylic acid
  • 2'-deoxy-7,8-dihydro-8-oxoguanosine 5'-monophosphate
  • 2'-Deoxy-7,8-dihydro-8-oxoguanosine 5'-monophosphoric acid
  • 2'-Deoxy-8-oxo-7,8-dihydroguanosine 5'-(dihydrogen phosphate)
  • 2'-Deoxy-8-oxo-7,8-dihydroguanosine 5'-(dihydrogen phosphoric acid)
  • 8-hydroxydeoxyguanosine 5'-monophosphate
  • 8-Hydroxydeoxyguanosine 5'-monophosphoric acid
  • 8-OH-Dgmp
  • 8-oxo-2'-deoxyguanosine-5'-monophosphate
  • 8-oxo-2'-Deoxyguanosine-5'-monophosphoric acid
  • 8-Oxo-7,8-dihydro-2'-deoxyguanosine 5'-triphosphate
  • 8-oxo-7,8-dihydro-2'-Deoxyguanosine 5'-triphosphoric acid
  • 8-Oxo-dGMP
  • 8OG
Chemical Formula: C10H14N5O8P
Average Molecular Weight: 363.2206
Monoisotopic Molecular Weight: 363.057998961
InChI Key: AQIVLFLYHYFRKU-VPENINKCSA-N
InChI:InChI=1S/C10H14N5O8P/c11-9-13-7-6(8(17)14-9)12-10(18)15(7)5-1-3(16)4(23-5)2-22-24(19,20)21/h3-5,16H,1-2H2,(H,12,18)(H2,19,20,21)(H3,11,13,14,17)/t3-,4+,5+/m0/s1
CAS number: Not Available
IUPAC Name:{[(2R,3S,5R)-5-(6,8-dihydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name: [(2R,3S,5R)-5-(6,8-dihydroxy-2-imino-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxyphosphonic acid
SMILES:[H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(O)=O)N1C(O)=NC2=C1NC(=N)N=C2O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine ribonucleotides
Direct Parent Purine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Purine
  • Imidazopyrimidine
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
  • purine 2'-deoxyribonucleoside 5'-monophosphate (CHEBI:63223 )
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.33 mg/mLALOGPS
logP-1.6ALOGPS
logP-1.3ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)5.31ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area202.74 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity86.02 m3·mol-1ChemAxon
Polarizability30.46 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-42f21e68a3b8a11d8f12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-de34592c0dc9520d28b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-0900000000-0ba8f7824c370f6cc73dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-5209000000-1cfe1dad9de4df88a5acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000000-e52ecd6c80029deb2695View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-9cd024afaf90bd3fd2bdView in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID63223
HMDB IDHMDB11670
Pubchem Compound ID447903
Kegg IDC19968
ChemSpider ID394863
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoG42