8-oxo-dGMP (ECMDB23234) (M2MDB003624)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (1)
Record Information
Version2.0
Creation Date2012-10-10 12:23:13 -0600
Update Date2015-06-03 17:26:14 -0600
Secondary Accession Numbers
  • ECMDB23234
Identification
Name:8-oxo-dGMP
Description8-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
MOLSDFPDBSMILESInChI
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
Weight:Average: 363.2206
Monoisotopic: 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
Description belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine deoxyribonucleotides
Direct ParentPurine 2'-deoxyribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside monophosphate
  • 6-oxopurine
  • Hypoxanthine
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Vinylogous amide
  • Tetrahydrofuran
  • Urea
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • purine 2'-deoxyribonucleoside 5'-monophosphate (CHEBI:63223 )
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.61 g/LALOGPS
logP-1.8ALOGPS
logP-1.1ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.29ChemAxon
pKa (Strongest Basic)0.33ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area202.74 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity86.02 m³·mol⁻¹ChemAxon
Polarizability30.46 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
8-oxo-dGTP + Water > 8-oxo-dGMP + Pyrophosphate
8-oxo-dGTP + Water <> 8-oxo-dGMP + Pyrophosphate
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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 IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoG42

Enzymes

Protein Details
1. Mutator mutT protein
General function:
Replication, recombination and repair
Specific function:
Involved in the GO system responsible for removing an oxidatively damaged form of guanine (7,8-dihydro-8-oxoguanine) from DNA and the nucleotide pool. 8-oxo-dGTP is inserted opposite dA and dC residues of template DNA with almost equal efficiency thus leading to A.T to G.C transversions. MutT specifically degrades 8-oxo-dGTP to the monophosphate
Gene Name:
mutT
Uniprot ID:
P08337
Molecular weight:
14927
Reactions
8-oxo-dGTP + H(2)O = 8-oxo-dGMP + diphosphate.