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Identification
YMDB IDYMDB00211
Name8-Oxo-dGTP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description8-Oxo-dGTP, also known as 8-OH-dGTP or 8-hydroxy-dGTP, belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. 8-Oxo-dGTP is a moderately basic compound (based on its pKa).
Structure
Thumb
Synonyms
  • 2'-deoxy-7,8-dihydro-8-oxo-Guanosine 5'-(tetrahydrogen triphosphate)
  • 8-Hydroxy-2'-deoxyguanosine 5'-triphosphate
  • 8-Oxo-2'-deoxyguanosine 5'-triphosphate
  • 8-Oxo-7,8-dihydro-2'-deoxyguanosine 5'-triphosphate
  • 8-Oxo-deoxyguanosine triphosphate
  • 8-Oxo-dGTP
  • 8-OH-dGTP
  • 8-Hydroxy-dGTP
  • ({[({[(3S)-5-(6,8-dihydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonate
CAS number139307-94-1
WeightAverage: 523.1804
Monoisotopic: 522.990659781
InChI KeyBUZOGVVQWCXXDP-KLFYCJEISA-N
InChIInChI=1S/C10H16N5O14P3/c11-9-13-7-6(8(17)14-9)12-10(18)15(7)5-1-3(16)4(27-5)2-26-31(22,23)29-32(24,25)28-30(19,20)21/h3-5,16H,1-2H2,(H,12,18)(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,17)/t3-,4?,5?/m0/s1
IUPAC Name({[({[(3S)-5-(2-amino-6,8-dioxo-6,7,8,9-tetrahydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional IUPAC Name({[(3S)-5-(2-amino-6,8-dioxo-3,7-dihydropurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
Chemical FormulaC10H16N5O14P3
SMILES[H]O[C@@]1([H])C([H])([H])C([H])(OC1([H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O[H])N1C(=O)N([H])C2=C1N([H])C(=NC2=O)N([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate 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 triphosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside triphosphate
  • 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 DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility10.3 g/LALOGPS
logP-0.38ALOGPS
logP-4.5ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)0.99ChemAxon
pKa (Strongest Basic)2.59ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area289.1 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity105.31 m³·mol⁻¹ChemAxon
Polarizability39.75 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Nucleus, Peroxisome
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054n-9573110000-daaf44eb7513200301d5JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03kc-7239120000-fb89512d66b2c0c73399JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-36f2c770086e2025286fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-abb035705d7ecec8a5ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-0900000000-69efc100442e712d235bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0330390000-a2ee834d8adc4368c864JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057u-6960010000-f32163c3a928e66f90daJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-8dfeadd910412236d96fJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB11615
Pubchem Compound ID107902
Kegg IDNot Available
ChemSpider ID24784983
FOODB IDFDB028320
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Coenzyme A diphosphatase which mediates the cleavage of CoA into 3',5'-ADP and 4'-phosphopantetheine. Has a strong preference for oxidized CoA disulfide (CoASSCoA) as substrate. May be required to remove potentially toxic oxidized CoA disulfide to maintain the capacity for beta-oxidation of fatty acids. Can degrade 8-oxo-dGTP in vitro; however, such activity may not be relevant in vivo
Gene Name:
PCD1
Uniprot ID:
Q12524
Molecular weight:
39754.5
Reactions
8-oxo-dGTP + H(2)O → 8-oxo-dGMP + diphosphate.