8-oxo-dGTP (PAMDB003623)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB003623
Identification
Name: 8-oxo-dGTP
Description:8-oxo-dGTP is a product of oxidative modification of dGTP that can be misincorporated into DNA, causing AT-->CG mutations. 8-Oxo-dG DNA lesions are formed in the cell by reactive oxygen species. These can be present due to normal oxidative metabolic processes such as UV ionizing radiation.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2R,3S,5R)-5-(2-amino-6,8-dioxo-3,7-dihydropurin-9-yl)-3-hydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl phosphono hydrogen phosphate
  • (2R,3S,5R)-5-(2-amino-6,8-dioxo-3,7-Dihydropurin-9-yl)-3-hydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl phosphono hydrogen phosphoric acid
  • 2'-deoxy-7,8-dihydro-8-oxo-Guanosine 5'-(tetrahydrogen triphosphate)
  • 2'-Deoxy-7,8-dihydro-8-oxo-guanosine 5'-(tetrahydrogen triphosphoric acid)
  • 2'-Deoxy-8-oxo-7,8-dihydroguanosine 5'-(tetrahydrogen triphosphate)
  • 2'-Deoxy-8-oxo-7,8-dihydroguanosine 5'-(tetrahydrogen triphosphoric acid)
  • 8-Hydroxy-2'-deoxyguanosine 5'-triphosphate
  • 8-Hydroxy-2'-deoxyguanosine 5'-triphosphoric acid
  • 8-Oxo-2'-deoxyguanosine 5'-triphosphate
  • 8-oxo-2'-Deoxyguanosine 5'-triphosphoric acid
  • 8-oxo-7,8-dihydro-2'-deoxyguanosine 5'-triphosphate
  • 8-oxo-7,8-dihydro-2'-Deoxyguanosine 5'-triphosphoric acid
  • 8-oxo-7,8-dihydro-2'-dGTP
  • 8-Oxo-deoxyguanosine triphosphate
  • 8-oxo-Deoxyguanosine triphosphoric acid
  • 8-Oxo-dGTP
  • 8-oxodeoxyguanosine triphosphate
  • 8-Oxodeoxyguanosine triphosphoric acid
Chemical Formula: C10H16N5O14P3
Average Molecular Weight: 523.1804
Monoisotopic Molecular Weight: 522.990659781
InChI Key: BUZOGVVQWCXXDP-VPENINKCSA-N
InChI:InChI=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
CAS number: 139307-94-1
IUPAC Name:({[({[(2R,3S,5R)-5-(6,8-dihydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional IUPAC Name: ({[(2R,3S,5R)-5-(6,8-dihydroxy-2-imino-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
SMILES:[H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(=O)OP(O)(=O)OP(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 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine deoxyribonucleotides
Direct Parent Purine 2'-deoxyribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside triphosphate
  • Organic pyrophosphate
  • Purine
  • Imidazopyrimidine
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • 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'-triphosphate (CHEBI:63220 )
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.39 mg/mLALOGPS
logP-0.77ALOGPS
logP-2.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)5.36ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area295.8 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity107.76 m3·mol-1ChemAxon
Polarizability39.14 Å3ChemAxon
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
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-fa699eeae800d358b363View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-03561090528e941efbc5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-0900000000-b0bdb44fd47c1a3b341fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0320290000-3c8695b8a4eb4e6b737eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057l-8950010000-3791d75d4282916b6533View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9810000000-91ff82c6a5066cb45fc5View in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID63220
HMDB IDHMDB11615
Pubchem Compound ID53481005
Kegg IDC19967
ChemSpider ID97031
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand Expo8DG