Showing metabocard for 8-Hydroxy-deoxyguanosine (BMDB0003333)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:03:44 UTC
Update Date2020-05-11 18:25:32 UTC
BMDB IDBMDB0003333
Secondary Accession Numbers
  • BMDB03333
Metabolite Identification
Common Name8-Hydroxy-deoxyguanosine
Description8-Hydroxy-deoxyguanosine, also known as 8-ohdg or 8-oxo-2'-DG, belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2. Based on a literature review a significant number of articles have been published on 8-Hydroxy-deoxyguanosine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7,8-Dihydro-2'-deoxy-8-oxoguanosineChEBI
8-HydroxydeoxyguanosineChEBI
8-OHdGChEBI
8-oxo-2'-DeoxyguanineChEBI
8-oxo-2'-DGChEBI
8-oxo-7,8-Dihydro-2'-deoxyguanosineChEBI
8-oxo-7-HydrodeoxyguanosineChEBI
8-oxo-DGChEBI
8-OxoguanosineChEBI
7,8-dihydro-8-oxo-2'-DeoxyguanosineHMDB, MeSH
7,8-dihydro-8-OxodeoxyguanosineHMDB
8-Hydroxy-2'-deoxyguanosineHMDB
8-Hydroxy-2'deoxyguanosineHMDB
8-Hydroxy-2-deoxyguanosineHMDB
8-Hydroxydeoxy-guanosineHMDB
8-HydroxydeoxyguanineHMDB
8-oxo-7,8-DihydrodeoxyguanosineHMDB, MeSH
8-OxodgHMDB, MeSH
OH8DgHMDB
2'-Deoxy-7,8-dihydro-8-oxoguanosineMeSH, HMDB
2'-Deoxy-8-oxo-7,8-dihydroguanosineMeSH, HMDB
8-OHdG compoundMeSH, HMDB
8-OxodGuoMeSH, HMDB
O-D-DGMeSH, HMDB
2'-Deoxy-8-oxoguanosineMeSH, HMDB
8-oxo-2'-DeoxyguanosineMeSH, HMDB
7-hydro-8-OxodeoxyguanosineMeSH, HMDB
8-OH-DGMeSH, HMDB
2'-Deoxy-8-hydroxyguanosineMeSH, HMDB
8-oxo-DGuoMeSH, HMDB
Chemical FormulaC10H13N5O5
Average Molecular Weight283.2407
Monoisotopic Molecular Weight283.091668551
IUPAC Name2-amino-8-hydroxy-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
Traditional Name8-hydroxy-2'-deoxyguanosine
CAS Registry Number88847-89-6
SMILES
NC1=NC2=C(N=C(O)N2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1
InChI Identifier
InChI=1S/C10H13N5O5/c11-9-13-7-6(8(18)14-9)12-10(19)15(7)5-1-3(17)4(2-16)20-5/h3-5,16-17H,1-2H2,(H,12,19)(H3,11,13,14,18)/t3-,4+,5+/m0/s1
InChI KeyHCAJQHYUCKICQH-VPENINKCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassPurine 2'-deoxyribonucleosides
Direct ParentPurine 2'-deoxyribonucleosides
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • N-substituted imidazole
  • Pyrimidine
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.7ALOGPS
logP-1.4ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.09ChemAxon
pKa (Strongest Basic)1.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.56 m³·mol⁻¹ChemAxon
Polarizability25.82 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9270000000-cbf066db8be0f3462b6dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-9503400000-ff14681f666eee936938View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-Ion Trap , Positivesplash10-0a4i-1649170600-b830f720eac21d5be0a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0900000000-bda7c71c752f3e3c4c51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-279a84bf501a3d5c6555View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-8b53d5aeced1f8b887aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-0900000000-1db539ae30cc3fae45efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0290000000-77880ee90b3d77e9f3f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-0920000000-8ab5275c7f1f98f7c143View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dm-4900000000-4c65e34bf57ca440e280View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-1df07afca955f854b771View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-0950000000-7088092794cc25cf636cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fxy-2900000000-16fdd2a07e854814fc6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0490000000-6a3ea27ba97cf9405385View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-d28ab0ab8ba89b944e85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ox-2910000000-d457b32e33bd1c0ab8f9View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003333
DrugBank IDDB02502
Phenol Explorer Compound IDNot Available
FooDB IDFDB023145
KNApSAcK IDNot Available
Chemspider ID66049
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link8-Oxo-2'-deoxyguanosine
METLIN ID6890
PubChem Compound73318
PDB IDNot Available
ChEBI ID40304
References
Synthesis ReferenceKawamoto T; Ikeuchi Y; Mikata Y; Kishigami M K; Yano S; Murayama C; Mori T; Yoneda F Promotion of radiation-induced formation of 8-oxo-7,8-dihydro-2'-deoxyguanosine by nitro 5-deazaflavin derivatives. Bioorganic & medicinal chemistry letters (2001), 11(13), 1745-8.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available