8-Hydroxyguanine (CHEM035307)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:39:07 UTC
Update Date2016-11-09 01:21:17 UTC
Accession NumberCHEM035307
Identification
Common Name8-Hydroxyguanine
ClassSmall Molecule
DescriptionAn oxopurine that is guanine in which the hydrogen at position 8 is replaced by an oxo group and in which the nitrogens at positions 7 and 9 each bear a hydrogen.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
8-OxoguanineChEBI
1H-Purine-6,8-dione, 2-amino-7,9-dihydro-1H-purine-6,8-dioneHMDB
2-amino-6,8-DihydroxypurineHMDB, MeSH
2-amino-7,9-dihydro-1H-Purine-6,8-dioneHMDB
2-amino-Purine-6,8-diolHMDB
2-Aminopurine-6,8-diolHMDB
7,8-dihydro-8-OxoguanineHMDB
oxo-8-GuaMeSH, HMDB
8-oxo-7,8-DihydroguanineMeSH, HMDB
8-HydroxyguanineChEBI
Chemical FormulaC5H5N5O2
Average Molecular Mass167.126 g/mol
Monoisotopic Mass167.044 g/mol
CAS Registry Number5614-64-2
IUPAC Name2-amino-6,7,8,9-tetrahydro-1H-purine-6,8-dione
Traditional Name8-hydroxyguanine
SMILESNC1=NC2=C(NC(=O)N2)C(=O)N1
InChI IdentifierInChI=1S/C5H5N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H5,6,7,8,9,10,11,12)
InChI KeyCLGFIVUFZRGQRP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurines and purine derivatives
Alternative Parents
Substituents
  • Purine
  • Hydroxypyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.94 g/LALOGPS
logP-1.6ALOGPS
logP-1.5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)7.35ChemAxon
pKa (Strongest Basic)3.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area108.61 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.81 m³·mol⁻¹ChemAxon
Polarizability14.26 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-3900000000-58549cee828db799d7b5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-6a4117b10e5530095707Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-89fdc38268686eaba66aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-107l-9600000000-7c79695abe7a15874725Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-ac22897692beb4981edeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2900000000-f3b3767a022d716580d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-9a8d26eff2e742411cb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-d3890f3472d103400e66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ri-1900000000-59a4be35534659234b6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-7d9830f9bdf455a84283Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-2907e7cb009d3747cf21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-5795d2965bc15c5daf00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00us-9200000000-fd1acc84bba1739821dbSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002032
FooDB IDFDB022809
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link8-Oxoguanine
Chemspider ID58661
ChEBI ID52617
PubChem Compound ID65154
Kegg Compound IDC20155
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Usacheva A M; Chernikov A V; Bruskov V I Formation of 8-hydroxyguanine upon damage of guanine nucleotides by gamma radiation. Molekuliarnaia biologiia (1995), 29(2), 446-51.
2. Lovell MA, Markesbery WR: Ratio of 8-hydroxyguanine in intact DNA to free 8-hydroxyguanine is increased in Alzheimer disease ventricular cerebrospinal fluid. Arch Neurol. 2001 Mar;58(3):392-6.
3. Shen Z, Wu W, Hazen SL: Activated leukocytes oxidatively damage DNA, RNA, and the nucleotide pool through halide-dependent formation of hydroxyl radical. Biochemistry. 2000 May 9;39(18):5474-82.
4. Flirski M, Sobow T: Biochemical markers and risk factors of Alzheimer's disease. Curr Alzheimer Res. 2005 Jan;2(1):47-64.