Record Information
Version1.0
Creation date2011-09-21 00:19:56 UTC
Update date2015-07-21 06:57:22 UTC
Primary IDFDB022809
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name8-Hydroxyguanine
DescriptionFormation of 8-hydroxyguanine (8-OHG), a mutagenic base which is a marker for OH-mediated DNA damage, requires peroxidase and halides and occurs in the presence of transition metal chelators (DTPA +/- desferrioxamine), and is inhibited by catalase, superoxide dismutase (SOD), and scavengers of hypohalous acids. (PMID 10820020) 8-Hydroxyguanine is an oxidative stress marker for diagnosis of Alzheimer's disease (AD). (PMID 15977989) [HMDB]
CAS Number5614-64-2
Structure
Thumb
Synonyms
SynonymSource
8-OxoguanineChEBI
2-Amino-6,8-dihydroxypurineHMDB
8-oxo-7,8-DihydroguanineHMDB
oxo-8-GuaHMDB
1H-Purine-6,8-dione, 2-amino-7,9-dihydro-1H-purine-6,8-dioneHMDB
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
8-HydroxyguanineChEBI
2-amino-7,9-dihydro-1H-Purine-6,8-dionehmdb
2-amino-Purine-6,8-diolhmdb
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H5N5O2
IUPAC name2-amino-6,7,8,9-tetrahydro-1H-purine-6,8-dione
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
Isomeric SMILESNC1=NC2=C(NC(=O)N2)C(=O)N1
Average Molecular Weight167.1255
Monoisotopic Molecular Weight167.044324429
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-3900000000-58549cee828db799d7b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-6a4117b10e5530095707JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-89fdc38268686eaba66aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-107l-9600000000-7c79695abe7a15874725JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-ac22897692beb4981edeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2900000000-f3b3767a022d716580d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-9a8d26eff2e742411cb2JSpectraViewer
ChemSpider ID58661
ChEMBL IDCHEMBL1328799
KEGG Compound IDC20155
Pubchem Compound ID65154
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02032
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference