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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:33 UTC
Update Date2019-07-23 05:45:15 UTC
HMDB IDHMDB0002032
Secondary Accession Numbers
  • HMDB0011613
  • HMDB02032
  • HMDB11613
Metabolite Identification
Common 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 ).
Structure
Data?1563860715
Synonyms
ValueSource
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
Chemical FormulaC5H5N5O2
Average Molecular Weight167.1255
Monoisotopic Molecular Weight167.044324429
IUPAC Name2-amino-6,7,8,9-tetrahydro-1H-purine-6,8-dione
Traditional Name8-hydroxyguanine
CAS Registry Number5614-64-2
SMILES
NC1=NC2=C(NC(=O)N2)C(=O)N1
InChI Identifier
InChI=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
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0001 +/- 0.00015 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.68 (0.49-0.87) uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.005 +/- 0.0007 uMAdult (>18 years old)BothDiabetes details
Cerebrospinal Fluid (CSF)Detected and Quantified0.19 (0.15-0.23) uMAdult (>18 years old)Not SpecifiedAlzheimer's disease details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  1. Shin CS, Moon BS, Park KS, Kim SY, Park SJ, Chung MH, Lee HK: Serum 8-hydroxy-guanine levels are increased in diabetic patients. Diabetes Care. 2001 Apr;24(4):733-7. [PubMed:11315839 ]
Alzheimer's disease
  1. 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. [PubMed:11255442 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022809
KNApSAcK IDNot Available
Chemspider ID58661
KEGG Compound IDC20155
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link8-Oxoguanine
METLIN IDNot Available
PubChem Compound65154
PDB IDNot Available
ChEBI ID52617
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceUsacheva 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:11255442 ]
  2. 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. [PubMed:10820020 ]
  3. Flirski M, Sobow T: Biochemical markers and risk factors of Alzheimer's disease. Curr Alzheimer Res. 2005 Jan;2(1):47-64. [PubMed:15977989 ]