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Human Metabolome Database Version 3.5

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Showing metabocard for 8-Hydroxyguanine (HMDB02032)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:33 -0600
Update Date 2013-02-08 17:11:13 -0700
HMDB ID HMDB02032
Secondary Accession Numbers
  • HMDB11613
Metabolite Identification
Common Name 8-Hydroxyguanine
Description Formation 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 Link_out). 8-Hydroxyguanine is an oxidative stress marker for diagnosis of Alzheimer's disease (AD). (PMID 15977989 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1H-Purine-6,8-dione, 2-amino-7,9-dihydro-1H-purine-6,8-dione
  2. 2-Amino-6,8-dihydroxypurine
  3. 2-Amino-7,9-dihydro-1H-Purine-6,8-dione
  4. 2-Amino-Purine-6,8-diol
  5. 2-Aminopurine-6,8-diol
  6. 7,8-Dihydro-8-oxoguanine
  7. 8-Hydroxyguanine
Chemical Formula C5H5N5O2
Average Molecular Weight 167.1255
Monoisotopic Molecular Weight 167.044324429
IUPAC Name 2-amino-6,7,8,9-tetrahydro-1H-purine-6,8-dione
Traditional IUPAC Name 8-hydroxyguanine
CAS Registry Number 5614-64-2
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 Key CLGFIVUFZRGQRP-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Imidazopyrimidines
Sub Class Purines and Purine Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Hypoxanthines
  • Organic Compounds
  • an aromatic compound(Cyc)
  • cyclic pseudoketone(ChEBI)
Substituents
  • Aminopyrimidine
  • Imidazole
  • Pyrimidine
  • Pyrimidone
Direct Parent Purinones
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.94 g/L ALOGPS
LogP -1.57 ALOGPS
LogP -1.5 ChemAxon
LogS -1.93 ALOGPS
pKa (strongest acidic) 7.35 ChemAxon
pKa (strongest basic) 3.95 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 108.61 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 47.81 ChemAxon
Polarizability 14.26 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.0001 +/- 0.00015 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.68 (0.49-0.87) uM Adult (>18 years old) Not Specified Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.005 +/- 0.0007 uM Adult (>18 years old) Both Diabetes Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.19 (0.15-0.23) uM Adult (>18 years old) Not Specified Alzheimer's disease Not Available
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  • 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 Link_out
    Diabetes mellitus type 2
    • 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 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB022809
      KNApSAcK ID Not Available
      Chemspider ID 58661 Link_out
      KEGG Compound ID C20155 Link_out
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Not Available
      NuGOwiki Link HMDB02032 Link_out
      Metagene Link HMDB02032 Link_out
      METLIN ID Not Available
      PubChem Compound 65154 Link_out
      PDB ID Not Available
      ChEBI ID 52617 Link_out
      References
      Synthesis Reference 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.
      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 Link_out