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Human Metabolome Database Version 3.5

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Showing metabocard for 8-Hydroxyguanosine (HMDB02044)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:33 -0600
Update Date 2013-02-08 17:11:14 -0700
HMDB ID HMDB02044
Secondary Accession Numbers None
Metabolite Identification
Common Name 8-Hydroxyguanosine
Description 8-hydroxyguanosine (8-OHG) is a marker for measuring the rate of oxidative damage to nucleic acids and lipids. Production of reactive oxygen species (ROS) damage proteins, lipid membranes, and nucleic acids (DNA and RNA), all critical functional components of living cells. The progressive accumulation of unrepaired free radical damage over time is believed to be a major contributor to the aging process and to a variety of age-related chronic diseases. Generation of most free radicals is a 'side effect' of normal metabolic processes, especially mitochondrial production of ROS, including superoxide anion, hydrogen peroxide, and hydroxyl radical, coincident to oxidative metabolism. (PMID 14607529 Link_out). 8-OHG (marker of oxidative damage to RNA) was found in the cerebral cortex in three of six cases of neuropathologically examined autopsy of subacute sclerosing panencephalitis patients. Subacute sclerosing panencephalitis is caused by persistent brain infection of mutated measles virus, showing inflammation, neuronal loss, and demyelination. (PMID 12546425 Link_out). The concentration of 8-OHG in CSF in Parkinson's disease (PD) patients is approximately three-fold that in controls. The concentration of 8-OHG in CSF decreased significantly with the duration of disease. However, the concentration of 8-OHG in serum was not significantly altered in PD patients compared to that in controls. (PMID 12499051 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 7,8-Dihydro-8-oxo-Guanosine
  2. 8-Hydroxyguanosine
  3. 8-Oxoguanosine
  4. Purine-6,8(1H,9H)-dione, 2-amino-9-.beta.-D-ribofuranosyl- (7CI,8CI)
  5. Purine-6,8(1H,9H)-dione, 2-amino-9-.beta.-delta-ribofuranosyl- (7CI,8CI)
Chemical Formula C10H13N5O6
Average Molecular Weight 299.2401
Monoisotopic Molecular Weight 299.086583173
IUPAC Name 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,7,8,9-tetrahydro-1H-purine-6,8-dione
Traditional IUPAC Name 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,7-dihydropurine-6,8-dione
CAS Registry Number 3868-31-3
SMILES NC1=NC2=C(NC(=O)N2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1
InChI Identifier InChI=1S/C10H13N5O6/c11-9-13-6-3(7(19)14-9)12-10(20)15(6)8-5(18)4(17)2(1-16)21-8/h2,4-5,8,16-18H,1H2,(H,12,20)(H3,11,13,14,19)/t2-,4-,5-,8-/m1/s1
InChI Key FPGSEBKFEJEOSA-UMMCILCDSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleosides and Analogues
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Aminopyrimidine
  • Glycosyl Compound
  • Hypoxanthine
  • Imidazole
  • Imidazopyrimidine
  • N Glycosyl Compound
  • Oxolane
  • Pentose Monosaccharide
  • Primary Alcohol
  • Purine
  • Purinone
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct Parent Purine Nucleosides and Analogues
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 9.79 g/L ALOGPS
LogP -2.08 ALOGPS
LogP -3 ChemAxon
LogS -1.49 ALOGPS
pKa (strongest acidic) 7.53 ChemAxon
pKa (strongest basic) 3.54 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 169.74 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 74.4 ChemAxon
Polarizability 26.94 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
0.00142 +/- 0.00059 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0001 +/- 0.00003 (0.00004 - 0.00014) uM Elderly (>65 years old) Not Specified Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.00149 +/- 0.00054 uM Adult (>18 years old) Both Parkinson's Disease Not Available
Blood Detected and Quantified
Article_icon
0.00153 +/- 0.00060 uM Adult (>18 years old) Both Alzheimer's disease Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.00050 +/- 0.00021 uM Elderly (>65 years old) Both Alzheimer's disease Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0003 +/- 0.00013 (0.00015 - 0.0004) uM Elderly (>65 years old) Not Specified Parkinson's disease Not Available
Associated Disorders and Diseases
Disease References
Parkinson's disease
  • Abe T, Isobe C, Murata T, Sato C, Tohgi H: Alteration of 8-hydroxyguanosine concentrations in the cerebrospinal fluid and serum from patients with Parkinson's disease. Neurosci Lett. 2003 Jan 16;336(2):105-8. Pubmed: 12499051 Link_out
    Alzheimer's disease
    • Abe T, Tohgi H, Isobe C, Murata T, Sato C: Remarkable increase in the concentration of 8-hydroxyguanosine in cerebrospinal fluid from patients with Alzheimer's disease. J Neurosci Res. 2002 Nov 1;70(3):447-50. Pubmed: 12391605 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB022815
      KNApSAcK ID Not Available
      Chemspider ID 58640 Link_out
      KEGG Compound ID Not Available
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Not Available
      NuGOwiki Link HMDB02044 Link_out
      Metagene Link HMDB02044 Link_out
      METLIN ID Not Available
      PubChem Compound 65131 Link_out
      PDB ID Not Available
      ChEBI ID 1177182 Link_out
      References
      Synthesis Reference Wong, Peter K.; Floyd, Robert A. photochemical synthesis of 8-hydroxyguanine nucleosides. Methods in Enzymology (1994), 234(Oxygen Radicals in Biological Systems, Pt. D), 59-65.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Abe T, Isobe C, Murata T, Sato C, Tohgi H: Alteration of 8-hydroxyguanosine concentrations in the cerebrospinal fluid and serum from patients with Parkinson's disease. Neurosci Lett. 2003 Jan 16;336(2):105-8. Pubmed: 12499051 Link_out