You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:33 UTC
Update Date2018-05-19 21:47:33 UTC
HMDB IDHMDB0002044
Secondary Accession Numbers
  • HMDB02044
Metabolite Identification
Common Name8-Hydroxyguanosine
Description8-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 ). 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 ). 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 ).
Structure
Thumb
Synonyms
ValueSource
7,8-dihydro-8-oxo-GuanosineHMDB
8-OxoguanosineHMDB
Purine-6,8(1H,9H)-dione, 2-amino-9-.beta.-D-ribofuranosyl- (7ci,8ci)HMDB
Purine-6,8(1H,9H)-dione, 2-amino-9-.beta.-delta-ribofuranosyl- (7ci,8ci)HMDB
7,8-dihydro-8-OxoguanosineMeSH
8-OxoGuoMeSH
8-oxo-7,8-DihydroguanosineMeSH
8-OxoG nucleosideMeSH
Chemical FormulaC10H13N5O6
Average Molecular Weight299.2401
Monoisotopic Molecular Weight299.086583173
IUPAC Name2-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 Name2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,7-dihydropurine-6,8-dione
CAS Registry Number3868-31-3
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 KeyFPGSEBKFEJEOSA-UMMCILCDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
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 Solubility9.79 g/LALOGPS
logP-2.1ALOGPS
logP-3ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)7.53ChemAxon
pKa (Strongest Basic)3.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area169.74 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity74.4 m³·mol⁻¹ChemAxon
Polarizability26.94 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-9160000000-b5d214bf9c0982dbbe63View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0uec-6902330000-d183539e2e438b4d7c80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-0f5c81fc8d1ea968575dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-0cbf4ce2e5de074bf971View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v6r-0900000000-625b8c3fb826dde8502aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-0490000000-d4f85e8ee7d5857f5de9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0920000000-8df43d9931a862018046View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dm-3900000000-5f141ad8cdd5265bd2e2View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00142 +/- 0.00059 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0001 +/- 0.00003 (0.00004 - 0.00014) uMElderly (>65 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00149 +/- 0.00054 uMAdult (>18 years old)BothParkinson's Disease details
BloodDetected and Quantified0.00153 +/- 0.00060 uMAdult (>18 years old)BothAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00050 +/- 0.00021 uMElderly (>65 years old)BothAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0003 +/- 0.00013 (0.00015 - 0.0004) uMElderly (>65 years old)Not SpecifiedParkinson's disease details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. 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 ]
Parkinson's disease
  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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022815
KNApSAcK IDNot Available
Chemspider ID58640
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link8-Hydroxyguanosine
METLIN IDNot Available
PubChem Compound65131
PDB IDNot Available
ChEBI ID1177182
References
Synthesis ReferenceWong, 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 ]
  2. Harman SM, Liang L, Tsitouras PD, Gucciardo F, Heward CB, Reaven PD, Ping W, Ahmed A, Cutler RG: Urinary excretion of three nucleic acid oxidation adducts and isoprostane F(2)alpha measured by liquid chromatography-mass spectrometry in smokers, ex-smokers, and nonsmokers. Free Radic Biol Med. 2003 Nov 15;35(10):1301-9. [PubMed:14607529 ]
  3. Hayashi M, Arai N, Satoh J, Suzuki H, Katayama K, Tamagawa K, Morimatsu Y: Neurodegenerative mechanisms in subacute sclerosing panencephalitis. J Child Neurol. 2002 Oct;17(10):725-30. [PubMed:12546425 ]