1.0 2011-09-21 00:20:04 UTC 2025-11-19 02:42:34 UTC FDB022815 8-Hydroxyguanosine 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) 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) [HMDB] 7,8-dihydro-8-oxo-Guanosine 8-hydroxyguanosine 8-Oxoguanosine Purine-6,8(1H,9H)-dione, 2-amino-9-.beta.-D-ribofuranosyl- (7CI,8CI) Purine-6,8(1H,9H)-dione, 2-amino-9-.beta.-delta-ribofuranosyl- (7CI,8CI) C10H13N5O6 299.2401 299.086583173 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 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,7-dihydropurine-6,8-dione 3868-31-3 NC1=NC2=C(NC(=O)N2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1 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 FPGSEBKFEJEOSA-UMMCILCDSA-N belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Purine nucleosides Organic compounds Nucleosides, nucleotides, and analogues Purine nucleosides Aromatic heteropolycyclic compounds Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hydroxypyrimidines N-substituted imidazoles Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Pentoses Primary alcohols Purines and purine derivatives Secondary alcohols Tetrahydrofurans Alcohol Aromatic heteropolycyclic compound Azacycle Azole Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydroxypyrimidine Imidazole Imidazopyrimidine Monosaccharide N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose monosaccharide Primary alcohol Purine Purine nucleoside Pyrimidine Secondary alcohol Tetrahydrofuran Solid logp -2.08 ALOGPS logs -1.49 ALOGPS solubility 9.79e+00 g/l ALOGPS logp -3 ChemAxon pka_strongest_acidic 7.53 ChemAxon pka_strongest_basic 3.54 ChemAxon iupac 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 ChemAxon average_mass 299.2401 ChemAxon mono_mass 299.086583173 ChemAxon smiles NC1=NC2=C(NC(=O)N2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1 ChemAxon formula C10H13N5O6 ChemAxon inchi 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 ChemAxon inchikey FPGSEBKFEJEOSA-UMMCILCDSA-N ChemAxon polar_surface_area 169.74 ChemAxon refractivity 74.4 ChemAxon polarizability 26.94 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 23372 Specdb::CMs 38241 Specdb::CMs 166716 Specdb::NmrOneD 109058 Specdb::NmrOneD 109059 Specdb::NmrOneD 109060 Specdb::NmrOneD 109061 Specdb::NmrOneD 109062 Specdb::NmrOneD 109063 Specdb::NmrOneD 109064 Specdb::NmrOneD 109065 Specdb::NmrOneD 109066 Specdb::NmrOneD 109067 Specdb::NmrOneD 109068 Specdb::NmrOneD 109069 Specdb::NmrOneD 109070 Specdb::NmrOneD 109071 Specdb::NmrOneD 109072 Specdb::NmrOneD 109073 Specdb::NmrOneD 109074 Specdb::NmrOneD 109075 Specdb::NmrOneD 109076 Specdb::NmrOneD 109077 Specdb::MsMs 317821 Specdb::MsMs 317822 Specdb::MsMs 317823 Specdb::MsMs 364417 Specdb::MsMs 364418 Specdb::MsMs 364419 Specdb::MsMs 2282155 Specdb::MsMs 2282156 Specdb::MsMs 2282157 Specdb::MsMs 3086236 Specdb::MsMs 3086237 Specdb::MsMs 3086238 HMDB02044 #<Reference:0x000055ce3072fa20> #<Reference:0x000055ce3072f868> #<Reference:0x000055ce3072f6b0> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823