8-Oxo-2'-deoxyguanosine

8-Oxo-2'-deoxyguanosine
Names
IUPAC name
2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,7-dihydropurine-6,8-dione
Other names
7,8-Dihydro-8-oxo-2'-deoxyguanosine; 7,8-Dihydro-8-oxodeoxyguanosine; 8-Hydroxy-2'-deoxyguanosine; 8-Hydroxydeoxyguanosine; 8-Oxo-2'-deoxyguanosine; 8-Oxo-7,8-dihydro-2'-deoxyguanosine; 8-Oxo-7,8-dihydrodeoxyguanosine; 8-Oxo-dG; 8-OH-dG
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C10H13N5O5/c11-9-13-7-6(8(18)14-9)12-10(19)15(7)5-1-3(17)4(2-16)20-5/h3-5,16-17H,1-2H2,(H,12,19)(H3,11,13,14,18)/t3-,4+,5+/m0/s1 checkY
    Key: HCAJQHYUCKICQH-VPENINKCSA-N checkY
  • InChI=1/C10H13N5O5/c11-9-13-7-6(8(18)14-9)12-10(19)15(7)5-1-3(17)4(2-16)20-5/h3-5,16-17H,1-2H2,(H,12,19)(H3,11,13,14,18)/t3-,4+,5+/m0/s1
    Key: HCAJQHYUCKICQH-VPENINKCBS
  • C1[C@@H]([C@H](O[C@H]1N2C3=C(C(=O)N=C(N3)N)NC2=O)CO)O
  • C1[C@@H]([C@H](O[C@H]1n2c3c(c(=O)nc([nH]3)N)[nH]c2=O)CO)O
Properties
C10H13N5O5
Molar mass 283.24 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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8-Oxo-2'-deoxyguanosine (8-oxo-dG) is an oxidized derivative of deoxyguanosine. 8-Oxo-dG is one of the major products of DNA oxidation.[1] Concentrations of 8-oxo-dG within a cell are a measurement of oxidative stress.

  1. ^ Nadja C. de Souza-Pinto; Lars Eide; Barbara A. Hogue; Tanja Thybo; Tinna Stevnsner; Erling Seeberg; Arne Klungland & Vilhelm A. Bohr (July 2001). "Repair of 8-Oxodeoxyguanosine Lesions in Mitochondrial DNA Depends on the Oxoguanine DNA Glycosylase (OGG1) Gene and 8-Oxoguanine Accumulates in the Mitochondrial DNA of OGG1-defective Mice". Cancer Research. 61 (14): 5378–5381. PMID 11454679.