oxo8GN – 8-Oxo-guanine; 8-hydroxyguanine

WID oxo8GN View in model
Name 8-Oxo-guanine; 8-hydroxyguanine View in model
Traditional name 2-amino-7,9-dihydro-3H-purine-6,8-dione
IUPAC name 2-amino-6,7,8,9-tetrahydro-3H-purine-6,8-dione
Cross references ChEBI: 52617, PubChem: 81058842
Type modified_nucleobase View in model
Empirical formula (pH 7.5) H5C5N5O2
SMILES (pH 7.5) N2C1=C(C(=O)N=C(N1)N)NC2=O
Charge (pH 7.5) 0
Is hydrophobic False View in model
Molecular weight (Da) 167.13 View in model
van der Waals volume 
(pH 7.5; Å3 molecule‑1)
pI 5.20
logP -1.82
logD (pH 7.5) -1.96
Reaction participant View in model
Comments most common DNA base lesion [PUB_0479]; 92-520 lesions per 10^7 bases [PUB_0479]; recognized by endonuclease III, FPG, UNG [PUB_0473]
  1. Guetens G, De Boeck G, Highley M, van Oosterom AT, de Bruijn EA. Oxidative DNA damage: biological significance and methods of analysis. Crit Rev Clin Lab Sci 39, 331-457 (2002). WholeCell: PUB_0479, PubMed: 12385502

  2. Hatahet Z, Kow YW, Purmal AA, Cunningham RP, Wallace SS. New substrates for old enzymes. 5-Hydroxy-2'-deoxycytidine and 5-hydroxy-2'-deoxyuridine are substrates for Escherichia coli endonuclease III and formamidopyrimidine DNA N-glycosylase, while 5-hydroxy-2'-deoxyuridine is a substrate for uracil DNA N-glycosylase. J Biol Chem 269, 18814-20 (1994). WholeCell: PUB_0473, PubMed: 8034633

Created 2012-10-01 15:07:05
Last updated 2012-10-01 15:12:27