ho5dU – 5-hydroxy-2'-deoxyuridine

Name
WID ho5dU View in model
Name 5-hydroxy-2'-deoxyuridine View in model
Traditional name 5-hydroxy-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
IUPAC name 5-hydroxy-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
Cross references CAS: 5168-36-5
 
Classification
Type modified_deoxyribonucleoside View in model
 
Structure
Empirical formula (pH 7.5) H12C9N2O6
SMILES (pH 7.5) C1C(C(OC1N2C=C(C(=O)NC2=O)O)CO)O
Charge (pH 7.5) 0
Is hydrophobic False View in model
Molecular weight (Da) 244.20 View in model
van der Waals volume 
(pH 7.5; Å3 molecule‑1)
197.52
pI 2.84
logP -1.76
logD (pH 7.5) -1.78
 
Function
Reaction participant View in model
 
Comments
Comments 6 lesions per 10^6 bases [PUB_0479]; recognized by endonuclease III, FPG, UNG [PUB_0473]
References
  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

 
Metadata
Created 2012-10-01 15:07:00
Last updated 2012-10-01 15:12:16