ho5CSN – 5-Hydroxycytosine

Name
WID ho5CSN View in model
Name 5-Hydroxycytosine View in model
Traditional name 4-amino-5-hydroxy-1H-pyrimidin-2-one
IUPAC name 4-amino-5-hydroxy-1,2-dihydropyrimidin-2-one
Cross references CAS: 13484-95-2, PubChem: 76231563
 
Classification
Type modified_nucleobase View in model
 
Structure
Empirical formula (pH 7.5) H5C4N3O2
SMILES (pH 7.5) N1C=C(C(=NC1=O)N)O
Charge (pH 7.5) 0
Is hydrophobic False View in model
Molecular weight (Da) 127.10 View in model
van der Waals volume 
(pH 7.5; Å3 molecule‑1)		 100.58
pI 10.86
logP -1.48
logD (pH 7.5) -1.49
 
Function
Reaction participant DNA radiation (gamma-ray) induced base oxidation (cytosine ==> 5-Hydroxycytosine; hydroxyl radical)
CSN[c] + gamma_radiation[e] + hydroxyl_radical[c] ⇒ H[c] + ho5CSN[c]		 View in model
 
Comments
Comments 36 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