FAPydG – N6-(2-Deoxy-α,β-d-erythro-pentofuranosyl)-2,6-diamino-4-hydroxy-5-formamidopyrimidine

Name
WID	FAPydG
Name	N6-(2-Deoxy-α,β-d-erythro-pentofuranosyl)-2,6-diamino-4-hydroxy-5-formamidopyrimidine
Traditional name	N-(2-amino-4-{[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]amino}-6-oxo-3H-pyrimidin-5-yl)formamide
IUPAC name	N-(2-amino-6-{[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]amino}-4-oxo-1,4-dihydropyrimidin-5-yl)formamide

Classification
Type	modified_deoxyribonucleoside

Structure
Empirical formula (pH 7.5)	H₁₅C₁₀N₅O₅
SMILES (pH 7.5)	C1C(C(OC1NC2=C(NC=O)C(N=C(N2)N)=O)CO)O
Charge (pH 7.5)	0
Is hydrophobic	False
Molecular weight (Da)	285.26
van der Waals volume (pH 7.5; Å³ molecule^‑1)	234.17
pI	11.30
logP	-3.19
logD (pH 7.5)	-3.20

Function
Reaction participant	5'-nucleotidase (N6-(2-Deoxy-α,β-d-erythro-pentofuranosyl)-2,6-diamino-4-hydroxy-5-formamidopyrimidine monophosphate) [c]: FAPydGMP + H2O ⇒ FAPydG + PI N6-(2-Deoxy-α,β-d-erythro-pentofuranosyl)-2,6-diamino-4-hydroxy-5-formamidopyrimidine transport FAPydG[e] ⇔ FAPydG[c]

Comments
Comments	78.5 lesions per 10^6 bases [PUB_0479]; recognized by endonuclease III, FPG, UNG [PUB_0473]
References	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 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 15:06:57
Last updated	2012-10-01 15:12:09