5-Hydroxyuracil

5-Hydroxyuracil
Names
	IUPAC name 2,4,5-Pyrimidinetriol
	Other names 5-Hydroxy-2,4(1H,3H)-pyrimidinedione
Identifiers
CAS Number	496-76-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29115;
ChEMBL	ChEMBL1561505;
ChemSpider	66014;
ECHA InfoCard	100.007.119
EC Number	207-829-9;
PubChem CID	73268;
UNII	438WJI1S49 ;
CompTox Dashboard (EPA)	DTXSID30174667 ;
	InChI InChI=1S/C4H4N2O3/c7-2-1-5-4(9)6-3(2)8/h1,7H,(H2,5,6,8,9) Key: OFJNVANOCZHTMW-UHFFFAOYSA-N;
	SMILES c1c(c(nc(n1)O)O)O;
Properties
Chemical formula	C4H4N2O3
Molar mass	128.087 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

5-Hydroxyuracil is an oxidized form of cytosine that is produced by the oxidative deamination of cytosines by reactive oxygen species.^[1] It does not distort the DNA molecule and is bypassed by replicative DNA polymerases. It can miscode for adenine and is potentially mutagenic.^[2]

References

^ Varatharasa Thiviyanathan; Anoma Somasunderam; David E. Volka & David G. Gorenstein (2005). "5-Hydroxyuracil can form stable base pairs with all four bases in a DNA duplex". Chem. Commun. (3): 400–402. doi:10.1039/B414474K. PMID 15645051.
^ Helmut Greim; Richard J. Albertini (2012). The Cellular Response to the Genotoxic Insult: The Question of Threshold for Genotoxic Carcinogens. Royal Society of Chemistry. ISBN 9781849731775. Retrieved July 20, 2015.

[MyUser_Pubs.rsc.org_July_20_2015c-1] Varatharasa Thiviyanathan; Anoma Somasunderam; David E. Volka & David G. Gorenstein (2005). "5-Hydroxyuracil can form stable base pairs with all four bases in a DNA duplex". Chem. Commun. (3): 400–402. doi:10.1039/B414474K. PMID 15645051.

[MyUser_Https:_July_20_2015c-2] Helmut Greim; Richard J. Albertini (2012). The Cellular Response to the Genotoxic Insult: The Question of Threshold for Genotoxic Carcinogens. Royal Society of Chemistry. ISBN 9781849731775. Retrieved July 20, 2015.

[1]

[2]