5-Hydroxyuracil

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]

5-Hydroxyuracil
Names
IUPAC name
2,4,5-Pyrimidinetriol
Other names
5-Hydroxy-2,4(1H,3H)-pyrimidinedione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.119
EC Number
  • 207-829-9
UNII
  • InChI=1S/C4H4N2O3/c7-2-1-5-4(9)6-3(2)8/h1,7H,(H2,5,6,8,9)
    Key: OFJNVANOCZHTMW-UHFFFAOYSA-N
  • c1c(c(nc(n1)O)O)O
Properties
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

References
  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.
  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.
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