5-Hydroxyuracil

{{Chembox

| ImageFile = 5-hydroxyuracil tautomer.svg

| ImageSize = 180px

| ImageAlt =

| IUPACName = 2,4,5-Pyrimidinetriol

| OtherNames = 5-Hydroxy-2,4(1H,3H)-pyrimidinedione

| Section1 = {{Chembox Identifiers

| CASNo = 496-76-4

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 438WJI1S49

| PubChem = 73268

| EINECS = 207-829-9

| ChemSpiderID = 66014

| ChEMBL = 1561505

| ChEBI = 29115

| SMILES = c1c(c(nc(n1)O)O)O

| StdInChI=1S/C4H4N2O3/c7-2-1-5-4(9)6-3(2)8/h1,7H,(H2,5,6,8,9)

| StdInChIKey=OFJNVANOCZHTMW-UHFFFAOYSA-N

}}

| Section2 = {{Chembox Properties

| C=4|H=4|N=2|O=3

| Appearance =

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| MeltingPt =

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| Section3 = {{Chembox Hazards

| MainHazards =

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5-Hydroxyuracil is an oxidized form of cytosine that is produced by the oxidative deamination of cytosines by reactive oxygen species.{{cite journal |url=http://pubs.rsc.org/en/Content/ArticleLanding/2005/CC/b414474k |title=5-Hydroxyuracil can form stable base pairs with all four bases in a DNA duplex| author = Varatharasa Thiviyanathan| author2 = Anoma Somasunderam| author3 = David E. Volka| author4 = David G. Gorenstein| name-list-style = amp | journal = Chem. Commun. |issue=3| date = 2005 | pages = 400–402 | doi = 10.1039/B414474K|pmid=15645051| url-access = subscription}} It does not distort the DNA molecule and is bypassed by replicative DNA polymerases. It can miscode for adenine and is potentially mutagenic.{{cite book |url=https://books.google.com/books?id=J7Kzz9kC8CkC&dq=5-hydroxycytosine&pg=PA119 |title=The Cellular Response to the Genotoxic Insult: The Question of Threshold for Genotoxic Carcinogens | author = Helmut Greim | author2 = Richard J. Albertini | publisher = Royal Society of Chemistry | date = 2012 | access-date= July 20, 2015|isbn=9781849731775 }}