5-Hydroxymethylcytosine

5-Hydroxymethylcytosine
Names
	Preferred IUPAC name 4-Amino-5-(hydroxymethyl)pyrimidin-2(1H)-one
Identifiers
CAS Number	1123-95-1 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:76792 ;
ChemSpider	63916 ;
PubChem CID	70751;
UNII	6CD2RLN1NK ;
CompTox Dashboard (EPA)	DTXSID70149990 ;
	InChI InChI=1S/C5H7N3O2/c6-4-3(2-9)1-7-5(10)8-4/h1,9H,2H2,(H3,6,7,8,10) Key: RYVNIFSIEDRLSJ-UHFFFAOYSA-N ; InChI=1/C5H7N3O2/c6-4-3(2-9)1-7-5(10)8-4/h1,9H,2H2,(H3,6,7,8,10) Key: RYVNIFSIEDRLSJ-UHFFFAOYAT;
	SMILES C1=NC(=O)NC(=C1CO)N; O=C1/N=C\C(=C(\N)N1)CO;
Properties
Chemical formula	C5H7N3O2
Molar mass	141.13 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

5-Hydroxymethylcytosine (5hmC) is a DNA pyrimidine nitrogen base derived from cytosine. It is potentially important in epigenetics, because the hydroxymethyl group on the cytosine can possibly switch a gene on and off. It was first seen in bacteriophages in 1952. However, in 2009 it was found to be abundant in human and mouse brains, as well as in embryonic stem cells. In mammals, it can be generated by oxidation of 5-methylcytosine, a reaction mediated by TET enzymes.