5-Methylcytosine
Chemical compound which is a modified DNA base / From Wikipedia, the free encyclopedia
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5-Methylcytosine is a methylated form of the DNA base cytosine (C) that regulates gene transcription and takes several other biological roles.[1] When cytosine is methylated, the DNA maintains the same sequence, but the expression of methylated genes can be altered (the study of this is part of the field of epigenetics). 5-Methylcytosine is incorporated in the nucleoside 5-methylcytidine.
Quick Facts Names, Identifiers ...
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Preferred IUPAC name
4-Amino-5-methylpyrimidin-2(1H)-one | |
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3D model (JSmol) |
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3DMet | |
120387 | |
ChEBI | |
ChemSpider |
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ECHA InfoCard | 100.008.236 |
EC Number |
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KEGG |
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MeSH | 5-Methylcytosine |
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CompTox Dashboard (EPA) |
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Properties | |
C5H7N3O | |
Molar mass | 125.131 g·mol−1 |
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GHS labelling: | |
Warning | |
H317, H319 | |
P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P333+P313, P337+P313, P363, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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In 5-methylcytosine, a methyl group is attached to the 5th atom in the 6-atom ring, counting counterclockwise from the NH-bonded nitrogen at the six o'clock position. This methyl group distinguishes 5-methylcytosine from cytosine.