4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2-dihydropyrimidin-2-one

• ChemBase ID: 125499
• Molecular Formular: C10H15N3O5
• Molecular Mass: 257.2432
• Monoisotopic Mass: 257.1011706
• SMILES: O=c1nc(N)c(cn1[C@@H]1O[C@@H]([C@@H](O)[C@H]1O)CO)C
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cc(C)c(nc1=O)N
• InChI: InChI=1S/C10H15N3O5/c1-4-2-13(10(17)12-8(4)11)9-7(16)6(15)5(3-14)18-9/h2,5-7,9,14-16H,3H2,1H3,(H2,11,12,17)/t5-,6-,7-,9-/m1/s1
• InChIKey: ZAYHVCMSTBRABG-JXOAFFINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 5-methylcytidine
• Synonyms: m^5C; 5-Methylcytidine; 5-Methylcytidine; 5-甲基胞苷

Database IDs

• CAS Number: 2140-61-6
• EC Number: 218-390-8
• MDL Number: MFCD00006548
• PubChem SID: 24896915; 162219849
• PubChem CID: 92918
• Chemspider ID: 83877
• Wikipedia Title: 5-Methylcytidine

CALCULATED PROPERTIES

• Acid pKa: 12.55323
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.4019687
• LogD (pH = 7.4): -2.40197
• Log P: -2.4019668
• Molar Refractivity: 58.9019 cm^3
• Polarizability: 23.29661 Å^3
• Polar Surface Area: 128.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 212-215 °C (dec.)(lit.)

Safety Information

• German water hazard class: 3

Product Information

• Purity: ≥99%; 99%
• Empirical Formula (Hill Notation): C10H15N3O5

DETAILS

Sigma Aldrich - M4254

Application
5-Methylcytidine is used in studies of DNA methylation processes (epigenetics).