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

• ChemBase ID: 154949
• Molecular Formular: C10H15N3O5
• Molecular Mass: 257.2432
• Monoisotopic Mass: 257.1011706
• SMILES: C[C@]1([C@@H]([C@H](O[C@H]1n1ccc(nc1=O)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@]([C@@H]1O)(C)O)n1ccc(nc1=O)N
• InChI: InChI=1S/C10H15N3O5/c1-10(17)7(15)5(4-14)18-8(10)13-3-2-6(11)12-9(13)16/h2-3,5,7-8,14-15,17H,4H2,1H3,(H2,11,12,16)/t5-,7-,8-,10-/m1/s1
• InChIKey: PPUDLEUZKVJXSZ-VPCXQMTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 4-amino-1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]pyrimidin-2-one
• Synonyms: 2′-C-Methyl Cytidine; NM107; 2’-C-Methylcytidine

Database IDs

• CAS Number: 20724-73-6
• MDL Number: MFCD02682947
• PubChem SID: 162249087
• PubChem CID: 500902

CALCULATED PROPERTIES

• Acid pKa: 12.432154
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.516942
• LogD (pH = 7.4): -2.5169446
• Log P: -2.5169406
• Molar Refractivity: 59.183 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

• Solubility: H2O: >20 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C10H15N3O5

DETAILS

Sigma Aldrich - M4949

Biochem/physiol Actions
2′-C-Methylcytidine is a potent inhibitor of the HCV NS5B RNA polymerase. 2′-C-Methylcytidine was the first nucleoside NS5B inhibitor that showed clinical efficacy. 2′-C-Methylcytidine was found to be effective against the 17D vaccine strain of yellow fever virus YFV in cell culture.