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

• ChemBase ID: 173493
• Molecular Formular: C10H15N3O5
• Molecular Mass: 257.2432
• Monoisotopic Mass: 257.1011706
• SMILES: [C@@H]1([C@H]([C@@H](O[C@@H]1CO)n1c(=O)nc(cc1)N)OC)O
• Canonical SMILES: CO[C@@H]1[C@H](O)[C@H](O[C@H]1n1ccc(nc1=O)N)CO
• InChI: InChI=1S/C10H15N3O5/c1-17-8-7(15)5(4-14)18-9(8)13-3-2-6(11)12-10(13)16/h2-3,5,7-9,14-15H,4H2,1H3,(H2,11,12,16)/t5-,7-,8-,9-/m1/s1
• InChIKey: RFCQJGFZUQFYRF-ZOQUXTDFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 2'-O-methylcytidine
• Synonyms: 2'-O-Methylcytidine; O2'-Methylcytidine; 2'-O-Methyl Cytidine

Database IDs

• CAS Number: 2140-72-9
• MDL Number: MFCD00056067
• PubChem SID: 164229403
• PubChem CID: 150971

CALCULATED PROPERTIES

• Acid pKa: 13.002485
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.1543922
• LogD (pH = 7.4): -2.1543918
• Log P: -2.1543908
• Molar Refractivity: 59.296 cm^3
• Polarizability: 23.362879 Å^3
• Polar Surface Area: 117.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 250-255°C (dec.)

Safety Information

• Storage Condition: Refrigerator

Product Information

• Purity: 98%

DETAILS

Toronto Research Chemicals - M294660

Cytidine analog. Used for preparation of nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase.

REFERENCES

• Eldrup, A.B., et al.: J. Med. Chem., 47, 2283 (2004)
• Shim, J., et al.: Antiviral Res., 243 (2004)
• Wang, M., et al.: J. Biol. Chem., 278, 9489 (2004)