3-methylbutyl N-{1-[(2R,4R,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate

• ChemBase ID: 165938
• Molecular Formular: C15H22FN3O6
• Molecular Mass: 359.3500832
• Monoisotopic Mass: 359.14926366
• SMILES: [C@H]1(C([C@@H](O[C@@H]1C)n1c(=O)nc(c(c1)F)NC(=O)OCCC(C)C)O)O
• Canonical SMILES: CC(CCOC(=O)Nc1nc(=O)n(cc1F)[C@@H]1O[C@@H]([C@@H](C1O)O)C)C
• InChI: InChI=1S/C15H22FN3O6/c1-7(2)4-5-24-15(23)18-12-9(16)6-19(14(22)17-12)13-11(21)10(20)8(3)25-13/h6-8,10-11,13,20-21H,4-5H2,1-3H3,(H,17,18,22,23)/t8-,10+,11?,13-/m1/s1
• InChIKey: PPVCPOIDSSQXMR-FSWKUEMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methylbutyl N-{1-[(2R,4R,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate
• IUPAC Traditional name: 3-methylbutyl N-{1-[(2R,4R,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl}carbamate
• Synonyms: [1-(5-Deoxy-β-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl]-carbamic Acid 3-Methylbutyl Ester; 5'-Deoxy-5-fluoro-N4-(isopentyloxycarbonyl)cytidine; 5'-Deoxy-5-fluoro-N-[(3-methylbutoxy)carbonyl]cytidine

Database IDs

• CAS Number: 162204-30-0
• PubChem SID: 162260071
• PubChem CID: 46780619

CALCULATED PROPERTIES

• Acid pKa: 8.226082
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.6097643
• LogD (pH = 7.4): 0.5574005
• Log P: 0.6104865
• Molar Refractivity: 82.6936 cm^3
• Polarizability: 32.438602 Å^3
• Polar Surface Area: 120.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 95-98°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D235350

5'-Desoxycytidine derivatives are used as antitumor agents. A CApecitabine (C175650) impurity,