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

• ChemBase ID: 165925
• Molecular Formular: C9H12FN3O4
• Molecular Mass: 245.2076832
• Monoisotopic Mass: 245.0811841
• SMILES: [C@H]1(C([C@@H](O[C@@H]1C)n1c(=O)nc(c(c1)F)N)O)O
• Canonical SMILES: C[C@H]1O[C@H](C([C@H]1O)O)n1cc(F)c(nc1=O)N
• InChI: InChI=1S/C9H12FN3O4/c1-3-5(14)6(15)8(17-3)13-2-4(10)7(11)12-9(13)16/h2-3,5-6,8,14-15H,1H3,(H2,11,12,16)/t3-,5+,6?,8-/m1/s1
• InChIKey: YSNABXSEHNLERR-BNVMRTHCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 4-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidin-2-one
• Synonyms: 5-Fluoro-5’-deoxycytidine, 5’-DFCR; 5'-Deoxy-5-fluoro Cytidine

Database IDs

• CAS Number: 66335-38-4
• PubChem SID: 162260058
• PubChem CID: 59859763

CALCULATED PROPERTIES

• Acid pKa: 12.587269
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.5511644
• LogD (pH = 7.4): -1.5511672
• Log P: -1.5511644
• Molar Refractivity: 53.204 cm^3
• Polarizability: 20.655432 Å^3
• Polar Surface Area: 108.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Hot Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 175-177°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D232950

A metabolite of Capecitabine.

REFERENCES

• Saji, S., et al.: Oncol., 72, 330 (2007)
• Desmoulin, F., et al.: Drug Metab. Lett., 1, 101 (2007)
• Albanell, J., et al.: Clin. Cancer Res., 14, 2726 (2007)
• Guichard, S., et al.: Eur. J. Cancer, 44, 310 (2007)