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

• ChemBase ID: 103272
• Molecular Formular: C9H12FN3O5
• Molecular Mass: 261.2070832
• Monoisotopic Mass: 261.07609872
• SMILES: Nc1nc(=O)n(cc1F)C1OC(CO)C(O)C1O
• Canonical SMILES: OCC1OC(C(C1O)O)n1cc(F)c(nc1=O)N
• InChI: InChI=1S/C9H12FN3O5/c10-3-1-13(9(17)12-7(3)11)8-6(16)5(15)4(2-14)18-8/h1,4-6,8,14-16H,2H2,(H2,11,12,17)
• InChIKey: STRZQWQNZQMHQR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: ara-fluorocytosine
• Synonyms: 5-FLUOROCYTIDINE

Database IDs

• CAS Number: 2341-22-2
• PubChem SID: 162090352
• PubChem CID: 352938

CALCULATED PROPERTIES

• Acid pKa: 12.553133
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.5980744
• LogD (pH = 7.4): -2.5980775
• Log P: -2.5980744
• Molar Refractivity: 54.7477 cm^3
• Polarizability: 21.37676 Å^3
• Polar Surface Area: 128.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: HA3890000

DETAILS

MP Biomedicals - 02151156

Reported anticancer properties.

REFERENCES

• M. Saneyoshi, Chem. Pharm. Bull., 26: 2990 (1978).