1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 169273
• Molecular Formular: C9H11FN2O6
• Molecular Mass: 262.1918432
• Monoisotopic Mass: 262.0601143
• SMILES: [C@H]1(C([C@@H]([C@@H](O1)n1c(=O)[nH]c(=O)c(c1)F)O)O)CO
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cc(F)c(=O)[nH]c1=O
• InChI: InChI=1S/C9H11FN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5?,6+,8-/m1/s1
• InChIKey: FHIDNBAQOFJWCA-TZLAVLDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-3H-pyrimidine-2,4-dione
• Synonyms: 5-FUrd; NSC 146604; NSC 519273; 5-Fluoro Uridine

Database IDs

• CAS Number: 316-46-1
• PubChem SID: 162263405
• PubChem CID: 54669724

CALCULATED PROPERTIES

• Acid pKa: 7.674215
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.2186642
• LogD (pH = 7.4): -2.3983889
• Log P: -2.2157993
• Molar Refractivity: 52.7685 cm^3
• Polarizability: 20.810516 Å^3
• Polar Surface Area: 119.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: 170-174°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F596500

5-Fluoro Uridine is an active metabolite of Doxifluridine (D556750).

REFERENCES

• Bollag, W., et al.: Eur. J. Cancer, 16, 427 (1980)
• Pinedo, H., et al.: J. Clin. Oncol., 6, 1653 (1980)
• Ishikawa, T., et al.: Biochem. Pharmacol., 55, 1091 (1980)
• Schuller, J., et al.: Cancer Chemother. Pharmacol., 45, 291 (1980)