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

• ChemBase ID: 165941
• Molecular Formular: C10H13FN2O4
• Molecular Mass: 244.2196232
• Monoisotopic Mass: 244.08593513
• SMILES: [C@H]1(C[C@@H](O[C@@H]1CO)n1c(=O)[nH]c(=O)c(c1)C)F
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1F)n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C10H13FN2O4/c1-5-3-13(10(16)12-9(5)15)8-2-6(11)7(4-14)17-8/h3,6-8,14H,2,4H2,1H3,(H,12,15,16)/t6-,7-,8-/m1/s1
• InChIKey: UXCAQJAQSWSNPQ-BWZBUEFSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4R,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-3H-pyrimidine-2,4-dione
• Synonyms: 1-(3'-Deoxy-3'-fluoro-β-D-pentofuranosyl)thymine; 3'-Fluoro-3'-deoxythymidine; 3'-Fluorodeoxythymidine; 3'-Fluorothymidine; Alovudine; CL 184824; FLT; MIV 310; NSC 140025; 3'-Deoxy-3'-fluoro Thymidine

Database IDs

• CAS Number: 25526-93-6
• PubChem SID: 162260074
• PubChem CID: 42104317

CALCULATED PROPERTIES

• Acid pKa: 9.710306
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.22798827
• LogD (pH = 7.4): -0.23005797
• Log P: -0.22796181
• Molar Refractivity: 53.7199 cm^3
• Polarizability: 21.151886 Å^3
• Polar Surface Area: 78.87 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 167-168°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D235475

An antiviral agent.

REFERENCES

• Hoffman, B., et al.: J. Med. Chem., 43, 4151 (2000)
• Narayanan, R., et al.: Bioorg. Med. Chem., 13, 3017 (2000)
• Abraham, M., et al.: J. Pharm. Sci., 95, 2091 (2000)