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

• ChemBase ID: 164837
• Molecular Formular: C10H13FN2O5
• Molecular Mass: 260.2190232
• Monoisotopic Mass: 260.08084975
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c(=O)[nH]c(=O)c(c1)C)CO)O)F
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)F)n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C10H13FN2O5/c1-4-2-13(10(17)12-8(4)16)9-6(11)7(15)5(3-14)18-9/h2,5-7,9,14-15H,3H2,1H3,(H,12,16,17)/t5-,6-,7?,9-/m1/s1
• InChIKey: GBBJCSTXCAQSSJ-PQLACBALSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,3R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-3H-pyrimidine-2,4-dione
• Synonyms: 1-(2'-Deoxy-2'-fluoro-β-L-arabinofuranosyl)-5-methyluracil; L-FMAU; 1-(2-Deoxy-2-fluoro-β-L-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione; Clevudine

Database IDs

• CAS Number: 163252-36-6
• PubChem SID: 162258971
• PubChem CID: 71314901

CALCULATED PROPERTIES

• Acid pKa: 9.704985
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.1286267
• LogD (pH = 7.4): -1.1307218
• Log P: -1.1285999
• Molar Refractivity: 55.2306 cm^3
• Polarizability: 21.866953 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 186-189°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C574150

Antiviral drug, used for the treatment of Hepatitis B.

REFERENCES

• Kwon, S., et al.: J. Virol., 84, 4494 (2010)
• Daga, P., et al.: Protein Sci., 19, 796 (2010)