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

• ChemBase ID: 169127
• Molecular Formular: C8H9FN2O4S
• Molecular Mass: 248.2314632
• Monoisotopic Mass: 248.026706
• SMILES: C1S[C@@H](O[C@@H]1n1cc(c(=O)[nH]c1=O)F)CO
• Canonical SMILES: OC[C@@H]1O[C@@H](CS1)n1cc(F)c(=O)[nH]c1=O
• InChI: InChI=1S/C8H9FN2O4S/c9-4-1-11(8(14)10-7(4)13)5-3-16-6(2-12)15-5/h1,5-6,12H,2-3H2,(H,10,13,14)/t5-,6+/m0/s1
• InChIKey: KOGYOPLNKQJQFM-NTSWFWBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-3H-pyrimidine-2,4-dione
• Synonyms: (2R-cis)-5-Fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)-pyrimidinedione; cis 5-Fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)- pyrimidinedione

Database IDs

• CAS Number: 145986-11-4
• PubChem SID: 162263259
• PubChem CID: 126768

CALCULATED PROPERTIES

• Acid pKa: 7.677286
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.5162344
• LogD (pH = 7.4): -0.6949329
• Log P: -0.5133895
• Molar Refractivity: 53.3882 cm^3
• Polarizability: 20.618954 Å^3
• Polar Surface Area: 78.87 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

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

DETAILS

Toronto Research Chemicals - F591850

Antiviral nucleoside analog

REFERENCES

• Jeong, L., et al.: J. Med. Chem., 36, 181 (1993)