5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2,3,4-tetrahydro(2-13C,1,3-15N2)pyrimidine-2,4-dione

• ChemBase ID: 169128
• Molecular Formular: C8H9FN2O4S
• Molecular Mass: 251.21093583
• Monoisotopic Mass: 251.02413062
• SMILES: C1S[C@@H](O[C@@H]1[15n]1cc(c(=O)[15nH][13c]1=O)F)CO
• Canonical SMILES: OC[C@@H]1O[C@@H](CS1)[15n]1cc(F)c(=O)[15nH][13c]1=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/i8+1,10+1,11+1
• InChIKey: KOGYOPLNKQJQFM-WHTUVWIHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2,3,4-tetrahydro(2-^1^3C,1,3-^1^5N₂)pyrimidine-2,4-dione
• IUPAC Traditional name: 5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl](2-^1^3C,1,3-^1^5N₂)-3H-pyrimidine-2,4-dione
• Synonyms: (2R-cis)-5-Fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)-pyrimidinedione-13C,15N2; cis 5-Fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)-pyrimidinedione-13C,15N2

Database IDs

• CAS Number: 1217728-33-0
• PubChem SID: 162263260
• PubChem CID: 46781616

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

Physical Property

• Solubility: Methanol; N,N-Dimethylformamide; Tetrahydrofuran
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - F591852

Antiviral nucleoside analog, Inhibition of human immunodeficiency and hepatitis B viruses.

REFERENCES

• Chinazi, R.F., et all.: Antimicrob. Ag. Chemother., 36, 2432 (1992)
• Jeong, L., et al.: J. Med. Chem., 36, 181 (1992)