4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-3-oxo-1,3λ4-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

• ChemBase ID: 167992
• Molecular Formular: C8H10FN3O4S
• Molecular Mass: 263.2461032
• Monoisotopic Mass: 263.03760504
• SMILES: [S@@]1(=O)C[C@H](O[C@H]1CO)n1c(=O)nc(c(c1)F)N
• Canonical SMILES: Nc1nc(=O)n(cc1F)[C@@H]1C[S@@](=O)[C@@H](O1)CO
• InChI: InChI=1S/C8H10FN3O4S/c9-4-1-12(8(14)11-7(4)10)5-3-17(15)6(2-13)16-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+,17+/m0/s1
• InChIKey: DMOMZPWPIDCLMB-WYDPKHCQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-3-oxo-1,3λ^4-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 4-amino-5-fluoro-1-[(2R,3R,5S)-2-(hydroxymethyl)-3-oxo-1,3λ^4-oxathiolan-5-yl]pyrimidin-2-one
• Synonyms: 4-Amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-3-oxido-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; [2R-(2α,5α)]-4-Amino-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone S-Oxide; [2R-(2α,5α)]-4-Amino-5-fluoro-1-[2-(hydroxymethyl)-3-oxido-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; Emtricitabine S-Oxide (Mixture of Diastereomers)

Database IDs

• CAS Number: 152128-77-3
• PubChem SID: 162262124
• PubChem CID: 71316322

CALCULATED PROPERTIES

• Acid pKa: 14.010272
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -2.2708213
• LogD (pH = 7.4): -2.2708216
• Log P: -2.2708213
• Molar Refractivity: 56.3255 cm^3
• Polarizability: 21.845541 Å^3
• Polar Surface Area: 105.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol (Sparingly); Water (Sparingly)
• Apperance: White Solid
• Melting Point: 212-213°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - E525030

A metabolite of (-)-Emtricitabine (E525000).

REFERENCES

• Schinazi, R.F., et al.: Antimicrob. Ag. Chemother., 36, 2423 (1992)
• Shockeor, J.P., et al.: Xenobioica, 26, 189 (1992)
• Feng, J.Y., et al.: FASEB J., 13, 1511 (1992)
• Molina, J.-M., et al.: J. Infec. Dis., 182, 599 (1992)