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

• ChemBase ID: 167986
• Molecular Formular: C8H10FN3O3S
• Molecular Mass: 247.2467032
• Monoisotopic Mass: 247.04269042
• SMILES: S1C[C@H](O[C@@H]1CO)n1c(=O)nc(c(c1)F)N
• Canonical SMILES: Nc1nc(=O)n(cc1F)[C@@H]1CS[C@H](O1)CO
• InChI: InChI=1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6-/m0/s1
• InChIKey: XQSPYNMVSIKCOC-WDSKDSINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-fluoro-1-[(2S,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 4-amino-5-fluoro-1-[(2S,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
• Synonyms: 4-Amino-5-fluoro-1-[(2S,5S)-2-hydroxymethyl)-1,3-oxathiolan-5-yl]-2-(1H-pyrimidinone; (2S-trans)-4-Amino-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; 2-epi-Emtricitabine

Database IDs

• CAS Number: 145416-34-8
• PubChem SID: 162262118
• PubChem CID: 22858382

CALCULATED PROPERTIES

• Acid pKa: 14.294606
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.8956647
• LogD (pH = 7.4): -0.89566475
• Log P: -0.8956647
• Molar Refractivity: 55.3674 cm^3
• Polarizability: 21.200071 Å^3
• Polar Surface Area: 88.15 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E524990

The 2-epi-enantiomer analogue of (-)-Emtricitabine (E525000) evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells.

REFERENCES

• Jeong, L.S., et al.: J. Med. Chem., 36, 2627 (1993)