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

• ChemBase ID: 167989
• Molecular Formular: C9H12FN3O2S2
• Molecular Mass: 277.3388832
• Monoisotopic Mass: 277.03549686
• SMILES: n1c(=O)n(cc(c1N)F)[C@@H]1CS[C@@H](O1)CSC
• Canonical SMILES: CSC[C@@H]1O[C@@H](CS1)n1cc(F)c(nc1=O)N
• InChI: InChI=1S/C9H12FN3O2S2/c1-16-4-7-15-6(3-17-7)13-2-5(10)8(11)12-9(13)14/h2,6-7H,3-4H2,1H3,(H2,11,12,14)/t6-,7+/m0/s1
• InChIKey: FVBDQZPRPOQFGT-NKWVEPMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-fluoro-1-[(2R,5S)-2-[(methylsulfanyl)methyl]-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 4-amino-5-fluoro-1-[(2R,5S)-2-[(methylsulfanyl)methyl]-1,3-oxathiolan-5-yl]pyrimidin-2-one
• Synonyms: (-)-2’,3’-Dideoxy-5-fluoro-3’-thiacytidine 6’-Disulfide; (-)-2'-Deoxy-5-fluoro-3'-thiacytidine 6’-Disulfide; Emtricitabine 6'-Disulfide

Database IDs

• PubChem SID: 162262121
• PubChem CID: 71316321

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.358105
• LogD (pH = 7.4): 0.358105
• Log P: 0.358105
• Molar Refractivity: 66.3114 cm^3
• Polarizability: 25.368074 Å^3
• Polar Surface Area: 67.92 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E525015

An impurity of Emtricitabine synthesis.