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

• ChemBase ID: 167988
• Molecular Formular: C8H10FN3O3S
• Molecular Mass: 247.2467032
• Monoisotopic Mass: 247.04269042
• SMILES: n1c(=O)n(cc(c1N)F)[C@H]1CS[C@H](O1)CO
• 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+/m1/s1
• InChIKey: XQSPYNMVSIKCOC-RITPCOANSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-fluoro-1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: racivir
• Synonyms: 4-Amino-5-fluoro-1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; (2S-cis)-4-Amino-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; (+)-2’-Deoxy-3’-thia-5-fluorocytidine; (+)-FTC; ent-Emtricitabine

Database IDs

• CAS Number: 137530-41-7
• PubChem SID: 162262120
• PubChem CID: 454858

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 - E525005

A reverse transcriptase inhibitor. It is an effective antiviral agent against HIV, HBV, and other viruses replicating in a similar manner. A nucleoside analog structurally related to Lamivudine (L172500).

REFERENCES

• Mellors, J., et al.: Science, 72, 1167 (1996)
• Reimann, K., et al.: J. Virol., 79, 8878 (1996)
• Rose, J., et al.: J. Biol. Chem., 280, 7413 (1996)
• Acierno, P., et al.: J. Immunol., 176, 5338 (1996)