(2S,3S,4S,5R,6R)-6-{[(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 167991
• Molecular Formular: C14H18FN3O9S
• Molecular Mass: 423.3708232
• Monoisotopic Mass: 423.07477839
• SMILES: S1C[C@H](O[C@H]1CO[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)n1c(=O)nc(c(c1)F)N
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC[C@H]2SC[C@H](O2)n2cc(F)c(nc2=O)N)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C14H18FN3O9S/c15-4-1-18(14(24)17-11(4)16)5-3-28-6(26-5)2-25-13-9(21)7(19)8(20)10(27-13)12(22)23/h1,5-10,13,19-21H,2-3H2,(H,22,23)(H2,16,17,24)/t5-,6+,7-,8-,9+,10-,13+/m0/s1
• InChIKey: KLILDKWVMCMYID-ANAKBQEJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (2R-cis)-[5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolan-2-yl]methyl β-D-Glucopyranosiduronic Acid; Emtricitabine O-β-D-Glucuronide

Database IDs

• CAS Number: 152128-78-4
• PubChem SID: 162262123
• PubChem CID: 10364982

CALCULATED PROPERTIES

• Acid pKa: 3.3002532
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -4.528841
• LogD (pH = 7.4): -5.7722793
• Log P: -2.3462257
• Molar Refractivity: 87.6481 cm^3
• Polarizability: 35.04363 Å^3
• Polar Surface Area: 184.37 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E525025

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)