bis(triethylamine); {[(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 167993
• Molecular Formular: C20H41FN5O6PS
• Molecular Mass: 529.6066042
• Monoisotopic Mass: 529.24991991
• SMILES: S1C[C@H](O[C@H]1COP(=O)(O)O)n1c(=O)nc(c(c1)F)N.N(CC)(CC)CC.N(CC)(CC)CC
• Canonical SMILES: Fc1cn([C@@H]2CS[C@@H](O2)COP(=O)(O)O)c(=O)nc1N.CCN(CC)CC.CCN(CC)CC
• InChI: InChI=1S/C8H11FN3O6PS.2C6H15N/c9-4-1-12(8(13)11-7(4)10)5-3-20-6(18-5)2-17-19(14,15)16;2*1-4-7(5-2)6-3/h1,5-6H,2-3H2,(H2,10,11,13)(H2,14,15,16);2*4-6H2,1-3H3/t5-,6+;;/m0../s1
• InChIKey: NBOLANBXSUBPLN-KXSOTYCDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(triethylamine); {[(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxyphosphonic acid; bis(triethylamine)
• Synonyms: Emtricitabine Monophosphate Di(Triethylammonium) Salt

Database IDs

• PubChem SID: 162262125
• PubChem CID: 71316323

CALCULATED PROPERTIES

• Acid pKa: 1.032578
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -3.497468
• LogD (pH = 7.4): -4.7175174
• Log P: -1.0192307
• Molar Refractivity: 66.2403 cm^3
• Polarizability: 25.796997 Å^3
• Polar Surface Area: 134.68 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - E525040

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

REFERENCES

• Paff, M. et al.; Antimicrob. Agents Ch. 38, 1230 (1994)