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

• ChemBase ID: 167990
• Molecular Formular: C8H13FN3O12P3S
• Molecular Mass: 487.1864062
• Monoisotopic Mass: 486.94168198
• SMILES: S1C[C@H](O[C@H]1COP(=O)(OP(=O)(O)OP(=O)(O)O)O)n1c(=O)nc(c(c1)F)N
• Canonical SMILES: Nc1nc(=O)n(cc1F)[C@@H]1CS[C@@H](O1)COP(=O)(OP(=O)(OP(=O)(O)O)O)O
• InChI: InChI=1S/C8H13FN3O12P3S/c9-4-1-12(8(13)11-7(4)10)5-3-28-6(22-5)2-21-26(17,18)24-27(19,20)23-25(14,15)16/h1,5-6H,2-3H2,(H,17,18)(H,19,20)(H2,10,11,13)(H2,14,15,16)/t5-,6+/m0/s1
• InChIKey: WIEOLFZNMKSGEX-NTSWFWBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
• IUPAC Traditional name: ({[(2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
• Synonyms: Triphosphoric Acid P-[[(2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolan-2-yl]methyl] Ester Sodium; Triphosphoric Acid (2R-cis)-P-[[5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolan-2-yl]methyl] Ester Sodium; Emtricitabine 5'-Triphosphate Sodium; Emtricitabine Triphosphate Sodium Salt

Database IDs

• PubChem SID: 162262122
• PubChem CID: 469172

CALCULATED PROPERTIES

• Acid pKa: 0.8948363
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -8.541702
• LogD (pH = 7.4): -9.273149
• Log P: -1.8628277
• Molar Refractivity: 87.9861 cm^3
• Polarizability: 35.411293 Å^3
• Polar Surface Area: 227.74 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Solid
• Melting Point: 180-184°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E525020

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

REFERENCES

• Barditch-Crovo, P., et al.: Antimicrob. Agents Chemother., 45, 2733 (2001)
• Ray, A., et al.: Antivir .Ther., 10, 451 (2001)
• Borroto-Esoda, K., et al.: Antivir. Ther., 11, 377 (2001)