triammonium ({[(2R,5S)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-oxathiolan-2-yl]methyl phosphonato}oxy)(hydrogen phosphonatooxy)phosphinate

• ChemBase ID: 172177
• Molecular Formular: C8H23N6O12P3S
• Molecular Mass: 520.287503
• Monoisotopic Mass: 520.0307511
• SMILES: S1C[C@H](O[C@H]1COP(=O)(OP(=O)(OP(=O)(O)[O-])[O-])[O-])n1c(=O)nc(cc1)N.[NH4+].[NH4+].[NH4+]
• Canonical SMILES: Nc1ccn(c(=O)n1)[C@@H]1CS[C@@H](O1)COP(=O)(OP(=O)(OP(=O)(O)[O-])[O-])[O-].[NH4+].[NH4+].[NH4+]
• InChI: InChI=1S/C8H14N3O12P3S.3H3N/c9-5-1-2-11(8(12)10-5)6-4-27-7(21-6)3-20-25(16,17)23-26(18,19)22-24(13,14)15;;;/h1-2,6-7H,3-4H2,(H,16,17)(H,18,19)(H2,9,10,12)(H2,13,14,15);3*1H3/t6-,7+;;;/m0.../s1
• InChIKey: WGYHYJAOTOCRPE-PXJNTPRPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: triammonium ({[(2R,5S)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-oxathiolan-2-yl]methyl phosphonato}oxy)(hydrogen phosphonatooxy)phosphinate
• IUPAC Traditional name: triammonium {[(2R,5S)-5-(4-amino-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methyl phosphonato}oxy(hydrogen phosphonatooxy)phosphinate
• Synonyms: Triphosphoric Acid P-[[(2R,5S)-5-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolan-2-yl]methyl] Ester Ammonium Salt; Lamivudine Triphosphate Ammonium Salt

Database IDs

• CAS Number: 1187058-42-9
• PubChem SID: 164228087
• PubChem CID: 71749720

CALCULATED PROPERTIES

• Acid pKa: 0.98006475
• H Acceptors: 11
• H Donor: 2
• LogD (pH = 5.5): -8.7410755
• LogD (pH = 7.4): -9.47259
• Log P: -2.4829042
• Molar Refractivity: 84.4181 cm^3
• Polarizability: 35.089672 Å^3
• Polar Surface Area: 236.23 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L172510

A metabolite of Lamivudine (L172500).

REFERENCES

• Burgess, K., et al.: Chem. Rev., 100, 2047 (2000)
• Gallois-Montbrun, S., et al.: Biochem. Pharmacol., 68, 1749 (2000)