diammonium [(2R,5S)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-oxathiolan-2-yl]methyl (hydrogen phosphonatooxy)phosphonate

• ChemBase ID: 172178
• Molecular Formular: C8H19N5O9P2S
• Molecular Mass: 423.277082
• Monoisotopic Mass: 423.03787147
• SMILES: S1C[C@H](O[C@H]1COP(=O)(OP(=O)(O)[O-])[O-])n1c(=O)nc(cc1)N.[NH4+].[NH4+]
• Canonical SMILES: Nc1ccn(c(=O)n1)[C@@H]1CS[C@@H](O1)COP(=O)(OP(=O)(O)[O-])[O-].[NH4+].[NH4+]
• InChI: InChI=1S/C8H13N3O9P2S.2H3N/c9-5-1-2-11(8(12)10-5)6-4-23-7(19-6)3-18-22(16,17)20-21(13,14)15;;/h1-2,6-7H,3-4H2,(H,16,17)(H2,9,10,12)(H2,13,14,15);2*1H3/t6-,7+;;/m0../s1
• InChIKey: XYMQOMHLQNDRJX-AUCRBCQYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diammonium [(2R,5S)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-oxathiolan-2-yl]methyl (hydrogen phosphonatooxy)phosphonate
• IUPAC Traditional name: diammonium [(2R,5S)-5-(4-amino-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methyl hydrogen phosphonatooxyphosphonate
• Synonyms: P-[[(2R,5S)-5-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolan-2-yl]methyl] Ester Diphosphoric Acid Ammonium Salt; Lamivudine Diphosphate Ammonium Salt

Database IDs

• CAS Number: 1187058-41-8
• PubChem SID: 164228088
• PubChem CID: 71749721

CALCULATED PROPERTIES

• Acid pKa: 1.7825153
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -6.0452323
• LogD (pH = 7.4): -6.674541
• Log P: -1.777337
• Molar Refractivity: 74.6669 cm^3
• Polarizability: 30.414097 Å^3
• Polar Surface Area: 186.87 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L172515

A metabolite of Lamivudine (L172500).

REFERENCES

• Soudeyns, H., et al.: Antimicrob. Agents Chemother., 35, 1386 (1991)
• Denapoli, L., et al.: Nucleosides Nucleotides, 12, 21 (1991)