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

• ChemBase ID: 172179
• Molecular Formular: C8H15N4O6PS
• Molecular Mass: 326.266661
• Monoisotopic Mass: 326.04499185
• SMILES: S1C[C@H](O[C@H]1COP(=O)(O)[O-])n1c(=O)nc(cc1)N.[NH4+]
• Canonical SMILES: [O-]P(=O)(OC[C@@H]1O[C@@H](CS1)n1ccc(nc1=O)N)O.[NH4+]
• InChI: InChI=1S/C8H12N3O6PS.H3N/c9-5-1-2-11(8(12)10-5)6-4-19-7(17-6)3-16-18(13,14)15;/h1-2,6-7H,3-4H2,(H2,9,10,12)(H2,13,14,15);1H3/t6-,7+;/m0./s1
• InChIKey: QVKKAWUJZGRQKI-UOERWJHTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ammonium [(2R,5S)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-oxathiolan-2-yl]methyl hydrogen phosphate
• IUPAC Traditional name: ammonium [(2R,5S)-5-(4-amino-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methyl hydrogen phosphate
• Synonyms: 4-Amino-1-[(2R,5S)-2-[(phosphonooxy)methyl]-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone Ammonium Salt; Lamivudine Monophosphate Ammonium Salt

Database IDs

• CAS Number: 1187058-40-7
• PubChem SID: 164228089
• PubChem CID: 71749722

CALCULATED PROPERTIES

• Acid pKa: 1.0930607
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -3.6968532
• LogD (pH = 7.4): -4.91696
• Log P: -1.5543764
• Molar Refractivity: 64.9157 cm^3
• Polarizability: 25.76865 Å^3
• Polar Surface Area: 137.51 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L172520

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)