(2R,5S)-5-[4-amino-2-oxo-1,2-dihydro(2-13C,1,3-15N2)pyrimidin-1-yl]-1,3-oxathiolane-2-carboxylic acid

• ChemBase ID: 172174
• Molecular Formular: C8H9N3O4S
• Molecular Mass: 246.21923263
• Monoisotopic Mass: 246.02880141
• SMILES: S1C[C@H](O[C@H]1C(=O)O)[15n]1[13c](=O)[15n]c(cc1)N
• Canonical SMILES: Nc1cc[15n]([13c](=O)[15n]1)[C@@H]1CS[C@@H](O1)C(=O)O
• InChI: InChI=1S/C8H9N3O4S/c9-4-1-2-11(8(14)10-4)5-3-16-7(15-5)6(12)13/h1-2,5,7H,3H2,(H,12,13)(H2,9,10,14)/t5-,7+/m0/s1/i8+1,10+1,11+1
• InChIKey: PIIRVEZNDVLYQA-FDHQWECPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,5S)-5-[4-amino-2-oxo-1,2-dihydro(2-^1^3C,1,3-^1^5N₂)pyrimidin-1-yl]-1,3-oxathiolane-2-carboxylic acid
• IUPAC Traditional name: (2R,5S)-5-[4-amino-2-oxo(2-^1^3C,1,3-^1^5N₂)pyrimidin-1-yl]-1,3-oxathiolane-2-carboxylic acid
• Synonyms: (2R-cis)-5-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic Acid-13C,15N2; Lamivudine Acid-13C,15N2

Database IDs

• PubChem SID: 164228084
• PubChem CID: 71749719

CALCULATED PROPERTIES

• Acid pKa: 3.270637
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -2.985684
• LogD (pH = 7.4): -4.2070246
• Log P: -0.774833
• Molar Refractivity: 55.0319 cm^3
• Polarizability: 21.34842 Å^3
• Polar Surface Area: 105.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L172492

Labelled Lamivudine Acid (L172490). Lamivudine Acid is an impurity of Lamivudine (L172500). Labelled Impurity A per European Pharmacopoeia.

REFERENCES

• Dwyer, O., et al.: Synlett, 11, 1163 (1995)