(2R,5S)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-oxathiolane-2-carboxylic acid

• ChemBase ID: 172173
• Molecular Formular: C8H9N3O4S
• Molecular Mass: 243.23976
• Monoisotopic Mass: 243.03137678
• SMILES: S1C[C@H](O[C@H]1C(=O)O)n1c(=O)nc(cc1)N
• Canonical SMILES: Nc1ccn(c(=O)n1)[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
• InChIKey: PIIRVEZNDVLYQA-CAHLUQPWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,5S)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-oxathiolane-2-carboxylic acid
• IUPAC Traditional name: (2R,5S)-5-(4-amino-2-oxopyrimidin-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; Lamivudine Acid

Database IDs

• CAS Number: 173829-09-9
• PubChem SID: 164228083
• PubChem CID: 15462288

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

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 230-233°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - L172490

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

REFERENCES

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