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

• ChemBase ID: 172180
• Molecular Formular: C16H18N6O8S2
• Molecular Mass: 486.47952
• Monoisotopic Mass: 486.06275357
• SMILES: S1C[C@@H](O[C@@H]1C(=O)O)n1c(=O)nc(cc1)N.S1C[C@H](O[C@H]1C(=O)O)n1c(=O)nc(cc1)N
• Canonical SMILES: OC(=O)[C@H]1SC[C@H](O1)n1ccc(nc1=O)N.OC(=O)[C@@H]1SC[C@@H](O1)n1ccc(nc1=O)N
• InChI: InChI=1S/2C8H9N3O4S/c2*9-4-1-2-11(8(14)10-4)5-3-16-7(15-5)6(12)13/h2*1-2,5,7H,3H2,(H,12,13)(H2,9,10,14)/t2*5-,7+/m10/s1
• InChIKey: YACUDLZGYXLWLK-BOJIXVGNSA-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; (2S,5R)-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; (2S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-1,3-oxathiolane-2-carboxylic acid
• Synonyms: cis-5-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic Acid; rac Lamivudine Acid

Database IDs

• CAS Number: 173602-25-0
• PubChem SID: 164228090
• PubChem CID: 71749723

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: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L172525

An impurity of the anti-viral Lamivudine (L172500).

REFERENCES

• Dwyer, O.: Synlett, 11, 1163 (1995)