4-amino-1-[(2S,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

• ChemBase ID: 168059
• Molecular Formular: C8H11N3O3S
• Molecular Mass: 229.25624
• Monoisotopic Mass: 229.05211223
• SMILES: S1C[C@H](O[C@@H]1CO)n1c(=O)nc(cc1)N
• Canonical SMILES: Nc1ccn(c(=O)n1)[C@@H]1CS[C@H](O1)CO
• InChI: InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7-/m0/s1
• InChIKey: JTEGQNOMFQHVDC-BQBZGAKWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2S,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 4-amino-1-[(2S,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
• Synonyms: 4-Amino-1-[(2S,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; (2S-trans)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; trans(-)-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane; 2'-Epi-Lamivudine

Database IDs

• CAS Number: 136846-20-3
• PubChem SID: 162262191
• PubChem CID: 6540852

CALCULATED PROPERTIES

• Acid pKa: 14.294606
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.0951098
• LogD (pH = 7.4): -1.0951077
• Log P: -1.0951076
• Molar Refractivity: 55.1645 cm^3
• Polarizability: 21.351086 Å^3
• Polar Surface Area: 88.15 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E588545

An epimer of Lamivudine (L172500); an antiviral that inhibits HIV-reverse transcriptase.

REFERENCES

• Lin, T. et al.: J. Med. Chem., 39, 1757 (1996)
• Schinazi, R.F. et al.: Antimicrob. Agents Chemother.,36, 672 (1996)