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

• ChemBase ID: 172176
• 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+/m1/s1
• InChIKey: JTEGQNOMFQHVDC-RQJHMYQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 2'3' dideoxy 3' thiacytidine
• Synonyms: 4-Amino-1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; (2S-cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; (+)-BCH 189; 2',3'-Dideoxy-3'-thiacytidine; 2'-Deoxy-3'-thiacytidine; 3TC; NSC 620753; cis(+)-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane; ent-Lamivudine; 4-amino-1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

Database IDs

• CAS Number: 134680-32-3
• MDL Number: MFCD00870542
• PubChem SID: 164228086
• PubChem CID: 73339

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

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 164-166°C; 176 - 178°C
• Hydrophobicity(logP): -1.462

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

Product Information

• Purity: 95%

DETAILS

Toronto Research Chemicals - L172505

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

REFERENCES

• Pepe, G. et al.: Eur. J. Med. Chem., 31, 775 (1996)
• Marr, E. et al.: Antiviral Res., 28, 1 (1996)
• Parikh, U.M. et al.: Antimicrob. Agents Chemother., 49, 1139 (1996)