2,2-dichloro-N-[(1S,2S)-1,3-dihydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide

• ChemBase ID: 178519
• Molecular Formular: C12H15Cl2NO5S
• Molecular Mass: 356.2222
• Monoisotopic Mass: 355.00479895
• SMILES: c1c(ccc(c1)[C@@H]([C@@H](NC(=O)C(Cl)Cl)CO)O)S(=O)(=O)C
• Canonical SMILES: OC[C@@H]([C@H](c1ccc(cc1)S(=O)(=O)C)O)NC(=O)C(Cl)Cl
• InChI: InChI=1S/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m0/s1
• InChIKey: OTVAEFIXJLOWRX-UWVGGRQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dichloro-N-[(1S,2S)-1,3-dihydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide
• IUPAC Traditional name: 2,2-dichloro-N-[(1S,2S)-1,3-dihydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide
• Synonyms: 2,2-Dichloro-N-[(1S,2S)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]acetamide; L-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-p-(methylsulfonyl)phenethyl]Acetamide; Thiamphenicol Epimer; Win 5063-3; ent-Thiamphenicol

Database IDs

• CAS Number: 19934-71-5
• PubChem SID: 164234429
• PubChem CID: 146678

CALCULATED PROPERTIES

• Acid pKa: 7.6499147
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.22368595
• LogD (pH = 7.4): -0.38777936
• Log P: -0.22097217
• Molar Refractivity: 79.8796 cm^3
• Polarizability: 31.870874 Å^3
• Polar Surface Area: 103.7 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T344210

The enatiomeric analogue of the antimicrobial agent Thiamphenicol (T344160).

REFERENCES

• Gal, J. et al.: J. Pharmac. Sci., 77, 1062 (1988)
• Martin, J. et al.: Anal. Biochem., 96, 215 (1988)