2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methanesulfonylphenyl)(2,3,3-2H3)propan-2-yl]acetamide

• ChemBase ID: 178509
• Molecular Formular: C12H15Cl2NO5S
• Molecular Mass: 356.2222
• Monoisotopic Mass: 355.00479895
• SMILES: c1c(ccc(c1)[C@H](C(NC(=O)C(Cl)Cl)CO)O)S(=O)(=O)C
• Canonical SMILES: OCC([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-VHSXEESVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methanesulfonylphenyl)(2,3,3-^2H₃)propan-2-yl]acetamide
• IUPAC Traditional name: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methanesulfonylphenyl)(2,3,3-^2H₃)propan-2-yl]acetamide
• Synonyms: 2,2-Dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl-d3)-2-[4-(methylsulfonyl)phenyl]ethyl]acetamide; D-d-threo-2-Dichloroacetamido-1-(4-methylsulfonylphenyl)-1,3-propanediol-d3; Dextrosulphenidol-d3; NSC 522822-d3; Thiocymetin-d3; Thiophenicol-d3; Win 5063-2-d3; Thiamphenicol-d3Discontinued See: T344163

Database IDs

• PubChem SID: 164234419
• PubChem CID: 46783058

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: 31.870953 Å^3
• Polar Surface Area: 103.7 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 164-166°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T344162

Labelled Thiamphenicol (T344160). Thiamphenicol is an antibiotic. Thiamphenicol is the methyl-sulfonyl analogue of chloramphenicol and has a similar spectrum of activity, but is 2.5 to 5 times as potent. Thiamphenicol is used particularly for the treatmen

REFERENCES

• Tikhonova, E., et al.: J. Biol. Chem., 279, 32116 (2004)
• Baucheron, S., et al.: J. Antimicrob. Chemother., 55, 707 (2004)
• Pages, J., et al.: Trends. Mol. Med., 11, 382 (2004)
• Lomovskaya, O., et al.: Biochem. Pharmacol., 71, 910 (2004)
• Samosorn, S.,