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

• ChemBase ID: 164052
• Molecular Formular: C11H12Cl2N2O5
• Molecular Mass: 323.12938
• Monoisotopic Mass: 322.01232685
• SMILES: c1c(ccc(c1)[C@@H]([C@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• Canonical SMILES: OC[C@@H]([C@H](c1ccc(cc1)[N+](=O)[O-])O)NC(=O)C(Cl)Cl
• InChI: InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m0/s1
• InChIKey: WIIZWVCIJKGZOK-IUCAKERBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dichloro-N-[(1S,2S)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
• IUPAC Traditional name: amphenicol
• Synonyms: 2,2-Dichloro-N-[(1S,2S)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide; (+)-Chloramphenicol; (1S,2S)-2-(2,2-Dichloroacetamido)-1-(4-nitrophenyl)-1,3-propanediol; Dextramycin; Dextromycetin; L-threo-Chloramphenicol; L-threo-Chloroamphenicol; L-threo-N-Dichloroacetyl-1-p-nitrophenyl-2-amino-1,3-propanediol; L-(+)-threo-Chloramphenicol

Database IDs

• CAS Number: 134-90-7
• PubChem SID: 162258187
• PubChem CID: 92099

CALCULATED PROPERTIES

• Acid pKa: 7.4943175
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.87482697
• LogD (pH = 7.4): 0.66041094
• Log P: 0.8787035
• Molar Refractivity: 73.2007 cm^3
• Polarizability: 27.817905 Å^3
• Polar Surface Area: 115.38 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C325025

The S,S-stereoisomer of Chloramphenicol (C325030). Broad spectrum antibiotic obtained from cultures of the soil bacterium Streptomyces venezuelae. It has a broad spectrum of activity against Gram-positive and gram-negative bacteria. Antibacterial; antiric

REFERENCES

• Bartz, et al.: J. Biol. Chem., et al.: 172, 445 (1948)
• Gottlieb, et al.: J. Bacteriol., 55, 409 (1948)
• Szulczewski, D., et al.: Anal. Profiles Drug Subs., 4, 47 (1948)
• Price, A., et al.: J. Antibiot., 43, 118 (1948)
• Shalit, I., et al.: Drugs, 28, 281