2,2-dichloro-N-[(1S,2R)-1,3-dihydroxy-1-[4-nitro(1,2,3,4,5,6-13C6)phenyl]propan-2-yl]acetamide

• ChemBase ID: 164053
• Molecular Formular: C11H12Cl2N2O5
• Molecular Mass: 329.08530903
• Monoisotopic Mass: 328.03245588
• SMILES: [13cH]1[13c]([13cH][13cH][13c]([13cH]1)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• Canonical SMILES: OC[C@H]([C@@H]([13c]1[13cH][13cH][13c]([13cH][13cH]1)[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-/m1/s1/i1+1,2+1,3+1,4+1,6+1,7+1
• InChIKey: WIIZWVCIJKGZOK-BNKGHQRYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dichloro-N-[(1S,2R)-1,3-dihydroxy-1-[4-nitro(1,2,3,4,5,6-^1^3C₆)phenyl]propan-2-yl]acetamide
• IUPAC Traditional name: 2,2-dichloro-N-[(1S,2R)-1,3-dihydroxy-1-[4-nitro(1,2,3,4,5,6-^1^3C₆)phenyl]propan-2-yl]acetamide
• Synonyms: 2,2-Dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl-13C6)ethyl]Acetamide; D-threo-N-Dichloroacetyl-1-p-nitro(phenyl-13C6)-2-amino- 1,3-propanediol; Anacetin-13C6; Aquamycetin-13C6; Chlorocid-13C6; Chloramphenicol-13C6

Database IDs

• CAS Number: 1217706-02-9
• PubChem SID: 162258188
• PubChem CID: 45038608

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

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: White Crystalline Powder
• Melting Point: 147-149°C

DETAILS

Toronto Research Chemicals - C325032

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; antirickettsial.

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