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

• ChemBase ID: 179844
• Molecular Formular: C11H12Cl2N2O5
• Molecular Mass: 323.12938
• Monoisotopic Mass: 322.01232685
• SMILES: [N+](=O)(c1ccc(C([C@H](NC(=O)C(Cl)Cl)CO)O)cc1)[O-]
• Canonical SMILES: OC[C@H](C(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?/m1/s1
• InChIKey: WIIZWVCIJKGZOK-VEDVMXKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dichloro-N-[(2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
• IUPAC Traditional name: 2,2-dichloro-N-[(2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
• Synonyms: Alficetyn; Chemicetin; Chlorcetin; Chlorocid; Chlorocidin C; Chloromycetin; Chloronitrin; Chloroptic; Detreomycin; Enteromycetin; Flamycin; Gloveticol; Halcetin; Kemicetine; Levomycetin; Normimycin V; Ophthochlor; Paraxin; Sintomicetin; Synthomycin; Umimycin; Chloramphenicol

Database IDs

• CAS Number: 56-75-7
• PubChem SID: 164235754
• PubChem CID: 16399516

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

Pharmacology Properties

• Mechanism of Action: Interferes with transfer of activated aminoacids from soluble RNA to ribosomes; Protein synthesis inhibitor

Product Information

• Biological Source: Metab. of the fungus Acrodontium salmoneum
• Application(s): Antibiotic

REFERENCES

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