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Substrate Report for: Chloramphenicol

Chloramphenicol is an antibiotic first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic. EstDL136 reactivated chloramphenicol from its acetyl derivates by counteracting the chloramphenicol acetyltransferase (CAT) activity. It catalyzed the deacetylation of 1- and 3- acetyl and 1,3-diacetyl derivates.EstDL136 also acts as a chloramphenicol hydrolase.It cleaves the amide linkage at C2 of chloramphenicol and thereby confers Cm resistance to bacteria


General
Type Antibiotic, pNP
Chemical_Nomenclature 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
Canonical SMILES C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
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-RKDXNWHRSA-N
Other name(s) Chloromycetin ; Chlornitromycin ; Levomycetin ; Chlorocid
________________________________________________________________________________________________
MW|323.12
Formula|C11H12Cl2N2O5
CAS_number|56-75-7
PubChem|5959
UniChem|WIIZWVCIJKGZOK-RKDXNWHRSA-N
IUPHAR|
Wikipedia|

Target
Families | Chloramphenicol ligand of proteins in family: Hormone-sensitive_lipase_like
Stucture | 1 structure: 6IEY: Crystal structure of Chloramphenicol-Metabolizing Enzyme EstDL136-Chloramphenicol complex
Protein | 9bact-g3cr02

References:
Search PubMed for references concerning: Chloramphenicol

2 more
    Title: Crystal structure of chloramphenicol-metabolizing enzyme EstDL136 from a metagenome
    Kim SH, Kang PA, Han K, Lee SW, Rhee S
    Ref: PLoS ONE, 14:e0210298, 2019 : PubMed

            

    Title: Inactivation of chloramphenicol and florfenicol by a novel chloramphenicol hydrolase
    Tao W, Lee MH, Wu J, Kim NH, Kim JC, Chung E, Hwang EC, Lee SW
    Ref: Applied Environmental Microbiology, 78:6295, 2012 : PubMed

            

    Title: Characterization of two metagenome-derived esterases that reactivate chloramphenicol by counteracting chloramphenicol acetyltransferase
    Tao W, Lee MH, Yoon MY, Kim JC, Malhotra S, Wu J, Hwang EC, Lee SW
    Ref: J Microbiol Biotechnol, 21:1203, 2011 : PubMed