chloramphenicol (CHEBI:17698)

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ChEBI Name	chloramphenicol

ChEBI ID	CHEBI:17698

Definition	An organochlorine compound that is dichloro-substituted acetamide containing a nitrobenzene ring, an amide bond and two alcohol functions.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:13965, CHEBI:47327, CHEBI:3603, CHEBI:23106, CHEBI:23108

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Formula

C11H12Cl2N2O5

Net Charge

Average Mass

323.130

Monoisotopic Mass

322.01233

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

SMILES

C1=C([C@H]([C@H](NC(C(Cl)Cl)=O)CO)O)C=CC(=C1)[N+]([O-])=O

Metabolite of Species	Details
Mycoplasma genitalium (NCBI:txid2097)	Binds L16 protein of the 50S ribosomal subunit and inhibits amino acid transfer to growing peptide chains See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Biological Role(s):	antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. protein synthesis inhibitor A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein. antibacterial drug A drug used to treat or prevent bacterial infections. Mycoplasma genitalium metabolite Any bacterial metabolite produced during a metabolic reaction in Mycoplasma genitalium.

Application(s):	antibacterial drug A drug used to treat or prevent bacterial infections. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

ChEBI Ontology
Outgoing	chloramphenicol (CHEBI:17698) has role Escherichia coli metabolite (CHEBI:76971) chloramphenicol (CHEBI:17698) has role Mycoplasma genitalium metabolite (CHEBI:131604) chloramphenicol (CHEBI:17698) has role antibacterial drug (CHEBI:36047) chloramphenicol (CHEBI:17698) has role antimicrobial agent (CHEBI:33281) chloramphenicol (CHEBI:17698) has role geroprotector (CHEBI:176497) chloramphenicol (CHEBI:17698) has role protein synthesis inhibitor (CHEBI:48001) chloramphenicol (CHEBI:17698) is a C-nitro compound (CHEBI:35716) chloramphenicol (CHEBI:17698) is a carboxamide (CHEBI:37622) chloramphenicol (CHEBI:17698) is a diol (CHEBI:23824) chloramphenicol (CHEBI:17698) is a organochlorine compound (CHEBI:36683)

Incoming	O-(4-trifluoroacetamidobenzylphosphonyl)chloramphenicol (CHEBI:47691) has functional parent chloramphenicol (CHEBI:17698) O³-(2-L-lysino-2-oxoethyl)-O¹-[4-(trifluoroacetamido)benzylcarbonyl]chloramphenicol (CHEBI:63766) has functional parent chloramphenicol (CHEBI:17698) chloramphenicol 3-acetate (CHEBI:16730) has functional parent chloramphenicol (CHEBI:17698) chloramphenicol palmitate (CHEBI:3605) has functional parent chloramphenicol (CHEBI:17698)

IUPAC Name

2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide

Synonyms	Sources
(−)-chloramphenicol	ChEBI
Chloramphenicol	KEGG COMPOUND
CHLORAMPHENICOL	PDBeChem
chloramphenicol	UniProt
chlornitromycin	ChEBI
D-(−)-2,2-dichloro-N-(β-hydroxy-α-(hydroxymethyl)-p-nitrophenylethyl)acetamide	ChemIDplus
D-(−)-threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propanediol	ChemIDplus
laevomycetinum	ChemIDplus
levomicetina	ChemIDplus
levomycetin	ChemIDplus

Last Modified

23 September 2021