CHEBI:17698 - chloramphenicol

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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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Formulae C11H12Cl2N2O5
C11H12Cl2N2O5
Net Charge 0
Average Mass 323.130
Monoisotopic Mass 322.012
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:2097) Binds L16 protein of the 50S ribosomal subunit and inhibits amino acid transfer to growing peptide chains See: PubMed
Escherichia coli (NCBI:562) 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.
View more via ChEBI Ontology
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 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
INNs Sources
chloramphenicol ChemIDplus
chloramphénicol ChEBI
chloramphenicolum ChemIDplus
cloramfenicol ChemIDplus
Synonyms Sources
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
Brand Names Sources
Chloramex ChemIDplus
Chlorocid ChemIDplus
Chlorocol ChemIDplus
Chloromycetin ChemIDplus
Fenicol ChemIDplus
Globenicol ChemIDplus
Halomycetin ChemIDplus
Oleomycetin ChemIDplus
Sificetina ChemIDplus
Database Links Databases
589 DrugCentral
C00918 KEGG COMPOUND
Chloramphenicol Wikipedia
CLM PDBeChem
D00104 KEGG DRUG
DB00446 DrugBank
GB795131 Patent
GB796901 Patent
LSM-5256 LINCS
US2483871 Patent
US2483884 Patent
US2483892 Patent
US2839577 Patent
View more database links
Registry Numbers Types Sources
2225532 Beilstein Registry Number Beilstein
56-75-7 CAS Registry Number KEGG COMPOUND
56-75-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11468347 PubMed citation Europe PMC
12217690 PubMed citation Europe PMC
16659995 PubMed citation Europe PMC
16897441 PubMed citation Europe PMC
17217404 PubMed citation Europe PMC
17692887 PubMed citation Europe PMC
18559535 PubMed citation Europe PMC
18657290 PubMed citation Europe PMC
18794387 PubMed citation Europe PMC
23142491 PubMed citation Europe PMC
23317719 PubMed citation Europe PMC
23395526 PubMed citation Europe PMC
23494278 PubMed citation Europe PMC
23512826 PubMed citation Europe PMC
657786 PubMed citation Europe PMC
6653106 PubMed citation Europe PMC
Last Modified
22 February 2017