chloramphenicol (CHEBI:17698)

CHEBI:17698 - chloramphenicol

ChEBI ID	CHEBI:17698
ChEBI Name	chloramphenicol
Stars
Definition	An organochlorine compound that is dichloro-substituted acetamide containing a nitrobenzene ring, an amide bond and two alcohol functions.
Secondary ChEBI IDs	CHEBI:3603, CHEBI:13965, CHEBI:23106, CHEBI:23108, CHEBI:47327
Last Modified	23 September 2021
Downloads	Molfile

Formula	C11H12Cl2N2O5
Net Charge	0
Average Mass	323.132
Monoisotopic Mass	322.01233
SMILES	O=C(N[C@H](CO)[C@H](O)c1ccc([N+](=O)[O-])cc1)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-RKDXNWHRSA-N

Wikipedia

Species of Metabolite	Component	Source	Comments
Escherichia coli (ncbitaxon:562)	-	PubMed (21988831)
Mycoplasma genitalium (ncbitaxon:2097)	-	PubMed (22817898)	Binds L16 protein of the 50S ribosomal subunit and inhibits amino acid transfer to growing peptide chains

Roles Classification

Mycoplasma genitalium metabolite Any bacterial metabolite produced during a metabolic reaction in Mycoplasma genitalium.

antibacterial drug A drug used to treat or prevent bacterial infections.

protein synthesis inhibitor A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.

Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.

antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.

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 Relation(s)
	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 Relation(s)
	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	Source
Chloramphenicol	KEGG COMPOUND
D-(−)-threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propanediol	ChemIDplus
D-(−)-2,2-dichloro-N-(β-hydroxy-α-(hydroxymethyl)-p-nitrophenylethyl)acetamide	ChemIDplus
CHLORAMPHENICOL	PDBeChem
levomycetin	ChemIDplus
laevomycetinum	ChemIDplus

UniProt Name	Source
chloramphenicol	UniProt

Citations