chloramphenicol (CHEBI:17698)

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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

Supplier Information	ChemicalBook:CB32502994, eMolecules:31228765, ZINC000004097420

Download	Molfile XML SDF

more structures >>

Molfile

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32 32 0 0 0 0 999 V2000

-2.9080 -2.5523 -1.1367 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.9120 -3.8657 -2.3707 Cl 0 0 0 0 0 0 0 0 0 0 0 0

-3.9018 -3.0576 0.2808 Cl 0 0 0 0 0 0 0 0 0 0 0 0

-1.4943 -2.2859 -0.6889 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.5788 -2.9247 -1.1619 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.2470 -1.3377 0.2358 N 0 0 0 0 0 0 0 0 0 0 0 0

0.1268 -1.0790 0.6700 C 0 0 2 0 0 0 0 0 0 0 0 0

0.4601 -1.9723 1.8668 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.4391 -1.6865 2.9396 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2666 0.3881 1.0756 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.6330 0.6747 2.1472 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.0612 1.2680 -0.1037 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3655 1.6867 -0.3075 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.6756 2.4904 -1.3811 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.6633 2.8852 -2.2721 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.9564 3.6701 -3.3249 N 0 3 0 0 0 0 0 0 0 0 0 0

-0.0765 4.0102 -4.0932 O 0 5 0 0 0 0 0 0 0 0 0 0

-2.1019 4.0401 -3.5078 O 0 0 0 0 0 0 0 0 0 0 0 0

0.6557 2.4550 -2.0560 C 0 0 0 0 0 0 0 0 0 0 0 0

0.9452 1.6566 -0.9725 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.3289 -1.6453 -1.5704 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.9797 -0.8270 0.6135 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8139 -1.2974 -0.1478 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4834 -1.7794 2.1910 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3611 -3.0187 1.5790 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1959 -2.2695 3.6717 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2892 0.5809 1.3990 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5248 0.4922 1.8200 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1423 1.3808 0.3776 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.6937 2.8155 -1.5380 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4407 2.7533 -2.7351 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9591 1.3244 -0.8053 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 3 1 0 0 0 0

1 4 1 0 0 0 0

1 21 1 0 0 0 0

4 5 2 0 0 0 0

4 6 1 0 0 0 0

6 7 1 0 0 0 0

6 22 1 0 0 0 0

7 8 1 0 0 0 0

7 10 1 0 0 0 0

7 23 1 0 0 0 0

8 9 1 0 0 0 0

8 24 1 0 0 0 0

8 25 1 0 0 0 0

9 26 1 0 0 0 0

10 11 1 0 0 0 0

10 12 1 0 0 0 0

10 27 1 0 0 0 0

11 28 1 0 0 0 0

12 13 4 0 0 0 0

12 20 4 0 0 0 0

13 14 4 0 0 0 0

13 29 1 0 0 0 0

14 15 4 0 0 0 0

14 30 1 0 0 0 0

15 16 1 0 0 0 0

15 19 4 0 0 0 0

16 17 1 0 0 0 0

16 18 2 0 0 0 0

19 20 4 0 0 0 0

19 31 1 0 0 0 0

20 32 1 0 0 0 0

M CHG 2 16 1 17 -1

M END): 20 ms

reading 32 atoms

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32 atoms created

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Wikipedia	License
[object Object]
Read full article at Wikipedia

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.

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 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

INNs	Sources
chloramphenicol	WHO MedNet
chloramphénicol	WHO MedNet
chloramphenicolum	WHO MedNet
cloramfenicol	WHO MedNet

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

Brand Names	Sources
Amphicol	KEGG DRUG
Chloramex	ChemIDplus
Chlorocid	ChemIDplus
Chlorocol	ChemIDplus
Chloromycetin	ChemIDplus
Econochlor	KEGG DRUG
Fenicol	ChemIDplus
Globenicol	ChemIDplus
Halomycetin	ChemIDplus
Oleomycetin	ChemIDplus
Sificetina	ChemIDplus

Manual Xrefs	Databases
1835	VSDB
5744	ChemSpider
589	DrugCentral
C00918	KEGG COMPOUND
chloramphenicol	Alan Wood's Pesticides
Chloramphenicol	Wikipedia
CHLORAMPHENICOL	MetaCyc
CLM	PDBeChem
D00104	KEGG DRUG
DB00446	DrugBank
GB795131	Patent
GB796901	Patent
HMDB0014589	HMDB
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	NIST Chemistry WebBook
56-75-7	CAS Registry Number	ChemIDplus

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
17963326	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
23698443	PubMed citation	Europe PMC
657786	PubMed citation	Europe PMC
6653106	PubMed citation	Europe PMC
7040026	PubMed citation	Europe PMC

Last Modified

23 September 2021

CHEBI:17698 - chloramphenicol

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