cycloheximide (CHEBI:27641)

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ChEBI Name	cycloheximide

ChEBI ID	CHEBI:27641

Definition	A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.

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

Secondary ChEBI IDs	CHEBI:23484, CHEBI:4015

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Formula

C15H23NO4

Net Charge

Average Mass

281.34740

Monoisotopic Mass

281.16271

InChI

InChI=1S/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9-,11-,12+/m0/s1

InChIKey

YPHMISFOHDHNIV-FSZOTQKASA-N

SMILES

C[C@H]1C[C@H](C)C(=O)[C@@H](C1)[C@H](O)CC1CC(=O)NC(=O)C1

Roles Classification
Biological Role(s):	bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. protein synthesis inhibitor A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein. antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. (via heterocyclic antibiotic ) fungicide A substance used to destroy fungal pests. (via antibiotic fungicide ) antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. (via antibiotic antifungal agent )

Application(s):	neuroprotective agent Any compound that can be used for the treatment of neurodegenerative disorders. fungicide A substance used to destroy fungal pests. (via antibiotic fungicide )

ChEBI Ontology
Outgoing	cycloheximide (CHEBI:27641) has functional parent piperidine-2,6-dione (CHEBI:5435) cycloheximide (CHEBI:27641) has role bacterial metabolite (CHEBI:76969) cycloheximide (CHEBI:27641) has role neuroprotective agent (CHEBI:63726) cycloheximide (CHEBI:27641) has role protein synthesis inhibitor (CHEBI:48001) cycloheximide (CHEBI:27641) is a antibiotic fungicide (CHEBI:87114) cycloheximide (CHEBI:27641) is a cyclic ketone (CHEBI:3992) cycloheximide (CHEBI:27641) is a dicarboximide (CHEBI:35356) cycloheximide (CHEBI:27641) is a piperidine antibiotic (CHEBI:49318) cycloheximide (CHEBI:27641) is a piperidones (CHEBI:48589) cycloheximide (CHEBI:27641) is a secondary alcohol (CHEBI:35681)

IUPAC Name

4-{(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl}piperidine-2,6-dione

Synonyms	Sources
3-((R)-2-((1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide	ChemIDplus
Cycloheximid	ChEBI
Cycloheximide	KEGG COMPOUND
cycloheximide	UniProt
naramycin	ChemIDplus
naramycin A	ChemIDplus
Zykloheximid	ChEBI

Citation	Type	Source
11972861	PubMed citation	Europe PMC

Last Modified

15 October 2019