cycloheximide (CHEBI:27641)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

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

Supplier Information

Download	Molfile XML SDF

more structures >>

Wikipedia	License

Read full article at Wikipedia

Formula

C15H23NO4

Net Charge

Average Mass

281.352

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

[H][C@]1(C[C@@H](C)C[C@H](C)C1=O)[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. anticoronaviral agent Any antiviral agent which inhibits the activity of coronaviruses. ferroptosis inhibitor Any substance that inhibits the process of ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms. 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 anticoronaviral agent (CHEBI:149553) cycloheximide (CHEBI:27641) has role bacterial metabolite (CHEBI:76969) cycloheximide (CHEBI:27641) has role ferroptosis inhibitor (CHEBI:173084) 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

Last Modified

27 May 2021