CHEBI:27641 - cycloheximide

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ChEBI Name cycloheximide
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 0
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
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 )
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.
A substance used to destroy fungal pests.
(via antibiotic fungicide )
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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)
INNs Sources
cicloheximida ChemIDplus
cicloheximide WHO MedNet
cicloheximide WHO MedNet
cicloheximidum ChemIDplus
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
Manual Xrefs Databases
1680 PPDB
3HE PDBeChem
C00047211 KNApSAcK
Cycloheximide Wikipedia
View more database links
Registry Numbers Types Sources
66-81-9 CAS Registry Number KEGG COMPOUND
66-81-9 CAS Registry Number ChemIDplus
88868 Beilstein Registry Number Beilstein
88868 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11972861 PubMed citation Europe PMC
16659174 PubMed citation Europe PMC
25209664 PubMed citation Europe PMC
26715760 PubMed citation Europe PMC
27192630 PubMed citation Europe PMC
27665925 PubMed citation Europe PMC
30154175 PubMed citation Europe PMC
30916348 PubMed citation Europe PMC
32299921 PubMed citation Europe PMC
33101237 PubMed citation Europe PMC
Last Modified
27 May 2021