CHEBI:27641 - cycloheximide

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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 0
Average Mass 281.34740
Monoisotopic Mass 281.163
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 )
View more via ChEBI Ontology
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
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
naramycin ChemIDplus
naramycin A ChemIDplus
Zykloheximid ChEBI
Manual Xrefs Databases
1680 PPDB
3HE PDBeChem
C00047211 KNApSAcK
C06685 KEGG COMPOUND
Cycloheximide Wikipedia
D03625 KEGG DRUG
LSM-2791 LINCS
View more database links
Registry Numbers Types Sources
66-81-9 CAS Registry Number KEGG COMPOUND
66-81-9 CAS Registry Number ChemIDplus
88868 Reaxys Registry Number Reaxys
88868 Beilstein Registry Number Beilstein
Citation Waiting for Citations Type Source
11972861 PubMed citation Europe PMC
Last Modified
25 February 2016