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
Supplier Information eMolecules:29817042, eMolecules:474920, ZINC000003872170
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Cycloheximide is a naturally occurring fungicide produced by the bacterium Streptomyces griseus. Cycloheximide exerts its effects by interfering with the translocation step in protein synthesis (movement of two tRNA molecules and mRNA in relation to the ribosome), thus blocking eukaryotic translational elongation. Cycloheximide is widely used in biomedical research to inhibit protein synthesis in eukaryotic cells studied in vitro (i.e. outside of organisms). It is inexpensive and works rapidly. Its effects are rapidly reversed by simply removing it from the culture medium. Due to significant toxic side effects, including DNA damage, teratogenesis, and other reproductive effects (including birth defects and toxicity to sperm), cycloheximide is generally used only in in vitro research applications, and is not suitable for human use as a therapeutic compound. Although it has been used as a fungicide in agricultural applications, this application is now decreasing as the health risks have become better understood. Because cycloheximide rapidly breaks down in a basic environment, decontamination of work surfaces and containers can be achieved by washing with a non-harmful alkali solution such as soapy water or aqueous sodium bicarbonate. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.
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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
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 )
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 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
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
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
Citations
Grubbs KJ, Surup F, Biedermann PHW, McDonald BR, Klassen JL, Carlson CM, Clardy J, Currie CR (2020)
Cycloheximide-Producing Streptomyces Associated With Xyleborinus saxesenii and Xyleborus affinis Fungus-Farming Ambrosia Beetles.
Frontiers in microbiology 11, 562140 [PubMed:33101237]
[show Abstract]
Buschauer R, Matsuo Y, Sugiyama T, Chen YH, Alhusaini N, Sweet T, Ikeuchi K, Cheng J, Matsuki Y, Nobuta R, Gilmozzi A, Berninghausen O, Tesina P, Becker T, Coller J, Inada T, Beckmann R (2020)
The Ccr4-Not complex monitors the translating ribosome for codon optimality.
Science (New York, N.Y.) 368, eaay6912 [PubMed:32299921]
[show Abstract]
Santos DA, Shi L, Tu BP, Weissman JS (2019)
Cycloheximide can distort measurements of mRNA levels and translation efficiency.
Nucleic acids research 47, 4974-4985 [PubMed:30916348]
[show Abstract]
Elliott A, Shaw SL (2018)
A Cycloheximide-Sensitive Step in Transverse Microtubule Array Patterning.
Plant physiology 178, 684-698 [PubMed:30154175]
[show Abstract]
Darvishi E, Woldemichael GM (2016)
Cycloheximide Inhibits Actin Cytoskeletal Dynamics by Suppressing Signaling via RhoA.
Journal of cellular biochemistry 117, 2886-2898 [PubMed:27192630]
[show Abstract]
Myasnikov AG, Kundhavai Natchiar S, Nebout M, Hazemann I, Imbert V, Khatter H, Peyron JF, Klaholz BP (2016)
Structure-function insights reveal the human ribosome as a cancer target for antibiotics.
Nature communications 7, 12856 [PubMed:27665925]
[show Abstract]
Schmidt C, Becker T, Heuer A, Braunger K, Shanmuganathan V, Pech M, Berninghausen O, Wilson DN, Beckmann R (2016)
Structure of the hypusinylated eukaryotic translation factor eIF-5A bound to the ribosome.
Nucleic acids research 44, 1944-1951 [PubMed:26715760]
[show Abstract]
Garreau de Loubresse N, Prokhorova I, Holtkamp W, Rodnina MV, Yusupova G, Yusupov M (2014)
Structural basis for the inhibition of the eukaryotic ribosome.
Nature 513, 517-522 [PubMed:25209664]
[show Abstract]
Tsuchida T, Kato T, Yamada A, Kawamoto K (2002)
Cycloheximide induces apoptosis of astrocytes.
Pathology international 52, 181-185 [PubMed:11972861]
[show Abstract]
McMahon D (1975)
Cycloheximide is not a specific inhibitor of protein synthesis in vivo.
Plant physiology 55, 815-821 [PubMed:16659174]
[show Abstract]
Last Modified
27 May 2021