Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 04:12:18 UTC
Update Date2025-10-07 16:04:15 UTC
Metabolite IDMMDBc0012752
Metabolite Identification
Common NameCycloheximide
DescriptionCycloheximide is a cyclohexylamide, specifically classified as a translation inhibitor that interferes with protein synthesis in eukaryotic cells. Its chemical structure features a cyclohexyl ring attached to an amide group, which is crucial for its biological activity. Cycloheximide is involved in various biochemical pathways, including the regulation of protein turnover and the modulation of gene expression. For instance, mechanistic studies utilizing transcriptomic and proteomic analyses have highlighted its role in protein stability and degradation, as seen in the investigation of FBXO2's contribution to tumor progression in hepatocellular carcinoma (HCC) (PMID:41035649 ). Additionally, it is used in experimental setups, such as culturing samples on selective media containing cycloheximide to inhibit fungal growth while allowing bacterial detection (PMID:41034097 ). Cycloheximide has also been employed to induce necroptosis in cancer cells, demonstrating its utility in studying cell death pathways (PMID:41030638 ). Furthermore, its effects on mRNA dynamics and protein degradation, including the acceleration of c-MYC degradation when co-treated with other compounds, underscore its significance in cellular processes (PMID:41014667 ; PMID:41028809 ).
Structure
SynonymsNot Available
Molecular FormulaC15H23NO4
Average Mass281.352
Monoisotopic Mass281.162708225
IUPAC Name4-[(2R)-2-[(1R,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-6-hydroxy-2,3,4,5-tetrahydropyridin-2-one
Traditional Name4-[(2R)-2-[(1R,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-6-hydroxy-4,5-dihydro-3H-pyridin-2-one
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(CC1CC(O)=NC(=O)C1)[C@@]1([H])C[C@@]([H])(C)C[C@]([H])(C)C1=O
InChI Identifier
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
InChI KeyYPHMISFOHDHNIV-GAIPPQHRSA-N