Cycloheximide (CED0001153)

Record Information
Version1.0
Creation Date2016-05-19 01:31:35 UTC
Update Date2026-08-19 12:32:21 UTC
Accession NumberCHEM003987
Identification
Common NameCycloheximide
ClassSmall Molecule
Description
Cycloheximide is an organic compound with the formula C15H23NO4 and an average molecular weight of 281.35 g/mol. Cycloheximide belongs to the hydropyridines, a subclass of pyridines and derivatives within the organic compounds. It is utilized as a biological drug (PMC6720308). The compound is identified in 32 recorded sources across various sectors. Within healthcare, pharmaceuticals, and veterinary products, it is found in antibiotics. In the category of food, food processing, and cookware, it appears in food preservation, the preparation of malt, the preparation of vinegar, the preparation of wine or sparkling wine, and fermentation processes for beer, among three other sources. Household cleaning and consumer product sources include soap detergents, perfumes within detergents and soaps, bleaching agents, tobacco smoke filters, and cigar cigarettes. Its presence is also recorded in building and construction materials such as tents or canopies and roofs, as well as in drinking water and water supply. Additionally, it is found in electrical and electronic equipment, including antennas, auxiliary devices, contacts, adjustable resistors, and conductors or conductive bodies characterised by the conductive materials, among 10 other sources. Recorded exposure routes for cycloheximide include oral and inhalation.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
3-((R)-2-((1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimideChEBI
CicloheximidaChEBI
CicloheximideChEBI
CicloheximidumChEBI
CycloheximidChEBI
NaramycinChEBI
Naramycin aChEBI
ZykloheximidChEBI
CycloheximideMeSH
ActidioneMeSH
Chemical FormulaC15H23NO4
Average Molecular Mass281.352 g/mol
Monoisotopic Mass281.163 g/mol
CAS Registry Number66-81-9
IUPAC Name4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-6-hydroxy-2,3,4,5-tetrahydropyridin-2-one
Traditional NameActiDione
SMILES[H][C@@](O)(CC1CC(O)=NC(=O)C1)[C@]1([H])C[C@@]([H])(C)C[C@]([H])(C)C1=O
InChI IdentifierInChI=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-FSZOTQKASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydropyridines. These are derivatives of pyridine in which two double bonds in the pyridine moiety are reduced by adding four hydrogen atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassHydropyridines
Direct ParentTetrahydropyridines
Alternative Parents
Substituents
  • Tetrahydropyridine
  • Ketone
  • Secondary alcohol
  • N-acylimine
  • Cyclic ketone
  • Lactim
  • Carboxylic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.97 g/LALOGPS
logP1.29ALOGPS
logP1.27ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.96 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity73.41 m³·mol⁻¹ChemAxon
Polarizability30.26 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03e9-0290000000-78279dc32021af511e9fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06tr-2940000000-57b034db6f6c951b850dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9600000000-6735c1ee2c0d2d860478Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0190000000-6b77cb5ecf21cc1ad8daNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01u0-1970000000-5d39546253193d6651ecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056u-6910000000-549689e72a6e59061929Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2733.0Log mg/kg[1500:4900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
499RoofsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
512ContactsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
COUP transcription factor 2 structureClick to view 3D structureCOUP transcription factor 2P24468HumansPredicted (SEA)0.622794
Click to view 3D structureLarge ribosomal subunit protein eL19AP0CX82Saccharomyces cerevisiae S288cPredicted (SEA)1.01204
Peptidyl-prolyl cis-trans isomerase FKBP1A structureClick to view 3D structurePeptidyl-prolyl cis-trans isomerase FKBP1AP62942HumansPredicted (SEA)5.3716
Click to view 3D structureHeat shock factor protein 1P38532Mus musculusPredicted (SEA)615.554
Click to view 3D structureDNA damage-inducible transcript 3 proteinP35639Mus musculusPredicted (SEA)716.602
X-box-binding protein 1 structureClick to view 3D structureX-box-binding protein 1P17861HumansPredicted (SEA)717.069
Solute carrier family 2, facilitated glucose transporter member 1 structureClick to view 3D structureSolute carrier family 2, facilitated glucose transporter member 1P11166HumansPredicted (SEA)746.341
Click to view 3D structureHexose transporter 1O97467Plasmodium falciparumPredicted (SEA)442.729
Click to view 3D structureGlucose transporterO61059Leishmania mexicanaPredicted (SEA)564.173
Click to view 3D structureSynaptic vesicle glycoprotein 2AQ02563Rattus norvegicusPredicted (SEA)6.61718
Click to view 3D structureOuter membrane protein MIPQ70YI1Legionella pneumophilaPredicted (SEA)12.378
Eukaryotic initiation factor 4A-I structureClick to view 3D structureEukaryotic initiation factor 4A-IP60842HumansPredicted (SEA)2.49118
Photoreceptor-specific nuclear receptor structureClick to view 3D structurePhotoreceptor-specific nuclear receptorQ9Y5X4HumansPredicted (SEA)4292.61
Proteasome assembly chaperone 3 structureClick to view 3D structureProteasome assembly chaperone 3Q9BT73HumansPredicted (SEA)29.2713
Click to view 3D structureHemagglutininP03438Influenza A virus (strain A/X-31 H3N2)Predicted (SEA)32.4631
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)6070.37
Click to view 3D structureCytochrome b-c1 complex subunit Rieske, mitochondrialG2YM83Botryotinia fuckeliana (strain T4) (Noble rot fungus) (Botrytiscinerea)Predicted (SEA)863.192
Click to view 3D structureTegument protein VP16P06492Herpes simplex virus (type 1 / strain 17)Predicted (SEA)4472.05
Click to view 3D structureHTH-type quorum-sensing regulator RhlRP54292Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)Predicted (SEA)136.937
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abQ98VG9Feline coronavirus (strain FIPV WSU-79/1146)Predicted (SEA)226.23
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)7494.08
Matrix metalloproteinase-9 structureClick to view 3D structureMatrix metalloproteinase-9P14780HumansPredicted (SEA)6435.72
RAC-gamma serine/threonine-protein kinase structureClick to view 3D structureRAC-gamma serine/threonine-protein kinaseQ9Y243HumansPredicted (SEA)7435.22
RAC-beta serine/threonine-protein kinase structureClick to view 3D structureRAC-beta serine/threonine-protein kinaseP31751HumansPredicted (SEA)7410.55
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)7550.99
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00047211
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCycloheximide
Chemspider IDNot Available
ChEBI ID27641
PubChem Compound ID6197
Kegg Compound IDC06685
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11972861