Cycloheximide (CHEM003987)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (25)XML
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
DescriptionCycloheximide 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 Sources
  • Clean Air Act Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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]piperidine-2,6-dione
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
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0290000000-78279dc32021af511e9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06tr-2940000000-57b034db6f6c951b850dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9600000000-6735c1ee2c0d2d860478Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0190000000-6b77cb5ecf21cc1ad8daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01u0-1970000000-5d39546253193d6651ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056u-6910000000-549689e72a6e59061929Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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