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ChemSpider 2D Image | Cycloheximide | C15H23NO4

Cycloheximide

  • Molecular FormulaC15H23NO4
  • Average mass281.347 Da
  • Monoisotopic mass281.162720 Da
  • ChemSpider ID5962

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

Featured data source
The Merck Index Online

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(-)-Cycloheximide
[1S-[1a(S*),3a,5b]]-4-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]-2,6-piperidinedione
2,6-Piperidinedione, 4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]- [ACD/Index Name]
200-636-0 [EINECS]
3-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide
3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide
4-[(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione
4-{(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl}-2,6-piperidindion [German] [ACD/IUPAC Name]
4-{(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl}-2,6-piperidinedione [ACD/IUPAC Name]
4-{(2R)-2-[(1S,3S,5S)-3,5-Diméthyl-2-oxocyclohexyl]-2-hydroxyéthyl}-2,6-pipéridinedione [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

98600C0908 [DBID]
MA4375000 [DBID]
01810_FLUKA [DBID]
01811_FLUKA [DBID]
18079_FLUKA [DBID]
46401_RIEDEL [DBID]
AI3-15541 [DBID]
AIDS004418 [DBID]
AIDS-004418 [DBID]
BPBio1_000990 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Appearance:

      white crystalline powder or colourless crystals OU Chemical Safety Data (No longer updated) More details

    • Stability:

      Stable. Combustible. Incompatible with strong oxidizing agents,acid chlorides, acid anhydrides, alkali. OU Chemical Safety Data (No longer updated) More details

    • Toxicity:

      Note low LD50s below. Very toxic if, ORL-RAT LD50 2 mg kg-1, IVN-RBT LD50 17 mg kg-1, ORL-DOG LD50 65 mg kg-1, SCU-MUS LD50 160 mg kg-1, IPR-CAT LD50 4 mg kg-1, IPR-GPG LD50 60 mg kg-1, IPR-HA M LD50 40 mg kg-1, ORL-MKY LD50 60 mg kg-1 OU Chemical Safety Data (No longer updated) More details

    • Safety:

      Safety glasses, gloves, good ventilation. OU Chemical Safety Data (No longer updated) More details

    • Target Organs:

      Antifungal TargetMol T1225

    • Chemical Class:

      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 i s an antibiotic produced by the bacterium <ital>Streptomyces griseus</ital>. ChEBI CHEBI:27641
      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 i s an antibiotic produced by the bacterium Streptomyces griseus. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:27641, CHEBI:27641

    • Bio Activity:

      <p>Widely-used eukaryotic protein synthesis inhibitor. Blocks the elongation phase of translation by binding to the E-site of the 60S ribosomal subunit to block eEF2-mediated tRNA translocation.</p> <p>Induces apoptosis in various cells but can also delay or inhibit apoptosis.</p><p>Also inhibits FKBP12 and shows potent antifungal and anti-mold activity.</p> Hello Bio HB2904
      Antibiotics Hello Bio HB2904
      Antifungal MedChem Express HY-12320
      Anti-infection MedChem Express HY-12320
      Anti-infection; MedChem Express HY-12320
      Cell Biology Tocris Bioscience 970
      Cell Metabolism Tocris Bioscience 970
      Cycloheximide is an inhibitor of protein biosynthesis in eukaryotic organisms, with IC50 of 532.5 nM.; IC50 value: 532.5 nM; Target: Antifungal; Cycloheximide is a highly effective antibiotic with activity against mold, yeast, and phytopathogenic fungi, with lower activity against bacteria. MedChem Express HY-12320
      Cycloheximide is an inhibitor of protein biosynthesis in eukaryotic organisms, with IC50 of 532.5 nM.;IC50 value: 532.5 nM;Target: AntifungalCycloheximide is a highly effective antibiotic with activity against mold, yeast, and phytopathogenic fungi, with lower activity against bacteria. It has been reported to inhibit the synthesis of both proteins and macromolecules, as well as affect apoptosis in eukaryotes. Inhibition of protein synthesis is believed to be mediated through DNA translation arrest, as demonstrated in rat thymocytes. Cycloheximide has also been reported to inhibit FKBP12 (peptidylprolylisomerase hFKBP12, PPIase hFKBP12) via competitive inhibition. Cycloheximide exerts its effect by interfering with the translocation step in protein synthesis (movement of two tRNA molecules and mRNA in relation to the ribosome) thus blocking translational elongation. MedChem Express HY-12320
      DNA, RNA and Protein Synthesis Tocris Bioscience 970
      Eukaryotic protein synthesis inhibitor Hello Bio HB2904
      Inhibitor of protein synthesis Tocris Bioscience 0970, 970
      Microbiology & Virology TargetMol T1225
      Others TargetMol T1225
      Selective inhibitor of eukaryotic (over prokaryotic) protein synthesis, blocking tRNA binding and release from ribosomes. Induces apoptosis in a variety of transformed and normal cell lines, including T cells. Competitively inhibits the PPIase hFKBP12 (Ki = 3.4 ?M). Antifungal antibiotic. Tocris Bioscience 970
      Selective inhibitor of eukaryotic (over prokaryotic) protein synthesis, blocking tRNA binding and release from ribosomes. Induces apoptosis in a variety of transformed and normal cell lines, including T cells. Competitively inhibits the PPIase hFKBP12 (Ki = 3.4 muM). Antifungal antibiotic. Tocris Bioscience 970
      Selective inhibitor of eukaryotic (over prokaryotic) protein synthesis, blocking tRNA binding and release from ribosomes. Induces apoptosis in a variety of transformed and normal cell lines, including T cells. Competitively inhibits the PPIase hFKBP12 (Ki = 3.4 ?M). Antifungal antibiotic. Tocris Bioscience 0970

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.1±0.1 g/cm3
Boiling Point: 491.8±10.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.8 mmHg at 25°C
Enthalpy of Vaporization: 87.4±6.0 kJ/mol
Flash Point: 251.2±19.0 °C
Index of Refraction: 1.499
Molar Refractivity: 72.7±0.3 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 0.56
ACD/LogD (pH 5.5): 0.83
ACD/BCF (pH 5.5): 2.52
ACD/KOC (pH 5.5): 67.44
ACD/LogD (pH 7.4): 0.83
ACD/BCF (pH 7.4): 2.52
ACD/KOC (pH 7.4): 67.44
Polar Surface Area: 83 Å2
Polarizability: 28.8±0.5 10-24cm3
Surface Tension: 40.0±3.0 dyne/cm
Molar Volume: 247.5±3.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™ 

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  0.08
    Log Kow (Exper. database match) =  0.55
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  554.89  (Adapted Stein & Brown method)
    Melting Pt (deg C):  238.24  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.45E-013  (Modified Grain method)
    MP  (exp database):  119 deg C
    Subcooled liquid VP: 3.8E-012 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  5337
       log Kow used: 0.55 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  72666 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Imides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.52E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.087E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.55  (exp database)
  Log Kaw used:  -12.842  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.392
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7792
   Biowin2 (Non-Linear Model)     :   0.4203
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7149  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5490  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2822
   Biowin6 (MITI Non-Linear Model):   0.0492
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0443
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  5.07E-010 Pa (3.8E-012 mm Hg)
  Log Koa (Koawin est  ): 13.392
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.92E+003 
       Octanol/air (Koa) model:  6.05 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.998 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  65.4983 E-12 cm3/molecule-sec
      Half-Life =     0.163 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.960 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  16.31
      Log Koc:  1.213 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 0.55 (expkow database)

 Volatilization from Water:
    Henry LC:  3.52E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  2.79E+011  hours   (1.162E+010 days)
    Half-Life from Model Lake : 3.044E+012  hours   (1.268E+011 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.000751        3.92         1000       
   Water     44.2            900          1000       
   Soil      55.7            1.8e+003     1000       
   Sediment  0.0878          8.1e+003     0          
     Persistence Time: 1e+003 hr

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