ChemSpider 2D Image | MG132 | C26H41N3O5

MG132

  • Molecular FormulaC26H41N3O5
  • Average mass475.621 Da
  • Monoisotopic mass475.304626 Da
  • ChemSpider ID406728

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

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

133407-82-6 [RN]
benzyl N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[(2S)-4-methyl-1-oxopentan-2-yl]carbamoyl}butyl]carbamoyl}butyl]carbamate
benzyloxycarbonyl-leucyl-leucyl-leucinal
benzyloxycarbonylleucyl-leucyl-leucine aldehyde
benzyloxycarbonyl-Leu-Leu-Leu-aldehyde
Cbz-Leu-Leu-Leu-CHO
Cbz-Leu-Leu-Leu-H [Formula]
L-Leucinamide, N-((phenylmethoxy)carbonyl)-L-leucyl-N-((1S)-1-formyl-3-methylbutyl)-
L-Leucinamide, N-[(phenylmethoxy)carbonyl]-L-leucyl-N-[(1S)-1-formyl-3-methylbutyl]- [ACD/Index Name]
MFCD00674886 [MDL number]
More...

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

AIDS031965 [DBID]
AIDS-031965 [DBID]
Bio2_000030 [DBID]
Bio2_000510 [DBID]
C2211_SIGMA [DBID]
CCRIS 4693 [DBID]
KBio2_000030 [DBID]
KBio2_002598 [DBID]
KBio2_005166 [DBID]
KBio3_000059 [DBID]
More...
  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A tripeptide that is <stereo>L</stereo>-leucyl-<stereo>L</stereo>-leucyl-<stereo>L</stereo>-leucine in which the <element>C</element>-terminal carboxy group has been reduced to the corresponding aldeh yde and the <element>N</element>-terminal amino group is protected as its benzyloxycarbonyl derivative. ChEBI CHEBI:75142
      A tripeptide that is L-leucyl-L-leucyl-L-leucine in which the C-terminal carboxy group has been reduced to the corresponding aldeh; yde and the N-terminal amino group is protected as its benzyloxycarb onyl derivative. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:75142
      A tripeptide that is L-leucyl-L-leucyl-L-leucine in which the C-terminal carboxy group has been reduced to the corresponding aldehyde and the N-terminal amino group is protected as its benzyloxycarbon yl derivative. ChEBI CHEBI:75142

    • Bio Activity:

      <p>MG-132 is a potent, cell-permeable proteasome inhibitor (IC<sub>50</sub> = 100 nM) which blocks the proteolytic activity of the 26S proteasome complex. It induces cell cycle arrest and triggers apoptosis to inhibit cell growth.</p> <p><br />Shows anti-cancer activity <em>in vivo</em> and is also calpain inhibitor.</p> <p><br />This is the (S),(S),(S)- stereoisomer.</p> Hello Bio HB4135
      Cell signaling/Ca<sup>2+</sup> signaling/Ca<sup>2+</sup>-sensitive protease Hello Bio HB4135
      Enzymes/Protease / Peptidase/Cathepsin/Cathepsin B Hello Bio HB4135
      Enzymes/Protease / Peptidase/Proteasome Hello Bio HB4135
      Metabolism/Protease MedChem Express HY-13259
      Metabolism/Protease; MedChem Express HY-13259
      MG-132 is an inhibitor of proteasome with IC50 of 100 nM, and also inhibits calpain with IC50 of 1.2 ?M.; IC50 value: 100 nM( proteasome); 1.2 uM(calpain) [1]; Target: proteasome; in vitro: MG-132 displays >1000 times more activity than ZLLal in inhibiting the ZLLL-MCA-degrading activity of 20S proteasome with IC50 of 100 nM versus 110 ?M. MedChem Express HY-13259
      Potent, cell-permeable proteasome inhibitor. Calpain inhibitor. Hello Bio HB4135
      Proteasome MedChem Express HY-13259
      Type/Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB4135

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

Density: 1.1±0.1 g/cm3
Boiling Point: 682.0±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 100.1±3.0 kJ/mol
Flash Point: 366.3±31.5 °C
Index of Refraction: 1.506
Molar Refractivity: 131.8±0.3 cm3
#H bond acceptors: 8
#H bond donors: 3
#Freely Rotating Bonds: 15
#Rule of 5 Violations: 1
ACD/LogP: 5.75
ACD/LogD (pH 5.5): 3.81
ACD/BCF (pH 5.5): 463.77
ACD/KOC (pH 5.5): 2819.31
ACD/LogD (pH 7.4): 3.81
ACD/BCF (pH 7.4): 463.60
ACD/KOC (pH 7.4): 2818.25
Polar Surface Area: 114 Å2
Polarizability: 52.2±0.5 10-24cm3
Surface Tension: 39.6±3.0 dyne/cm
Molar Volume: 443.1±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) =  3.76

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  646.36  (Adapted Stein & Brown method)
    Melting Pt (deg C):  280.97  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.61E-015  (Modified Grain method)
    Subcooled liquid VP: 4.47E-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):  0.6305
       log Kow used: 3.76 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  255.66 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.71E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.561E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.76  (KowWin est)
  Log Kaw used:  -13.955  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.715
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.4337
   Biowin2 (Non-Linear Model)     :   1.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0373  (months      )
   Biowin4 (Primary Survey Model) :   3.9675  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2496
   Biowin6 (MITI Non-Linear Model):   0.0068
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.8380
 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):  5.96E-010 Pa (4.47E-012 mm Hg)
  Log Koa (Koawin est  ): 17.715
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.03E+003 
       Octanol/air (Koa) model:  1.27E+005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  93.4892 E-12 cm3/molecule-sec
      Half-Life =     0.114 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.373 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    :  8.247E+004
      Log Koc:  4.916 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.505E-004  L/mol-sec
  Kb Half-Life at pH 8:     145.912  years  
  Kb Half-Life at pH 7:    1459.123  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.195 (BCF = 156.7)
       log Kow used: 3.76 (estimated)

 Volatilization from Water:
    Henry LC:  2.71E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.712E+012  hours   (1.963E+011 days)
    Half-Life from Model Lake :  5.14E+013  hours   (2.142E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              20.42  percent
    Total biodegradation:        0.24  percent
    Total sludge adsorption:    20.18  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       0.00051         2.75         1000       
   Water     8.83            1.44e+003    1000       
   Soil      89.7            2.88e+003    1000       
   Sediment  1.46            1.3e+004     0          
     Persistence Time: 2.86e+003 hr

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