ChemSpider 2D Image | Bortezomib | C19H25BN4O4

Bortezomib

  • Molecular FormulaC19H25BN4O4
  • Average mass384.237 Da
  • Monoisotopic mass384.196899 Da
  • ChemSpider ID343402
  • defined stereocentres - 2 of 2 defined stereocentres


More details:



Featured data source



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

[(1R)-3-methyl-1-({(2S)-3-phenyl-2-[(pyrazin-2-ylcarbonyl)amino]propanoyl}amino)butyl]boronic acid
[(1R)-3-Methyl-1-({(2S)-3-phenyl-2-[(pyrazin-2-ylcarbonyl)amino]propanoyl}amino)butyl]boronsäure [German]
179324-69-7 [RN]
8331
acide [(1R)-3-méthyl-1-({(2S)-3-phényl-2-[(pyrazin-2-ylcarbonyl)amino]propanoyl}amino)butyl]boronique [French]
Boronic acid, ((1R)-3-methyl-1-(((2S)-1-oxo-3-phenyl-2-((pyrazinylcarbonyl)amino)propyl)amino)butyl)-
boronic acid, [(1R)-3-methyl-1-[[(2S)-1-oxo-3-phenyl-2-[(pyrazinylcarbonyl)amino]propyl]amino]butyl]-
Boronic acid, B-[(1R)-3-methyl-1-[[(2S)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)amino]propyl]amino]butyl]- [ACD/Index Name]
N-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-Nα-(pyrazin-2-ylcarbonyl)-L-phenylalaninamide
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

69G8BD63PP [DBID]
LDP-341 [DBID]
PS-341 [DBID]
AIDS004352 [DBID]
AIDS-004352 [DBID]
D03150 [DBID]
LPD 341 [DBID]
LPD-341 [DBID]
MLN-341 [DBID]
NCI60_029010 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1810
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1810
      IRRITANT Matrix Scientific 094031
      L01XX32 Wikidata Q419319
      no pictogram Axon Medchem 1810
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1810
      Warning Axon Medchem 1810
    • Target Organs:

      Protease inhibitor TargetMol T2399
    • Chemical Class:

      <stereo>L</stereo>-Phenylalaninamide substituted at the amide nitrogen by a 1-(dihydroxyboranyl)-3-methylbutyl group and at <element>N</element><smallsup><locant>alpha</locant></smallsup> by a pyrazin -2-ylcarbonyl group. It is a dipeptidyl boronic acid that reversibly inhibits the 26S proteasome. ChEBI CHEBI:52717
    • Bio Activity:

      20S proteasome TargetMol T2399
      Bortezomib (PS-341) is a potent 20S proteasome inhibitor with Ki of 0.6 nM. MedChem Express
      Bortezomib (PS-341) is a potent 20S proteasome inhibitor with Ki of 0.6 nM.; IC50 value: 0.6 nM (Ki) [1]; Target: 20S proteasome; in vitro: The average growth inhibition of 50% value for Bortezomib across the entire panel of 60 cancer cell lines derived from multiple human tumors from the US National Cancer Institute (NCI) is 7 nM. MedChem Express HY-10227
      Metabolism/Protease MedChem Express HY-10227
      Metabolism/Protease; MedChem Express HY-10227
      Proteases/Proteasome TargetMol T2399
      Proteasome MedChem Express HY-10227

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.2±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.564
Molar Refractivity: 103.0±0.3 cm3
#H bond acceptors: 8
#H bond donors: 4
#Freely Rotating Bonds: 9
#Rule of 5 Violations: 0
ACD/LogP: 2.45
ACD/LogD (pH 5.5): 1.87
ACD/BCF (pH 5.5): 15.65
ACD/KOC (pH 5.5): 249.27
ACD/LogD (pH 7.4): 1.87
ACD/BCF (pH 7.4): 15.60
ACD/KOC (pH 7.4): 248.40
Polar Surface Area: 124 Å2
Polarizability: 40.8±0.5 10-24cm3
Surface Tension: 53.2±3.0 dyne/cm
Molar Volume: 316.5±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) =  2.00

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  684.30  (Adapted Stein & Brown method)
    Melting Pt (deg C):  298.69  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.1E-020  (Modified Grain method)
    Subcooled liquid VP: 5.76E-017 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):  75.78
       log Kow used: 2.00 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   Incomplete
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.403E-022 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Can Not Estimate (can not calculate HenryLC)

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1677
   Biowin2 (Non-Linear Model)     :   0.9951
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1888  (months      )
   Biowin4 (Primary Survey Model) :   3.6406  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2695
   Biowin6 (MITI Non-Linear Model):   0.0030
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.5974
 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):  7.68E-015 Pa (5.76E-017 mm Hg)
  Log Koa (): not available
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.91E+008 
       Octanol/air (Koa) model:  not available
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  not available

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  46.1238 E-12 cm3/molecule-sec
      Half-Life =     0.232 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.783 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    :  3.193E+004
      Log Koc:  4.504 

 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 = 0.836 (BCF = 6.857)
       log Kow used: 2.00 (estimated)

 Volatilization from Water:
    Henry LC:  3.4E-022 atm-m3/mole  (calculated from VP/WS)
    Half-Life from Model River: 3.373E+018  hours   (1.405E+017 days)
    Half-Life from Model Lake :  3.68E+019  hours   (1.533E+018 days)

 Removal In Wastewater Treatment:
    Total removal:               2.25  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.15  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       8.49e-005       5.57         1000       
   Water     23.2            1.44e+003    1000       
   Soil      76.8            2.88e+003    1000       
   Sediment  0.0915          1.3e+004     0          
     Persistence Time: 1.89e+003 hr




                    

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