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
The Merck Index Online

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

Bortezomib [INN] [JAN] [USAN] [Wiki]
((R)-3-Methyl-1-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butyl)boronic acid
(1R)-3-Methyl-1-({(2S)-3-phenyl-2-[(2-pyrazinylcarbonyl)amino]propanoyl}amino)butylboronic acid
[(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]
[(1R)-3-methyl-1-[(2S)-3-phenyl-2-[(pyrazin-2-yl)formamido]propanamido]butyl]boronic acid
179324-69-7 [RN]
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]-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

69G8BD63PP [DBID]
8331 [DBID]
LDP-341 [DBID]
PS-341 [DBID]
AIDS004352 [DBID]
AIDS-004352 [DBID]
D03150 [DBID]
LPD 341 [DBID]
LPD-341 [DBID]
MLN-341 [DBID]
More...
  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      L01XX32 Wikidata Q419319

    • 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
      L-Phenylalaninamide substituted at the amide nitrogen by a 1-(dihydroxyboranyl)-3-methylbutyl group and at N(alpha) by a pyrazin-2-ylcarbonyl group. It is a dipeptidyl boronic acid that reversibly inh ibits the 26S proteasome. ChEBI CHEBI:52717

    • Bio Activity:

      20S proteasome TargetMol T2399
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB4036
      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
      Enzymes/Protease / Peptidase/Proteasome Hello Bio HB4036
      Highly potent, selective and reversible cell permeable inhibitor of the proteasome. Inhibits the chymotrypsin-like and caspase-like peptidase activity of the proteasome. Calpain and cathepsin inhibitor. Autophagy activator. Anticancer compound. Inhibits proliferation and migration of several tumor cell lines with nanomolar potency. Apoptosis inducer. Hello Bio HB4036
      Highly potent, selective, reversible and cell permeable proteasome inhibitor Hello Bio HB4036
      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, version: 14.00

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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