ChemSpider 2D Image | b-AP15 | C22H17N3O6

b-AP15

  • Molecular FormulaC22H17N3O6
  • Average mass419.387 Da
  • Monoisotopic mass419.111725 Da
  • ChemSpider ID4508454
  • Double-bond stereo - Double-bond stereo


More details:






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

(3E,5E)-1-Acryloyl-3,5-bis(4-nitrobenzyliden)-4-piperidinon [German] [ACD/IUPAC Name]
(3E,5E)-1-Acryloyl-3,5-bis(4-nitrobenzylidene)-4-piperidinone [ACD/IUPAC Name]
(3E,5E)-1-Acryloyl-3,5-bis(4-nitrobenzylidène)-4-pipéridinone [French] [ACD/IUPAC Name]
(3E,5E)-1-acryloyl-3,5-bis(4-nitrobenzylidene)piperidin-4-one
1009817-63-3 [RN]
4-Piperidinone, 3,5-bis[(4-nitrophenyl)methylene]-1-(1-oxo-2-propen-1-yl)-, (3E,5E)- [ACD/Index Name]
b-AP15
(3E,5E)-3,5-bis[(4-nitrophenyl)methylidene]-1-(prop-2-enoyl)piperidin-4-one
(3E,5E)-3,5-bis[(4-nitrophenyl)methylidene]-1-prop-2-enoylpiperidin-4-one
[1009817-63-3]
More...

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

CCRIS 4693 [DBID]
NSC687852 [DBID]
PubChem Substance ID 329825761 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 2228
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 2228
      no pictogram Axon Medchem 2228
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 2228
      Warning Axon Medchem 2228
    • Bio Activity:

      b-AP15(NSC687852) is a specific inhibitor of the deubiquitinating enzymes UCHL5 and Usp14 of the 26S proteasome. MedChem Express HY-13989, http://www.medchemexpress.com/nvp-tnks656.html
      b-AP15(NSC687852) is a specific inhibitor of the deubiquitinating enzymes UCHL5 and Usp14 of the 26S proteasome. It blocks the deubiquitinating activity of the 26S proteasome.;IC50 value: ;Target: UCHL5/Usp14;In vitro: b-AP15 abrogates the deubiquitinating activity of the 19S regulatory particle.b-AP15 inhibited the activity of two 19S regulatory-particle-associated deubiquitinases, ubiquitin C-terminal hydrolase 5 (UCHL5) and ubiquitin-specific peptidase 14 (USP14), resulting in accumulation of polyubiquitin. b-AP15 induced tumor cell apoptosis that was insensitive to TP53 status and overexpression of the apoptosis inhibitor BCL2 [1]. b-AP15 triggers time- and dose-dependent apoptosis of the human multiple myeloma (MM) cell lines RPMI8226 and U266, as determined by phosphatidylserine exposure. Apoptosis was dependent on caspase activation and was partially dependent on cathepsin D. Furthermore, b-AP15 triggered processing of pro-caspase-3 and cleavage of poly (ADP-ribose) polymera MedChem Express HY-13989
      Cell Cycle/DNA Damage MedChem Express HY-13989
      Cell Cycle/DNA Damage; MedChem Express HY-13989
      Deubiquitinase MedChem Express HY-13989
      Deubiquitinating Enzymes Tocris Bioscience 4566
      Enzymes Tocris Bioscience 4566
      Inhibitor of 19S regulatory particle associated deubiquitinating enzymes (DUBs), UCHL5 and USP14. Shows minimal inhibition of UCHL-1, UCHL-3, USP2, USP7, USP, BAP1 and proteasome activity. Induces apoptosis by cathepsin D-dependent caspase-cleavage (IC50 = 0.5 ?M). Displays antitumor activity in vivo. Tocris Bioscience 4566
      Inhibitor of 19S regulatory particle associated deubiquitinating enzymes (DUBs), UCHL5 and USP14. Shows minimal inhibition of UCHL-1, UCHL-3, USP2, USP7, USP, BAP1 and proteasome activity. Induces apoptosis by cathepsin D-dependent caspase-cleavage (IC50 = 0.5 muM). Displays antitumor activity in vivo. Tocris Bioscience 4566
      Inhibitor of 19S regulatory particle associated deubiquitylating enzymes (DUBs), UCHL5 and USP14. Shows minimal inhibition of UCHL-1, UCHL-3, USP2, USP7, USP, BAP1 and proteasome activity. Induces apo ptosis by cathepsin D-dependent caspase-cleavage (IC50 = 0.5 ?M). Displays antitumor activity in vivo. Tocris Bioscience 4566
      Inhibitor of UCHL5 and USP14 Tocris Bioscience 4566
      Proteases Tocris Bioscience 4566

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

Density: 1.4±0.1 g/cm3
Boiling Point: 670.4±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization: 98.5±3.0 kJ/mol
Flash Point: 359.3±31.5 °C
Index of Refraction: 1.702
Molar Refractivity: 114.7±0.3 cm3
#H bond acceptors: 9
#H bond donors: 0
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 4.24
ACD/LogD (pH 5.5): 3.49
ACD/BCF (pH 5.5): 263.56
ACD/KOC (pH 5.5): 1881.37
ACD/LogD (pH 7.4): 3.49
ACD/BCF (pH 7.4): 263.56
ACD/KOC (pH 7.4): 1881.37
Polar Surface Area: 129 Å2
Polarizability: 45.5±0.5 10-24cm3
Surface Tension: 69.9±3.0 dyne/cm
Molar Volume: 296.1±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) =  3.19

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  596.21  (Adapted Stein & Brown method)
    Melting Pt (deg C):  257.54  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.68E-013  (Modified Grain method)
    Subcooled liquid VP: 9.26E-011 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):  1.8
       log Kow used: 3.19 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.32403 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Ketones
       Acrylamides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.35E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.216E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.19  (KowWin est)
  Log Kaw used:  -17.258  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.448
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1548
   Biowin2 (Non-Linear Model)     :   0.0033
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8565  (months      )
   Biowin4 (Primary Survey Model) :   3.2091  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.5302
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.9229
 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):  1.23E-008 Pa (9.26E-011 mm Hg)
  Log Koa (Koawin est  ): 20.448
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  243 
       Octanol/air (Koa) model:  6.89E+007 
   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 =  93.1520 E-12 cm3/molecule-sec
      Half-Life =     0.115 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.378 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    27.474998 E-17 cm3/molecule-sec
      Half-Life =     0.042 Days (at 7E11 mol/cm3)
      Half-Life =      1.001 Hrs
   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    :  8.136E+004
      Log Koc:  4.910 

 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 = 1.753 (BCF = 56.56)
       log Kow used: 3.19 (estimated)

 Volatilization from Water:
    Henry LC:  1.35E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.882E+015  hours   (3.701E+014 days)
    Half-Life from Model Lake : 9.689E+016  hours   (4.037E+015 days)

 Removal In Wastewater Treatment:
    Total removal:               7.67  percent
    Total biodegradation:        0.14  percent
    Total sludge adsorption:     7.53  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       1.13e-008       0.734        1000       
   Water     9.96            1.44e+003    1000       
   Soil      89.6            2.88e+003    1000       
   Sediment  0.395           1.3e+004     0          
     Persistence Time: 2.75e+003 hr




                    

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