ChemSpider 2D Image | SMI 4a | C11H6F3NO2S

SMI 4a

  • Molecular FormulaC11H6F3NO2S
  • Average mass273.231 Da
  • Monoisotopic mass273.007141 Da
  • ChemSpider ID1139805
  • Double-bond stereo - Double-bond stereo


More details:






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

(5Z)-5-[[3-(Trifluoromethyl)phenyl]methylene]-2,4-thiazolidinedione
(5Z)-5-[3-(Trifluormethyl)benzyliden]-1,3-thiazolidin-2,4-dion [German] [ACD/IUPAC Name]
(5Z)-5-[3-(Trifluoromethyl)benzylidene]-1,3-thiazolidine-2,4-dione [ACD/IUPAC Name]
(5Z)-5-[3-(Trifluorométhyl)benzylidène]-1,3-thiazolidine-2,4-dione [French] [ACD/IUPAC Name]
(Z)-5-(3-Trifluoromethylbenzylidene)thiazolidine-2,4-dione
2,4-Thiazolidinedione, 5-[[3-(trifluoromethyl)phenyl]methylene]-, (5Z)- [ACD/Index Name]
438190-29-5 [RN]
MFCD01152003
SMI 4a
SMI-4a
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

PubChem Substance ID 329825761 [DBID]
ZINC01204064 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1923
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1923
      no pictogram Axon Medchem 1923
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1923
      Warning Axon Medchem 1923
    • Bio Activity:

      Enzymes Tocris Bioscience 3714
      JAK/STAT Signaling MedChem Express HY-16576A
      JAK/STAT Signaling; MedChem Express HY-16576A
      Kinases Tocris Bioscience 3714
      Pim MedChem Express HY-16576A
      Pim Kinase Tocris Bioscience 3714
      Selective, ATP-competitive Pim kinase inhibitor Tocris Bioscience 3714
      Selective, ATP-competitive Pim kinase inhibitor (IC50 values are 24 and 100 nM for Pim-1 and Pim-2 respectively). Displays selectivity over a panel of ~50 other kinases tested. Exhibits cytotoxicity i n PC3 prostate carcinoma cells in vitro (IC50 = 17 ?M). Tocris Bioscience 3714
      Selective, ATP-competitive Pim kinase inhibitor (IC50 values are 24 and 100 nM for Pim-1 and Pim-2 respectively). Displays selectivity over a panel of ~50 other kinases tested. Exhibits cytotoxicity in PC3 prostate carcinoma cells in vitro (IC50 = 17 ?M). Tocris Bioscience 3714
      Selective, ATP-competitive Pim kinase inhibitor (IC50 values are 24 and 100 nM for Pim-1 and Pim-2 respectively). Displays selectivity over a panel of ~50 other kinases tested. Exhibits cytotoxicity in PC3 prostate carcinoma cells in vitro (IC50 = 17 muM). Tocris Bioscience 3714
      SMI-4a is a selective ATP-competitive Pim-1 kinase inhibitor with an IC50 of 21 nM for Pim-1 compared to an IC50 of 100 nM for Pim-2 and with little or no activity against a panel of 50 other kinases tested.; IC50 value: 21 nM (Pim1); 100 nM (Pim2) [1]; Target: Pim-1; in vitro: Incubation of pre-T-LBL cells with SMI-4a induced G1 phase cell-cycle arrest secondary to a dose-dependent induction of p27(Kip1), apoptosis through the mitochondrial pathway, and inhibition of the mammalian target of rapamycin C1 (mTORC1) pathway based on decreases in phospho-p70 S6K and phospho-4E-BP1, 2 substrates of this enzyme. MedChem Express HY-16576A
      SMI-4a is a selective ATP-competitive Pim-1 kinase inhibitor with an IC50 of 21 nM for Pim-1 compared to an IC50 of 100 nM for Pim-2 and with little or no activity against a panel of 50 other kinases tested.;IC50 value: 21 nM (Pim1); 100 nM (Pim2) [1];Target: Pim-1;In vitro: Incubation of pre-T-LBL cells with SMI-4a induced G1 phase cell-cycle arrest secondary to a dose-dependent induction of p27(Kip1), apoptosis through the mitochondrial pathway, and inhibition of the mammalian target of rapamycin C1 (mTORC1) pathway based on decreases in phospho-p70 S6K and phospho-4E-BP1, 2 substrates of this enzyme. In addition, treatment of these cells with SMI-4a was found to induce phosphorylation of extracellular signal-related kinase1/2 (ERK1/2), and the combination of SMI-4a and a mitogen-activated protein kinase kinase 1/2 (MEK1/2) inhibitor was highly synergistic in killing pre-T-LBL cells [1]. Ectopic expression of phosphomimetic mutants of eIF4B conferred resistance to apoptosis by t MedChem Express HY-16576A

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

Density: 1.5±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.602
Molar Refractivity: 61.2±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 2.30
ACD/LogD (pH 5.5): 2.03
ACD/BCF (pH 5.5): 20.48
ACD/KOC (pH 5.5): 301.02
ACD/LogD (pH 7.4): 1.73
ACD/BCF (pH 7.4): 10.19
ACD/KOC (pH 7.4): 149.76
Polar Surface Area: 71 Å2
Polarizability: 24.3±0.5 10-24cm3
Surface Tension: 48.6±3.0 dyne/cm
Molar Volume: 178.5±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) =  2.71

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  486.78  (Adapted Stein & Brown method)
    Melting Pt (deg C):  206.42  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.09E-010  (Modified Grain method)
    Subcooled liquid VP: 5.92E-008 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):  85.17
       log Kow used: 2.71 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  38.761 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.07E-007  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.993E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.71  (KowWin est)
  Log Kaw used:  -4.431  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.141
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.0970
   Biowin2 (Non-Linear Model)     :   0.0014
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0824  (months      )
   Biowin4 (Primary Survey Model) :   3.1791  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0095
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.3808
 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):  7.89E-006 Pa (5.92E-008 mm Hg)
  Log Koa (Koawin est  ): 7.141
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.38 
       Octanol/air (Koa) model:  3.4E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.932 
       Mackay model           :  0.968 
       Octanol/air (Koa) model:  0.000272 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  30.7835 E-12 cm3/molecule-sec
      Half-Life =     0.347 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     4.170 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     2.100000 E-17 cm3/molecule-sec
      Half-Life =     0.546 Days (at 7E11 mol/cm3)
      Half-Life =     13.097 Hrs
   Fraction sorbed to airborne particulates (phi): 0.95 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1706
      Log Koc:  3.232 

 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 = 1.386 (BCF = 24.3)
       log Kow used: 2.71 (estimated)

 Volatilization from Water:
    Henry LC:  9.07E-007 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:       1069  hours   (44.53 days)
    Half-Life from Model Lake :  1.18E+004  hours   (491.5 days)

 Removal In Wastewater Treatment:
    Total removal:               3.91  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.75  percent
    Total to Air:                0.05  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.127           5.1          1000       
   Water     17.1            1.44e+003    1000       
   Soil      82.6            2.88e+003    1000       
   Sediment  0.223           1.3e+004     0          
     Persistence Time: 1.57e+003 hr




                    

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