ChemSpider 2D Image | Entinostat | C21H20N4O3


  • Molecular FormulaC21H20N4O3
  • Average mass376.409 Da
  • Monoisotopic mass376.153534 Da
  • ChemSpider ID4111

More details:

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

((4-(((2-Aminophenyl)amino)carbonyl)phenyl)methyl)carbamic Acid 3-Pyridinylmethyl Ester
{4-[(2-Aminophényl)carbamoyl]benzyl}carbamate de 3-pyridinylméthyle [French] [ACD/IUPAC Name]
209783-80-2 [RN]
3-pyridinylmethyl [[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]carbamate
3-Pyridinylmethyl {4-[(2-aminophenyl)carbamoyl]benzyl}carbamate [ACD/IUPAC Name]
3-Pyridinylmethyl-{4-[(2-aminophenyl)carbamoyl]benzyl}carbamat [German] [ACD/IUPAC Name]
Carbamic acid, N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-, 3-pyridinylmethyl ester [ACD/Index Name]
entinostat [French] [INN]

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

MS 27-275 [DBID]
MS-27-275 [DBID]
MS-275 [DBID]
MS 275 [DBID]
MS275 [DBID]
NCI60_038022 [DBID]
NSC706995 [DBID]
NSC-706995 [DBID]
  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1803
      GHS07 Biosynth W-201831
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1803
      H315; H319; H335 Biosynth W-201831
      H319, H314, H314 LKT Labs [E5477]
      no pictogram Axon Medchem 1803
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1803
      P261; P305+P351+P338 Biosynth W-201831
      R36/37/38 LKT Labs [E5477]
      Warning Biosynth W-201831
      Warning Axon Medchem 1803
      Xi LKT Labs [E5477]
    • Chemical Class:

      A member of the class of benzamides resulting from the formal condensation of the carboxy group of the pyridin-3-ylmethyl carbamate derivative of <ital>p</ital>-(aminomethyl)benzoic acid with one of t he amino groups of benzene-1,2-diamine. It is an inhibitor of histone deacetylase isoform 1 (HDAC1) and isoform 3 (HDAC3). ChEBI CHEBI:132082
    • Bio Activity:

      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB3983]
      Cell Cycle/DNA Damage MedChem Express HY-12163
      Cell Cycle/DNA Damage; MedChem Express HY-12163
      Class I HDAC inhibitor (IC50 values are 0.18, 0.74, 44.9 and >100 muM for HDAC1, 3, 8 and 6, respectively). Exhibits antiproliferative effects and induces apoptosis in a range of tumor cell lines in vitro and in vivo. Increases estrogen receptor alpha- and aromatase expression in breast cancer cells. Inhibits PCB-induced neuronal cell death by preventing HDAC3 binding and histone deacetylation within the synapsin-1 promoter. Tocris Bioscience 6208
      Deacetylases Tocris Bioscience 6208
      Entinostat (MS-275; SNDX 275) strongly inhibits HDAC1 and HDAC3 with IC50 of 0.51 ?M and 1.7 ?M.; IC50 Value: 0.51 ?M(HDAC1); 1.7 ?M(HDAC3); Target: HDAC1/3; in vitro: MS-275 shows inhibitory to HDACs by 2'-amino group. MedChem Express HY-12163
      Enzymes Tocris Bioscience 6208
      Enzymes/Deacetylase/Histone deacetylase (HDAC) Hello Bio [HB3983]
      HDAC MedChem Express HY-12163
      HDAC (Class I) inhibitor Tocris Bioscience 6208
      HDAC 1 inhibitor Hello Bio [HB3983]
      HDAC 1 inhibitor. Antitumor compound. Antiproliferative. TGF-beta type II receptor inducer. Apoptosis inducer. Anti-inflammatory. Angiogenesis inhibitor. Promotes either self-renewal or differentiation of embryonic stem cells. Hello Bio [HB3983]
      Histone Deacetylases Tocris Bioscience 6208

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

Density: 1.3±0.1 g/cm3
Boiling Point: 566.7±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 85.1±3.0 kJ/mol
Flash Point: 296.6±30.1 °C
Index of Refraction: 1.672
Molar Refractivity: 107.2±0.3 cm3
#H bond acceptors: 7
#H bond donors: 4
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 1.46
ACD/LogD (pH 5.5): 1.86
ACD/BCF (pH 5.5): 14.92
ACD/KOC (pH 5.5): 232.67
ACD/LogD (pH 7.4): 1.92
ACD/BCF (pH 7.4): 16.82
ACD/KOC (pH 7.4): 262.36
Polar Surface Area: 106 Å2
Polarizability: 42.5±0.5 10-24cm3
Surface Tension: 63.6±3.0 dyne/cm
Molar Volume: 286.1±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) =  2.27

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  593.33  (Adapted Stein & Brown method)
    Melting Pt (deg C):  256.19  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.31E-013  (Modified Grain method)
    Subcooled liquid VP: 1.1E-010 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):  978.3
       log Kow used: 2.27 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  91.275 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aromatic Amines

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.41E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.676E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.27  (KowWin est)
  Log Kaw used:  -17.415  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.685
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4697
   Biowin2 (Non-Linear Model)     :   0.1015
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9173  (months      )
   Biowin4 (Primary Survey Model) :   3.5766  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.5285
   Biowin6 (MITI Non-Linear Model):   0.0005
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5284
 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):  1.47E-008 Pa (1.1E-010 mm Hg)
  Log Koa (Koawin est  ): 19.685
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  205 
       Octanol/air (Koa) model:  1.19E+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 =  75.8362 E-12 cm3/molecule-sec
      Half-Life =     0.141 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.692 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    :  5.447E+004
      Log Koc:  4.736 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.921E-003  L/mol-sec
  Kb Half-Life at pH 8:       7.518  years  
  Kb Half-Life at pH 7:      75.178  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.050 (BCF = 11.22)
       log Kow used: 2.27 (estimated)

 Volatilization from Water:
    Henry LC:  9.41E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.207E+016  hours   (5.03E+014 days)
    Half-Life from Model Lake : 1.317E+017  hours   (5.487E+015 days)

 Removal In Wastewater Treatment:
    Total removal:               2.59  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.49  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       8.36e-009       3.38         1000       
   Water     18              1.44e+003    1000       
   Soil      81.9            2.88e+003    1000       
   Sediment  0.103           1.3e+004     0          
     Persistence Time: 2.16e+003 hr


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