ChemSpider 2D Image | Tacedinaline | C15H15N3O2

Tacedinaline

  • Molecular FormulaC15H15N3O2
  • Average mass269.298 Da
  • Monoisotopic mass269.116425 Da
  • ChemSpider ID2644

More details:






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

Tacedinaline [INN] [USAN]
112522-64-2 [RN]
4-(Acetylamino)-N-(2-aminophenyl)benzamide
4-Acetamido-N-(2-aminophenyl)benzamid [German] [ACD/IUPAC Name]
4-Acetamido-N-(2-aminophenyl)benzamide [ACD/IUPAC Name]
4-Acétamido-N-(2-aminophényl)benzamide [French] [ACD/IUPAC Name]
4-acetylamino-n-(2'-aminophenyl)benzamide
acetyldinaline
Benzamide, 4-(acetylamino)-N-(2-aminophenyl)- [ACD/Index Name]
MFCD00866266 [MDL number]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

8328 [DBID]
CI-994 [DBID]
GOE 5549 [DBID]
PD 123654 [DBID]
UMF554N5FG [DBID]
Acetyldinaline;Tacedinaline;PD 123654;Goe 5549;CI 994;CI994 [DBID]
C.I. 994 [DBID]
D05988 [DBID]
GOE-5549 [DBID]
PD-123654 [DBID]
More...
  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 2014
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 2014
      no pictogram Axon Medchem 2014
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 2014
      Warning Axon Medchem 2014
    • Target Organs:

      HDAC inhibitor TargetMol T1888
    • Chemical Class:

      A benzamide obtained by formal condensation of the carboxy group of 4-acetamidobenzoic acid with one of the amino groups of 1,2-phenylenediamine. An oral cytostatic drug with impressive differential a ctivity against leukemic cells and normal stem-cells. Also used in combination therapy for selected tumors including non-smoll cell lung, pancreatic, breast, and colorectal cancers. ChEBI CHEBI:90195, https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:90195
    • Bio Activity:

      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB1385]
      Cell Cycle/DNA Damage MedChem Express HY-50934
      Cell Cycle/DNA Damage; MedChem Express HY-50934
      Chromatin/Epigenetic TargetMol T1888
      CI-994 (Tacedinaline) is an anti-cancer drug which inhibits HDAC1 with IC50 of 0.57 ?M and causes G1 cell cycle arrest. MedChem Express HY-50934
      Class I histone deacetylase inhibitor; orally active Tocris Bioscience 2952
      Deacetylases Tocris Bioscience 2952
      Enzymes Tocris Bioscience 2952
      Enzymes/Deacetylase/Histone deacetylase (HDAC) Hello Bio [HB1385]
      HDAC MedChem Express HY-50934
      HDAC1 TargetMol T1888
      Histone Deacetylases Tocris Bioscience 2952
      Orally active class I histone deacetylase (HDAC) inhibitor (Ki values are 0.41, 0.75, >100 and >100 ?M for HDAC1, HDAC3, HDAC6 and HDAC8 respectively). Mediates G1 cell cycle arrest, inhibits prolifer ation and induces apoptosis in vitro and in vivo. Increases neuroplasticity during memory extinction. Tocris Bioscience 2952
      Orally active class I histone deacetylase (HDAC) inhibitor (Ki values are 0.41, 0.75, >100 and >100 ?M for HDAC1, HDAC3, HDAC6 and HDAC8 respectively). Mediates G1 cell cycle arrest, inhibits proliferation and induces apoptosis in vitro and in vivo. Increases neuroplasticity during memory extinction. Tocris Bioscience 2952
      Orally active class I histone deacetylase (HDAC) inhibitor (Ki values are 0.41, 0.75, >100 and >100 muM for HDAC1, HDAC3, HDAC6 and HDAC8 respectively). Mediates G1 cell cycle arrest, inhibits proliferation and induces apoptosis in vitro and in vivo. Increases neuroplasticity during memory extinction. Tocris Bioscience 2952
      Potent and selective histone deacetylase (HDAC) inhibitor. Inhibits HDAC1, 3, 6 and 8 (IC<sub>50</sub> values are 0.41, 0.75, >100 and >100 &micro;M respectively). Induces histone H3 hyperacetylation and cell differentiation. Shows anti-proliferative and apoptotic actions. Cell-permeable. Hello Bio [HB1385]
      Potent, selective HDAC inhibitor Hello Bio [HB1385]

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

Density: 1.3±0.1 g/cm3
Boiling Point: 450.6±30.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 71.0±3.0 kJ/mol
Flash Point: 226.3±24.6 °C
Index of Refraction: 1.707
Molar Refractivity: 79.3±0.3 cm3
#H bond acceptors: 5
#H bond donors: 4
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 0.96
ACD/LogD (pH 5.5): 1.16
ACD/BCF (pH 5.5): 4.44
ACD/KOC (pH 5.5): 100.54
ACD/LogD (pH 7.4): 1.17
ACD/BCF (pH 7.4): 4.53
ACD/KOC (pH 7.4): 102.70
Polar Surface Area: 84 Å2
Polarizability: 31.5±0.5 10-24cm3
Surface Tension: 64.2±3.0 dyne/cm
Molar Volume: 203.7±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) =  1.19

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  540.50  (Adapted Stein & Brown method)
    Melting Pt (deg C):  231.52  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.53E-011  (Modified Grain method)
    Subcooled liquid VP: 2.55E-009 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):  1777
       log Kow used: 1.19 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  16.909 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.84E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.051E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.19  (KowWin est)
  Log Kaw used:  -13.494  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.684
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8059
   Biowin2 (Non-Linear Model)     :   0.9346
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3607  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7617  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0727
   Biowin6 (MITI Non-Linear Model):   0.0236
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.4205
 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):  3.4E-007 Pa (2.55E-009 mm Hg)
  Log Koa (Koawin est  ): 14.684
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  8.82 
       Octanol/air (Koa) model:  119 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.997 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  67.7327 E-12 cm3/molecule-sec
      Half-Life =     0.158 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.895 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.998 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  827.3
      Log Koc:  2.918 

 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 = 0.216 (BCF = 1.644)
       log Kow used: 1.19 (estimated)

 Volatilization from Water:
    Henry LC:  7.84E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.226E+012  hours   (5.106E+010 days)
    Half-Life from Model Lake : 1.337E+013  hours   (5.571E+011 days)

 Removal In Wastewater Treatment:
    Total removal:               1.91  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.82  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       5.22e-006       3.79         1000       
   Water     38.2            900          1000       
   Soil      61.7            1.8e+003     1000       
   Sediment  0.0846          8.1e+003     0          
     Persistence Time: 1.09e+003 hr




                    

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