ChemSpider 2D Image | (E)-entacapone | C14H15N3O5

(E)-entacapone

  • Molecular FormulaC14H15N3O5
  • Average mass305.286 Da
  • Monoisotopic mass305.101166 Da
  • ChemSpider ID4444537
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

(E)-entacapone
(2E)-2-Cyan-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylacrylamid [German] [ACD/IUPAC Name]
(2E)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylacrylamide [ACD/IUPAC Name]
(2E)-2-Cyano-3-(3,4-dihydroxy-5-nitrophényl)-N,N-diéthylacrylamide [French] [ACD/IUPAC Name]
(2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide
(E)-2-Cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide
(E)-a-Cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide
130929-57-6 [RN]
2-Propenamide, 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-, (2E)- [ACD/Index Name]
Entacapona [Spanish] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

4975G9NM6T [DBID]
C07943 [DBID]
COM-998 [DBID]
D00781 [DBID]
LS-123327 [DBID]
OR 611 [DBID]
OR-611 [DBID]
UNII:4975G9NM6T [DBID]
UNII-4975G9NM6T [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      N04BX02 Wikidata Q416444
    • Target Organs:

      COMT inhibitor TargetMol T2216, T3083
      Histone Methyltransferase inhibitor TargetMol T2216, T3083
    • Chemical Class:

      A monocarboxylic acid amide that is <element>N</element>,<element>N</element>-diethylprop-2-enamide in which the hydrogen at position 2 is substituted by a cyano group and the hydrogen at the 3<stereo >E</stereo> position is substituted by a 3,4-dihydroxy-5-nitrophenyl group. ChEBI CHEBI:4798
    • Therapeutical Effect:

      Antiparkinson Agents,Enzyme Inhibitors Sean Ekins
    • Bio Activity:

      Catechol O-Methyltransferase Tocris Bioscience 4720
      catechol-O-methyl transferase TargetMol T2216, T3083
      Chromatin/Epigenetic TargetMol T2216, T3083
      COMT MedChem Express HY-14280
      COMT TargetMol T2216, T3083
      Entacapone is a specific, potent, peripherally acting catechol-O-methyltransferase (COMT) inhibitor with IC50 of 151 nM for PD treatment. MedChem Express
      Enzymes Tocris Bioscience 4720
      Neuroscience TargetMol T2216, T3083
      Potent catechol O-methyltransferase (COMT) inhibitor (IC50 values are 14.3, 20.1 and 73.3 nM for rat liver soluble COMT, total COMT and membrane-bound COMT respectively). Increases bioavailability of levodopa when given as an adjunct therapy for Parkinson's disease. Inhibits ?-synuclein aggregation in an in vitro assay; blocks ?-synuclein-induced cell death in PC-12 cells. Tocris Bioscience 4720
      Potent catechol O-methyltransferase (COMT) inhibitor (IC50 values are 14.3, 20.1 and 73.3 nM for rat liver soluble COMT, total COMT and membrane-bound COMT respectively). Increases bioavailability of levodopa when given as an adjunct therapy for Parkinson's disease. Inhibits ?-synuclein aggregation in an in vitro assay; blocks ?-synuclein-induced cell death in PC-12 cells. Tocris Bioscience 4720
      Potent catechol O-methyltransferase (COMT) inhibitor (IC50 values are 14.3, 20.1 and 73.3 nM for rat liver soluble COMT, total COMT and membrane-bound COMT respectively). Increases bioavailability of levodopa when given as an adjunct therapy for Parkinson's disease. Inhibits alpha-synuclein aggregation in an in vitro assay; blocks alpha-synuclein-induced cell death in PC-12 cells. Tocris Bioscience 4720
      Potent COMT inhibitor; blocks ?-synuclein aggregation Tocris Bioscience 4720
      Potent COMT inhibitor; blocks alpha-synuclein aggregation Tocris Bioscience 4720
      Transferases Tocris Bioscience 4720

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

Density: 1.4±0.1 g/cm3
Boiling Point: 526.6±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 83.1±3.0 kJ/mol
Flash Point: 272.3±30.1 °C
Index of Refraction: 1.642
Molar Refractivity: 79.1±0.3 cm3
#H bond acceptors: 8
#H bond donors: 2
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 2.38
ACD/LogD (pH 5.5): 1.60
ACD/BCF (pH 5.5): 7.89
ACD/KOC (pH 5.5): 118.84
ACD/LogD (pH 7.4): -0.04
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 2.73
Polar Surface Area: 130 Å2
Polarizability: 31.4±0.5 10-24cm3
Surface Tension: 68.2±3.0 dyne/cm
Molar Volume: 219.2±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) =  2.22

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  507.37  (Adapted Stein & Brown method)
    Melting Pt (deg C):  216.04  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.25E-012  (Modified Grain method)
    Subcooled liquid VP: 3.53E-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):  78.35
       log Kow used: 2.22 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  16400 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Allylic/Vinyl Nitriles
       Phenols
       Acrylamides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.76E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.666E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.22  (KowWin est)
  Log Kaw used:  -16.559  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.779
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0459
   Biowin2 (Non-Linear Model)     :   0.9951
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3311  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5185  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0653
   Biowin6 (MITI Non-Linear Model):   0.0044
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1560
 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):  4.71E-008 Pa (3.53E-010 mm Hg)
  Log Koa (Koawin est  ): 18.779
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  63.7 
       Octanol/air (Koa) model:  1.48E+006 
   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 =  30.0245 E-12 cm3/molecule-sec
      Half-Life =     0.356 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     4.275 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.105000 E-17 cm3/molecule-sec
      Half-Life =    10.914 Days (at 7E11 mol/cm3)
   Reaction With Nitrate Radicals May Be Important!
   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    :  5159
      Log Koc:  3.713 

 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 = 1.012 (BCF = 10.29)
       log Kow used: 2.22 (estimated)

 Volatilization from Water:
    Henry LC:  6.76E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.513E+015  hours   (6.305E+013 days)
    Half-Life from Model Lake : 1.651E+016  hours   (6.879E+014 days)

 Removal In Wastewater Treatment:
    Total removal:               2.51  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.41  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       2.15e-008       8.28         1000       
   Water     19.4            900          1000       
   Soil      80.5            1.8e+003     1000       
   Sediment  0.1             8.1e+003     0          
     Persistence Time: 1.53e+003 hr




                    

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