ChemSpider 2D Image | tolcapone | C14H11NO5

tolcapone

  • Molecular FormulaC14H11NO5
  • Average mass273.241 Da
  • Monoisotopic mass273.063721 Da
  • ChemSpider ID3848682

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

(3,4-Dihydroxy-5-nitrophenyl)(4-methylphenyl)methanon [German] [ACD/IUPAC Name]
(3,4-Dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone [ACD/IUPAC Name]
(3,4-Dihydroxy-5-nitrophényl)(4-méthylphényl)méthanone [French] [ACD/IUPAC Name]
134308-13-7 [RN]
6873
CIF6334OLY
Methanone, (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)- [ACD/Index Name]
tolcapone [Wiki]
tolcapone [INN_en]
(3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)-methanone
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:63630 [DBID]
C07949 [DBID]
CCRIS 7904 [DBID]
D00786 [DBID]
LS-91226 [DBID]
PubChem Substance ID 329831176 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      GHS09 Biosynth Q-201841
      H410 Biosynth Q-201841
      N04BX01 Wikidata Q413840
      P273; P501 Biosynth Q-201841
      Warning Biosynth Q-201841
    • Chemical Class:

      Benzophenone substituted on one of the phenyl rings at C-3 and C-4 by hydroxy groups and at C-5 by a nitro group, and on the other phenyl ring by a methyl group at C-4. It is an inhibitor of catechol <element>O</element>-methyltransferase. ChEBI CHEBI:63630
    • Therapeutical Effect:

      Antiparkinson Agents,Enzyme Inhibitors Sean Ekins
    • Drug Status:

      withdrawn BIONET-Key Organics KS-1314
    • Bio Activity:

      Catechol O-Methyltransferase Tocris Bioscience 5864
      COMT MedChem Express HY-17406
      COMT inhibitor. Inhibits both brain and peripheral COMT. Also binds transthyretin (TTR) with high affinity (Kd1 and Kd2 values are 21 and 58 nM, respectively). Inhibits TTR aggregation in human plasma and prevents TTR-induced cytotoxicity in vitro. Stabilizes TTR in mice and humans in vivo. Orally bioavailable. Tocris Bioscience 5864
      COMT inhibitor; also inhibits transthyretin aggregation Tocris Bioscience 5864
      Enzymes Tocris Bioscience 5864
      Others MedChem Express HY-17406
      Tolcapone(Ro 40-7592) is an orally active selective, potent catechol-O-methyltransferase (COMT) inhibitor. MedChem Express HY-17406, http://www.medchemexpress.com/terbinafine.html
      Tolcapone(Ro 40-7592) is an orally active selective, potent catechol-O-methyltransferase (COMT) inhibitor. ;IC50 value:;Target: COMT;Tolcapone inhibits both central and peripheral COMT. Tolcapone caused a rapid and reversible inhibition of COMT activity in erythrocytes in parallel with a dose-dependent decrease in the formation of 3-OMD. Tolcapone increased the area under the concentration-time curve and elimination half-life of levodopa. Tolcapone crosses the blood-brain barrier, and has been used for L-DOPA adjunct therapy in the treatment of Parkinson's disease. MedChem Express HY-17406
      Transferases Tocris Bioscience 5864
  • Gas Chromatography

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

Density: 1.4±0.1 g/cm3
Boiling Point: 485.6±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 78.0±3.0 kJ/mol
Flash Point: 205.7±17.2 °C
Index of Refraction: 1.661
Molar Refractivity: 71.2±0.3 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 4.07
ACD/LogD (pH 5.5): 2.92
ACD/BCF (pH 5.5): 71.44
ACD/KOC (pH 5.5): 511.85
ACD/LogD (pH 7.4): 1.22
ACD/BCF (pH 7.4): 1.41
ACD/KOC (pH 7.4): 10.13
Polar Surface Area: 103 Å2
Polarizability: 28.2±0.5 10-24cm3
Surface Tension: 66.6±3.0 dyne/cm
Molar Volume: 192.5±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) =  3.13

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  441.87  (Adapted Stein & Brown method)
    Melting Pt (deg C):  185.44  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.96E-010  (Modified Grain method)
    Subcooled liquid VP: 2.83E-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):  37.22
       log Kow used: 3.13 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  254.23 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.90E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.757E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.13  (KowWin est)
  Log Kaw used:  -10.926  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.056
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6055
   Biowin2 (Non-Linear Model)     :   0.1917
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4412  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3338  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0486
   Biowin6 (MITI Non-Linear Model):   0.0072
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5528
 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):  3.77E-006 Pa (2.83E-008 mm Hg)
  Log Koa (Koawin est  ): 14.056
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.795 
       Octanol/air (Koa) model:  27.9 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.966 
       Mackay model           :  0.985 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   5.9012 E-12 cm3/molecule-sec
      Half-Life =     1.812 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    21.750 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.975 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5501
      Log Koc:  3.740 

 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 = 0.870 (BCF = 7.407)
       log Kow used: 3.13 (estimated)

 Volatilization from Water:
    Henry LC:  2.9E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.337E+009  hours   (1.391E+008 days)
    Half-Life from Model Lake : 3.641E+010  hours   (1.517E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               6.96  percent
    Total biodegradation:        0.13  percent
    Total sludge adsorption:     6.83  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       8.82e-005       43.5         1000       
   Water     12.4            900          1000       
   Soil      87.2            1.8e+003     1000       
   Sediment  0.379           8.1e+003     0          
     Persistence Time: 1.8e+003 hr




                    

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