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ChemSpider 2D Image | Vorapaxar | C29H33FN2O4

Vorapaxar

  • Molecular FormulaC29H33FN2O4
  • Average mass492.582 Da
  • Monoisotopic mass492.242432 Da
  • ChemSpider ID8252668
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 7 of 7 defined stereocentres


More details:



Featured data source



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

[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-{(E)-2-[5-(3-Fluorophényl)-2-pyridinyl]vinyl}-1-méthyl-3-oxododécahydronaphto[2,3-c]furan-6-yl]carbamate d'éthyle [French] [ACD/IUPAC Name]
618385-01-6 [RN]
8852
Carbamic acid, [(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(1E)-2-[5-(3-fluorophenyl)-2- pyridinyl]ethenyl]dodecahydro-1-methyl-3-oxonaphtho[2,3-c]furan-6-yl]-, ethyl ester
Carbamic acid, N-[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(E)-2-[5-(3-fluorophenyl)-2-pyridinyl]ethenyl]dodecahydro-1-methyl-3-oxonaphtho[2,3-c]furan-6-yl]-, ethyl ester [ACD/Index Name]
Ethyl [(1R,3aR,4aR,6R,8aR,9S,9aS)-9-{(E)-2-[5-(3-fluorophenyl)-2-pyridinyl]vinyl}-1-methyl-3-oxododecahydronaphtho[2,3-c]furan-6-yl]carbamate [ACD/IUPAC Name]
ethyl [(1R,3aR,4aR,6R,8aR,9S,9aS)-9-{(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl}-1-methyl-3-oxododecahydronaphtho[2,3-c]furan-6-yl]carbamate
Ethyl [(1R,3aR,4aR,6R,8aR,9S,9aS)-9-{(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]vinyl}-1-methyl-3-oxododecahydronaphtho[2,3-c]furan-6-yl]carbamate
Ethyl-[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-{(E)-2-[5-(3-fluorphenyl)-2-pyridinyl]vinyl}-1-methyl-3-oxododecahydronaphtho[2,3-c]furan-6-yl]carbamat [German] [ACD/IUPAC Name]
UNII-ZCE93644N2
More...

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

SCH 530348 [DBID]
SCH-530348 [DBID]
TRA-SCH 530348 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1755
      B01AC26 Wikidata Q7941753
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1755
      no pictogram Axon Medchem 1755
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1755
      Warning Axon Medchem 1755
    • Chemical Class:

      A carbamate ester that is the ethyl ester of [(1<stereo>R</stereo>,3a<stereo>R</stereo>,4a<stereo>R</stereo>,6<stereo>R</stereo>,8a<stereo>R</stereo>,9<stereo>S</stereo>,9a<stereo>S</stereo>)-9-{(<ste reo>E</stereo>)-2-[5-(3-fluorophenyl)pyridin-2-yl]ethynyl}-1-methyl-3-oxododecahydronaphtho[2,3-<ital>c</ital>]furan-6-yl]carbamic acid. A protease-activated receptor-1 antagonist used (as its sulfate salt) for the reduction of thrombotic cardiovascular events in patients with a history of myocardial infarction (MI) or with peripheral arterial disease. It has been shown to reduce the rate of a com bined endpoint of cardiovascular death, MI, stroke and urgent coronary revascularisation. ChEBI CHEBI:82702
    • Bio Activity:

      GPCR/G protein; MedChem Express HY-10119
      Protease-Activated Receptors(PARs) MedChem Express HY-10119
      Vorapaxar is a thrombin receptor (protease-activated receptor, PAR-1) antagonist.;Target: PAR-1Vorapaxar is an oral protease-activated receptor antagonist, is a novel antiplatelet drug that has been recently approved to provide further risk reduction. Vorapaxar has a high bioavailability after oral administration of >90% with a half-life of 126 h-296 h. It binds reversibly to a PAR-1; however, it slowly dissociates making it functionally irreversible. Vorapaxar is a potential antithrombotic drug. MedChem Express HY-10119

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

Density: 1.3±0.1 g/cm3
Boiling Point: 676.0±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 99.3±3.0 kJ/mol
Flash Point: 362.6±31.5 °C
Index of Refraction: 1.594
Molar Refractivity: 133.7±0.4 cm3
#H bond acceptors: 6
#H bond donors: 1
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 4.54
ACD/LogD (pH 5.5): 4.75
ACD/BCF (pH 5.5): 2390.70
ACD/KOC (pH 5.5): 9053.29
ACD/LogD (pH 7.4): 4.76
ACD/BCF (pH 7.4): 2451.45
ACD/KOC (pH 7.4): 9283.33
Polar Surface Area: 78 Å2
Polarizability: 53.0±0.5 10-24cm3
Surface Tension: 53.1±5.0 dyne/cm
Molar Volume: 394.2±5.0 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) =  5.21

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  613.44  (Adapted Stein & Brown method)
    Melting Pt (deg C):  265.59  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.55E-014  (Modified Grain method)
    Subcooled liquid VP: 3.28E-011 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):  0.02818
       log Kow used: 5.21 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.015778 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.76E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.737E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.21  (KowWin est)
  Log Kaw used:  -12.948  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.158
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.1978
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5830  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.5544  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1830
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4969
 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):  4.37E-009 Pa (3.28E-011 mm Hg)
  Log Koa (Koawin est  ): 18.158
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  686 
       Octanol/air (Koa) model:  3.53E+005 
   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 = 111.7624 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 119.3624 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.148 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.075 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     6.825000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    13.650000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     4.030 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     2.015 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   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    :  5.391E+006
      Log Koc:  6.732 

 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 = 3.314 (BCF = 2063)
       log Kow used: 5.21 (estimated)

 Volatilization from Water:
    Henry LC:  2.76E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.708E+011  hours   (1.962E+010 days)
    Half-Life from Model Lake : 5.136E+012  hours   (2.14E+011 days)

 Removal In Wastewater Treatment:
    Total removal:              83.33  percent
    Total biodegradation:        0.71  percent
    Total sludge adsorption:    82.62  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       0.000183        1.46         1000       
   Water     2.54            4.32e+003    1000       
   Soil      78              8.64e+003    1000       
   Sediment  19.5            3.89e+004    0          
     Persistence Time: 9.97e+003 hr




                    

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