ChemSpider 2D Image | Benzoylecgonine | C16H19NO4

Benzoylecgonine

  • Molecular FormulaC16H19NO4
  • Average mass289.326 Da
  • Monoisotopic mass289.131409 Da
  • ChemSpider ID395095
  • defined stereocentres - 4 of 4 defined stereocentres


More details:






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

(1R,2R,3S,5S)-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octan-2-carbonsäure [German] [ACD/IUPAC Name]
(1R,2R,3S,5S)-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid [ACD/IUPAC Name]
208-263-5 [EINECS]
3b-Hydroxy-1aH,5aH-tropane-2b-carboxylic Acid Benzoate
519-09-5 [RN]
5353I8I6YS
8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, (1R,2R,3S,5S)- [ACD/Index Name]
Acide (1R,2R,3S,5S)-3-(benzoyloxy)-8-méthyl-8-azabicyclo[3.2.1]octane-2-carboxylique [French] [ACD/IUPAC Name]
Benzoylecgonine [Wiki]
Ecgonine Benzoate
More...

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

DEA No. 9180 [DBID]
B4147_SIGMA [DBID]
B8900_SIGMA [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A benzoate ester metabolite of cocaine formed by hydrolysis of the methyl ester group, catalysed by carboxylesterases. ChEBI CHEBI:41001

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

Density: 1.3±0.1 g/cm3
Boiling Point: 442.4±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 73.8±3.0 kJ/mol
Flash Point: 221.4±28.7 °C
Index of Refraction: 1.599
Molar Refractivity: 76.3±0.4 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 2.71
ACD/LogD (pH 5.5): -0.21
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.32
ACD/LogD (pH 7.4): -0.21
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.33
Polar Surface Area: 67 Å2
Polarizability: 30.2±0.5 10-24cm3
Surface Tension: 56.3±5.0 dyne/cm
Molar Volume: 223.1±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) =  -1.32

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  489.11  (Adapted Stein & Brown method)
    Melting Pt (deg C):  305.36  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.77E-011  (Modified Grain method)
    Subcooled liquid VP: 5.17E-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):  1605
       log Kow used: -1.32 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  8112.6 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines-acid
       Esters-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.03E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.942E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.32  (KowWin est)
  Log Kaw used:  -11.376  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.056
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7795
   Biowin2 (Non-Linear Model)     :   0.9608
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8318  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7617  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4419
   Biowin6 (MITI Non-Linear Model):   0.0933
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4209
 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):  6.89E-006 Pa (5.17E-008 mm Hg)
  Log Koa (Koawin est  ): 10.056
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.435 
       Octanol/air (Koa) model:  0.00279 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.94 
       Mackay model           :  0.972 
       Octanol/air (Koa) model:  0.183 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  54.6199 E-12 cm3/molecule-sec
      Half-Life =     0.196 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.350 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.956 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  353.2
      Log Koc:  2.548 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  3.986E-003  L/mol-sec
  Kb Half-Life at pH 8:       5.511  years  
  Kb Half-Life at pH 7:      55.105  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -1.32 (estimated)

 Volatilization from Water:
    Henry LC:  1.03E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.669E+009  hours   (4.029E+008 days)
    Half-Life from Model Lake : 1.055E+011  hours   (4.395E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       0.0001          4.7          1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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