ChemSpider 2D Image | Abiraterone acetate | C26H33NO2

Abiraterone acetate

  • Molecular FormulaC26H33NO2
  • Average mass391.546 Da
  • Monoisotopic mass391.251129 Da
  • ChemSpider ID7997598
  • defined stereocentres - 6 of 6 defined stereocentres


More details:






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

(3aS,3bR,7S,9aR,9bS,11aS)-9a,11a-dimethyl-1-(pyridin-3-yl)-3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-yl acetate
(3β)-17-(3-Pyridinyl)androsta-5,16-dien-3-yl acetate [ACD/IUPAC Name]
(3β)-17-(3-Pyridinyl)androsta-5,16-dien-3-yl-acetat [German] [ACD/IUPAC Name]
(3β)-17-(pyridin-3-yl)androsta-5,16-dien-3-yl acetate
154229-18-2 [RN]
17-(pyridin-3-yl)androsta-5,16-dien-3β-yl acetate
Abiraterone acetate [USAN]
Acétate de (3β)-17-(3-pyridinyl)androsta-5,16-dién-3-yle [French] [ACD/IUPAC Name]
Androsta-5,16-dien-3-ol, 17-(3-pyridinyl)-, acetate (ester), (3β)- [ACD/Index Name]
EM5OCB9YJ6
More...

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

CB 7598 [DBID]
CB7630 [DBID]
CB 7630 [DBID]
CB-7630 [DBID]
JNJ 212082 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A sterol ester obtained by formal condensation of the 3-hydroxy group of abiraterone with the carboxy group of acetic acid. A prodrug that is converted <ital>in vivo </ital> to abiraterone. Used for t reatment of metastatic castrate-resistant prostate cancer. ChEBI CHEBI:68639
      A sterol ester obtained by formal condensation of the 3-hydroxy group of abiraterone with the carboxy group of acetic acid. A prodrug that is converted in vivo into abiraterone. Used for treatment of metastatic castrate-resistant prostate cancer. ChEBI CHEBI:68639
    • Bio Activity:

      Abiraterone acetate (CB-7598) is a potent steroidal cytochrome P450 17alpha-hydroxylase-17,20-lyase (CYP17) inhibitor with an IC50 at 4 nM. MedChem Express http://www.medchemexpress.com/vx-222.html, HY-75054
      Cytochrome P450 MedChem Express HY-75054
      Metabolism/Protease MedChem Express HY-75054
      Metabolism/Protease; MedChem Express HY-75054

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.1±0.1 g/cm3
Boiling Point: 506.7±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 77.7±3.0 kJ/mol
Flash Point: 260.2±30.1 °C
Index of Refraction: 1.584
Molar Refractivity: 114.8±0.4 cm3
#H bond acceptors: 3
#H bond donors: 0
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 1
ACD/LogP: 6.55
ACD/LogD (pH 5.5): 5.66
ACD/BCF (pH 5.5): 10434.96
ACD/KOC (pH 5.5): 22731.74
ACD/LogD (pH 7.4): 5.87
ACD/BCF (pH 7.4): 17020.97
ACD/KOC (pH 7.4): 37078.84
Polar Surface Area: 39 Å2
Polarizability: 45.5±0.5 10-24cm3
Surface Tension: 47.5±5.0 dyne/cm
Molar Volume: 343.0±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) =  6.40

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  457.08  (Adapted Stein & Brown method)
    Melting Pt (deg C):  192.55  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.71E-009  (Modified Grain method)
    Subcooled liquid VP: 3.28E-007 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):  0.01191
       log Kow used: 6.40 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.0473 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.82E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.470E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.40  (KowWin est)
  Log Kaw used:  -5.624  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.024
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2129
   Biowin2 (Non-Linear Model)     :   0.0277
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8357  (months      )
   Biowin4 (Primary Survey Model) :   3.1862  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2271
   Biowin6 (MITI Non-Linear Model):   0.0139
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4692
 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-005 Pa (3.28E-007 mm Hg)
  Log Koa (Koawin est  ): 12.024
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0686 
       Octanol/air (Koa) model:  0.259 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.712 
       Mackay model           :  0.846 
       Octanol/air (Koa) model:  0.954 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 197.4363 E-12 cm3/molecule-sec
      Half-Life =     0.054 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.650 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    21.043749 E-17 cm3/molecule-sec
      Half-Life =     0.054 Days (at 7E11 mol/cm3)
      Half-Life =      1.307 Hrs
   Fraction sorbed to airborne particulates (phi): 0.779 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5.171E+006
      Log Koc:  6.714 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  6.266E-002  L/mol-sec
  Kb Half-Life at pH 8:     128.021  days   
  Kb Half-Life at pH 7:       3.505  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 4.225 (BCF = 1.679e+004)
       log Kow used: 6.40 (estimated)

 Volatilization from Water:
    Henry LC:  5.82E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.991E+004  hours   (829.5 days)
    Half-Life from Model Lake : 2.173E+005  hours   (9056 days)

 Removal In Wastewater Treatment:
    Total removal:              93.28  percent
    Total biodegradation:        0.77  percent
    Total sludge adsorption:    92.51  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       0.00706         0.652        1000       
   Water     2.09            1.44e+003    1000       
   Soil      33.3            2.88e+003    1000       
   Sediment  64.6            1.3e+004     0          
     Persistence Time: 4.27e+003 hr




                    

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