ChemSpider 2D Image | Megestrol acetate | C24H32O4

Megestrol acetate

  • Molecular FormulaC24H32O4
  • Average mass384.509 Da
  • Monoisotopic mass384.230072 Da
  • ChemSpider ID11192
  • defined stereocentres - 6 of 6 defined stereocentres


More details:



Featured data source



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

(1R,3aS,3bR,9aR,9bS,11aS)-1-acetyl-5,9a,11a-trimethyl-7-oxo-1H,2H,3H,3aH,3bH,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl acetate
(8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate
(8R,9S,10R,13S,14S,17R)-17-Acetyl-6,10,13-trimethyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylacetat
17-(acetyloxy)-6-methylpregna-4,6-diene-3,20-dione
17a-Acetoxy-6-methylpregna-4,6-diene-3,20-dione
17α-Acetoxy-6-methyl-4,6-pregnadiene-3,20-dione
17α-Acetoxy-6-methyl-4,6-pregnadiene-3,20-dione
17α-Acetoxy-6-methylpregna-4,6-diene-3,20-dione
17α-Hydroxy-6-methyl-4,6-pregnadiene-3,20-dione 17-acetate
17α-Hydroxy-6-methyl-6-dehydroprogesterone 17-acetate
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

MJ 5071 [DBID]
TJ2M0FR8ES [DBID]
46420_RIEDEL [DBID]
BDH 1298 [DBID]
C08151 [DBID]
CCRIS 372 [DBID]
D00952 [DBID]
DRG-0063 [DBID]
M0513_SIGMA [DBID]
MLS000028633 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      Glucocorticoid Receptor agonist; Estrogen/progestogen Receptor agonist TargetMol T1284
    • Chemical Class:

      A steroid ester resulting from the formal condensation of the hydroxy group of megestrol with the carboxy group of acetic acid. It is an appetite stimulant used for the treatment of anorexia and cache xia. Also used for birth control and for the treatment of breast cancer. ChEBI CHEBI:6723
    • Bio Activity:

      Endocrinology/ Hormones TargetMol T1284
      Glucocorticoid receptor;Estrogen/progestogen Receptor TargetMol T1284
      Megestrol Acetate is a synthetic progesteronal agent with an IC50 of 260 ?M for the inhibition of HegG2.; Target: Progesterone Receptor; Megestrol acetate, also known as 17?-acetoxy-6-dehydro-6-methyl progesterone, and sometimes abbreviated as MGA or MA, is a steroidal progestin and progesterone derivative (specifically, a 17-hydroxylated progesterone) with predominantly progestational and antigona dotropic effects. MedChem Express HY-13676
      Nuclear Receptors Tocris Bioscience 6285
      Others MedChem Express HY-13676
      Progesterone Receptor Tocris Bioscience 6285
      Progesterone Receptor MedChem Express HY-13676
      Synthetic progesterone analog Tocris Bioscience 6285
      Synthetic progesterone analog. Dose-dependently inhibits growth of HepG2 cells (IC50 = 260 muM) in vitro and in vivo and reduces tumor volume. High dosages improve weight gain in tumor-bearing nude mice. Orally bioavailable. Tocris Bioscience 6285

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

Density: 1.2±0.1 g/cm3
Boiling Point: 507.1±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: 218.5±30.2 °C
Index of Refraction: 1.551
Molar Refractivity: 106.4±0.4 cm3
#H bond acceptors: 4
#H bond donors: 0
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 3.82
ACD/LogD (pH 5.5): 3.83
ACD/BCF (pH 5.5): 477.41
ACD/KOC (pH 5.5): 2878.41
ACD/LogD (pH 7.4): 3.83
ACD/BCF (pH 7.4): 477.41
ACD/KOC (pH 7.4): 2878.41
Polar Surface Area: 60 Å2
Polarizability: 42.2±0.5 10-24cm3
Surface Tension: 44.3±5.0 dyne/cm
Molar Volume: 333.4±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) =  4.00

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  451.58  (Adapted Stein & Brown method)
    Melting Pt (deg C):  189.98  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.37E-009  (Modified Grain method)
    MP  (exp database):  214 deg C
    Subcooled liquid VP: 4.49E-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):  1.459
       log Kow used: 4.00 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  2 mg/L (37 deg C)
        Exper. Ref:  MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5.9778 mg/L
    Wat Sol (Exper. database match) =  2.00
       Exper. Ref:  MERCK INDEX (1996)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters
       Vinyl/Allyl Ketones

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.23E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.515E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.00  (KowWin est)
  Log Kaw used:  -7.299  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.299
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2005
   Biowin2 (Non-Linear Model)     :   0.0116
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8083  (months      )
   Biowin4 (Primary Survey Model) :   3.0172  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5204
   Biowin6 (MITI Non-Linear Model):   0.1111
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.9252
 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):  5.99E-005 Pa (4.49E-007 mm Hg)
  Log Koa (Koawin est  ): 11.299
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0501 
       Octanol/air (Koa) model:  0.0489 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.644 
       Mackay model           :  0.8 
       Octanol/air (Koa) model:  0.796 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 255.4102 E-12 cm3/molecule-sec
      Half-Life =     0.042 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.503 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    34.222500 E-17 cm3/molecule-sec
      Half-Life =     0.033 Days (at 7E11 mol/cm3)
      Half-Life =     48.221 Min
   Fraction sorbed to airborne particulates (phi): 0.722 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5721
      Log Koc:  3.757 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  9.548E-002  L/mol-sec
  Kb Half-Life at pH 8:      84.020  days   
  Kb Half-Life at pH 7:       2.300  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.381 (BCF = 240.7)
       log Kow used: 4.00 (estimated)

 Volatilization from Water:
    Henry LC:  1.23E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.334E+005  hours   (3.889E+004 days)
    Half-Life from Model Lake : 1.018E+007  hours   (4.243E+005 days)

 Removal In Wastewater Treatment:
    Total removal:              30.06  percent
    Total biodegradation:        0.32  percent
    Total sludge adsorption:    29.74  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       0.00908         0.447        1000       
   Water     12              1.44e+003    1000       
   Soil      84.4            2.88e+003    1000       
   Sediment  3.61            1.3e+004     0          
     Persistence Time: 1.9e+003 hr




                    

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