ChemSpider 2D Image | Gestodene | C21H26O2

Gestodene

  • Molecular FormulaC21H26O2
  • Average mass310.430 Da
  • Monoisotopic mass310.193268 Da
  • ChemSpider ID2298532
  • defined stereocentres - 6 of 6 defined stereocentres


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

(17a)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,15-dien-20-yn-3-one
(8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one [ACD/IUPAC Name]
(8R,9S,10R,13S,14S,17R)-13-Éthyl-17-éthynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,17-dodécahydro-3H-cyclopenta[a]phénanthrén-3-one [French] [ACD/IUPAC Name]
(8R,9S,10R,13S,14S,17R)-17-Ethinyl-13-ethyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-on [German] [ACD/IUPAC Name]
17a-Ethynyl-13-ethyl-17b-hydroxy-4,15-gonadien-3-one
17a-Ethynyl-17b-hydroxy-18-methyl-4,15-estradien-3-one
60282-87-3 [RN]
Gestoden [German]
Gestodène [French] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

SH-546 [DBID]
SHB-331 [DBID]
SHT-546 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      P261; P262 Biosynth Q-101426
    • Bio Activity:

      Gestodene(SHB 331;WL 70) is a progestogen hormonal contraceptive. MedChem Express
      Gestodene(SHB 331;WL 70) is a progestogen hormonal contraceptive.;Target: Estrogen Receptor/ERRGestodene is androgenically neutral, meaning that contraceptive pills containing gestodene do not exhibit the androgenic side effects (e.g. acne, hirsutism, weight gain) often associated with second-generation contraceptive pills, such as those containing levonorgestrel. When 40 micrograms of gestodene was taken, six out of seven women did not ovulate, and one out of seven had a cycle with luteal insufficiency. These data indicate that 40 micrograms of gestodene is the borderline dose for inhibition of ovulation. A combination of 75 micrograms gestodene with 30 micrograms ethinyl estradiol was found to inhibit ovulation in ten subjects, and no follicular maturation was noted [1]. gestodene bound with high affinity to the progesterone receptor, as did other synthetic and natural progestogens. However, gestodene did not bind to the estradiol receptor. The relative binding affinities of all MedChem Express HY-B0110
      Progesterone Receptor MedChem Express HY-B0110

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

Density: 1.2±0.1 g/cm3
Boiling Point: 462.7±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.6 mmHg at 25°C
Enthalpy of Vaporization: 83.5±6.0 kJ/mol
Flash Point: 196.9±21.3 °C
Index of Refraction: 1.588
Molar Refractivity: 90.1±0.4 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 3.65
ACD/LogD (pH 5.5): 3.12
ACD/BCF (pH 5.5): 138.06
ACD/KOC (pH 5.5): 1184.32
ACD/LogD (pH 7.4): 3.12
ACD/BCF (pH 7.4): 138.06
ACD/KOC (pH 7.4): 1184.30
Polar Surface Area: 37 Å2
Polarizability: 35.7±0.5 10-24cm3
Surface Tension: 49.8±5.0 dyne/cm
Molar Volume: 267.6±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) =  3.26

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  413.40  (Adapted Stein & Brown method)
    Melting Pt (deg C):  169.54  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.13E-009  (Modified Grain method)
    MP  (exp database):  197.9 deg C
    Subcooled liquid VP: 7.47E-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):  56.21
       log Kow used: 3.26 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  7.6465 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Ketones
       Vinyl/Allyl Alcohols
       Propargyl Alc-hindered

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.77E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.212E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.26  (KowWin est)
  Log Kaw used:  -7.558  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.818
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2387
   Biowin2 (Non-Linear Model)     :   0.0050
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0664  (months      )
   Biowin4 (Primary Survey Model) :   3.0707  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2781
   Biowin6 (MITI Non-Linear Model):   0.0333
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.0607
 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):  9.96E-006 Pa (7.47E-008 mm Hg)
  Log Koa (Koawin est  ): 10.818
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.301 
       Octanol/air (Koa) model:  0.0161 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.916 
       Mackay model           :  0.96 
       Octanol/air (Koa) model:  0.564 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 165.8297 E-12 cm3/molecule-sec
      Half-Life =     0.064 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.774 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     8.534250 E-17 cm3/molecule-sec
      Half-Life =     0.134 Days (at 7E11 mol/cm3)
      Half-Life =      3.223 Hrs
   Fraction sorbed to airborne particulates (phi): 0.938 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5353
      Log Koc:  3.729 

 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 = 1.814 (BCF = 65.15)
       log Kow used: 3.26 (estimated)

 Volatilization from Water:
    Henry LC:  6.77E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.524E+006  hours   (6.349E+004 days)
    Half-Life from Model Lake : 1.662E+007  hours   (6.926E+005 days)

 Removal In Wastewater Treatment:
    Total removal:               8.62  percent
    Total biodegradation:        0.15  percent
    Total sludge adsorption:     8.47  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       0.0229          1.05         1000       
   Water     13.7            1.44e+003    1000       
   Soil      85.7            2.88e+003    1000       
   Sediment  0.644           1.3e+004     0          
     Persistence Time: 1.78e+003 hr




                    

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