ChemSpider 2D Image | Allopregnanolone | C21H34O2

Allopregnanolone

  • Molecular FormulaC21H34O2
  • Average mass318.493 Da
  • Monoisotopic mass318.255890 Da
  • ChemSpider ID83760
  • defined stereocentres - 8 of 8 defined stereocentres


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

(+)-3a-Hydroxy-5a-pregnan-20-one
(+)-3α-Hydroxy-5α-pregnan-20-one
(3α,5α)-3-Hydroxypregnan-20-on [German] [ACD/IUPAC Name]
(3α,5α)-3-Hydroxypregnan-20-one [ACD/IUPAC Name]
(3α,5α)-3-Hydroxyprégnan-20-one [French] [ACD/IUPAC Name]
3a-Hydroxy-5a-pregnan-20-one
3a-Hydroxy-5a-pregnane-20-one
3α,5α-Tetrahydroprogesterone
3α,5α-THP
More...

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

10446 [DBID]
BRN 3211363 [DBID]
C13712 [DBID]
CHEBI:32924 [DBID]
P8887_SIGMA [DBID]
ZINC04081043 [DBID]
  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A 3-hydroxy-5alpha-pregnan-20-one in which the hydroxy group at position 3 has alpha-configuration. It is a metabolite of the sex hormone progesterone and used for th; e treatment of postpartum depres sion in women. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50169
      A 3-hydroxy-5alpha-pregnan-20-one in which the hydroxy group at position 3 has alpha-configuration. It is a metabolite of the sex hormone progesterone and used for the treatment of postpartum depressi on in women. ChEBI CHEBI:50169
    • Bio Activity:

      Biochemicals & small molecules/Agonists & activators Hello Bio [HB0932]
      GABAA and A-rho Receptors Tocris Bioscience 3653
      GABAA receptor positive allosteric modulator Tocris Bioscience 3653
      GABAA receptor positive allosteric modulator. Neuroactive steroid. Deuterated analog also available. Tocris Bioscience 3653
      Ion Channels Tocris Bioscience 3653
      Ion channels/Ligand-gated ion channel/GABA<sub>A</sub> Hello Bio [HB0932]
      Ligand-gated Ion Channels Tocris Bioscience 3653
      Potent GABA<sub>A</sub> receptor positive allosteric modulator Hello Bio [HB0932]
      Potent GABA<sub>A</sub> receptor positive allosteric modulator. Endogenous neurosteroid; shows sedative, anticonvulsive, antidepressant and anxiolytic actions. Shows neurogenic effects in Alzheimer's disease and Parkinson's disease. Hello Bio [HB0932]

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

Density: 1.1±0.1 g/cm3
Boiling Point: 431.2±18.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.3 mmHg at 25°C
Enthalpy of Vaporization: 79.3±6.0 kJ/mol
Flash Point: 183.9±13.8 °C
Index of Refraction: 1.524
Molar Refractivity: 92.6±0.3 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 4.89
ACD/LogD (pH 5.5): 4.28
ACD/BCF (pH 5.5): 1046.69
ACD/KOC (pH 5.5): 5048.77
ACD/LogD (pH 7.4): 4.28
ACD/BCF (pH 7.4): 1046.69
ACD/KOC (pH 7.4): 5048.77
Polar Surface Area: 37 Å2
Polarizability: 36.7±0.5 10-24cm3
Surface Tension: 39.0±3.0 dyne/cm
Molar Volume: 302.4±3.0 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) =  3.97

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  395.91  (Adapted Stein & Brown method)
    Melting Pt (deg C):  150.39  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.04E-009  (Modified Grain method)
    MP  (exp database):  194.5 deg C
    Subcooled liquid VP: 2.44E-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):  12.48
       log Kow used: 3.97 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  51.301 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.12E-008  atm-m3/mole
   Group Method:   3.08E-010  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.357E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.97  (KowWin est)
  Log Kaw used:  -6.339  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.309
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3936
   Biowin2 (Non-Linear Model)     :   0.0134
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2086  (months      )
   Biowin4 (Primary Survey Model) :   3.1886  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4321
   Biowin6 (MITI Non-Linear Model):   0.0677
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.1736
 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):  3.25E-005 Pa (2.44E-007 mm Hg)
  Log Koa (Koawin est  ): 10.309
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0922 
       Octanol/air (Koa) model:  0.005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.769 
       Mackay model           :  0.881 
       Octanol/air (Koa) model:  0.286 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  39.0618 E-12 cm3/molecule-sec
      Half-Life =     0.274 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.286 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.825 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4273
      Log Koc:  3.631 

 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 = 2.360 (BCF = 229.3)
       log Kow used: 3.97 (estimated)

 Volatilization from Water:
    Henry LC:  3.08E-010 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 3.392E+006  hours   (1.414E+005 days)
    Half-Life from Model Lake : 3.701E+007  hours   (1.542E+006 days)

 Removal In Wastewater Treatment:
    Total removal:              28.71  percent
    Total biodegradation:        0.31  percent
    Total sludge adsorption:    28.40  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       0.0171          6.57         1000       
   Water     9.02            1.44e+003    1000       
   Soil      88.4            2.88e+003    1000       
   Sediment  2.51            1.3e+004     0          
     Persistence Time: 2.72e+003 hr




                    

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