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ChemSpider 2D Image | Levonorgestrel | C21H28O2

Levonorgestrel

  • Molecular FormulaC21H28O2
  • Average mass312.446 Da
  • Monoisotopic mass312.208923 Da
  • ChemSpider ID12560
  • defined stereocentres - 6 of 6 defined stereocentres


More details:



Featured data source



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

(-)-Norgestrel
(−)-Norgestrel
(17a)-(-)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one
(17a)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one
(8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one [ACD/IUPAC Name]
(8R,9S,10R,13S,14S,17R)-13-éthyl-17-éthynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tétradécahydro-3H-cyclopenta[a]phénanthrén-3-one
(8R,9S,10R,13S,14S,17R)-13-Éthyl-17-éthynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tétradécahydro-3H-cyclopenta[a]phénanthrén-3-one [French] [ACD/IUPAC Name]
(8R,9S,10R,13S,14S,17R)-17-Ethinyl-13-ethyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-on
(8R,9S,10R,13S,14S,17R)-17-Ethinyl-13-ethyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-on [German] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

WY 5104 [DBID]
284858_ALDRICH [DBID]
BRN 2391114 [DBID]
C08149 [DBID]
C08153 [DBID]
CCRIS 6525 [DBID]
D00950 [DBID]
D00954 [DBID]
HSDB 3595 [DBID]
HSDB 6483 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Toxicity:

      Organic Compound; Ester; Drug; Metabolite; Contraceptive, Oral, Synthetic; Synthetic Compound; Contraceptive Agent; Contraceptive Agent, Female Toxin, Toxin-Target Database T3D4749
    • Safety:

      5 Axon Medchem 2065
      G03AC03 Wikidata Q416950
      G03AD01 Wikidata Q416950
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 2065
      no pictogram Axon Medchem 2065
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 2065
      Warning Axon Medchem 2065
    • Target Organs:

      Estrogen/Progestogen Receptor agonist TargetMol T1263
      Estrogen/Progestogen receptor agonist TargetMol T2597
    • Bio Activity:

      Endocrinology/ Hormones TargetMol T1263, T2597
      Estrogen/Progestogen receptor TargetMol T1263, T2597
      Levonorgestrel is a synthetic progestogen used as an active ingredient in some hormonal contraceptives. MedChem Express
      Levonorgestrel is a synthetic progestogen used as an active ingredient in some hormonal contraceptives.;Target: Progesterone ReceptorA synthetic progestational hormone with actions similar to those of progesterone and about twice as potent as its racemic or (+-)-isomer (norgestrel). It is used for contraception, control of menstrual disorders, and treatment of endometriosis. It is usually supplied in a racemic mixture (Norgestrel, 6533-00-2). Only the levonorgestrel isomer is active. Levonorgestrel is marketed mostly as a combination oral contraceptive under several brand names such as Alesse, Triphasil, and Min-Ovral [1]. MedChem Express HY-B0257
      Nuclear Receptors Tocris Bioscience 4833
      Progesterone Receptor Tocris Bioscience 4833
      Progesterone Receptor MedChem Express HY-B0257
      SRD5A1;Estrogen/Progestogen receptor TargetMol T1263, T2597
      Synthetic progesterone analog Tocris Bioscience 4833
      Synthetic progesterone analog; binds to the progesterone receptor (relative binding affinities are < 0.02, 7.5, 17, 58 and 323 % for estrogen receptors, glucocorticoid receptors, mineralocorticoid rec eptors, androgen receptors and progesterone receptors respectively). Tocris Bioscience 4833
      Synthetic progesterone analog; binds to the progesterone receptor (relative binding affinities are < 0.02, 7.5, 17, 58 and 323 % for estrogen receptors, glucocorticoid receptors, mineralocorticoid receptors, androgen receptors and progesterone receptors respectively). Tocris Bioscience 4833
      Tocolytic; Zerenex Molecular [ZBioX-0468]

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

Density: 1.1±0.1 g/cm3
Boiling Point: 459.1±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.6 mmHg at 25°C
Enthalpy of Vaporization: 83.0±6.0 kJ/mol
Flash Point: 195.4±21.3 °C
Index of Refraction: 1.571
Molar Refractivity: 90.2±0.4 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 3.92
ACD/LogD (pH 5.5): 3.32
ACD/BCF (pH 5.5): 195.10
ACD/KOC (pH 5.5): 1516.96
ACD/LogD (pH 7.4): 3.32
ACD/BCF (pH 7.4): 195.10
ACD/KOC (pH 7.4): 1516.96
Polar Surface Area: 37 Å2
Polarizability: 35.8±0.5 10-24cm3
Surface Tension: 48.3±5.0 dyne/cm
Molar Volume: 274.3±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) =  3.48

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  411.88  (Adapted Stein & Brown method)
    Melting Pt (deg C):  168.68  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1E-009  (Modified Grain method)
    MP  (exp database):  206 deg C
    Subcooled liquid VP: 8.28E-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):  35.84
       log Kow used: 3.48 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  8.991 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.70E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.147E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.48  (KowWin est)
  Log Kaw used:  -7.502  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.982
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2378
   Biowin2 (Non-Linear Model)     :   0.0048
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0620  (months      )
   Biowin4 (Primary Survey Model) :   3.0678  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2992
   Biowin6 (MITI Non-Linear Model):   0.0469
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.1537
 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):  1.1E-005 Pa (8.28E-008 mm Hg)
  Log Koa (Koawin est  ): 10.982
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.272 
       Octanol/air (Koa) model:  0.0236 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.908 
       Mackay model           :  0.956 
       Octanol/air (Koa) model:  0.653 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 113.5600 E-12 cm3/molecule-sec
      Half-Life =     0.094 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.130 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.396749 E-17 cm3/molecule-sec
      Half-Life =     0.155 Days (at 7E11 mol/cm3)
      Half-Life =      3.718 Hrs
   Fraction sorbed to airborne particulates (phi): 0.932 (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 = 1.979 (BCF = 95.38)
       log Kow used: 3.48 (estimated)

 Volatilization from Water:
    Henry LC:  7.7E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.344E+006  hours   (5.6E+004 days)
    Half-Life from Model Lake : 1.466E+007  hours   (6.109E+005 days)

 Removal In Wastewater Treatment:
    Total removal:              12.58  percent
    Total biodegradation:        0.18  percent
    Total sludge adsorption:    12.40  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       0.0293          1.41         1000       
   Water     13              1.44e+003    1000       
   Soil      85.9            2.88e+003    1000       
   Sediment  1.06            1.3e+004     0          
     Persistence Time: 1.83e+003 hr




                    

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