ChemSpider 2D Image | Mifepristone | C29H35NO2

Mifepristone

  • Molecular FormulaC29H35NO2
  • Average mass429.594 Da
  • Monoisotopic mass429.266785 Da
  • ChemSpider ID49889
  • defined stereocentres - 5 of 5 defined stereocentres


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

(11b,17b)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-17-(1-propynyl)estra-4,9-dien-3-one
(11β,17β)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-17-(prop-1-in-1-yl)estra-4,9-dien-3-on [German]
(11β,17β)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-17-(prop-1-yn-1-yl)estra-4,9-dien-3-one
(11β,17β)-11-[4-(dimethylamino)phenyl]-17-hydroxy-17-prop-1-yn-1-ylestra-4,9-dien-3-one
(8S,11R,13S,14S,17S)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-13-methyl-17-(1-propin-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-on [German] [ACD/IUPAC Name]
(8S,11R,13S,14S,17S)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-13-methyl-17-(1-propin-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-on (non-preferred name) [German] [ACD/IUPAC Name]
(8S,11R,13S,14S,17S)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-13-methyl-17-(1-propyn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one [ACD/IUPAC Name]
(8S,11R,13S,14S,17S)-11-[4-(Diméthylamino)phényl]-17-hydroxy-13-méthyl-17-(1-propyn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodécahydro-3H-cyclopenta[a]phénanthrén-3-one [French] [ACD/IUPAC Name]
(8S,11R,13S,14S,17S)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-13-methyl-17-(1-propyn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one (non-preferred name) [ACD/IUPAC Name]
(8S,11R,13S,14S,17S)-11-[4-(Diméthylamino)phényl]-17-hydroxy-13-méthyl-17-(1-propyn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodécahydro-3H-cyclopenta[a]phénanthrén-3-one (non-preferred name) [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CDB 2477 [DBID]
ZK 98296 [DBID]
320T6RNW1F [DBID]
AIDS025200 [DBID]
AIDS-025200 [DBID]
BRN 5779404 [DBID]
C07652 [DBID]
C-1073 [DBID]
CI-1073 [DBID]
D00585 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1502
      G03XB01 Wikidata Q411240
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1502
      no pictogram Axon Medchem 1502
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1502
      Warning Axon Medchem 1502
    • Target Organs:

      Estrogen/Progestogen Receptor antagonist; Glucocorticoid Receptor antagonist; MRP inhibitor TargetMol T1102
    • Bio Activity:

      Endocrinology/ Hormones TargetMol T1102
      Estrogen/progestogen Receptor ;Glucocorticoid receptor;MRP1 TargetMol T1102
      Mifepristone(RU-38486; RU486) is a progesterone receptor antagonist(IC50= 0.2 nM) used as an abortifacient in the first months of pregnancy, and in smaller doses as an emergency contraceptive. MedChem Express
      Mifepristone(RU-38486; RU486) is a progesterone receptor antagonist(IC50= 0.2 nM) used as an abortifacient in the first months of pregnancy, and in smaller doses as an emergency contraceptive.;IC50 Value: 0.2 nM (Progesterone receptor); 2.6 nM (Glucocorticoid receptor) [1];Target: Progesterone receptorMifepristone is a synthetic steroid compound used as a pharmaceutical. It is a progesterone receptor antagonist used as an abortifacient in the first months of pregnancy, and in smaller doses as an emergency contraceptive. Mifepristone is also a powerful glucocorticoid receptor antagonist, and has occasionally been used in refractory Cushing's Syndrome.;In vitro: Mifepristone had no effect onHeLa cell proliferation inhibition rate during 24 and 48 hours (p > 0.05). Mifepristone at low concentrations (< or = 10 micromol/l) combined withcisplatin can significantly enhance the inhibitory effect of cisplatin on HeLa cell line [2]. The effect of mifepristone on cytotoxicity of cisplatin MedChem Express HY-13683
      Nuclear Receptors Tocris Bioscience 1479
      Progesterone and glucocorticoid receptor antagonist Tocris Bioscience 1479
      Progesterone Receptor Tocris Bioscience 1479
      Progesterone Receptor MedChem Express HY-13683
      Selective antagonist at progesterone (PR) and glucocorticoid (GR) receptors in vitro and in vivo. Is a silent antagonist at PR and has a higher affinity than progesterone. Has higher affinity for GR t han dexamethasone (Cat. No. 1126). Tocris Bioscience 1479
      Selective antagonist at progesterone (PR) and glucocorticoid (GR) receptors in vitro and in vivo. Is a silent antagonist at PR and has a higher affinity than progesterone. Has higher affinity for GR than dexamethasone (Cat. No. 1126). Tocris Bioscience 1479

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

Density: 1.2±0.1 g/cm3
Boiling Point: 628.6±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 97.8±3.0 kJ/mol
Flash Point: 334.0±31.5 °C
Index of Refraction: 1.623
Molar Refractivity: 127.7±0.4 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 4.95
ACD/LogD (pH 5.5): 4.88
ACD/BCF (pH 5.5): 2579.45
ACD/KOC (pH 5.5): 7998.66
ACD/LogD (pH 7.4): 5.16
ACD/BCF (pH 7.4): 4896.89
ACD/KOC (pH 7.4): 15184.86
Polar Surface Area: 41 Å2
Polarizability: 50.6±0.5 10-24cm3
Surface Tension: 54.1±5.0 dyne/cm
Molar Volume: 362.0±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) =  5.39

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  537.74  (Adapted Stein & Brown method)
    Melting Pt (deg C):  230.23  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.04E-014  (Modified Grain method)
    Subcooled liquid VP: 1.29E-011 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):  0.04972
       log Kow used: 5.39 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.0674 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 :   4.97E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.141E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.39  (KowWin est)
  Log Kaw used:  -10.692  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.082
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.0314
   Biowin2 (Non-Linear Model)     :   0.0002
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.4734  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.5423  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2039
   Biowin6 (MITI Non-Linear Model):   0.0011
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.9152
 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):  1.72E-009 Pa (1.29E-011 mm Hg)
  Log Koa (Koawin est  ): 16.082
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.74E+003 
       Octanol/air (Koa) model:  2.96E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 506.2820 E-12 cm3/molecule-sec
      Half-Life =     0.021 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    15.211 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =  1445.903687 E-17 cm3/molecule-sec
      Half-Life =     0.001 Days (at 7E11 mol/cm3)
      Half-Life =      1.141 Min
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  8.927E+004
      Log Koc:  4.951 

 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 = 3.452 (BCF = 2832)
       log Kow used: 5.39 (estimated)

 Volatilization from Water:
    Henry LC:  4.97E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.442E+009  hours   (1.017E+008 days)
    Half-Life from Model Lake : 2.664E+010  hours   (1.11E+009 days)

 Removal In Wastewater Treatment:
    Total removal:              86.73  percent
    Total biodegradation:        0.74  percent
    Total sludge adsorption:    85.99  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       0.000131        0.0183       1000       
   Water     3.15            4.32e+003    1000       
   Soil      61.9            8.64e+003    1000       
   Sediment  35              3.89e+004    0          
     Persistence Time: 6.71e+003 hr




                    

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