ChemSpider 2D Image | Parthenolide | C15H20O3

Parthenolide

  • Molecular FormulaC15H20O3
  • Average mass248.318 Da
  • Monoisotopic mass248.141251 Da
  • ChemSpider ID20126246
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 4 of 4 defined stereocentres


More details:






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

(1aR,4E,7aS,10aS,10bS)-1a,5-Dimethyl-8-methylen-2,3,6,7,7a,8,10a,10b-octahydrooxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-on [German] [ACD/IUPAC Name]
(1aR,4E,7aS,10aS,10bS)-1a,5-Dimethyl-8-methylene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one [ACD/IUPAC Name]
(1aR,4E,7aS,10aS,10bS)-1a,5-Diméthyl-8-méthylène-2,3,6,7,7a,8,10a,10b-octahydrooxiréno[9,10]cyclodéca[1,2-b]furan-9(1aH)-one [French] [ACD/IUPAC Name]
Oxireno(9,10)cyclodeca(1,2-b)furan-9(1aH)-one, 2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methylene-, (1aR,4E,7aS,10aS,10bS)-
Oxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one, 2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methylene-, (1aR,4E,7aS,10aS,10bS)- [ACD/Index Name]
Parthenolide [Wiki]
(1aR,7aS,10aS,10bS,E)-1a,5-dimethyl-8-methylene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2',3':9,10]cyclodeca[1,2-b]furan-9(1aH)-one
(1S,2S,4R,7E,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one
(E)-(1S,2S,4R,11S)-4,8-Dimethyl-12-methylene-3,14-dioxa-tricyclo[9.3.0.0*2,4*]tetradec-7-en-13-one
[1aR-(1aR*,4E,7aS*,10aS*,-10bR*)]-2,3-6,7,7a,8,10a,10b-Octahydro-1a,5-dimethyl-8-methyleneoxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Compound Source:

      Constit. of Chrysanthemum parthenium (feverfew) and Michelia champaca Zerenex Molecular [ZBioX-0492]
    • Bio Activity:

      5-HT Receptors Tocris Bioscience 610
      5-HT release inhibitor Tocris Bioscience 0610, 610
      5-HT-Related Tocris Bioscience 610
      7-TM Receptors Tocris Bioscience 610
      Antineoplastic agent; Zerenex Molecular [ZBioX-0492]
      The active principle of feverfew (Chrysanthemum parthenium), widely used as a herbal remedy for arthritis and migraine and as a febrifuge. Antisecretory, anti-inflammatory and spasmolytic; inhibits th e release of 5-HT from blood platelets. Also inhibits generation of leukotriene B4 and thromboxane B2. Tocris Bioscience 0610
      The active principle of feverfew (Chrysanthemum parthenium), widely used as a herbal remedy for arthritis and migraine and as a febrifuge. Antisecretory, anti-inflammatory and spasmolytic; inhibits the release of 5-HT from blood platelets. Also inhibits generation of leukotriene B4 and thromboxane B2. Tocris Bioscience 610
      The active principle of feverfew (Chrysanthemum parthenium). Antisecretory, anti-inflammatory and spasmolytic; inhibits the release of 5-HT from blood platelets. Also inhibits activation of NF-kappaB, and generation of leukotriene B4 and thromboxane B2. Tocris Bioscience 610

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

Density: 1.1±0.1 g/cm3
Boiling Point: 394.1±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 64.4±3.0 kJ/mol
Flash Point: 166.3±22.5 °C
Index of Refraction: 1.533
Molar Refractivity: 68.1±0.4 cm3
#H bond acceptors: 3
#H bond donors: 0
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 2.42
ACD/LogD (pH 5.5): 2.61
ACD/BCF (pH 5.5): 56.90
ACD/KOC (pH 5.5): 627.96
ACD/LogD (pH 7.4): 2.61
ACD/BCF (pH 7.4): 56.90
ACD/KOC (pH 7.4): 627.96
Polar Surface Area: 39 Å2
Polarizability: 27.0±0.5 10-24cm3
Surface Tension: 38.6±5.0 dyne/cm
Molar Volume: 219.7±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) =  2.70

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  359.44  (Adapted Stein & Brown method)
    Melting Pt (deg C):  112.29  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.09E-005  (Modified Grain method)
    Subcooled liquid VP: 7.87E-005 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):  119
       log Kow used: 2.70 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  62.101 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Acrylates
       Epoxides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.11E-007  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.993E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.70  (KowWin est)
  Log Kaw used:  -4.602  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.302
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2722
   Biowin2 (Non-Linear Model)     :   0.1693
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5698  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5552  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5218
   Biowin6 (MITI Non-Linear Model):   0.2274
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3250
 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):  0.0105 Pa (7.87E-005 mm Hg)
  Log Koa (Koawin est  ): 7.302
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000286 
       Octanol/air (Koa) model:  4.92E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0102 
       Mackay model           :  0.0224 
       Octanol/air (Koa) model:  0.000393 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 119.1364 E-12 cm3/molecule-sec
      Half-Life =     0.090 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.077 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    44.137501 E-17 cm3/molecule-sec
      Half-Life =     0.026 Days (at 7E11 mol/cm3)
      Half-Life =     37.389 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.0163 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  376.3
      Log Koc:  2.576 

 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 = 1.381 (BCF = 24.02)
       log Kow used: 2.70 (estimated)

 Volatilization from Water:
    Henry LC:  6.11E-007 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:       1512  hours   (62.98 days)
    Half-Life from Model Lake : 1.662E+004  hours   (692.6 days)

 Removal In Wastewater Treatment:
    Total removal:               3.85  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.70  percent
    Total to Air:                0.03  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.0244          0.483        1000       
   Water     21.5            900          1000       
   Soil      78.2            1.8e+003     1000       
   Sediment  0.259           8.1e+003     0          
     Persistence Time: 967 hr




                    

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