ChemSpider 2D Image | Eupatolide | C15H20O3

Eupatolide

  • Molecular FormulaC15H20O3
  • Average mass248.318 Da
  • Monoisotopic mass248.141251 Da
  • ChemSpider ID4444802

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 3 of 3 defined stereocentres

More details:

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

(3aR,4R,6E,10E,11aR)-4-Hydroxy-6,10-dimethyl-3-methylen-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-on [German] [ACD/IUPAC Name]
(3aR,4R,6E,10E,11aR)-4-Hydroxy-6,10-dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one [ACD/IUPAC Name]
(3aR,4R,6E,10E,11aR)-4-Hydroxy-6,10-diméthyl-3-méthylène-3a,4,5,8,9,11a-hexahydrocyclodéca[b]furan-2(3H)-one [French] [ACD/IUPAC Name]
6750-25-0 [RN]
Cyclodeca[b]furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-4-hydroxy-6,10-dimethyl-3-methylene-, (3aR,4R,6E,10E,11aR)- [ACD/Index Name]
Eupatolide
(3aR,4R,6E,10E,11aR)-4-hydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
eupatolid
https://www.ebi.ac.uk/chembl/compoundreportcard/CHEMBL485296/

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

C09440 [DBID]
  • Miscellaneous

    • Chemical Class:

      A germacranolide with formula C15H20O3, isolated from several Inula species. It exhibits anti-cancer properties. ChEBI CHEBI:4935

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

Density: 1.1±0.1 g/cm3
Boiling Point: 438.7±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.4 mmHg at 25°C
Enthalpy of Vaporization: 80.3±6.0 kJ/mol
Flash Point: 186.7±21.5 °C
Index of Refraction: 1.538
Molar Refractivity: 69.6±0.4 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 2.82
ACD/LogD (pH 5.5): 2.43
ACD/BCF (pH 5.5): 41.65
ACD/KOC (pH 5.5): 502.29
ACD/LogD (pH 7.4): 2.43
ACD/BCF (pH 7.4): 41.65
ACD/KOC (pH 7.4): 502.29
Polar Surface Area: 47 Å2
Polarizability: 27.6±0.5 10-24cm3
Surface Tension: 40.5±5.0 dyne/cm
Molar Volume: 222.5±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) =  2.56

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  391.21  (Adapted Stein & Brown method)
    Melting Pt (deg C):  128.92  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.06E-008  (Modified Grain method)
    Subcooled liquid VP: 3.35E-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):  510.7
       log Kow used: 2.56 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  198.94 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.89E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.958E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.56  (KowWin est)
  Log Kaw used:  -6.112  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.672
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9622
   Biowin2 (Non-Linear Model)     :   0.9908
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9506  (weeks       )
   Biowin4 (Primary Survey Model) :   3.8479  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6003
   Biowin6 (MITI Non-Linear Model):   0.3277
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4458
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  4.47E-005 Pa (3.35E-007 mm Hg)
  Log Koa (Koawin est  ): 8.672
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0672 
       Octanol/air (Koa) model:  0.000115 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.708 
       Mackay model           :  0.843 
       Octanol/air (Koa) model:  0.00914 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 210.2430 E-12 cm3/molecule-sec
      Half-Life =     0.051 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.610 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    87.137497 E-17 cm3/molecule-sec
      Half-Life =     0.013 Days (at 7E11 mol/cm3)
      Half-Life =     18.938 Min
   Fraction sorbed to airborne particulates (phi): 0.776 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  203
      Log Koc:  2.307 

 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 = 1.270 (BCF = 18.63)
       log Kow used: 2.56 (estimated)

 Volatilization from Water:
    Henry LC:  1.89E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.882E+004  hours   (2034 days)
    Half-Life from Model Lake : 5.327E+005  hours   (2.22E+004 days)

 Removal In Wastewater Treatment:
    Total removal:               3.28  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     3.17  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       0.0262          0.251        1000       
   Water     26.9            360          1000       
   Soil      72.9            720          1000       
   Sediment  0.206           3.24e+003    0          
     Persistence Time: 452 hr

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