ChemSpider 2D Image | Ergolide | C17H22O5

Ergolide

  • Molecular FormulaC17H22O5
  • Average mass306.354 Da
  • Monoisotopic mass306.146729 Da
  • ChemSpider ID161502

  • defined stereocentres - 6 of 6 defined stereocentres

More details:

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

(3aR,4S,4aR,7aS,8R,9aS)-4a,8-Dimethyl-3-methylen-2,5-dioxododecahydroazuleno[6,5-b]furan-4-yl-acetat [German] [ACD/IUPAC Name]
(3aR,4S,4aR,7aS,8R,9aS)-4a,8-Dimethyl-3-methylene-2,5-dioxododecahydroazuleno[6,5-b]furan-4-yl acetate [ACD/IUPAC Name]
(3AR,4S,4AR,7AS,8R,9AS)-4A,8-DIMETHYL-3-METHYLIDENE-2,5-DIOXO-DODECAHYDROAZULENO[6,5-B]FURAN-4-YL ACETATE
54999-07-4 [RN]
Acétate de (3aR,4S,4aR,7aS,8R,9aS)-4a,8-diméthyl-3-méthylène-2,5-dioxododécahydroazuléno[6,5-b]furan-4-yle [French] [ACD/IUPAC Name]
Azuleno[6,5-b]furan-2,5-dione, 4-(acetyloxy)decahydro-4a,8-dimethyl-3-methylene-, (3aR,4S,4aR,7aS,8R,9aS)- [ACD/Index Name]
Ergolide
(3aR)-(3aα,4α,4aβ,7aα,8α,9aβ)-4-(acetyloxy)decahydro-4a,8-dimethyl-3-methylene-azuleno(6,5-b)furan-2,5-dione
(3aR,4S,4aR,7aR,8R,9aS)-4a,8-dimethyl-3-methylidene-2,5-dioxo-2,3,3a,4,4a,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-yl acetate
(3AR,4S,4AR,7AS,8R,9AS)-4A,8-DIMETHYL-3-METHYLIDENE-2,5-DIOXODODECAHYDROAZULENO[6,5-B]FURAN-4-YL ACETATE
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  • Miscellaneous

    • Chemical Class:

      A sesquiterpene lactone that is decahydroazuleno[6,5-<ital>b</ital>]furan-2,5-dione subtituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetyloxy group at posit ion 4. It has been isolated from the aerial parts of <ital>Inula hupehensis</ital>. ChEBI CHEBI:69340
      A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetyloxy group at position 4. It ha s been isolated from the aerial parts of Inula hupehensis. ChEBI CHEBI:69340
      A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2,5-dione subtituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetyloxy group at posit; ion 4. It h as been isolated from the aerial parts of Inula hupehensis. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:69340

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

Density: 1.2±0.1 g/cm3
Boiling Point: 456.8±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 71.7±3.0 kJ/mol
Flash Point: 202.0±28.8 °C
Index of Refraction: 1.525
Molar Refractivity: 77.9±0.4 cm3
#H bond acceptors: 5
#H bond donors: 0
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 1.76
ACD/LogD (pH 5.5): 1.53
ACD/BCF (pH 5.5): 8.57
ACD/KOC (pH 5.5): 161.95
ACD/LogD (pH 7.4): 1.53
ACD/BCF (pH 7.4): 8.57
ACD/KOC (pH 7.4): 161.95
Polar Surface Area: 70 Å2
Polarizability: 30.9±0.5 10-24cm3
Surface Tension: 42.8±5.0 dyne/cm
Molar Volume: 254.1±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) =  1.12

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  418.49  (Adapted Stein & Brown method)
    Melting Pt (deg C):  156.20  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.34E-007  (Modified Grain method)
    Subcooled liquid VP: 2.94E-006 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):  1247
       log Kow used: 1.12 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  83.919 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.92E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.332E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.12  (KowWin est)
  Log Kaw used:  -8.105  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.225
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7730
   Biowin2 (Non-Linear Model)     :   0.9904
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5680  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6880  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8086
   Biowin6 (MITI Non-Linear Model):   0.4959
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0949
 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):  0.000392 Pa (2.94E-006 mm Hg)
  Log Koa (Koawin est  ): 9.225
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00765 
       Octanol/air (Koa) model:  0.000412 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.217 
       Mackay model           :  0.38 
       Octanol/air (Koa) model:  0.0319 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  53.5964 E-12 cm3/molecule-sec
      Half-Life =     0.200 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.395 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   Fraction sorbed to airborne particulates (phi): 0.298 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  164
      Log Koc:  2.215 

 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 = 0.162 (BCF = 1.452)
       log Kow used: 1.12 (estimated)

 Volatilization from Water:
    Henry LC:  1.92E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.337E+006  hours   (2.224E+005 days)
    Half-Life from Model Lake : 5.823E+007  hours   (2.426E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               1.90  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.81  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       0.00321         4            1000       
   Water     39.3            900          1000       
   Soil      60.7            1.8e+003     1000       
   Sediment  0.0853          8.1e+003     0          
     Persistence Time: 1.07e+003 hr

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