ChemSpider 2D Image | Inuviscolide | C15H20O3

Inuviscolide

  • Molecular FormulaC15H20O3
  • Average mass248.318 Da
  • Monoisotopic mass248.141251 Da
  • ChemSpider ID153715

  • defined stereocentres - 5 of 5 defined stereocentres

More details:

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

(3aR,4aR,5R,7aS,9aS)-5-Hydroxy-5-methyl-3,8-bis(methylene)decahydroazuleno[6,5-b]furan-2(3H)-one [ACD/IUPAC Name]
(3aR,4aR,5R,7aS,9aS)-5-Hydroxy-5-methyl-3,8-dimethylendecahydroazuleno[6,5-b]furan-2(3H)-on [German] [ACD/IUPAC Name]
(3aR,4aR,5R,7aS,9aS)-5-Hydroxy-5-méthyl-3,8-diméthylènedécahydroazuléno[6,5-b]furan-2(3H)-one [French] [ACD/IUPAC Name]
Azuleno[6,5-b]furan-2(3H)-one, decahydro-5-hydroxy-5-methyl-3,8-bis(methylene)-, (3aR,4aR,5R,7aS,9aS)- [ACD/Index Name]
Inuviscolide
(3aR,4aR,5R,7aS,9aS)-5-hydroxy-5-methyl-3,8-dimethylidenedecahydroazuleno[6,5-b]furan-2(3H)-one
63109-30-8 [RN]
https://www.ebi.ac.uk/chembl/compoundreportcard/CHEMBL521960/
  • Miscellaneous

    • Chemical Class:

      A sesquiterpene lactone that is decahydroazuleno[6,5-<ital>b</ital>]furan-2(3<element>H</element>)-one substituted by a hydroxy group at position 5, a mthyl group at position 5 and methylidene groups at positions 3 and 8 (the 3a<stereo>R</stereo>,4a<stereo>R</stereo>,5<stereo>R</stereo>,7a<stereo>S</stereo>,9a<stereo>S</stereo> stereoisomer). Isolated from the aerial parts of <ital>Inula hupehensi s</ital>, it exhibits anti-inflammatory activity. ChEBI CHEBI:69345
      A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2(3H)-one substituted by a hydroxy group at position 5, a methyl group at position 5 and methylidene groups at positions 3 and 8 (the 3aR,4 aR,5R,7aS,9aS stereoisomer). Isolated from the aerial parts of Inula hupehensis, it exhibits anti-inflammatory activity. ChEBI CHEBI:69345
      A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2(3H)-one substituted by a hydroxy group at position 5, a mthyl group at position 5 and methylidene groups ; at positions 3 and 8 (the 3aR, 4aR,5R,7aS,9aS stereoisomer). Isolated from the aerial parts of Inula hupehensi; s, it exhibits anti-inflammatory activity. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:69345

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

Density: 1.2±0.1 g/cm3
Boiling Point: 416.4±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 77.4±6.0 kJ/mol
Flash Point: 176.9±21.5 °C
Index of Refraction: 1.547
Molar Refractivity: 67.8±0.4 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 1.73
ACD/LogD (pH 5.5): 1.88
ACD/BCF (pH 5.5): 15.84
ACD/KOC (pH 5.5): 251.45
ACD/LogD (pH 7.4): 1.88
ACD/BCF (pH 7.4): 15.84
ACD/KOC (pH 7.4): 251.45
Polar Surface Area: 47 Å2
Polarizability: 26.9±0.5 10-24cm3
Surface Tension: 42.1±5.0 dyne/cm
Molar Volume: 213.5±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) =  1.81

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  371.14  (Adapted Stein & Brown method)
    Melting Pt (deg C):  128.15  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.2E-007  (Modified Grain method)
    Subcooled liquid VP: 1.28E-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):  2205
       log Kow used: 1.81 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  62.837 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.79E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.778E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.81  (KowWin est)
  Log Kaw used:  -6.557  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.367
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6196
   Biowin2 (Non-Linear Model)     :   0.8628
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5785  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5650  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5386
   Biowin6 (MITI Non-Linear Model):   0.2251
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0222
 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):  0.000171 Pa (1.28E-006 mm Hg)
  Log Koa (Koawin est  ): 8.367
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0176 
       Octanol/air (Koa) model:  5.71E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.388 
       Mackay model           :  0.584 
       Octanol/air (Koa) model:  0.00455 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  90.2072 E-12 cm3/molecule-sec
      Half-Life =     0.119 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.423 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     2.337500 E-17 cm3/molecule-sec
      Half-Life =     0.490 Days (at 7E11 mol/cm3)
      Half-Life =     11.766 Hrs
   Fraction sorbed to airborne particulates (phi): 0.486 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  182.4
      Log Koc:  2.261 

 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 = 0.697 (BCF = 4.982)
       log Kow used: 1.81 (estimated)

 Volatilization from Water:
    Henry LC:  6.79E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.359E+005  hours   (5662 days)
    Half-Life from Model Lake : 1.482E+006  hours   (6.177E+004 days)

 Removal In Wastewater Treatment:
    Total removal:               2.10  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     2.01  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       0.0628          2.29         1000       
   Water     30.1            900          1000       
   Soil      69.7            1.8e+003     1000       
   Sediment  0.0953          8.1e+003     0          
     Persistence Time: 1e+003 hr

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