ChemSpider 2D Image | (-)-Bakkenolide B | C22H30O6

(-)-Bakkenolide B

  • Molecular FormulaC22H30O6
  • Average mass390.470 Da
  • Monoisotopic mass390.204254 Da
  • ChemSpider ID9340308

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 6 of 6 defined stereocentres

More details:

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

(-)-Bakkenolide B
(2Z)-2-Méthyl-2-buténoate de (3R,3'R,3a'R,4'S,7'S,7a'R)-3'-acétoxy-7',7a'-diméthyl-4-méthylène-2-oxodécahydrospiro[furan-3,2'-inden]-4'-yle [French] [ACD/IUPAC Name]
(3R,3'R,3a'R,4'S,7'S,7a'R)-3'-Acetoxy-7',7a'-dimethyl-4-methylen-2-oxodecahydrospiro[furan-3,2'-inden]-4'-yl-(2Z)-2-methyl-2-butenoat [German] [ACD/IUPAC Name]
(3R,3'R,3a'R,4'S,7'S,7a'R)-3'-Acetoxy-7',7a'-dimethyl-4-methylene-2-oxodecahydrospiro[furan-3,2'-inden]-4'-yl (2Z)-2-methyl-2-butenoate [ACD/IUPAC Name]
18455-98-6 [RN]
2-Butenoic acid, 2-methyl-, (3R,3'R,3a'R,4'S,7'S,7a'R)-3'-(acetyloxy)decahydro-7',7'a-dimethyl-4-methylene-2-oxospiro[furan-3(2H),2'-[2H]inden]-4'-yl ester, (2Z)- [ACD/Index Name]
Bakkenolide B
Fukinolide

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

Density: 1.2±0.1 g/cm3
Boiling Point: 503.0±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 77.2±3.0 kJ/mol
Flash Point: 217.1±30.2 °C
Index of Refraction: 1.526
Molar Refractivity: 102.5±0.4 cm3
#H bond acceptors: 6
#H bond donors: 0
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 4.07
ACD/LogD (pH 5.5): 3.02
ACD/BCF (pH 5.5): 116.75
ACD/KOC (pH 5.5): 1050.40
ACD/LogD (pH 7.4): 3.02
ACD/BCF (pH 7.4): 116.75
ACD/KOC (pH 7.4): 1050.40
Polar Surface Area: 79 Å2
Polarizability: 40.6±0.5 10-24cm3
Surface Tension: 42.5±5.0 dyne/cm
Molar Volume: 334.1±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) =  4.67

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  447.47  (Adapted Stein & Brown method)
    Melting Pt (deg C):  142.82  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.65E-008  (Modified Grain method)
    Subcooled liquid VP: 5.68E-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):  0.3599
       log Kow used: 4.67 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.62646 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.91E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.211E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.67  (KowWin est)
  Log Kaw used:  -6.925  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.595
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7163
   Biowin2 (Non-Linear Model)     :   0.9981
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3326  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6644  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8662
   Biowin6 (MITI Non-Linear Model):   0.5001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2575
 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):  7.57E-005 Pa (5.68E-007 mm Hg)
  Log Koa (Koawin est  ): 11.595
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0396 
       Octanol/air (Koa) model:  0.0966 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.589 
       Mackay model           :  0.76 
       Octanol/air (Koa) model:  0.885 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 100.0976 E-12 cm3/molecule-sec
      Half-Life =     0.107 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.282 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     8.531250 E-17 cm3/molecule-sec
      Half-Life =     0.134 Days (at 7E11 mol/cm3)
      Half-Life =      3.224 Hrs
   Fraction sorbed to airborne particulates (phi): 0.674 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  9.054E+004
      Log Koc:  4.957 

 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 = 2.896 (BCF = 787.8)
       log Kow used: 4.67 (estimated)

 Volatilization from Water:
    Henry LC:  2.91E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.976E+005  hours   (1.657E+004 days)
    Half-Life from Model Lake : 4.337E+006  hours   (1.807E+005 days)

 Removal In Wastewater Treatment:
    Total removal:              64.58  percent
    Total biodegradation:        0.58  percent
    Total sludge adsorption:    63.99  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       0.0257          1.43         1000       
   Water     11.8            900          1000       
   Soil      75.2            1.8e+003     1000       
   Sediment  13              8.1e+003     0          
     Persistence Time: 1.56e+003 hr

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