ChemSpider 2D Image | Versicolactone B | C15H22O3

Versicolactone B

  • Molecular FormulaC15H22O3
  • Average mass250.333 Da
  • Monoisotopic mass250.156891 Da
  • ChemSpider ID4943433

  • 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

(1R,4S,5E,8R,9R)-4-Hydroxy-8-isopropenyl-5-methyl-10-oxabicyclo[7.2.1]dodec-5-en-11-on [German] [ACD/IUPAC Name]
(1R,4S,5E,8R,9R)-4-Hydroxy-8-isopropenyl-5-methyl-10-oxabicyclo[7.2.1]dodec-5-en-11-one [ACD/IUPAC Name]
(1R,4S,5E,8R,9R)-4-Hydroxy-8-isopropényl-5-méthyl-10-oxabicyclo[7.2.1]dodéc-5-én-11-one [French] [ACD/IUPAC Name]
10-Oxabicyclo[7.2.1]dodec-5-en-11-one, 4-hydroxy-5-methyl-8-(1-methylethenyl)-, (1R,4S,5E,8R,9R)- [ACD/Index Name]
Versicolactone B
(1R,4S,5E,8R,9R)-4-hydroxy-5-methyl-8-(prop-1-en-2-yl)-10-oxabicyclo[7.2.1]dodec-5-en-11-one
104613-44-7 [RN]
10-Oxabicyclo(7.2.1)dodec-5-en-11-one, 4-hydroxy-5-methyl-8-(1-methylethenyl)-, (1R-(1R*,4S*,5E,8R*,9R*))-
  • Miscellaneous

    • Chemical Class:

      A sesquiterpene lactone with formula C<smallsub>15</smallsub>H<smallsub>22</smallsub>O<smallsub>3</smallsub> that is isolated from <ital>Viola yedoensis</ital> and <ital>Aristolochia versicolor</ital> . ChEBI CHEBI:132826

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

Density: 1.1±0.1 g/cm3
Boiling Point: 420.5±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 77.9±6.0 kJ/mol
Flash Point: 176.4±21.5 °C
Index of Refraction: 1.505
Molar Refractivity: 69.8±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 2.16
ACD/LogD (pH 5.5): 2.81
ACD/BCF (pH 5.5): 80.74
ACD/KOC (pH 5.5): 806.67
ACD/LogD (pH 7.4): 2.81
ACD/BCF (pH 7.4): 80.74
ACD/KOC (pH 7.4): 806.67
Polar Surface Area: 47 Å2
Polarizability: 27.7±0.5 10-24cm3
Surface Tension: 35.8±3.0 dyne/cm
Molar Volume: 235.2±3.0 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) =  2.64

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  385.11  (Adapted Stein & Brown method)
    Melting Pt (deg C):  105.44  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.24E-008  (Modified Grain method)
    Subcooled liquid VP: 5.05E-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):  420.9
       log Kow used: 2.64 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  148.62 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.41E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.449E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.64  (KowWin est)
  Log Kaw used:  -5.856  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.496
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9613
   Biowin2 (Non-Linear Model)     :   0.9905
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9461  (weeks       )
   Biowin4 (Primary Survey Model) :   3.8450  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6203
   Biowin6 (MITI Non-Linear Model):   0.3322
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4387
 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):  6.73E-005 Pa (5.05E-007 mm Hg)
  Log Koa (Koawin est  ): 8.496
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0446 
       Octanol/air (Koa) model:  7.69E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.617 
       Mackay model           :  0.781 
       Octanol/air (Koa) model:  0.00612 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 158.4658 E-12 cm3/molecule-sec
      Half-Life =     0.067 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.810 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    44.200001 E-17 cm3/molecule-sec
      Half-Life =     0.026 Days (at 7E11 mol/cm3)
      Half-Life =     37.336 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.699 (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 = 1.336 (BCF = 21.67)
       log Kow used: 2.64 (estimated)

 Volatilization from Water:
    Henry LC:  3.41E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.717E+004  hours   (1132 days)
    Half-Life from Model Lake : 2.965E+005  hours   (1.235E+004 days)

 Removal In Wastewater Treatment:
    Total removal:               3.56  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.46  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       0.0459          0.45         1000       
   Water     26.4            360          1000       
   Soil      73.3            720          1000       
   Sediment  0.232           3.24e+003    0          
     Persistence Time: 457 hr

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