ChemSpider 2D Image | Burchellin | C20H20O5

Burchellin

  • Molecular FormulaC20H20O5
  • Average mass340.370 Da
  • Monoisotopic mass340.131073 Da
  • ChemSpider ID9079184

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

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

(2S,3S,3aR)-3a-Allyl-2-(1,3-benzodioxol-5-yl)-5-methoxy-3-methyl-3,3a-dihydro-1-benzofuran-6(2H)-on [German] [ACD/IUPAC Name]
(2S,3S,3aR)-3a-Allyl-2-(1,3-benzodioxol-5-yl)-5-methoxy-3-methyl-3,3a-dihydro-1-benzofuran-6(2H)-one [ACD/IUPAC Name]
(2S,3S,3aR)-3a-Allyl-2-(1,3-benzodioxol-5-yl)-5-méthoxy-3-méthyl-3,3a-dihydro-1-benzofuran-6(2H)-one [French] [ACD/IUPAC Name]
38276-59-4 [RN]
6(2H)-Benzofuranone, 2-(1,3-benzodioxol-5-yl)-3,3a-dihydro-5-methoxy-3-methyl-3a-(2-propen-1-yl)-, (2S,3S,3aR)- [ACD/Index Name]
Burchellin
(2S,3S,3Ar)-2-(1,3-benzodioxol-5-yl)-5-methoxy-3-methyl-3a-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one
(2S,3S,3aR)-2-(2H-1,3-benzodioxol-5-yl)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-3,3a-dihydro-1-benzofuran-6(2H)-one
  • Miscellaneous

    • Chemical Class:

      A neolignan with formula C<smallsub>20</smallsub>H<smallsub>20</smallsub>O<smallsub>5</smallsub> that is isolated from <ital>Ocotea cymbarum</ital> and <ital>Piper wallichii</ital>. It is active again st a variety of parasites including <ital>T. cruzi</ital>, the vector for Chagas disease. ChEBI CHEBI:132650
      A neolignan with formula C20H20O5 that is isolated from Ocotea cymbarum and Piper wallichii. It is active again; st a variety of parasites including T. cruzi, the vector for Chagas disease. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:132650
      A neolignan with formula C20H20O5 that is isolated from Ocotea cymbarum and Piper wallichii. It is active against a variety of parasites including T. cruzi, the vector for Chagas disease. ChEBI CHEBI:132650

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

Density: 1.3±0.1 g/cm3
Boiling Point: 491.0±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 75.8±3.0 kJ/mol
Flash Point: 216.4±28.8 °C
Index of Refraction: 1.603
Molar Refractivity: 91.6±0.4 cm3
#H bond acceptors: 5
#H bond donors: 0
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 3.05
ACD/LogD (pH 5.5): 3.06
ACD/BCF (pH 5.5): 124.65
ACD/KOC (pH 5.5): 1100.79
ACD/LogD (pH 7.4): 3.06
ACD/BCF (pH 7.4): 124.65
ACD/KOC (pH 7.4): 1100.79
Polar Surface Area: 54 Å2
Polarizability: 36.3±0.5 10-24cm3
Surface Tension: 49.7±5.0 dyne/cm
Molar Volume: 266.7±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) =  2.06

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  436.70  (Adapted Stein & Brown method)
    Melting Pt (deg C):  183.03  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.18E-008  (Modified Grain method)
    Subcooled liquid VP: 2.75E-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):  123.9
       log Kow used: 2.06 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  407.42 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Ketones
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.40E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.234E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.06  (KowWin est)
  Log Kaw used:  -6.242  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.302
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.9810
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1777  (months      )
   Biowin4 (Primary Survey Model) :   3.1420  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0351
   Biowin6 (MITI Non-Linear Model):   0.0030
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.6815
 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):  0.000367 Pa (2.75E-006 mm Hg)
  Log Koa (Koawin est  ): 8.302
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00818 
       Octanol/air (Koa) model:  4.92E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.228 
       Mackay model           :  0.396 
       Octanol/air (Koa) model:  0.00392 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 392.4944 E-12 cm3/molecule-sec
      Half-Life =     0.027 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    19.621 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    12.589999 E-17 cm3/molecule-sec
      Half-Life =     0.091 Days (at 7E11 mol/cm3)
      Half-Life =      2.185 Hrs
   Fraction sorbed to airborne particulates (phi): 0.312 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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 = 0.884 (BCF = 7.657)
       log Kow used: 2.06 (estimated)

 Volatilization from Water:
    Henry LC:  1.4E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.716E+004  hours   (3215 days)
    Half-Life from Model Lake : 8.419E+005  hours   (3.508E+004 days)

 Removal In Wastewater Treatment:
    Total removal:               2.30  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.21  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       0.0189          0.503        1000       
   Water     27.7            1.44e+003    1000       
   Soil      72.1            2.88e+003    1000       
   Sediment  0.118           1.3e+004     0          
     Persistence Time: 1.18e+003 hr

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