ChemSpider 2D Image | futokadsurin C | C21H24O5

futokadsurin C

  • Molecular FormulaC21H24O5
  • Average mass356.412 Da
  • Monoisotopic mass356.162384 Da
  • ChemSpider ID7827829
  • defined stereocentres - 4 of 4 defined stereocentres


More details:






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

1,3-Benzodioxole, 5-[(2R,3R,4S,5S)-5-(3,4-dimethoxyphenyl)tetrahydro-3,4-dimethyl-2-furanyl]- [ACD/Index Name]
5-[(2R,3R,4S,5S)-5-(3,4-Dimethoxyphenyl)-3,4-dimethyltetrahydro-2-furanyl]-1,3-benzodioxol [German] [ACD/IUPAC Name]
5-[(2R,3R,4S,5S)-5-(3,4-Dimethoxyphenyl)-3,4-dimethyltetrahydro-2-furanyl]-1,3-benzodioxole [ACD/IUPAC Name]
5-[(2R,3R,4S,5S)-5-(3,4-Diméthoxyphényl)-3,4-diméthyltétrahydro-2-furanyl]-1,3-benzodioxole [French] [ACD/IUPAC Name]
futokadsurin C
(7R,8R,7'S,8'S)-3',4'-dimethoxy-3,4-methylenedioxy-7,7'-epoxylignan
5-[(2R,3R,4S,5S)-5-(3,4-dimethoxyphenyl)-3,4-dimethyltetrahydrofuran-2-yl]-1,3-benzodioxole
852459-91-7 [RN]
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65938
  • Miscellaneous
    • Chemical Class:

      A lignan that is tetrahydrofuran substituted by methyl groups at positions 3 and 4, a 3,4-dimethoxyphenyl group at position 5 and a 1,3-benzodioxol-5-yl moiety at position 2 (the 2<stereo>R</stereo>,3 <stereo>R</stereo>,4<stereo>S</stereo>,5<stereo>S</stereo> stereoisomer). Isolated from the aerial parts of <ital>Piper futokadsura</ital>, it exhibits inhibitory activity against production of nitric oxide (NO). ChEBI CHEBI:65938
      A lignan that is tetrahydrofuran substituted by methyl groups at positions 3 and 4, a 3,4-dimethoxyphenyl group at position 5 and a 1,3-benzodioxol-5-yl moiety at position 2 (the 2R,3; R,4S,5S stereoi somer). Isolated from the aerial parts of Piper futokadsura, it exhibits inhibitory activity against production of nitric; oxide (NO). ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65938

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

Density: 1.2±0.1 g/cm3
Boiling Point: 467.5±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 70.2±3.0 kJ/mol
Flash Point: 189.1±28.6 °C
Index of Refraction: 1.550
Molar Refractivity: 97.9±0.3 cm3
#H bond acceptors: 5
#H bond donors: 0
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 4.64
ACD/LogD (pH 5.5): 4.08
ACD/BCF (pH 5.5): 737.78
ACD/KOC (pH 5.5): 3930.66
ACD/LogD (pH 7.4): 4.08
ACD/BCF (pH 7.4): 737.78
ACD/KOC (pH 7.4): 3930.66
Polar Surface Area: 46 Å2
Polarizability: 38.8±0.5 10-24cm3
Surface Tension: 41.3±3.0 dyne/cm
Molar Volume: 307.3±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) =  3.36

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  438.32  (Adapted Stein & Brown method)
    Melting Pt (deg C):  173.96  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.74E-008  (Modified Grain method)
    Subcooled liquid VP: 9.57E-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):  7.613
       log Kow used: 3.36 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5.3736 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.32E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.688E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.36  (KowWin est)
  Log Kaw used:  -7.588  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.948
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.2004
   Biowin2 (Non-Linear Model)     :   0.0004
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2693  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4585  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1388
   Biowin6 (MITI Non-Linear Model):   0.0081
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3734
 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):  0.000128 Pa (9.57E-007 mm Hg)
  Log Koa (Koawin est  ): 10.948
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0235 
       Octanol/air (Koa) model:  0.0218 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.459 
       Mackay model           :  0.653 
       Octanol/air (Koa) model:  0.635 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 342.2882 E-12 cm3/molecule-sec
      Half-Life =     0.031 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    22.499 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     9.639999 E-17 cm3/molecule-sec
      Half-Life =     0.119 Days (at 7E11 mol/cm3)
      Half-Life =      2.853 Hrs
   Fraction sorbed to airborne particulates (phi): 0.556 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  108.7
      Log Koc:  2.036 

 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 = 1.889 (BCF = 77.48)
       log Kow used: 3.36 (estimated)

 Volatilization from Water:
    Henry LC:  6.32E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.749E+006  hours   (7.287E+004 days)
    Half-Life from Model Lake : 1.908E+007  hours   (7.95E+005 days)

 Removal In Wastewater Treatment:
    Total removal:              10.22  percent
    Total biodegradation:        0.16  percent
    Total sludge adsorption:    10.06  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       0.00722         0.594        1000       
   Water     13.6            900          1000       
   Soil      85.7            1.8e+003     1000       
   Sediment  0.709           8.1e+003     0          
     Persistence Time: 1.52e+003 hr




                    

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