ChemSpider 2D Image | futokadsurin A | C21H26O5

futokadsurin A

  • Molecular FormulaC21H26O5
  • Average mass358.428 Da
  • Monoisotopic mass358.178009 Da
  • ChemSpider ID7827827
  • defined stereocentres - 4 of 4 defined stereocentres


More details:



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4-[(2R,3S,4S,5S)-5-(3,4-Dimethoxyphenyl)-3,4-dimethyltetrahydro-2-furanyl]-2-methoxyphenol [German] [ACD/IUPAC Name]
4-[(2R,3S,4S,5S)-5-(3,4-Diméthoxyphényl)-3,4-diméthyltétrahydro-2-furanyl]-2-méthoxyphénol [French] [ACD/IUPAC Name]
4-[(2R,3S,4S,5S)-5-(3,4-Dimethoxyphenyl)-3,4-dimethyltetrahydro-2-furanyl]-2-methoxyphenolato [ACD/IUPAC Name]
futokadsurin A
Phenol, 4-[(2R,3S,4S,5S)-5-(3,4-dimethoxyphenyl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxy- [ACD/Index Name]
4-[rel-(2R,3S,4S,5S)-5-(3,4-dimethoxyphenyl)-3,4-dimethyltetrahydrofuran-2-yl]-2-methoxyphenol
rel-(7S,8S,7'R,8'S)-3,4,3'-trimethoxy-4'-hydroxy-7,7'-epoxylignan
  • Miscellaneous
    • Chemical Class:

      A lignan that is tetrahydrofuran substituted by methyl groups at positions 3 and 4 (relatively <stereo>trans</stereo> configuration), a 3,4-dimethoxyphenyl moiety at position 5 (relatively <stereo>tra ns</stereo> to the methyl group at position 4) and a 4-hydroxy-3-methoxyphenyl group at position 2 (relatively <stereo>cis</stereo> to the methyl group at position 3). Isolated from the aerial parts of <ital>Piper futokadsura</ital>, it exhibits inhibitory activity against production of nitric oxide (NO). ChEBI CHEBI:65936
      A lignan that is tetrahydrofuran substituted by methyl groups at positions 3 and 4 (relatively trans configuration), a 3,4-dimethoxyphenyl moiety at position 5 (relatively tra; ns to the methyl group at position 4) and a 4-hydroxy-3-methoxyphenyl group at position 2 (relatively cis to the methyl group at position 3). Isolated from the aerial parts ; of Piper futokadsura, it exhibits inhibitory ac tivity against production of nitric oxide (NO). ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65936

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

Density: 1.1±0.1 g/cm3
Boiling Point: 492.8±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 78.9±3.0 kJ/mol
Flash Point: 251.8±28.7 °C
Index of Refraction: 1.542
Molar Refractivity: 100.3±0.3 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 3.75
ACD/LogD (pH 5.5): 3.90
ACD/BCF (pH 5.5): 544.54
ACD/KOC (pH 5.5): 3162.65
ACD/LogD (pH 7.4): 3.90
ACD/BCF (pH 7.4): 542.88
ACD/KOC (pH 7.4): 3152.97
Polar Surface Area: 57 Å2
Polarizability: 39.8±0.5 10-24cm3
Surface Tension: 38.8±3.0 dyne/cm
Molar Volume: 318.5±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) =  4.03

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  454.82  (Adapted Stein & Brown method)
    Melting Pt (deg C):  190.89  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.1E-009  (Modified Grain method)
    Subcooled liquid VP: 6.05E-008 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):  1.991
       log Kow used: 4.03 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2.2625 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.09E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.606E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.03  (KowWin est)
  Log Kaw used:  -12.068  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.098
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7411
   Biowin2 (Non-Linear Model)     :   0.8950
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2804  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5919  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3539
   Biowin6 (MITI Non-Linear Model):   0.0840
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.3682
 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):  8.07E-006 Pa (6.05E-008 mm Hg)
  Log Koa (Koawin est  ): 16.098
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.372 
       Octanol/air (Koa) model:  3.08E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.931 
       Mackay model           :  0.967 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 104.6043 E-12 cm3/molecule-sec
      Half-Life =     0.102 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.227 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.949 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5.201E+004
      Log Koc:  4.716 

 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 = 2.403 (BCF = 253.1)
       log Kow used: 4.03 (estimated)

 Volatilization from Water:
    Henry LC:  2.09E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.304E+010  hours   (2.21E+009 days)
    Half-Life from Model Lake : 5.786E+011  hours   (2.411E+010 days)

 Removal In Wastewater Treatment:
    Total removal:              31.45  percent
    Total biodegradation:        0.33  percent
    Total sludge adsorption:    31.12  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       2.97e-006       2.46         1000       
   Water     10.9            900          1000       
   Soil      86.3            1.8e+003     1000       
   Sediment  2.76            8.1e+003     0          
     Persistence Time: 1.89e+003 hr




                    

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