ChemSpider 2D Image | (−)-Arctigenin | C21H24O6

(−)-Arctigenin

  • Molecular FormulaC21H24O6
  • Average mass372.412 Da
  • Monoisotopic mass372.157288 Da
  • ChemSpider ID58506

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

(−)-Arctigenin
(-)-Arctigenin
(3R,4R)-4-(3,4-Dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydro-2(3H)-furanon [German] [ACD/IUPAC Name]
(3R,4R)-4-(3,4-Dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydro-2(3H)-furanone [ACD/IUPAC Name]
(3R,4R)-4-(3,4-Diméthoxybenzyl)-3-(4-hydroxy-3-méthoxybenzyl)dihydro-2(3H)-furanone [French] [ACD/IUPAC Name]
(3R,4R)-4-(3,4-Dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one
(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
(3R,4R)-4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone
144901-91-7 [RN]
2(3H)-Furanone [ACD/Index Name] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

A1854_SIGMA [DBID]
AIDS002466 [DBID]
AIDS-002466 [DBID]
C10545 [DBID]
NCGC00025291-01 [DBID]
Tocris-1777 [DBID]
  • Experimental Physico-chemical Properties

    • Experimental Solubility:

      Soluble to 25 mM in ethanol and to 100 mM in DMSO Tocris Bioscience 1777
      Soluble to 25 mM in ethanol with gentle warming and to 100 mM in DMSO Tocris Bioscience 1777
  • Miscellaneous

    • Target Organs:

      Others TargetMol T2957

    • Compound Source:

      arctigenin and isoarctigenin biosynthesis PlantCyc CPD-17600
      Linum usitatissimum PlantCyc CPD-17600

    • Bio Activity:

      Antioxidant, anti-inflammatory, antiproliferative and antiviral agent. Inhibits LPS-induced iNOS expression via inhibition of I?B? phosphorylation and p65 nuclear translocation (IC50 = 10 nM). Inhibit s HIV-1 replication in vitro. Also potently inhibits MKK1 (MEK1) (IC50 = 0.5 nM) and provides neuroprotection by binding to kainate receptors. Tocris Bioscience 1777
      Antioxidant, anti-inflammatory, antiproliferative and antiviral agent. Inhibits LPS-induced iNOS expression via inhibition of I?B? phosphorylation and p65 nuclear translocation (IC50 = 10 nM). Inhibits HIV-1 replication in vitro. Also potently inhibits MKK1 (MEK1) (IC50 = 0.5 nM) and provides neuroprotection by binding to kainate receptors. Tocris Bioscience 1777
      Antioxidant, anti-inflammatory, antiproliferative and antiviral agent. Inhibits LPS-induced iNOS expression via inhibition of IkappaBalpha phosphorylation and p65 nuclear translocation (IC50 = 10 nM). Inhibits HIV-1 replication in vitro. Also potently inhibits MKK1 (MEK1) (IC50 = 0.5 nM) and provides neuroprotection by binding to kainate receptors. Tocris Bioscience 1777
      Arctigenin is a lignan found in certain plants of the Asteraceae; it has shown antiviral and anticancer effects in glass; it is the aglycone of arctiin. MedChem Express
      Arctigenin is a lignan found in certain plants of the Asteraceae; it has shown antiviral and anticancer effects in glass; it is the aglycone of arctiin.; IC50 value: ; Target: anticancer agent; Arctiin and its aglucone, arctigenin from the fruits of Arctium lappa L. MedChem Express HY-N0035
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB0119]
      Enzymes Tocris Bioscience 1777
      Enzymes/Kinase/ERK/ERK2 / MAPK1 Hello Bio [HB0119]
      Kinases Tocris Bioscience 1777
      MEK Tocris Bioscience 1777
      Others MedChem Express HY-N0035
      Others TargetMol T2957
      Potent MAP kinase kinase (MKK/MEK) inhibitor Hello Bio [HB0119]
      Potent MAP kinase kinase (MKK/MEK) inhibitor (IC<sub>50</sub> = 1 nM for MKK1/MEK1). Antiviral, anti-cancer, antioxidant and anti-inflammatory compound. Inhibits iNOS expression by suppressing 1-&kappa;B&alpha; phosphorylation and nuclear translocation of p65 (IC<sub>50</sub> = 10 nM). Shows neuroprotective actions. Hello Bio [HB0119]
      Potent MEK1 inhibitor. Also inhibits I?B? phosphorylation Tocris Bioscience 1777
      Potent MEK1 inhibitor. Also inhibits IkappaBalpha phosphorylation Tocris Bioscience 1777
      S-adenosyl-L-methionine + (-)-matairesinol -> arctigenin + S-adenosyl-L-homocysteine + H+ PlantCyc CPD-17600

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

Density: 1.2±0.1 g/cm3
Boiling Point: 567.0±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 88.3±3.0 kJ/mol
Flash Point: 198.8±22.2 °C
Index of Refraction: 1.576
Molar Refractivity: 100.4±0.3 cm3
#H bond acceptors: 6
#H bond donors: 1
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 2.47
ACD/LogD (pH 5.5): 2.51
ACD/BCF (pH 5.5): 47.64
ACD/KOC (pH 5.5): 552.95
ACD/LogD (pH 7.4): 2.51
ACD/BCF (pH 7.4): 47.53
ACD/KOC (pH 7.4): 551.68
Polar Surface Area: 74 Å2
Polarizability: 39.8±0.5 10-24cm3
Surface Tension: 48.6±3.0 dyne/cm
Molar Volume: 303.3±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) =  2.68

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  515.71  (Adapted Stein & Brown method)
    Melting Pt (deg C):  219.94  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.09E-011  (Modified Grain method)
    Subcooled liquid VP: 1.32E-009 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):  23.08
       log Kow used: 2.68 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.92699 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.54E-014  atm-m3/mole
   Group Method:   1.94E-012  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  2.314E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.68  (KowWin est)
  Log Kaw used:  -11.984  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.664
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.3653
   Biowin2 (Non-Linear Model)     :   1.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2487  (months      )
   Biowin4 (Primary Survey Model) :   3.6734  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5816
   Biowin6 (MITI Non-Linear Model):   0.3067
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5267
 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):  1.76E-007 Pa (1.32E-009 mm Hg)
  Log Koa (Koawin est  ): 14.664
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  17 
       Octanol/air (Koa) model:  113 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.998 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  92.0024 E-12 cm3/molecule-sec
      Half-Life =     0.116 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.395 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  9.267E+004
      Log Koc:  4.967 

 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 = 1.367 (BCF = 23.29)
       log Kow used: 2.68 (estimated)

 Volatilization from Water:
    Henry LC:  1.94E-012 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 5.824E+008  hours   (2.427E+007 days)
    Half-Life from Model Lake : 6.354E+009  hours   (2.647E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               3.73  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.62  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       0.00908         2.79         1000       
   Water     13.4            1.44e+003    1000       
   Soil      86.4            2.88e+003    1000       
   Sediment  0.164           1.3e+004     0          
     Persistence Time: 2.33e+003 hr

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