ChemSpider 2D Image | (+)-lyoniresinol | C22H28O8

(+)-lyoniresinol

  • Molecular FormulaC22H28O8
  • Average mass420.453 Da
  • Monoisotopic mass420.178406 Da
  • ChemSpider ID9886175

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

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(+)-lyoniresinol
(6R,7R,8S)-8-(4-Hydroxy-3,5-diméthoxyphényl)-6,7-bis(hydroxyméthyl)-1,3-diméthoxy-5,6,7,8-tétrahydro-2-naphtalénol [French] [ACD/IUPAC Name]
(6R,7R,8S)-8-(4-Hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydro-2-naphthalenol [ACD/IUPAC Name]
(6R,7R,8S)-8-(4-Hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydro-2-naphthalinol [German] [ACD/IUPAC Name]
2,3-Naphthalenedimethanol, 1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-dimethoxy-, (1S,2R,3R)- [ACD/Index Name]
Lyoniresinol
(6R,7R,8S)-8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-ol
[14464-90-5] [RN]
[144655-81-2] [RN]
14464-90-5 [RN]
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  • Miscellaneous

    • Chemical Class:

      A lignan that is tetralin substituted by a 4-hydroxy-3,5-dimethoxy group at position 4, hydroxymethyl groups at positions 2 and 3, methoxy groups at positions 5 and 7 and a hydroxy group at position 6 . Isolated from <ital>Machilus robusta</ital> and <ital>Sinocalamus affinis</ital>, it exhibits antineoplastic activity. ChEBI CHEBI:68168
      A lignan that is tetralin substituted by a 4-hydroxy-3,5-dimethoxy group at position 4, hydroxymethyl groups at positions 2 and 3, methoxy groups at positions 5 and 7 and a hydroxy group at position 6 . Isolated from Machilus robusta and Sinocalamus affinis, it exhibits antineoplastic activity. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:68168, CHEBI:68168

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

Density: 1.3±0.1 g/cm3
Boiling Point: 617.6±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 96.3±3.0 kJ/mol
Flash Point: 327.3±31.5 °C
Index of Refraction: 1.583
Molar Refractivity: 110.4±0.3 cm3
#H bond acceptors: 8
#H bond donors: 4
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 0.81
ACD/LogD (pH 5.5): 1.44
ACD/BCF (pH 5.5): 7.33
ACD/KOC (pH 5.5): 144.85
ACD/LogD (pH 7.4): 1.44
ACD/BCF (pH 7.4): 7.30
ACD/KOC (pH 7.4): 144.33
Polar Surface Area: 118 Å2
Polarizability: 43.8±0.5 10-24cm3
Surface Tension: 51.6±3.0 dyne/cm
Molar Volume: 330.5±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) =  1.73

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  587.77  (Adapted Stein & Brown method)
    Melting Pt (deg C):  253.60  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.9E-016  (Modified Grain method)
    Subcooled liquid VP: 8.97E-014 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):  76.53
       log Kow used: 1.73 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  223.01 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.29E-022  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.096E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.73  (KowWin est)
  Log Kaw used:  -20.278  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  22.008
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.7334
   Biowin2 (Non-Linear Model)     :   1.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3205  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7508  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7775
   Biowin6 (MITI Non-Linear Model):   0.4599
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.2983
 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):  1.2E-011 Pa (8.97E-014 mm Hg)
  Log Koa (Koawin est  ): 22.008
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.51E+005 
       Octanol/air (Koa) model:  2.5E+009 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 222.6753 E-12 cm3/molecule-sec
      Half-Life =     0.048 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.576 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  9546
      Log Koc:  3.980 

 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 = -0.020 (BCF = 0.9547)
       log Kow used: 1.73 (estimated)

 Volatilization from Water:
    Henry LC:  1.29E-022 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.307E+018  hours   (3.878E+017 days)
    Half-Life from Model Lake : 1.015E+020  hours   (4.23E+018 days)

 Removal In Wastewater Treatment:
    Total removal:               2.06  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.97  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       2.33e-008       1.15         1000       
   Water     28.3            900          1000       
   Soil      71.6            1.8e+003     1000       
   Sediment  0.0836          8.1e+003     0          
     Persistence Time: 1.29e+003 hr

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