ChemSpider 2D Image | (2S)-2'-methoxykurarinone | C27H32O6

(2S)-2'-methoxykurarinone

  • Molecular FormulaC27H32O6
  • Average mass452.539 Da
  • Monoisotopic mass452.219879 Da
  • ChemSpider ID10155208

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

(2S)-2'-methoxykurarinone
(2S)-7-Hydroxy-2-(4-hydroxy-2-methoxyphenyl)-8-[(2R)-2-isopropenyl-5-methyl-4-hexen-1-yl]-5-methoxy-2,3-dihydro-4H-chromen-4-on [German] [ACD/IUPAC Name]
(2S)-7-Hydroxy-2-(4-hydroxy-2-methoxyphenyl)-8-[(2R)-2-isopropenyl-5-methyl-4-hexen-1-yl]-5-methoxy-2,3-dihydro-4H-chromen-4-one [ACD/IUPAC Name]
(2S)-7-Hydroxy-2-(4-hydroxy-2-méthoxyphényl)-8-[(2R)-2-isopropényl-5-méthyl-4-hexén-1-yl]-5-méthoxy-2,3-dihydro-4H-chromén-4-one [French] [ACD/IUPAC Name]
4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2R)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]-, (2S)- [ACD/Index Name]
(2S)-2`-METHOXYKURARINONE
(2S)-7,4'-Dihydroxy-8-lavandulyl-5,2'-dimethoxyflavanone
(2S)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2R)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]-2,3-dihydro-4H-chromen-4-one
(2S)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2R)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]-2,3-dihydrochromen-4-one
[270249-38-2] [RN]
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  • Miscellaneous

    • Chemical Class:

      A dimethoxyflavanone that is (2<stereo>S</stereo>)-(<minus/>)-kurarinone in which the hydroxy group at position 2' is replaced by a methoxy group. Isolated from the roots of <ital>Sophora flavescens</ ital>, it exhibits cytotoxicity against human myeloid leukemia HL-60 cells. ChEBI CHEBI:66151
      A dimethoxyflavanone that is (2S)-(-)-kurarinone in which the hydroxy group at position 2' is replaced by a methoxy group. Isolated from the roots of Sophora flavescens, it exhibits cytotoxicity again st human myeloid leukemia HL-60 cells. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:66151, CHEBI:66151

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

Density: 1.2±0.1 g/cm3
Boiling Point: 643.6±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization: 98.4±3.0 kJ/mol
Flash Point: 213.2±25.0 °C
Index of Refraction: 1.575
Molar Refractivity: 127.8±0.3 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 1
ACD/LogP: 7.05
ACD/LogD (pH 5.5): 6.57
ACD/BCF (pH 5.5): 57816.41
ACD/KOC (pH 5.5): 88923.02
ACD/LogD (pH 7.4): 6.32
ACD/BCF (pH 7.4): 32205.16
ACD/KOC (pH 7.4): 49532.31
Polar Surface Area: 85 Å2
Polarizability: 50.7±0.5 10-24cm3
Surface Tension: 45.5±3.0 dyne/cm
Molar Volume: 386.4±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) =  7.13

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  578.35  (Adapted Stein & Brown method)
    Melting Pt (deg C):  249.20  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.95E-015  (Modified Grain method)
    Subcooled liquid VP: 2.72E-012 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):  0.004425
       log Kow used: 7.13 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.065894 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.01E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.339E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  7.13  (KowWin est)
  Log Kaw used:  -15.384  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  22.514
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2209
   Biowin2 (Non-Linear Model)     :   0.9949
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0402  (months      )
   Biowin4 (Primary Survey Model) :   3.4148  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2042
   Biowin6 (MITI Non-Linear Model):   0.0325
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2090
 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):  3.63E-010 Pa (2.72E-012 mm Hg)
  Log Koa (Koawin est  ): 22.514
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  8.27E+003 
       Octanol/air (Koa) model:  8.02E+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 = 392.8941 E-12 cm3/molecule-sec
      Half-Life =     0.027 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    19.601 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    44.200001 E-17 cm3/molecule-sec
      Half-Life =     0.026 Days (at 7E11 mol/cm3)
      Half-Life =     37.336 Min
   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    :  2.589E+006
      Log Koc:  6.413 

 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 = 3.788 (BCF = 6144)
       log Kow used: 7.13 (estimated)

 Volatilization from Water:
    Henry LC:  1.01E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.233E+014  hours   (5.138E+012 days)
    Half-Life from Model Lake : 1.345E+015  hours   (5.605E+013 days)

 Removal In Wastewater Treatment:
    Total removal:              93.89  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.12  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       1.23e-005       0.319        1000       
   Water     1.26            1.44e+003    1000       
   Soil      42.8            2.88e+003    1000       
   Sediment  56              1.3e+004     0          
     Persistence Time: 6.14e+003 hr

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