ChemSpider 2D Image | desmethylxanthohumol | C20H20O5

desmethylxanthohumol

  • Molecular FormulaC20H20O5
  • Average mass340.370 Da
  • Monoisotopic mass340.131073 Da
  • ChemSpider ID4947362
  • Double-bond stereo - Double-bond stereo


More details:






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

(2E)-3-(4-Hydroxyphenyl)-1-[2,4,6-trihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-2-propen-1-on [German] [ACD/IUPAC Name]
(2E)-3-(4-Hydroxyphenyl)-1-[2,4,6-trihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-2-propen-1-one [ACD/IUPAC Name]
(2E)-3-(4-Hydroxyphényl)-1-[2,4,6-trihydroxy-3-(3-méthyl-2-butén-1-yl)phényl]-2-propén-1-one [French] [ACD/IUPAC Name]
115063-39-3 [RN]
2-Propen-1-one, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl)-, (2E)-
2-Propen-1-one, 3-(4-hydroxyphenyl)-1-[2,4,6-trihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-, (2E)- [ACD/Index Name]
desmethylxanthohumol
(2E)-3-(4-hydroxyphenyl)-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-en-1-one
(E)-3-(4-hydroxyphenyl)-1-[2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl]prop-2-en-1-one
2-Propen-1-one,3-(4-hydroxyphenyl)-1-[2,4,6-trihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-,(2E)-
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  • Miscellaneous
    • Chemical Class:

      A member of the class of chalcones that is <stereo>trans</stereo>-chalcone substituted by hydroxy groups at positions 4, 2', 4', and 6' and a 3-methylbut-2-en-1-yl group at position 3'. ChEBI CHEBI:80489
      A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2', 4', and 6' and a 3-methylbut-2-en-1-yl group at position 3'. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:80489
    • Compound Source:

      Linum usitatissimum PlantCyc CPD-7120
      xanthohumol biosynthesis PlantCyc CPD-7120
    • Bio Activity:

      naringenin chalcone + dimethylallyl diphosphate -> desmethylxanthohumol + diphosphate + diphosphate + H+ + H+ PlantCyc CPD-7120
      S-adenosyl-L-methionine + desmethylxanthohumol -> S-adenosyl-L-homocysteine + xanthohumol + S-adenosyl-L-homocysteine + H+ + H+ PlantCyc CPD-7120

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

Density: 1.3±0.1 g/cm3
Boiling Point: 570.7±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 88.8±3.0 kJ/mol
Flash Point: 313.0±26.6 °C
Index of Refraction: 1.680
Molar Refractivity: 98.0±0.3 cm3
#H bond acceptors: 5
#H bond donors: 4
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: 5.22
ACD/LogD (pH 5.5): 4.46
ACD/BCF (pH 5.5): 1431.91
ACD/KOC (pH 5.5): 6279.06
ACD/LogD (pH 7.4): 4.01
ACD/BCF (pH 7.4): 510.16
ACD/KOC (pH 7.4): 2237.12
Polar Surface Area: 98 Å2
Polarizability: 38.8±0.5 10-24cm3
Surface Tension: 62.9±3.0 dyne/cm
Molar Volume: 259.3±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) =  5.64

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  529.46  (Adapted Stein & Brown method)
    Melting Pt (deg C):  226.36  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.44E-013  (Modified Grain method)
    Subcooled liquid VP: 7.85E-011 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):  0.4077
       log Kow used: 5.64 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  20.338 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.53E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.976E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.64  (KowWin est)
  Log Kaw used:  -14.204  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.844
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1102
   Biowin2 (Non-Linear Model)     :   0.8737
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5752  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4247  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0789
   Biowin6 (MITI Non-Linear Model):   0.0196
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2116
 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):  1.05E-008 Pa (7.85E-011 mm Hg)
  Log Koa (Koawin est  ): 19.844
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  287 
       Octanol/air (Koa) model:  1.71E+007 
   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 = 308.4060 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 311.0660 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =   24.971 Min (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =   24.757 Min (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    44.049999 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    45.099998 E-17 cm3/molecule-sec [Trans-]
      Half-Life =    37.463 Min (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =    36.591 Min (at 7E11 mol/cm3) [Trans-isomer]
   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    :  4.415E+005
      Log Koc:  5.645 

 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 = 2.806 (BCF = 639.1)
       log Kow used: 5.64 (estimated)

 Volatilization from Water:
    Henry LC:  1.53E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  7.06E+012  hours   (2.942E+011 days)
    Half-Life from Model Lake : 7.702E+013  hours   (3.209E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              89.81  percent
    Total biodegradation:        0.75  percent
    Total sludge adsorption:    89.05  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       1.2e-005        0.357        1000       
   Water     4.74            900          1000       
   Soil      56.1            1.8e+003     1000       
   Sediment  39.2            8.1e+003     0          
     Persistence Time: 2.93e+003 hr




                    

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