ChemSpider 2D Image | Taxifolin | C15H12O7

Taxifolin

  • Molecular FormulaC15H12O7
  • Average mass304.252 Da
  • Monoisotopic mass304.058289 Da
  • ChemSpider ID388626
  • defined stereocentres - 2 of 2 defined stereocentres


More details:






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

(+)-Taxifolin
(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-chromen-4-on [German] [ACD/IUPAC Name]
(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-chromen-4-one [ACD/IUPAC Name]
(2R,3R)-2-(3,4-Dihydroxyphényl)-3,5,7-trihydroxy-2,3-dihydro-4H-chromén-4-one [French] [ACD/IUPAC Name]
207-543-4 [EINECS]
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)- [ACD/Index Name]
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R-trans)-
5-18-05-00451 [Beilstein]
9SOB9E3987
Dihydroquercetin
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:17948 [DBID]
78666_FLUKA [DBID]
AIDS003061 [DBID]
AIDS-003061 [DBID]
BRN 0093548 [DBID]
C01617 [DBID]
T4512_SIGMA [DBID]
ZINC00105077 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      Adrenergic Receptor antagonist;NGF inhibitor;TNF-alpha inhibitor TargetMol T1738
    • Chemical Class:

      A taxifolin that has (2<stereo>R</stereo>,3<stereo>R</stereo>)-configuration. ChEBI CHEBI:17948
    • Compound Source:

      Isolated from a plant Susan Richardson [Structure found in ChemSpider, confirmed from ACD/Dictionary]
      Pterogyne nitens (Fabaceae) Susan Richardson [Structure found in ChemSpider, confirmed from ACD/Dictionary]
    • Bio Activity:

      ??-adrenergic receptor;Beta-nerve growth factor; TNF TargetMol T1738
      GPCR/G Protein; Neuroscience; Immunology/Inflammation TargetMol T1738
      Others MedChem Express HY-N0136
      Taxifolin(Dihydroquercetin) is a flavanonol, a type of flavonoid; exhibits antitumor and antidiabetic properties. MedChem Express
      Taxifolin(Dihydroquercetin) is a flavanonol, a type of flavonoid; exhibits antitumor and antidiabetic properties.; IC50 value:; Target: ; in vitro: EGF receptor (EGFR), phosphoinositide 3-kinase (PI3K), and Src are potential targets for taxifolin. MedChem Express HY-N0136
      Taxifolin(Dihydroquercetin) is a flavanonol, a type of flavonoid; exhibits antitumor and antidiabetic properties.;IC50 value:;Target: ;In vitro: EGF receptor (EGFR), phosphoinositide 3-kinase (PI3K), and Src are potential targets for taxifolin. Pull-down assay results showed that EGFR, PI3K, and Src directly interacted with taxifolin in vitro, whereas taxifolin bound to EGFR and PI3K, but not to Src in cells. ATP competition and in vitro kinase assay data revealed that taxifolin interacted with EGFR and PI3K at the ATP-binding pocket and inhibited their kinase activities [1]. The lipid radical production detected by coumarin C-525-activated chemiluminescence decreased under the action of rutin and taxifolin in a dose-dependent manner, so that a 50% inhibition of chemiluminescence was observed at the antioxidant concentrations of 3.7 and 10 microM, respectively [3].;In vivo: Topical treatment of taxifolin to the dorsal skin significantly suppressed tumor incidence, volume, and mult MedChem Express HY-N0136

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

Density: 1.7±0.1 g/cm3
Boiling Point: 687.6±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.3 mmHg at 25°C
Enthalpy of Vaporization: 105.9±3.0 kJ/mol
Flash Point: 264.2±25.0 °C
Index of Refraction: 1.763
Molar Refractivity: 73.7±0.3 cm3
#H bond acceptors: 7
#H bond donors: 5
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 1
ACD/LogP: 1.82
ACD/LogD (pH 5.5): 1.64
ACD/BCF (pH 5.5): 10.31
ACD/KOC (pH 5.5): 183.56
ACD/LogD (pH 7.4): 1.15
ACD/BCF (pH 7.4): 3.31
ACD/KOC (pH 7.4): 58.88
Polar Surface Area: 127 Å2
Polarizability: 29.2±0.5 10-24cm3
Surface Tension: 100.4±3.0 dyne/cm
Molar Volume: 178.7±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) =  0.59
    Log Kow (Exper. database match) =  0.95
       Exper. Ref:  Perrissoud,D & Testa,B (1986)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  531.64  (Adapted Stein & Brown method)
    Melting Pt (deg C):  227.38  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.34E-013  (Modified Grain method)
    Subcooled liquid VP: 1.99E-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):  2.203e+004
       log Kow used: 0.95 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.0497e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.76E-022  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.435E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.95  (exp database)
  Log Kaw used:  -19.711  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.661
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.3634
   Biowin2 (Non-Linear Model)     :   0.9947
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8317  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7519  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5818
   Biowin6 (MITI Non-Linear Model):   0.3988
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6732
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  2.65E-009 Pa (1.99E-011 mm Hg)
  Log Koa (Koawin est  ): 20.661
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.13E+003 
       Octanol/air (Koa) model:  1.12E+008 
   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 = 253.1164 E-12 cm3/molecule-sec
      Half-Life =     0.042 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.507 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    :  540.1
      Log Koc:  2.733 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 0.95 (expkow database)

 Volatilization from Water:
    Henry LC:  4.76E-022 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.146E+018  hours   (8.94E+016 days)
    Half-Life from Model Lake : 2.341E+019  hours   (9.752E+017 days)

 Removal In Wastewater Treatment:
    Total removal:               1.88  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.79  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       7.16e-010       1.01         1000       
   Water     35              360          1000       
   Soil      65              720          1000       
   Sediment  0.0694          3.24e+003    0          
     Persistence Time: 607 hr




                    

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