ChemSpider 2D Image | (−)-Epigallocatechin gallate | C22H18O11

(−)-Epigallocatechin gallate

  • Molecular FormulaC22H18O11
  • Average mass458.372 Da
  • Monoisotopic mass458.084900 Da
  • ChemSpider ID58575

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(−)-Epigallocatechin gallate
(-)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate
(-)-cis-3,3',4',5,5',7-Hexahydroxy-flavane-3-gallate
(-)-EGCG
(-)-epigallocatechin 3-gallate
(-)-Epigallocatechin 3-O-gallate
(-)-Epigallocatechin gallat [German]
(-)-Epigallocatechin gallate
(-)-Epigallocatechin-3-o-gallate
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BQM438CTEL [DBID]
50299_FLUKA [DBID]
AIDS000674 [DBID]
AIDS-000674 [DBID]
C09731 [DBID]
CCRIS 3729 [DBID]
CHEBI:4806 [DBID]
DivK1c_006373 [DBID]
E4143_SIAL [DBID]
E4268_SIAL [DBID]
More...
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Appearance:

      solid OU Chemical Safety Data (No longer updated) More details

    • Stability:

      Stable, but may be light sensitive. Incompatible with strongoxidizing agents. OU Chemical Safety Data (No longer updated) More details

    • Toxicity:

      ORL-MUS LD50 2170 mg kg-1 OU Chemical Safety Data (No longer updated) More details

    • Safety:

      Minimize exposure. OU Chemical Safety Data (No longer updated) More details

    • Target Organs:

      Others TargetMol T2988

    • Chemical Class:

      A gallate ester obtained by the formal condensation of gallic acid with the (3<stereo>R</stereo>)-hydroxy group of (<minus/>)-epigallocatechin. ChEBI CHEBI:4806
      A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4806, CHEBI:4806
      Flavanols Phenol-Explorer 129
      Flavonoids Phenol-Explorer 129

    • Compound Source:

      Chrysophyllum marginatum (Sapotaceae) Susan Richardson [Structure found in ChemSpider, confirmed from The Merck Index Online, Natural product Updates, ChEBI and ChEMBL]
      galloylated catechin biosynthesis PlantCyc CPD-15291
      Isolated from a plant Susan Richardson [Structure found in ChemSpider, confirmed from The Merck Index Online, Natural product Updates, ChEBI and ChEMBL]
      Linum usitatissimum PlantCyc CPD-15291

    • Bio Activity:

      (-)-epigallocatechin-3-O-gallate -> (-)-gallocatechin-3-O-gallate PlantCyc CPD-15291
      1-O-galloyl-beta-D-glucose + (-)-epigallocatechin -> (-)-epigallocatechin-3-O-gallate + D-glucopyranose PlantCyc CPD-15291
      Amyloid Beta Peptides Tocris Bioscience 4524
      Apoptosis MedChem Express HY-13653
      Apoptosis inducer MedChem Express HY-13653
      Apoptosis; MedChem Express HY-13653
      beta-secretase inhibitor (IC50 = 1.6 muM); inhibits amyloid assembly. Inhibits the formation of amyloid fibrils by proteins such as Abeta, alpha-synuclein and huntingtin. Reduces Abeta42-induced cell death in three different cell types. Also inhibits glutamate dehydrogenase. Inhibits cell growth and selectively induces apoptosis in A431 and human pancreatic cancer cells. Also a DNMT1 inhibitor. Tocris Bioscience 4524
      beta-secretase inhibitor; inhibits amyloid assembly Tocris Bioscience 4524
      Cell Biology Tocris Bioscience 4524
      Cell Metabolism Tocris Bioscience 4524
      Enzymes Tocris Bioscience 4524
      Epigallocatechol Gallate(EGCG) is an antioxidant polyphenol flavonoid that inhibits telomerase and DNA methyltransferase. MedChem Express http://www.medchemexpress.com/_-_-epigallocatechin-gallate.html, HY-13653
      Epigallocatechol Gallate(EGCG) is an antioxidant polyphenol flavonoid that inhibits telomerase and DNA methyltransferase. EGCG blocks the activation of EGF receptors and HER-2 receptors.;IC50 value:;Target: apoptosis inducer(-)-Epigallocatechin Gallate (EGCG) is a strong polyphenol catechin antioxidant found in green tea, with broad efficacy against many conditions generated from oxidative damage. Extensive oxidation of low density lipoproteins (LDL) is correlated to cardiovascular diseases, and EGCG is reported to strongly inhibit Cu(2+)-mediated oxidative modification of LDLs. The antiapoptotic proteins Bcl-2 and Bcl-x(L) are observed to suppress apoptosis and convey survival to heavily damaged and mutated cells, and EGCG (along with the other catechins) is shown to directly inhibit these proteins, reestablishing the normal apoptotic pathway in the cell. After treating with EGCG, the expressions of HES1 and Notch2 was obviously inhibited, this indicated that EGCG inhibited color MedChem Express HY-13653
      Inhibitor of amyloid assembly; inhibits the formation of amyloid fibrils by proteins such as A?, ?-synuclein and huntingtin. Reduces A?42-induced cell death in three different cell types. Also inhibit s ?-secretase (IC50 = 1.6 ?M) and glutamate dehydrogenase GDH. Inhibits cell growth and selectively induces apoptosis in A431 and human pancreatic cancer cells. Also a DNMT1 inhibitor. Tocris Bioscience 4524
      Inhibitor of amyloid assembly; inhibits the formation of amyloid fibrils by proteins such as A?, ?-synuclein and huntingtin. Reduces A?42-induced cell death in three different cell types. Also inhibits ?-secretase (IC50 = 1.6 ?M) and glutamate dehydrogenase GDH. Inhibits cell growth and selectively induces apoptosis in A431 and human pancreatic cancer cells. Also a DNMT1 inhibitor. Tocris Bioscience 4524
      Inhibits formation of amyloid fibrils Tocris Bioscience 4524
      Other Proteases Tocris Bioscience 4524
      Others TargetMol T2988
      Proteases Tocris Bioscience 4524

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

Density: 1.9±0.1 g/cm3
Boiling Point: 909.1±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.3 mmHg at 25°C
Enthalpy of Vaporization: 136.7±3.0 kJ/mol
Flash Point: 320.0±27.8 °C
Index of Refraction: 1.857
Molar Refractivity: 108.4±0.4 cm3
#H bond acceptors: 11
#H bond donors: 8
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 2
ACD/LogP: 2.08
ACD/LogD (pH 5.5): 1.83
ACD/BCF (pH 5.5): 14.47
ACD/KOC (pH 5.5): 235.14
ACD/LogD (pH 7.4): 1.62
ACD/BCF (pH 7.4): 8.96
ACD/KOC (pH 7.4): 145.65
Polar Surface Area: 197 Å2
Polarizability: 43.0±0.5 10-24cm3
Surface Tension: 149.7±5.0 dyne/cm
Molar Volume: 241.2±5.0 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) =  2.56

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  720.48  (Adapted Stein & Brown method)
    Melting Pt (deg C):  315.59  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.39E-020  (Modified Grain method)
    Subcooled liquid VP: 1.18E-016 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):  32.77
       log Kow used: 2.56 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.013596 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.08E-040  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.176E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.56  (KowWin est)
  Log Kaw used:  -38.355  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  40.915
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.8166
   Biowin2 (Non-Linear Model)     :   1.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6445  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7415  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3975
   Biowin6 (MITI Non-Linear Model):   0.0910
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.2099
 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):  1.57E-014 Pa (1.18E-016 mm Hg)
  Log Koa (Koawin est  ): 40.915
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.91E+008 
       Octanol/air (Koa) model:  2.02E+028 
   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 = 221.5207 E-12 cm3/molecule-sec
      Half-Life =     0.048 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.579 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    :  8.643E+006
      Log Koc:  6.937 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  4.907E-004  L/mol-sec
  Kb Half-Life at pH 8:      44.760  years  
  Kb Half-Life at pH 7:     447.602  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.270 (BCF = 18.61)
       log Kow used: 2.56 (estimated)

 Volatilization from Water:
    Henry LC:  1.08E-040 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.161E+037  hours   (4.836E+035 days)
    Half-Life from Model Lake : 1.266E+038  hours   (5.276E+036 days)

 Removal In Wastewater Treatment:
    Total removal:               3.28  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     3.17  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       1.66e-023       1.16         1000       
   Water     15.5            900          1000       
   Soil      84.4            1.8e+003     1000       
   Sediment  0.142           8.1e+003     0          
     Persistence Time: 1.67e+003 hr

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