ChemSpider 2D Image | Isoliquiritigenin | C15H12O4

Isoliquiritigenin

  • Molecular FormulaC15H12O4
  • Average mass256.253 Da
  • Monoisotopic mass256.073547 Da
  • ChemSpider ID553829
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

(2E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-on [German] [ACD/IUPAC Name]
(2E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one [ACD/IUPAC Name]
(2E)-1-(2,4-Dihydroxyphényl)-3-(4-hydroxyphényl)-2-propén-1-one [French] [ACD/IUPAC Name]
(2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one [ACD/IUPAC Name]
(E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one [ACD/IUPAC Name]
2',4,4'-Trihydroxychalcone [ACD/IUPAC Name]
237-316-5 [EINECS]
2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-, (2E)- [ACD/Index Name]
961-29-5 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS035379 [DBID]
AIDS-035379 [DBID]
AIDS226290 [DBID]
AIDS-226290 [DBID]
BRN 1914295 [DBID]
C08650 [DBID]
CCRIS 7676 [DBID]
CPD-3041 [DBID]
DivK1c_006858 [DBID]
EU-0100681 [DBID]
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  • Spectroscopy
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Yellow crystals Indofine [T-503]
    • Safety:

      26-37 Alfa Aesar H26920
      36/37/38 Alfa Aesar H26920
      H315-H319-H335 Alfa Aesar H26920
      None LKT Labs [I7559]
      P261; P262 Biosynth Q-100904
      P261-P280-P305+P351+P338-P304+P340-P405-P501a Alfa Aesar H26920
      Warning Alfa Aesar H26920
      WARNING: Irritates lungs, eyes, skin Alfa Aesar H26920
    • Target Organs:

      Aldose reductase inhibitor TargetMol T0725
    • Chemical Class:

      A member of the class of chalcones that is <stereo>trans</stereo>-chalcone hydroxylated at C-2', -4 and -4'. ChEBI CHEBI:310312
      chalcone Microsource [01504200]
    • Drug Status:

      experimental Microsource [01504200]
    • Compound Source:

      widespread in Fabaceae Microsource [01504200]
    • Bio Activity:

      Aldose Reductase MedChem Express HY-N0102
      Aldose reductase TargetMol T0725
      Enzyme TargetMol T0725
      Isoliquiritigenin(GU-17; Isoliquiritigen) is a licorice chalconoid, a type of natural phenols; is a sirtuin-activating compound. MedChem Express
      Isoliquiritigenin(GU-17; Isoliquiritigen) is a licorice chalconoid, a type of natural phenols; is a sirtuin-activating compound.; IC50 Value: 320 nM [1]; Target: Aldose reductase; Anti-cancer; in vitro: GU-17(isoliquiritigenin) had the most potent aldose reductase inhibiting activity. MedChem Express HY-N0102
      Isoliquiritigenin(GU-17; Isoliquiritigen) is a licorice chalconoid, a type of natural phenols; is a sirtuin-activating compound.;IC50 Value: 320 nM [1];Target: Aldose reductase; Anti-cancer;In vitro: GU-17(isoliquiritigenin) had the most potent aldose reductase inhibiting activity. Isoliquiritigenin inhibited rat lens aldose reductase with an IC50 of 3.2 x 10(-7) M, using DL-glyceraldehyde as a substrate. It inhibited sorbitol accumulation in human red blood cells in vitro, with an IC50 of 2.0 x 10(-6) M. Isoliquiritigenin also showed the most potent inhibition of mouse rectal contraction induced by CCh with an IC50 value of 1.70+/-0.07 microM [2]. Isoliquiritigenin (ISL) treatment markedly ameliorated cardiomyocytes contractile dysfunction caused by hypoxia. ISL significantly stimulated cardioprotective signaling, AMP-activated protein kinase (AMPK), and extracellular signal-regulated kinase (ERK) signaling pathways. The ROS fluorescent probe H2DCFDA determination indicated that MedChem Express HY-N0102
      Metabolic Enzyme/Protease; MedChem Express HY-N0102
      Others MedChem Express HY-N0102
  • Gas Chromatography

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

Density: 1.4±0.1 g/cm3
Boiling Point: 504.0±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 80.3±3.0 kJ/mol
Flash Point: 272.7±24.4 °C
Index of Refraction: 1.715
Molar Refractivity: 72.8±0.3 cm3
#H bond acceptors: 4
#H bond donors: 3
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 3.11
ACD/LogD (pH 5.5): 3.10
ACD/BCF (pH 5.5): 132.11
ACD/KOC (pH 5.5): 1142.36
ACD/LogD (pH 7.4): 2.73
ACD/BCF (pH 7.4): 57.61
ACD/KOC (pH 7.4): 498.19
Polar Surface Area: 78 Å2
Polarizability: 28.8±0.5 10-24cm3
Surface Tension: 70.3±3.0 dyne/cm
Molar Volume: 185.1±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) =  2.99

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  436.21  (Adapted Stein & Brown method)
    Melting Pt (deg C):  182.80  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.3E-010  (Modified Grain method)
    Subcooled liquid VP: 4.11E-008 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):  230.3
       log Kow used: 2.99 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3176.6 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 :   3.29E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.362E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.99  (KowWin est)
  Log Kaw used:  -13.871  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.861
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9798
   Biowin2 (Non-Linear Model)     :   0.8379
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7795  (weeks       )
   Biowin4 (Primary Survey Model) :   3.5749  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3301
   Biowin6 (MITI Non-Linear Model):   0.1577
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1287
 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):  5.48E-006 Pa (4.11E-008 mm Hg)
  Log Koa (Koawin est  ): 16.861
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.547 
       Octanol/air (Koa) model:  1.78E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.952 
       Mackay model           :  0.978 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 220.1600 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 222.8200 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.583 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.576 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.050000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     2.100000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     1.091 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =    13.097 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.965 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.557E+004
      Log Koc:  4.192 

 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 = 0.765 (BCF = 5.825)
       log Kow used: 2.99 (estimated)

 Volatilization from Water:
    Henry LC:  3.29E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.849E+012  hours   (1.187E+011 days)
    Half-Life from Model Lake : 3.108E+013  hours   (1.295E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               5.61  percent
    Total biodegradation:        0.12  percent
    Total sludge adsorption:     5.48  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       1.6e-007        1.12         1000       
   Water     16.9            360          1000       
   Soil      82.8            720          1000       
   Sediment  0.277           3.24e+003    0          
     Persistence Time: 774 hr




                    

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