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)-2-propen-1-one
(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]
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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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  • References
  • 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
      A member of the class of chalcones that is trans-chalcone hydroxylated at C-2', -4 and -4'. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:310312
      chalcone Microsource [01504200]
      Flavonoids Phenol-Explorer 918
      Isoflavonoids Phenol-Explorer 918
    • Drug Status:

      experimental Microsource [01504200]
    • Compound Source:

      widespread in Fabaceae Microsource [01504200]
    • Bio Activity:

      Aldose Reductase MedChem Express HY-N0102
      Aldose reductase TargetMol T0725
      Biochemicals & small molecules/Agonists & activators Hello Bio [HB4213]
      Enzyme TargetMol T0725
      Flovonoid. Positive allosteric GABA<sub>A</sub> recetor modulator. Hello Bio [HB4213]
      Ion channels/Ligand-gated ion channel/GABA<sub>A</sub> Hello Bio [HB4213]
      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
      Positive allosteric GABA<sub>A</sub> recetor modulator. Anticancer. Apoptosis inducer and cell proliferation inhibitor. Autophagy inducer. Anti-angiogenic. VEGF/VEGFR-2 signaling inhibitor. Antioxidant and antibacterial. AMPK-mediated GSK3beta inhibitor. Anti-inflammatory. Inhibits translocation and activation of NF-kappaB by blocking phosphorylation and subsequent degradation of IkappaBalpha. Downregulates TRIF-dependent signaling pathways of TLRs by inhibiting TBK1 kinase activity. Blocks LPS-induced TLR4/MD2 complex signaling. NLRP3 inflammasome activation inhibitor. Inhibits NLRP3-activated ASC oligomerization. Can block the NLRP3 inflammasome at both the priming step and the activation step. H(2) histamine receptor signaling inhibitor. Anti-diabetic. Antihyperglycemic. Aldose reductase inhibitor. Vasorelaxant. Soluble guanylyl cyclase activator. Potent cystic fibrosis transmembrane conductance regulator (CFTR) inhibitor. Shown to inhibit breast cancer stem cells through WIF1 demethylation. Shows outstanding matrix properties for MALDI-TOF-MS analysis of oligosaccharides. Hello Bio [HB4213]
  • 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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