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Details

Stereochemistry ACHIRAL
Molecular Formula C15H12O4
Molecular Weight 256.2539
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TRIHYDROXYCHALCONE

SMILES

c1cc(ccc1/C(/[H])=C(\[H])/C(=O)c2ccc(cc2O)O)O

InChI

InChIKey=DXDRHHKMWQZJHT-FPYGCLRLSA-N
InChI=1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+

HIDE SMILES / InChI

Molecular Formula C15H12O4
Molecular Weight 256.2539
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Trihydroxychalcone (Isoliquiritigenin, ISL) is a flavonoid found in licorice root and several other plants that displays antioxidant,anti-inflammatory,and antitumor activities as well as hepatoprotection against steatosis-induced oxidative stress. Trihydroxychalcone is a potent antimetastatic agent, which can markedly inhibit the metastatic and invasive capacity of prostate cancer cells. The inhibition of JNK/AP-1 signaling may be one of the mechanisms by which ISL inhibits cancer cell invasion and migration. Trihydroxychalcone has been shown to be a BACE1 inhibitor, which could ameliorate memory impairment in mice, and is expected to be potentially used as a lead compound for further anti-AD reagent development.

Approval Year

PubMed

PubMed

TitleDatePubMed
Metabolism and excretion of butein, 2',3,4-trihydroxychalcone, 3-O-methylbutein, 4-O-methylbutein and 2',4',4-trihydroxychalcone in the rat.
1983 Nov
The potent anti-tumor-promoting agent isoliquiritigenin.
1991 Feb
Studies on cancer chemoprevention by traditional folk medicines XXV. Inhibitory effect of isoliquiritigenin on azoxymethane-induced murine colon aberrant crypt focus formation and carcinogenesis.
2002 Feb
Isoliquiritigenin inhibits cell proliferation and induces apoptosis in human hepatoma cells.
2005 Feb
Isoliquiritigen enhances the antitumour activity and decreases the genotoxic effect of cyclophosphamide.
2013 Jul 24
Patents

Sample Use Guides

In APP-PS1 double transgenic mice model the treatment of 9 mg/kg/day of Trihydroxychalcone could obviously decrease Abeta production and Abeta plaque formation, while efficiently improve the memory impairment based on Morris water maze test.
Route of Administration: Intraperitoneal
DU145 cells were cultured in the presence of 0-20 umol/L Trihydroxychalcone with or without 10 ug/L epidermal growth factor (EGF). Trihydroxychalcone inhibited basal and EGF-induced cell migration, invasion and adhesion dose dependently. Trihydroxychalcone decreased EGF-induced secretion of urokinase-type plasminogen activator (uPA), matrix metalloproteinase (MMP)-9, tissue inhibitor of metalloproteinase-1 (TIMP-1), and vascular endothelial growth factor (VEGF), but increased TIMP-2 secretion in a concentration-dependent manner.
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:51:35 UTC 2021
Edited
by admin
on Sat Jun 26 13:51:35 UTC 2021
Record UNII
B9CTI9GB8F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIHYDROXYCHALCONE
INCI  
INCI  
Official Name English
GU 17
Code English
ILG
Brand Name English
2-PROPEN-1-ONE, 1-(2,4-DIHYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-, (2E)-
Systematic Name English
2-PROPEN-1-ONE, 1-(2,4-DIHYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-, (E)-
Systematic Name English
ISOLIQUIRITIGEN
Common Name English
ISOLIQUIRITIGENIN
Common Name English
CHALCONE, 2',4,4'-TRIHYDROXY-
Systematic Name English
2',4,4'-TRIHYDROXYCHALCONE
Systematic Name English
TRIHYDROXYCHALCONE [INCI]
Common Name English
Code System Code Type Description
CAS
13745-20-5
Created by admin on Sat Jun 26 13:51:35 UTC 2021 , Edited by admin on Sat Jun 26 13:51:35 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
PUBCHEM
638278
Created by admin on Sat Jun 26 13:51:35 UTC 2021 , Edited by admin on Sat Jun 26 13:51:35 UTC 2021
PRIMARY
MESH
C040920
Created by admin on Sat Jun 26 13:51:35 UTC 2021 , Edited by admin on Sat Jun 26 13:51:35 UTC 2021
PRIMARY
EPA CompTox
961-29-5
Created by admin on Sat Jun 26 13:51:35 UTC 2021 , Edited by admin on Sat Jun 26 13:51:35 UTC 2021
PRIMARY
FDA UNII
B9CTI9GB8F
Created by admin on Sat Jun 26 13:51:35 UTC 2021 , Edited by admin on Sat Jun 26 13:51:35 UTC 2021
PRIMARY
EVMPD
SUB130946
Created by admin on Sat Jun 26 13:51:35 UTC 2021 , Edited by admin on Sat Jun 26 13:51:35 UTC 2021
PRIMARY
ECHA (EC/EINECS)
237-316-5
Created by admin on Sat Jun 26 13:51:35 UTC 2021 , Edited by admin on Sat Jun 26 13:51:35 UTC 2021
PRIMARY
EU FOOD ADDITIVES
ISOLIQUIRITIGENIN
Created by admin on Sat Jun 26 13:51:35 UTC 2021 , Edited by admin on Sat Jun 26 13:51:35 UTC 2021
PRIMARY A group of neolignan lipid esters and phenolic compounds isolated from the roots and stolons of liquorice (Glycyrrhiza glabra) were found to have chemopreventive properties. Of these compounds, hispaglabridin B isoliquiritigenin, and paratocarpin B were found to be the most potent anti-oxidant agents (Chin et al. 2007).
CAS
961-29-5
Created by admin on Sat Jun 26 13:51:35 UTC 2021 , Edited by admin on Sat Jun 26 13:51:35 UTC 2021
PRIMARY
DRUG BANK
DB03285
Created by admin on Sat Jun 26 13:51:35 UTC 2021 , Edited by admin on Sat Jun 26 13:51:35 UTC 2021
PRIMARY
WIKIPEDIA
ISOLIQUIRITIGENIN
Created by admin on Sat Jun 26 13:51:35 UTC 2021 , Edited by admin on Sat Jun 26 13:51:35 UTC 2021
PRIMARY
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Showed anti-HCV activity, with an IC50 of 3.7mg/mL.
METABOLIC ENZYME -> SUBSTRATE
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A group of neolignan lipid esters and phenolic compounds isolated from the roots and stolons of liquorice (Glycyrrhiza glabra) were found to have chemopreventive properties. Of these compounds, hispaglabridin B isoliquiritigenin, and paratocarpin B were found to be the most potent anti-oxidant agents (Chin et al. 2007).
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isoliquiritigenin was tested for antithrombotic activity.
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