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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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
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
Isoliquiritigenin inhibits cell proliferation and induces apoptosis in human hepatoma cells.
2005 Feb
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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PARENT -> CONSTITUENT ALWAYS PRESENT
isoliquiritigenin was tested for antithrombotic activity.
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