TRIHYDROXYCHALCONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H12O4
Molecular Weight	256.2534
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(\C=C\C(=O)C2=C(O)C=C(O)C=C2)C=C1

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	256.2534
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18824345 | https://www.ncbi.nlm.nih.gov/pubmed/20412384

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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 1A 1 Target ID: CHEMBL3544905 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15664435	Inhibitor 8297
Aldose reductase 44 Target ID: CHEMBL1900 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11370705 \| https://www.ncbi.nlm.nih.gov/pubmed/10220294	Inhibitor 8297	320.0 nM [IC50]
Monoamine oxidase A 49 Target ID: CHEMBL3358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11501051	Inhibitor 8297	13.9 µM [IC50]
Monoamine oxidase B 72 Target ID: CHEMBL2993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11501051	Inhibitor 8297	47.2 µM [IC50]
Beta-secretase 1 21 Target ID: CHEMBL4822 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20412384	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20412384	Primary		Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20068129 https://www.ncbi.nlm.nih.gov/pubmed/1899810	Preventing		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
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	6673378
The potent anti-tumor-promoting agent isoliquiritigenin.	1991 Feb	1899810
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	11853176
Isoliquiritigenin inhibits cell proliferation and induces apoptosis in human hepatoma cells.	2005 Feb	15729620
Isoliquiritigen enhances the antitumour activity and decreases the genotoxic effect of cyclophosphamide.	2013 Jul 24	23887720

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Fri Dec 15 18:01:30 UTC 2023` Edited by `admin` on `Fri Dec 15 18:01:30 UTC 2023`
Record UNII	B9CTI9GB8F
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TRIHYDROXYCHALCONE

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