4-HYDROXYCHALCONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H12O2
Molecular Weight	224.2546
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=CC=CC=C2)C=C1

InChI

InChIKey=PWWCDTYUYPOAIU-DHZHZOJOSA-N

InChI=1S/C15H12O2/c16-14-9-6-12(7-10-14)8-11-15(17)13-4-2-1-3-5-13/h1-11,16H/b11-8+

HIDE SMILES / InChI

Molecular Formula	C15H12O2
Molecular Weight	224.2546
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/11205867 | http://www.hmdb.ca/metabolites/HMDB32584 | https://www.ncbi.nlm.nih.gov/pubmed/21703248 | https://www.ncbi.nlm.nih.gov/pubmed/25003119

4-Hydroxychalcone is found in herbs and spices. 4-Hydroxychalcone is a constituent of Glycyrrhiza glabra (licorice) roots. 4-hydroxychalcone is a 17beta-hydroxysteroid dehydrogenase inhibitor. 4-hydroxychalcone inhibits TNFα-induced NF-κB activation via proteasome inhibition. Treatment with 40 mg/kg 4HCH reduced systolic hypertension, serum IL-1β, and TNF-α levels and suppressed the activation of nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) and renal injury. The impact of 4-Hydroxychalcone on the hyperaldosteronism, inflammation, and kidney injury provides new insights for the future development of therapeutic strategies in resistant hypertension.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Peroxisome proliferator-activated receptor alpha 62 Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20957597	Agonist 2678
Tyrosinase 41 Target ID: CHEMBL1973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15231412	Inhibitor 8297
17beta-hydroxysteroid dehydrogenase 1 Target ID: 17beta-hydroxysteroid dehydrogenase Sources: https://www.ncbi.nlm.nih.gov/pubmed/11205867	Inhibitor 8297	16.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25003119	Preventing		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003 Oct	14565775
Metabolism of the alpha,beta-unsaturated ketones, chalcone and trans-4-phenyl-3-buten-2-one, by rat liver microsomes and estrogenic activity of the metabolites.	2005 Aug	15863696
Hydroxychalcones exhibit differential effects on XRE transactivation.	2005 Feb 14	15596260
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities.	2012 Nov 19	23013281
Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein.	2015 Feb	25349334

Patents

Sample Use Guides

In Vivo Use Guide

The cryptochrome-null mice received high-salt treatment and were treated orally with 4-hydroxychalcone (4HCH) 10 mg/kg, 4HCH 20 mg/kg, and 4HCH 40 mg/kg, respectively.

Route of Administration: Oral

In Vitro Use Guide

4-hydroxychalcone (22 ug/ml) suppressed several steps of angiogenesis, including endothelial cell proliferation, migration and tube formation without showing any signs of cytotoxicity. 4-hydroxychalcone significantly suppressed both VEGF/TNF-a- and bFGF/TNF-a-induced endothelial tube formation when tested at the concentration of 22 ug/ml in hMVEC.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:51:49 GMT 2023` Edited by `admin` on `Sat Dec 16 05:51:49 GMT 2023`
Record UNII	JO97Q47VBU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

4-HYDROXYCHALCONE

Systematic Name

English

4-HYDROXYSTYRYL PHENYL KETONE

Systematic Name

English

2-PROPEN-1-ONE, 3-(4-HYDROXYPHENYL)-1-PHENYL-

Systematic Name

English

2-PROPEN-1-ONE, 3-(4-HYDROXYPHENYL)-1-PHENYL-, (2E)-

Systematic Name

English

1-PHENYL-3-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE

Systematic Name

English

TRANS-4-HYDROXYCHALCONE

Systematic Name

English

(2E)-3-(4-HYDROXYPHENYL)-1-PHENYLPROP-2-EN-1-ONE

Systematic Name

English

(E)-3-(4-HYDROXYPHENYL)-1-PHENYL-2-PROPEN-1-ONE

Systematic Name

English

CHALCONE, 4-HYDROXY-

Systematic Name

English

(E)-4-HYDROXYCHALCONE

Systematic Name

English

(4-HYDROXYBENZYLIDENE)ACETOPHENONE

Systematic Name

English

3-(4-HYDROXYPHENYL)-1-PHENYL-2-PROPEN-1-ONE

Systematic Name

English

NSC-170282

Code

English

(4-HYDROXYBENZAL)ACETOPHENONE

Systematic Name

English

NSC-60593

Code

English

2-PROPEN-1-ONE, 3-(4-HYDROXYPHENYL)-1-PHENYL-, (E)-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID3022453