4'-METHOXYCHALCONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H14O2
Molecular Weight	238.2812
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1)C(=O)\C=C\C2=CC=CC=C2

InChI

InChIKey=KJHHAPASNNVTSN-KPKJPENVSA-N

InChI=1S/C16H14O2/c1-18-15-10-8-14(9-11-15)16(17)12-7-13-5-3-2-4-6-13/h2-12H,1H3/b12-7+

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24046186
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28528971 | https://www.ncbi.nlm.nih.gov/pubmed/24352006

4’-Methoxychalcone (4-MC) is chalcone derivative that has shown diverse pharmacological properties, including anti-tumor and anti-inflammatory activities. 4’-Methoxychalcone significantly enhances differentiation of preadipocytes, which is accompanied by the induction of adipogenic genes including PPARgamma and adiponectin. 4’-Methoxychalcone considerably upregulated PPARgamma-induced transcriptional activity and reversed the inhibitory effect of TNF-alpha on adipocyte differentiation and adiponectin expression. 4’-Methoxychalcone could be utilized for the prevention and treatment of metabolic syndrome and diabetes.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Monoamine oxidase B 72 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26337020	Inhibitor 8297		0.471 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28528971	Primary		Basic research	Unknown Approved Use Unknown
Metabolic syndrome 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28528971	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

Rats were treated with 4’-Methoxychalcone as a single dose 100 mg/kg

Route of Administration: Oral

In Vitro Use Guide

A549 and HEK 293 cells were seeded in 48-well plates, incubated for 24 h, then fed with fresh medium for cisplatin treatment. At the end of the treatment, the medium was removed, and MTT (0.5 mg/ml) was added to each well for at least 4 h. The purple formazan precipitate was dissolved with DMSO, and the color intensity was measured at 550 nm with a Versamax microplate reader

Name

Type

Language

4'-METHOXYCHALCONE

Official Name

English

1-(P-METHOXYPHENYL)-3-PHENYL-2-PROPEN-1-ONE

Common Name

English

.ALPHA.-STYRYL P-ANISYL KETONE

Common Name

English

4-METHOXYPHENYL STYRYL KETONE

Systematic Name

English

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

Systematic Name

English

4'-METHOXYCHALCONE [INCI]

Common Name

English

NSC-37157

Code

English

METHOXYCHALCONE, TRANS-4'-

Systematic Name

English

1-(4-METHOXYPHENYL)-3-PHENYLPROPENONE

Common Name

English

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

Systematic Name

English

CHALCONE, 4'-METHOXY-

Systematic Name

English

Code System Code Type Description

PUBCHEM

641818