DIHYDROXYMETHOXYCHALCONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H14O4
Molecular Weight	270.28
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(O)=CC(O)=C1C(=O)\C=C\C2=CC=CC=C2

InChI

InChIKey=NYSZJNUIVUBQMM-BQYQJAHWSA-N

InChI=1S/C16H14O4/c1-20-15-10-12(17)9-14(19)16(15)13(18)8-7-11-5-3-2-4-6-11/h2-10,17,19H,1H3/b8-7+

HIDE SMILES / InChI

Molecular Formula	C16H14O4
Molecular Weight	270.28
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/24433078

Dihydroxymethoxychalcone (also known as cardamonin) is a chalcone, which is found in many plants, including the cardamom spice. Several studies demonstrated that the drug has anti-inflammatory, antineoplastic, and antioxidant activity. Preclinical experiments have shown that the drug may be a promising agent for the treatment of colorectal cancer, nasopharyngeal carcinoma, and ischemia-reperfusion injury.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
NF-kappa B signaling pathway 84 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24433078	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Colorectal cancer 101 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29066742	Primary	Preclinical	Unknown Approved Use Unknown
Nasopharyngeal carcinoma 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29048425	Primary	Preclinical	Unknown Approved Use Unknown
Ischemia reperfusion injury 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28966130	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
An overview on cardamonin.	2014 Jun	24433078
Cardamonin induces ROS-mediated G2/M phase arrest and apoptosis through inhibition of NF-κB pathway in nasopharyngeal carcinoma.	2017 Aug 31	29048425
Effect of cardamonin on hepatic ischemia reperfusion induced in rats: Role of nitric oxide.	2017 Nov 15	28966130
Cardamonin inhibits colonic neoplasia through modulation of MicroRNA expression.	2017 Oct 24	29066742

Patents

Sample Use Guides

In Vivo Use Guide

In a preclinical study, mice with nasopharyngeal carcinoma were given 5 mg/kg dihydroxymethoxychalcone every day.

Route of Administration: Intravenous

In Vitro Use Guide

In a prolifiration assay, CNE-1, CNE-2, HONE-1 and SUNE-1 cells were treated with 6.125, 12.5, 25, 50, 100 uM of dihydroxymethoxychalcone for 24, 48 and 72 h. In a cell viability assay, CNE-2 cells were cultured with 10, 20, 30 uM of the drug for 24, 48 and 72 h.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:36:17 GMT 2023` Edited by `admin` on `Fri Dec 15 18:36:17 GMT 2023`
Record UNII	H8KP1OJ8JX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIHYDROXYMETHOXYCHALCONE

Official Name

English

ALPINETIN CHALCONE

Common Name

English

DIHYDROXYMETHOXYCHALCONE [INCI]

Common Name

English

CARDAMOMIN

Common Name

English

CARDAMONIN

Common Name

English

PHYTO-DKK1

Common Name

English

2-PROPEN-1-ONE, 1-(2,4-DIHYDROXY-6-METHOXYPHENYL)-3-PHENYL-, (2E)-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID201029726