METOCHALCONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H18O4
Molecular Weight	298.3331
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=HVAKUYCEWDPRCA-IZZDOVSWSA-N

InChI=1S/C18H18O4/c1-20-14-7-4-13(5-8-14)6-11-17(19)16-10-9-15(21-2)12-18(16)22-3/h4-12H,1-3H3/b11-6+

HIDE SMILES / InChI

Description
Sources: Dressler, H. (2013) Resorcinol: Its Uses and Derivatives, page 182, retrieved from: https://books.google.ru/books?id=6IkHCAAAQBAJ | DOI: 10.1039/C7RA08639C | https://www.ncbi.nlm.nih.gov/pubmed/13571107 | Buckingham, J. (1994) Dictionary of Natural Products, page 130, retrieved from: https://books.google.ru/books?id=QQ00Uu4_-dIC

Metochalcone is a chalcone. It was isolated from heartwood of Pterocarpus marsupium. It has been approved for clinical use as choleretic and diuretic agent. It was made from 2,4-dihydroxybenzaldehyde (beta-resorcaldehide).

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Biliary tract diseases 11 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13571107	Primary		Approved 8583	Lesidrin Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP1 116 BCRP 910 P-gp 1741 CYP1A2 2153 CYP19A1 429 CYP2C19 2057	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6063342#section=Biological-Test-Results Page: 7.0	inconclusive [IC50 9.7717 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6063342#section=Biological-Test-Results Page: 12.0	no [IC50 13.3332 uM]
MRP1 232	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMDA0IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM2NTg0In19	no [IC50 >10 uM]
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6063342#section=Biological-Test-Results Page: 236.0	no
BCRP 985	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MzkzIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM2NTg0In19	yes [IC50 1.91 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6063342#section=Biological-Test-Results Page: 3.0	yes [IC50 3.0901 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6063342#section=Biological-Test-Results Page: 3.0	yes [IC50 3.8902 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6063342#section=Biological-Test-Results Page: 4.0	yes [IC50 4.3649 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6063342#section=Biological-Test-Results Page: 4.0	yes [IC50 4.5646 uM]
P-gp 1932	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM2NTg0In19	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6063342#section=Biological-Test-Results Page: 15 \| 222	inconclusive

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6063342#section=Biological-Test-Results Page: 169.0

PubMed

Title	Date	PubMed
Cytotoxic 3,4,5-trimethoxychalcones as mitotic arresters and cell migration inhibitors.	2013-05	23524161
Identification of 3',4',5'-trimethoxychalcone analogues as potent inhibitors of Helicobacter pylori-induced inflammation in human gastric epithelial cells.	2010-09-15	20705463
A new trimethoxychalcone from Crotalaria ramosissima.	2007-09	17616261
[Research on the properties of 2', 4, 4'-trimethoxychalcone. I. Toxicity].	1958	13603405

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

METOCHALCONE

Official Name

English

NSC-97905

Preferred Name

English

2',4,4'-TRIMETHOXYCHALCONE

Systematic Name

English

METOCHALCONE [MI]

Common Name

English

METOCHALCONE [MART.]

Common Name

English

metochalcone [INN]

Common Name

English

Metochalcone [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1937