4-METHYLESCULETIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H8O4
Molecular Weight	192.1681
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC(=O)OC2=C1C=C(O)C(O)=C2

InChI

InChIKey=KVOJTUXGYQVLAJ-UHFFFAOYSA-N

InChI=1S/C10H8O4/c1-5-2-10(13)14-9-4-8(12)7(11)3-6(5)9/h2-4,11-12H,1H3

HIDE SMILES / InChI

Molecular Formula	C10H8O4
Molecular Weight	192.1681
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29217385
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17354230 | https://www.ncbi.nlm.nih.gov/pubmed/25424619

4-Methylesculetin is one of the coumarin derivatives with great anti-oxidant and anti-inflammatory activities. This molecule has been shown non-toxic effects and a promising potentiality to treat inflammatory diseases, especially those related to reactive oxygen species (ROS). 4-Methylesculetin (4-ME) causes the relaxation or inhibits the Angiotensin II (ATN 2) induced contraction in the smooth muscle, mediated by prostacyclin release. 4-methylesculetin showed similar efficacy to that obtained with either prednisolone or sulphasalazine, both in the acute phase of colitis as well as following a curative protocol. The intestinal anti-inflammatory activity by 4-methylesculetin is likely related to its ability in reduce colonic oxidative stress and inhibit pro-inflammatory cytokine production.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Aldose reductase 45 Target ID: CHEMBL1900 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20805028	Inhibitor 8504	64.4 µM [IC50]
Sorbitol dehydrogenase 1 Target ID: CHEMBL2275 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20805028	Inhibitor 8504	212.0 µM [IC50]
Xanthine dehydrogenase 33 Target ID: CHEMBL1929 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17316915	Inhibitor 8504	246.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17354230	Primary		Basic research	Unknown Approved Use Unknown
Colitis 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20380826	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The hepatitis B virus ribonuclease H is sensitive to inhibitors of the human immunodeficiency virus ribonuclease H and integrase enzymes.	2013-01	23349632
Suppression of TNBS-induced colitis in rats by 4-methylesculetin, a natural coumarin: comparison with prednisolone and sulphasalazine.	2012-01-05	22119283
Structure-activity relationship of dihydroxy-4-methylcoumarins as powerful antioxidants: correlation between experimental & theoretical data and synergistic effect.	2010-09	20600568
Intestinal anti-inflammatory activity of esculetin and 4-methylesculetin in the trinitrobenzenesulphonic acid model of rat colitis.	2010-07-30	20380826
Synthesis, characterisation and antimicrobial activity of copper(II) and manganese(II) complexes of coumarin-6,7-dioxyacetic acid (cdoaH2) and 4-methylcoumarin-6,7-dioxyacetic acid (4-MecdoaH2): X-ray crystal structures of [Cu(cdoa)(phen)2].8.8H(2)O and [Cu(4-Mecdoa)(phen)2].13H2O (phen=1,10-phenanthroline).	2007-08	17555821
Inhibitory effect of 4-methylesculetin on hyaluronan synthesis slows the development of human pancreatic cancer in vitro and in nude mice.	2007-06-15	17354230
Structural requirements of hydroxylated coumarins for in vitro anti-Helicobacter pylori activity.	2003-11-06	14598616
Protection of coumarins against linoleic acid hydroperoxide-induced cytotoxicity.	2003-01-06	12453663
In vitro activity of polyhydroxycarboxylates against herpesviruses and HIV.	2001-11	12018678
[Sensitization and crossreaction of simple coumarins].	2001-01	11201168

Patents

Sample Use Guides

In Vivo Use Guide

Mice were treated with 4-Methylesculetin orally 5 or 25 mg/kg of 4-methylesculetin daily

Route of Administration: Oral

In Vitro Use Guide

An aliquot of 2 x 10^5 PBL was plated into 24-well plates in 2 ml RPMI culture medium per well at 37◦C and incubated with tests compounds for 4 h at concentrations of 2, 8, or 32 μg/ml and MMS at 75 μM (positive control). The concentrations were selected due to the absence of toxicity in trypan blue exclusion test. Each experiment was performed three times (with separate blood from two donors) and in duplicate.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:52:26 GMT 2025` Edited by `admin` on `Mon Mar 31 18:52:26 GMT 2025`
Record UNII	132H8N0A91
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

4-METHYLESCULETIN

Common Name

English

NSC-11828

Preferred Name

English

METHYLESCULETIN, 4-

Common Name

English

NSC-688807

Code

English

Code System Code Type Description

FDA UNII

132H8N0A91