EUPATORIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H16O7
Molecular Weight	344.3154
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(C(=O)C=C(O2)C3=CC(O)=C(OC)C=C3)C(O)=C1OC

InChI

InChIKey=KLAOKWJLUQKWIF-UHFFFAOYSA-N

InChI=1S/C18H16O7/c1-22-12-5-4-9(6-10(12)19)13-7-11(20)16-14(25-13)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3

HIDE SMILES / InChI

Molecular Formula	C18H16O7
Molecular Weight	344.3154
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/22516932 | https://www.ncbi.nlm.nih.gov/pubmed/22698713 | https://www.ncbi.nlm.nih.gov/pubmed/25442272 | https://www.ncbi.nlm.nih.gov/pubmed/26983579 | https://www.ncbi.nlm.nih.gov/pubmed/27370961

Eupatorin is a natural flavonoid isolated from the herbs of Eupatorium semiserratum. It has the anti-inflammatory and anti-proliferative properties, which may be utilized in the development of novel anti-inflammatory and anti-tumor treatments. Eupatorin moderately inhibited human cytochrome P450 1A2 (CYP1A2). Eupatorin showed IC50 values of 0.4 ug/mL on T. cruzi epimastigotes and 61.8 ug/mL on trypomastigotes, respectively. It was demonstrated, that eupatorin exerts a vasorelaxative effect on aortic rings through the NO/sGC/cGMP and PGI2 pathways, calcium and potassium channels, muscarinic and beta-adrenergic receptors.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Apoptosis 156 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25390937	Activator 1447
Cytochrome P450 1A2 73 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25442272	Inhibitor 8504	50.8 µM [IC50]
G2/M transition of mitotic cell cycle 2 Target ID: GO:0000086 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22698713	Blocker 555

Conditions

Condition	Modality	Highest Phase	Product
Leukemia 72 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25390937	Primary	Basic research	Unknown Approved Use Unknown
Hypertension 575 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27370961	Primary	Basic research	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22698713	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids.	2011-05-01	21482471
In vitro effects of active constituents and extracts of Orthosiphon stamineus on the activities of three major human cDNA-expressed cytochrome P450 enzymes.	2011-03-15	21276781
In vitro modulatory effects of Andrographis paniculata, Centella asiatica and Orthosiphon stamineus on cytochrome P450 2C19 (CYP2C19).	2011-01-27	21093571
Flavones and rosmarinic acid from Salvia limbata.	2010-12	21108116
Bioactivity-guided isolation of antiproliferative compounds from Centaurea arenaria.	2010-11	21031625
HPLC and anti-inflammatory studies of the flavonoid rich chloroform extract fraction of Orthosiphon stamineus leaves.	2010-06-21	20657453
The methoxylated flavones eupatorin and cirsiliol induce CYP1 enzyme expression in MCF7 cells.	2009-08	19601638
Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention.	2009-06-16	19531241
Evaluation of the anti-pyretic potential of Orthosiphon stamineus Benth standardized extract.	2009-02	19127348
Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1-mediated metabolism.	2008	18454852
Diterpenoids and flavonoids from the fruits of Vitex agnus-castus and antioxidant activity of the fruit extracts and their constituents.	2007-04	17262892
New Bisabolane-Type Sesquiterpenes from the Aerial Parts of Lippia dulcis.	2005-09	16141591
Determination of flavonoids from Orthosiphon stamineus in plasma using a simple HPLC method with ultraviolet detection.	2005-02-25	15664346
Phytochemical and pharmacological studies on Orthosiphon stamineus Benth. (Lamiaceae) hydroalcoholic extracts.	2003-09-15	12946538
Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship.	2002-07	12132661

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 50 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

Eupatorin (0.04-2.29 гM) caused the concentration-dependent vasorelaxation of PEcontracted aortic rings (pD2=6.66±0.13 and EMAX=99.72±6.39%).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:06:16 GMT 2025` Edited by `admin` on `Mon Mar 31 20:06:16 GMT 2025`
Record UNII	3J474AV6MY
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

NSC-106402

Preferred Name

English

EUPATORIN

Common Name

English

FLAVONE, 3',5-DIHYDROXY-4',6,7-TRIMETHOXY-

Systematic Name

English

3',5-DIHYDROXY-4',6,7-TRIMETHOXYFLAVONE

Systematic Name

English

EUPATORIN [MI]

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-6,7-DIMETHOXY-

Systematic Name

English

6-METHOXYLUTEOLIN 4',7-DIMETHYL ETHER

Common Name

English

EUPATORINE

Common Name

English

5,3'-DIHYDROXY-6,7,4'-TRIMETHOXYFLAVONE

Systematic Name

English

Code System Code Type Description

PUBCHEM

97214