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=CC=C(C=C1O)C2=CC(=O)C3=C(O2)C=C(OC)C(OC)=C3O

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

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 155 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25390937	Activator 1430
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25442272	Inhibitor 8297	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 537

Conditions

Condition	Modality	Highest Phase	Product
Leukemia 87 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25390937	Primary	Basic research	Unknown Approved Use Unknown
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27370961	Primary	Basic research	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22698713	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship.	2002 Jul	12132661
Determination of flavonoids from Orthosiphon stamineus in plasma using a simple HPLC method with ultraviolet detection.	2005 Feb 25	15664346

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%).

Name

Type

Language

EUPATORIN

Common Name

English

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

Systematic Name

English

NSC-106402

Code

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