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

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 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
Phytochemical and pharmacological studies on Orthosiphon stamineus Benth. (Lamiaceae) hydroalcoholic extracts.	2003 Sep 15	12946538
Determination of flavonoids from Orthosiphon stamineus in plasma using a simple HPLC method with ultraviolet detection.	2005 Feb 25	15664346
New Bisabolane-Type Sesquiterpenes from the Aerial Parts of Lippia dulcis.	2005 Sep	16141591
Diterpenoids and flavonoids from the fruits of Vitex agnus-castus and antioxidant activity of the fruit extracts and their constituents.	2007 Apr	17262892
Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1-mediated metabolism.	2008	18454852
The methoxylated flavones eupatorin and cirsiliol induce CYP1 enzyme expression in MCF7 cells.	2009 Aug	19601638
Evaluation of the anti-pyretic potential of Orthosiphon stamineus Benth standardized extract.	2009 Feb	19127348
Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention.	2009 Jun 16	19531241
Flavones and rosmarinic acid from Salvia limbata.	2010 Dec	21108116
HPLC and anti-inflammatory studies of the flavonoid rich chloroform extract fraction of Orthosiphon stamineus leaves.	2010 Jun 21	20657453
Bioactivity-guided isolation of antiproliferative compounds from Centaurea arenaria.	2010 Nov	21031625
In vitro modulatory effects of Andrographis paniculata, Centella asiatica and Orthosiphon stamineus on cytochrome P450 2C19 (CYP2C19).	2011 Jan 27	21093571
In vitro effects of active constituents and extracts of Orthosiphon stamineus on the activities of three major human cDNA-expressed cytochrome P450 enzymes.	2011 Mar 15	21276781
Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids.	2011 May 1	21482471

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 `Fri Dec 15 20:16:48 GMT 2023` Edited by `admin` on `Fri Dec 15 20:16:48 GMT 2023`
Record UNII	3J474AV6MY
Record Status	`Validated (UNII)`
Record Version

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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