eupatilin (CHEBI:4932)

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ChEBI Name	eupatilin

ChEBI ID	CHEBI:4932

Definition	A trimethoxyflavone that is flavone substituted by hydroxy groups at C-5 and C-7 and methoxy groups at C-6, C-3' and C-4' respectively. Isolated from Citrus reticulata and Salvia tomentosa, it exhibits anti-inflammatory, anti-ulcer and antineoplastic activities.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:65882

Supplier Information

Download	Molfile XML SDF

Formula

C18H16O7

Net Charge

Average Mass

344.31540

Monoisotopic Mass

344.08960

InChI

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

InChIKey

DRRWBCNQOKKKOL-UHFFFAOYSA-N

SMILES

COc1ccc(cc1OC)-c1cc(=O)c2c(O)c(OC)c(O)cc2o1

Metabolite of Species	Details
Eupatorium altissimum (IPNI:1076340-2)	Found in whole plant (BTO:0001461). See: PubMed
Artemisia asiatica (IPNI:179234-1)	See: PubMed
Salvia tomentosa (IPNI:457405-1)	Found in leaf (BTO:0000713). See: DOI
Citrus reticulata (IPNI:772038-1)	Found in exocarp (BTO:0000733). Previous component: fruit peel; See: PubMed
Sideritis mugronensis (IPNI:900993-1)	Found in aerial part (BTO:0001658). See: DOI
Sideritis gomeraea (NCBI:txid155247)	See: J. NAT. PROD., 1978, 41, 279
Merrillia caloxylon (NCBI:txid159055)	Found in root (BTO:0001188). See: DOI
Orthosiphon stamineus (NCBI:txid260636)	See: PubMed
Salvia lavanduloides (NCBI:txid392669)	Found in whole plant (BTO:0001461). See: REV. LANTINOAM. QUIM., 1974, 5, 41
Otostegia limbata (NCBI:txid483858)	See: DOI

Roles Classification
Biological Role(s):	EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor A lipoxygenase inhibitor that interferes with the action of arachidonate 5-lipoxygenase (EC 1.13.11.34). metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

Application(s):	anti-ulcer drug One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. anti-inflammatory agent Any compound that has anti-inflammatory effects.

ChEBI Ontology
Outgoing	eupatilin (CHEBI:4932) has role anti-inflammatory agent (CHEBI:67079) eupatilin (CHEBI:4932) has role anti-ulcer drug (CHEBI:49201) eupatilin (CHEBI:4932) has role antineoplastic agent (CHEBI:35610) eupatilin (CHEBI:4932) has role EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor (CHEBI:64964) eupatilin (CHEBI:4932) has role metabolite (CHEBI:25212) eupatilin (CHEBI:4932) is a dihydroxyflavone (CHEBI:38686) eupatilin (CHEBI:4932) is a trimethoxyflavone (CHEBI:27124)

IUPAC Name

2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one

Synonyms	Sources
2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one	ChemIDplus
5,7-dihydroxy-3',4',6-trimethoxyflavone	ChEBI
Eupatilin	KEGG COMPOUND

Last Modified

16 February 2018