eupatorin (CHEBI:136666)

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ChEBI Name	eupatorin

ChEBI ID	CHEBI:136666

Definition	A trimethoxyflavone that is 6-hydroxyluteolin in which the phenolic hydogens at positions 4', 6 and 7 have been replaced by methyl groups.

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

Supplier Information

Download	Molfile XML SDF

Formula

C18H16O7

Net Charge

Average Mass

344.316

Monoisotopic Mass

344.08960

InChI

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

InChIKey

KLAOKWJLUQKWIF-UHFFFAOYSA-N

SMILES

O1C=2C(=C(O)C(OC)=C(OC)C2)C(=O)C=C1C3=CC(O)=C(OC)C=C3

Metabolite of Species	Details
Eupatorium semiserratum (NCBI:txid103755)	See: PubMed
Artemisia incisa (NCBI:txid1177119)	Found in aerial part (BTO:0001658). See: PubMed
Centaurea virgata (NCBI:txid124936)	See: PubMed
Veronica austriaca subsp. teucrium (NCBI:txid1483217)	Found in aerial part (BTO:0001658). See: PubMed
Merrillia caloxylon (NCBI:txid159055)	See: PubMed
Veronica officinalis (NCBI:txid160511)	Found in aerial part (BTO:0001658). See: PubMed
Salvia connivens (NCBI:txid2026474)	See: PubMed
Salvia filipes (NCBI:txid2026484)	Found in aerial part (BTO:0001658). See: PubMed
Orthosiphon stamineus (NCBI:txid260636)	Found in leaf (BTO:0000713). See: PubMed
Achillea alpina (NCBI:txid282718)	Found in aerial part (BTO:0001658). See: PubMed
Croton ciliatoglandulifer (NCBI:txid323039)	See: PubMed
Brassica napus (NCBI:txid3708)	See: PubMed
Brassica napus (NCBI:txid3708)	See: MetaboLights Study
Salvia plebeia (NCBI:txid424424)	See: PubMed
Veronica orchidea (NCBI:txid996481)	Found in aerial part (BTO:0001658). See: PubMed

Roles Classification
Biological Role(s):	Brassica napus metabolite Any plant metabolite that is produced by rapeseed (Brassica napus). apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. calcium channel blocker One of a class of drugs that acts by selective inhibition of calcium influx through cell membranes or on the release and binding of calcium in intracellular pools. P450 inhibitor An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.

Application(s):	vasodilator agent A drug used to cause dilation of the blood vessels. anti-inflammatory agent Any compound that has anti-inflammatory effects. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	eupatorin (CHEBI:136666) has functional parent 6-hydroxyluteolin (CHEBI:2197) eupatorin (CHEBI:136666) has role Brassica napus metabolite (CHEBI:140165) eupatorin (CHEBI:136666) has role anti-inflammatory agent (CHEBI:67079) eupatorin (CHEBI:136666) has role antineoplastic agent (CHEBI:35610) eupatorin (CHEBI:136666) has role apoptosis inducer (CHEBI:68495) eupatorin (CHEBI:136666) has role calcium channel blocker (CHEBI:38215) eupatorin (CHEBI:136666) has role P450 inhibitor (CHEBI:50183) eupatorin (CHEBI:136666) has role vasodilator agent (CHEBI:35620) eupatorin (CHEBI:136666) is a dihydroxyflavone (CHEBI:38686) eupatorin (CHEBI:136666) is a polyphenol (CHEBI:26195) eupatorin (CHEBI:136666) is a trimethoxyflavone (CHEBI:27124)

IUPAC Name

5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-1-benzopyran-4-one

Synonyms	Sources
3',5-Dihydroxy-4',6,7-trimethoxyflavone	KNApSAcK
eupatorin	UniProt
Eupatorine	ChemIDplus

Last Modified

21 July 2022