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CHEBI:4932 - eupatilin

Default Structure
ChEBI IDCHEBI:4932
ChEBI Nameeupatilin
Stars
DefinitionA 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.
Secondary ChEBI IDCHEBI:65882
Last Modified16 February 2018
DownloadsMolfile
FormulaC18H16O7
Net Charge0
Average Mass344.319
Monoisotopic Mass344.08960
SMILESCOc1ccc(-c2cc(=O)c3c(O)c(OC)c(O)cc3o2)cc1OC
InChIInChI=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
InChIKeyDRRWBCNQOKKKOL-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Artemisia asiatica (IPNI:179234-1) - PubMed (17404061)
Citrus reticulata (IPNI:772038-1) exocarp (BTO:0000733) PubMed (7463312) Previous component: fruit peel;
Eupatorium altissimum (IPNI:1076340-2) whole plant (BTO:0001461) PubMed (856983)
Merrillia caloxylon (ncbitaxon:159055) root (BTO:0001188) DOI (10.1016/0031-9422(74)80328-6)
Orthosiphon stamineus (ncbitaxon:260636) - PubMed (4798539)
Otostegia limbata (ncbitaxon:483858) - DOI (10.1055/s-0028-1097328)
Salvia lavanduloides (ncbitaxon:392669) whole plant (BTO:0001461) Article (REV. LANTINOAM. QUIM., 1974, 5, 41)
Salvia tomentosa (IPNI:457405-1) leaf (BTO:0000713) DOI (10.1021/np50003a002)
Sideritis gomeraea (ncbitaxon:155247) - Article (J. NAT. PROD., 1978, 41, 279)
Sideritis mugronensis (IPNI:900993-1) aerial part (BTO:0001658) DOI (10.1016/S0031-9422(00)89273-0)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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).
Applications:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-oneChemIDplus
5,7-dihydroxy-3',4',6-trimethoxyflavoneChEBI
EupatilinKEGG COMPOUND
Manual XrefsDatabases
C00003845KNApSAcK
C10040KEGG COMPOUND
Registry NumbersSources
Reaxys:1354453Reaxys
CAS:22368-21-4ChemIDplus
CAS:22368-21-4KEGG COMPOUND
Citations