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CHEBI:4932 - eupatilin

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
Sideritis mugronensis (IPNI:900993-1) aerial part (BTO:0001658) DOI (10.1016/S0031-9422(00)89273-0)
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)
Artemisia asiatica (IPNI:179234-1) - PubMed (17404061)
Eupatorium altissimum (IPNI:1076340-2) whole plant (BTO:0001461) PubMed (856983)
Citrus reticulata (IPNI:772038-1) exocarp (BTO:0000733) PubMed (7463312) Previous component: fruit peel;
Otostegia limbata (ncbitaxon:483858) - DOI (10.1055/s-0028-1097328)
Merrillia caloxylon (ncbitaxon:159055) root (BTO:0001188) DOI (10.1016/0031-9422(74)80328-6)
Orthosiphon stamineus (ncbitaxon:260636) - PubMed (4798539)
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:
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.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
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
EupatilinKEGG COMPOUND
2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-oneChemIDplus
5,7-dihydroxy-3',4',6-trimethoxyflavoneChEBI
Manual XrefsDatabases
C10040KEGG COMPOUND
C00003845KNApSAcK
Registry NumbersSources
Reaxys:1354453Reaxys
CAS:22368-21-4KEGG COMPOUND
CAS:22368-21-4ChemIDplus
Citations