CHEBI:66685 - matsudone A

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ChEBI Name matsudone A
ChEBI ID CHEBI:66685
Definition A glycosyloxyflavone that is 5,3',4'-trihydroxyflavone substituted by a β-D-glucopyranosyloxy group at position 3 and a 2'',2''-dimethylpyrano ring fused across positions 7 and 8. Isolated from the leaves of Salix matsudana, it acts as a cyclooxygenase 2 inhibitor.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C26H26O12
Net Charge 0
Average Mass 530.47740
Monoisotopic Mass 530.14243
InChI InChI=1S/C26H26O12/c1-26(2)6-5-11-15(38-26)8-14(30)17-19(32)24(37-25-21(34)20(33)18(31)16(9-27)35-25)22(36-23(11)17)10-3-4-12(28)13(29)7-10/h3-8,16,18,20-21,25,27-31,33-34H,9H2,1-2H3/t16-,18-,20+,21-,25+/m1/s1
InChIKey IVILUDSFUSZAPC-HWZJXXSZSA-N
SMILES CC1(C)Oc2cc(O)c3c(oc(-c4ccc(O)c(O)c4)c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c3=O)c2C=C1
Metabolite of Species Details
Salix matsudana (NCBI:txid349989) Found in leaf (BTO:0000713). See: PubMed
Roles Classification
Biological Role(s): cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing matsudone A (CHEBI:66685) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
matsudone A (CHEBI:66685) has role metabolite (CHEBI:25212)
matsudone A (CHEBI:66685) is a β-D-glucoside (CHEBI:22798)
matsudone A (CHEBI:66685) is a extended flavonoid (CHEBI:71037)
matsudone A (CHEBI:66685) is a glycosyloxyflavone (CHEBI:50018)
matsudone A (CHEBI:66685) is a monosaccharide derivative (CHEBI:63367)
matsudone A (CHEBI:66685) is a pyranochromane (CHEBI:74632)
matsudone A (CHEBI:66685) is a trihydroxyflavone (CHEBI:27116)
IUPAC Name
2-(3,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-4-oxo-4H,8H-pyrano[2,3-f]chromen-3-yl β-D-glucopyranoside
Synonym Source
7,8-(2'',2''-dimethylpyrano)-5,3',4'-trihydroxyflavone-3-O-β-D-glucopyranoside ChEBI
Registry Number Type Source
18597782 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
18794770 PubMed citation Europe PMC
Last Modified
12 July 2013