matsudone A (CHEBI:66685)

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CHEBI:66685 - matsudone A

ChEBI ID	CHEBI:66685
ChEBI Name	matsudone A
Stars
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.
Last Modified	12 July 2013
Downloads	Molfile

Formula	C26H26O12
Net Charge	0
Average Mass	530.482
Monoisotopic Mass	530.14243
SMILES	CC1(C)C=Cc2c(cc(O)c3c(=O)c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c(-c4ccc(O)c(O)c4)oc23)O1
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

Species of Metabolite	Component	Source	Comments
Salix matsudana (ncbitaxon:349989)	leaf (BTO:0000713)	PubMed (18794770)

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.

cyclooxygenase 2 inhibitor A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.

ChEBI Ontology

Outgoing Relation(s)
	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 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)
	matsudone A (CHEBI:66685) is a β-D-glucoside (CHEBI:22798)

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 Numbers	Sources
Reaxys:18597782	Reaxys

Citations