CHEBI:66605 - (+)-lyoniresinol 4,4'-bis-O-β-D-glucopyranoside

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ChEBI Name (+)-lyoniresinol 4,4'-bis-O-β-D-glucopyranoside
ChEBI ID CHEBI:66605
ChEBI ASCII Name (+)-lyoniresinol 4,4'-bis-O-beta-D-glucopyranoside
Definition A lignan that consists of (+)-lyoniresinol attached to two β-D-glucopyranosyl units at positions 4 and 4' via glycosidic linkages. Isolated from Indigofera heterantha, it exhibits inhibitory activity against lipoxygenase.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C34H48O18
Net Charge 0
Average Mass 744.73410
Monoisotopic Mass 744.28406
InChI InChI=1S/C34H48O18/c1-45-17-7-14(8-18(46-2)30(17)51-33-28(43)26(41)24(39)20(11-37)49-33)22-16(10-36)15(9-35)5-13-6-19(47-3)31(32(48-4)23(13)22)52-34-29(44)27(42)25(40)21(12-38)50-34/h6-8,15-16,20-22,24-29,33-44H,5,9-12H2,1-4H3/t15-,16-,20+,21+,22+,24+,25+,26-,27-,28+,29+,33-,34-/m0/s1
InChIKey WDBFWRZVSDUFTE-AUWKFTQZSA-N
SMILES COc1cc(cc(OC)c1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@H]1[C@@H](CO)[C@H](CO)Cc2cc(OC)c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(OC)c12
Metabolite of Species Details
Indigofera heterantha (NCBI:txid198880) Found in whole plant (BTO:0001461). See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
lipoxygenase inhibitor
A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (+)-lyoniresinol 4,4'-bis-O-β-D-glucopyranoside (CHEBI:66605) has functional parent (+)-lyoniresinol (CHEBI:68168)
(+)-lyoniresinol 4,4'-bis-O-β-D-glucopyranoside (CHEBI:66605) has role lipoxygenase inhibitor (CHEBI:35856)
(+)-lyoniresinol 4,4'-bis-O-β-D-glucopyranoside (CHEBI:66605) has role metabolite (CHEBI:25212)
(+)-lyoniresinol 4,4'-bis-O-β-D-glucopyranoside (CHEBI:66605) is a β-D-glucoside (CHEBI:22798)
(+)-lyoniresinol 4,4'-bis-O-β-D-glucopyranoside (CHEBI:66605) is a dimethoxybenzene (CHEBI:51681)
(+)-lyoniresinol 4,4'-bis-O-β-D-glucopyranoside (CHEBI:66605) is a lignan (CHEBI:25036)
(+)-lyoniresinol 4,4'-bis-O-β-D-glucopyranoside (CHEBI:66605) is a primary alcohol (CHEBI:15734)
(+)-lyoniresinol 4,4'-bis-O-β-D-glucopyranoside (CHEBI:66605) is a tetralins (CHEBI:36786)
IUPAC Name
4-[(1S,2R,3R)-7-(β-D-glucopyranosyloxy)-2,3-bis(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-1-yl]-2,6-dimethoxyphenyl β-D-glucopyranoside
Registry Number Type Source
10142896 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15744094 PubMed citation Europe PMC
Last Modified
27 March 2013