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

ChEBI IDCHEBI:66605
ChEBI Name(+)-lyoniresinol 4,4'-bis-O-β-D-glucopyranoside
Stars
ASCII Name(+)-lyoniresinol 4,4'-bis-O-beta-D-glucopyranoside
DefinitionA 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.
Last Modified27 March 2013
DownloadsMolfile
FormulaC34H48O18
Net Charge0
Average Mass744.740
Monoisotopic Mass744.28406
SMILESCOc1cc([C@H]2c3c(cc(OC)c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c3OC)C[C@@H](CO)[C@@H]2CO)cc(OC)c1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChIInChI=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
InChIKeyWDBFWRZVSDUFTE-AUWKFTQZSA-N
Species of MetaboliteComponentSourceComments
Indigofera heterantha (ncbitaxon:198880) whole plant (BTO:0001461) PubMed (15744094)
Roles Classification
Biological Roles:
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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
(+)-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 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)
(+)-lyoniresinol 4,4'-bis-O-β-D-glucopyranoside (CHEBI:66605) is a β-D-glucoside (CHEBI:22798)
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 NumbersSources
Reaxys:10142896Reaxys
Citations