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

Default Structure
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:
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.
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