CHEBI:66606 - (+)-lyoniresinol-3-α-O-β-D-glucopyranoside

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ChEBI Name (+)-lyoniresinol-3-α-O-β-D-glucopyranoside
ChEBI ID CHEBI:66606
ChEBI ASCII Name (+)-lyoniresinol-3-alpha-O-beta-D-glucopyranoside
Definition A lignan that is (+)-lyoniresinol substituted by a β-D-glucopyranosyl moiety at position 3 via a glycosidic linkage. Isolated from the root barks of Stemmadenia minima and Lycium chinense, it exhibits antimicrobial activities.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H38O13
Net Charge 0
Average Mass 582.59350
Monoisotopic Mass 582.23124
InChI InChI=1S/C28H38O13/c1-36-16-7-13(8-17(37-2)22(16)31)20-15(11-40-28-26(35)25(34)23(32)19(10-30)41-28)14(9-29)5-12-6-18(38-3)24(33)27(39-4)21(12)20/h6-8,14-15,19-20,23,25-26,28-35H,5,9-11H2,1-4H3/t14-,15-,19+,20+,23+,25-,26+,28+/m0/s1
InChIKey PQQRNPDHSJDAGV-HQSXISOASA-N
SMILES COc1cc(cc(OC)c1O)[C@@H]1[C@@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](CO)Cc2cc(OC)c(O)c(OC)c12
Metabolite of Species Details
Stemmadenia minima (IPNI:81813-1) Found in stem (BTO:0001300). Previous component: stem bark; See: PubMed
Lycium chinense (NCBI:txid112883) Found in root (BTO:0001188). Previous component: root bark; 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.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (+)-lyoniresinol-3-α-O-β-D-glucopyranoside (CHEBI:66606) has functional parent (+)-lyoniresinol (CHEBI:68168)
(+)-lyoniresinol-3-α-O-β-D-glucopyranoside (CHEBI:66606) has role antibacterial agent (CHEBI:33282)
(+)-lyoniresinol-3-α-O-β-D-glucopyranoside (CHEBI:66606) has role antifungal agent (CHEBI:35718)
(+)-lyoniresinol-3-α-O-β-D-glucopyranoside (CHEBI:66606) has role metabolite (CHEBI:25212)
(+)-lyoniresinol-3-α-O-β-D-glucopyranoside (CHEBI:66606) is a β-D-glucoside (CHEBI:22798)
(+)-lyoniresinol-3-α-O-β-D-glucopyranoside (CHEBI:66606) is a dimethoxybenzene (CHEBI:51681)
(+)-lyoniresinol-3-α-O-β-D-glucopyranoside (CHEBI:66606) is a lignan (CHEBI:25036)
(+)-lyoniresinol-3-α-O-β-D-glucopyranoside (CHEBI:66606) is a monosaccharide derivative (CHEBI:63367)
(+)-lyoniresinol-3-α-O-β-D-glucopyranoside (CHEBI:66606) is a polyphenol (CHEBI:26195)
(+)-lyoniresinol-3-α-O-β-D-glucopyranoside (CHEBI:66606) is a primary alcohol (CHEBI:15734)
(+)-lyoniresinol-3-α-O-β-D-glucopyranoside (CHEBI:66606) is a tetralins (CHEBI:36786)
IUPAC Name
[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methyl β-D-glucopyranoside
Synonyms Sources
(+)-lyoniresinol 9'-O-β-D-glucopyranoside ChEBI
pteleifoside G ChEBI
Manual Xref Database
HMDB0038922 HMDB
View more database links
Registry Number Type Source
6168345 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16212233 PubMed citation Europe PMC
17226467 PubMed citation Europe PMC
Last Modified
27 March 2013