CHEBI:68168 - (+)-lyoniresinol

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ChEBI Name (+)-lyoniresinol
Definition A lignan that is tetralin substituted by a 4-hydroxy-3,5-dimethoxy group at position 4, hydroxymethyl groups at positions 2 and 3, methoxy groups at positions 5 and 7 and a hydroxy group at position 6. Isolated from Machilus robusta and Sinocalamus affinis, it exhibits antineoplastic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C22H28O8
Net Charge 0
Average Mass 420.45290
Monoisotopic Mass 420.17842
InChI InChI=1S/C22H28O8/c1-27-15-7-12(8-16(28-2)20(15)25)18-14(10-24)13(9-23)5-11-6-17(29-3)21(26)22(30-4)19(11)18/h6-8,13-14,18,23-26H,5,9-10H2,1-4H3/t13-,14-,18+/m0/s1
SMILES COc1cc(cc(OC)c1O)[C@@H]1[C@@H](CO)[C@H](CO)Cc2cc(OC)c(O)c(OC)c12
Metabolite of Species Details
Sinocalamus affinis (IPNI:421970-1) Found in stem (BTO:0001300). 95% Ethanolic extract of skin-removed, air-dried, powdered stems. See: PubMed
Machilus robusta (NCBI:txid460780) Found in bark (BTO:0001301). 95%aqueous EtOH extract of air-dried 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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (+)-lyoniresinol (CHEBI:68168) has role antineoplastic agent (CHEBI:35610)
(+)-lyoniresinol (CHEBI:68168) has role metabolite (CHEBI:25212)
(+)-lyoniresinol (CHEBI:68168) is a dimethoxybenzene (CHEBI:51681)
(+)-lyoniresinol (CHEBI:68168) is a lignan (CHEBI:25036)
(+)-lyoniresinol (CHEBI:68168) is a polyphenol (CHEBI:26195)
(+)-lyoniresinol (CHEBI:68168) is a primary alcohol (CHEBI:15734)
(+)-lyoniresinol (CHEBI:68168) is a tetralins (CHEBI:36786)
Incoming (+)-lyoniresinol 4,4'-bis-O-β-D-glucopyranoside (CHEBI:66605) has functional parent (+)-lyoniresinol (CHEBI:68168)
(+)-lyoniresinol-3-α-O-β-D-glucopyranoside (CHEBI:66606) has functional parent (+)-lyoniresinol (CHEBI:68168)
Manual Xref Database
JP2010150152 Patent
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Registry Number Type Source
2191984 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
21469695 PubMed citation Europe PMC
21627109 PubMed citation Europe PMC
Last Modified
27 March 2013