(-)-matairesinol (CHEBI:6698)

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ChEBI Name	(−)-matairesinol

ChEBI ID	CHEBI:6698

ChEBI ASCII Name	(-)-matairesinol

Definition	A lignan that is γ-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Kristian Axelsen

Secondary ChEBI IDs	CHEBI:43819, CHEBI:65005

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Formula

C20H22O6

Net Charge

Average Mass

358.390

Monoisotopic Mass

358.14164

InChI

InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1

InChIKey

MATGKVZWFZHCLI-LSDHHAIUSA-N

SMILES

COC1=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O)C(OC)=C2)=CC=C1O

Roles Classification
Biological Role(s):	phytoestrogen Any compound produced by a plant that happens to have estrogenic activity. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

Application(s):	angiogenesis inhibitor An agent and endogenous substances that antagonize or inhibit the development of new blood vessels. anti-asthmatic agent Any compound that has anti-asthmatic effects.

ChEBI Ontology
Outgoing	(−)-matairesinol (CHEBI:6698) has role angiogenesis inhibitor (CHEBI:48422) (−)-matairesinol (CHEBI:6698) has role anti-asthmatic agent (CHEBI:65023) (−)-matairesinol (CHEBI:6698) has role phytoestrogen (CHEBI:76989) (−)-matairesinol (CHEBI:6698) has role plant metabolite (CHEBI:76924) (−)-matairesinol (CHEBI:6698) is a γ-lactone (CHEBI:37581) (−)-matairesinol (CHEBI:6698) is a lignan (CHEBI:25036) (−)-matairesinol (CHEBI:6698) is a polyphenol (CHEBI:26195)

Incoming	matairesinoside (CHEBI:132820) has functional parent (−)-matairesinol (CHEBI:6698)

IUPAC Name

(3R,4R)-3,4-bis(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one

Synonyms	Sources
(−)-matairesinol	UniProt
3R,4R-Bis((4-hydroxy-3-methoxyphenyl)methyl)dihydro-2(3H)-furanone	ChemIDplus
Artigenin congener	DrugBank
Matairesinol	KEGG COMPOUND

Last Modified

21 June 2021