CHEBI:6698 - (−)-matairesinol

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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 0
Average Mass 358.38510
Monoisotopic Mass 358.142
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 COc1cc(C[C@H]2COC(=O)[C@@H]2Cc2ccc(O)c(OC)c2)ccc1O
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.
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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
Manual Xrefs Databases
C00000606 KNApSAcK
C10682 KEGG COMPOUND
CPD-8912 MetaCyc
DB04200 DrugBank
Matairesinol Wikipedia
MAX PDBeChem
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Registry Numbers Types Sources
580-72-3 CAS Registry Number ChemIDplus
93883 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
23 January 2017