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CHEBI:6698 - (−)-matairesinol

ChEBI IDCHEBI:6698
ChEBI Name(−)-matairesinol
Stars
ASCII Name(-)-matairesinol
DefinitionA lignan that is γ-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).
Secondary ChEBI IDsCHEBI:43819, CHEBI:65005
Last Modified21 June 2021
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC20H22O6
Net Charge0
Average Mass358.390
Monoisotopic Mass358.14164
SMILESCOc1cc(C[C@H]2COC(=O)[C@@H]2Cc2ccc(O)c(OC)c2)ccc1O
InChIInChI=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
InChIKeyMATGKVZWFZHCLI-LSDHHAIUSA-N
Wikipedia
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
phytoestrogen  Any compound produced by a plant that happens to have estrogenic activity.
Applications:
anti-asthmatic agent  Any compound that has anti-asthmatic effects.
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
ChEBI Ontology
Outgoing Relation(s)
(−)-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 lignan (CHEBI:25036)
(−)-matairesinol (CHEBI:6698) is a polyphenol (CHEBI:26195)
(−)-matairesinol (CHEBI:6698) is a γ-lactone (CHEBI:37581)
Incoming Relation(s)
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  Source
MatairesinolKEGG COMPOUND
Artigenin congenerDrugBank
3R,4R-Bis((4-hydroxy-3-methoxyphenyl)methyl)dihydro-2(3H)-furanoneChemIDplus
UniProt Name  Source
(−)-matairesinolUniProt
Manual XrefsDatabases
CPD-8912MetaCyc
MAXPDBeChem
C10682KEGG COMPOUND
DB04200DrugBank
MatairesinolWikipedia
C00000606KNApSAcK
106491ChemSpider
Registry NumbersSources
Reaxys:93883Reaxys
CAS:580-72-3KEGG COMPOUND
CAS:580-72-3ChemIDplus
Citations