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CHEBI:67644 - (−)-medioresinol

ChEBI IDCHEBI:67644
ChEBI Name(−)-medioresinol
Stars
ASCII Name(-)-medioresinol
DefinitionA lignan that is tetrahydro-1H,3H-furo[3,4-c]furan substituted by a 4-hydroxy-3,5-dimethoxyphenyl group at position 1 and a 4-hydroxy-3-methoxyphenyl group at position 4. It has been isolated from the stems of Sinocalamus affinis.
Last Modified10 October 2014
DownloadsMolfile
FormulaC21H24O7
Net Charge0
Average Mass388.416
Monoisotopic Mass388.15220
SMILES[H][C@]12CO[C@H](c3cc(OC)c(O)c(OC)c3)[C@@]1([H])CO[C@@H]2c1ccc(O)c(OC)c1
InChIInChI=1S/C21H24O7/c1-24-16-6-11(4-5-15(16)22)20-13-9-28-21(14(13)10-27-20)12-7-17(25-2)19(23)18(8-12)26-3/h4-8,13-14,20-23H,9-10H2,1-3H3/t13-,14-,20+,21+/m0/s1
InChIKeyVJOBNGRIBLNUKN-BMHXQBNDSA-N
Species of MetaboliteComponentSourceComments
Sinocalamus affinis (IPNI:421970-1) stem (BTO:0001300) PubMed (21469695) 95% Ethanolic extract of skin-removed, air-dried, powdered stems.
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
(−)-medioresinol (CHEBI:67644) has role plant metabolite (CHEBI:76924)
(−)-medioresinol (CHEBI:67644) is a dimethoxybenzene (CHEBI:51681)
(−)-medioresinol (CHEBI:67644) is a furofuran (CHEBI:47790)
(−)-medioresinol (CHEBI:67644) is a lignan (CHEBI:25036)
(−)-medioresinol (CHEBI:67644) is a polyphenol (CHEBI:26195)
IUPAC Name 
4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3-methoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-2,6-dimethoxyphenol
Registry NumbersSources
Reaxys:4569869Reaxys
Citations