CHEBI:67648 - (−)-5'-methoxyisolariciresinol

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ChEBI Name (−)-5'-methoxyisolariciresinol
ChEBI ID CHEBI:67648
ChEBI ASCII Name (-)-5'-methoxyisolariciresinol
Definition A lignan that is 5,6,7,8-tetrahydronaphthalen-2-ol substituted by two hydroxymethyl groups at positions 6 and 7, a methoxy group at position 3 and a 4-hydroxy-3,5-dimethoxyphenyl group at position 8. It has been isolated from the stems of Sinocalamus affinis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H26O7
Net Charge 0
Average Mass 390.42690
Monoisotopic Mass 390.16785
InChI InChI=1S/C21H26O7/c1-26-17-5-11-4-13(9-22)15(10-23)20(14(11)8-16(17)24)12-6-18(27-2)21(25)19(7-12)28-3/h5-8,13,15,20,22-25H,4,9-10H2,1-3H3/t13-,15-,20-/m1/s1
InChIKey JUJIQKRWLCSYQD-WAWZGNHOSA-N
SMILES COc1cc2C[C@H](CO)[C@@H](CO)[C@H](c3cc(OC)c(O)c(OC)c3)c2cc1O
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
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-5'-methoxyisolariciresinol (CHEBI:67648) has role plant metabolite (CHEBI:76924)
(−)-5'-methoxyisolariciresinol (CHEBI:67648) is a dimethoxybenzene (CHEBI:51681)
(−)-5'-methoxyisolariciresinol (CHEBI:67648) is a lignan (CHEBI:25036)
(−)-5'-methoxyisolariciresinol (CHEBI:67648) is a polyphenol (CHEBI:26195)
IUPAC Name
(6S,7S,8R)-8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ol
Registry Number Type Source
7357972 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21469695 PubMed citation Europe PMC
Last Modified
10 October 2014