CHEBI:67246 - (+)-lariciresinol

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ChEBI Name (+)-lariciresinol
ChEBI ID CHEBI:67246
Definition A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter KAX
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Formula C20H24O6
Net Charge 0
Average Mass 360.40100
Monoisotopic Mass 360.157
InChI InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1
InChIKey MHXCIKYXNYCMHY-AUSJPIAWSA-N
SMILES COc1cc(C[C@H]2CO[C@@H]([C@H]2CO)c2ccc(O)c(OC)c2)ccc1O
Metabolite of Species Details
Rubia yunnanensis (IPNI:765385-1) Found in root (BTO:0001188). Methanolic extract of air dried powdered roots. See: PubMed
Taxus yunnanensis (NCBI:txid147275) Found in xylem (BTO:0001468). Previous component: wood; Aqueous extract of air-dried, powdered wood See: PubMed
Roles Classification
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing (+)-lariciresinol (CHEBI:67246) has role antifungal agent (CHEBI:35718)
(+)-lariciresinol (CHEBI:67246) has role plant metabolite (CHEBI:76924)
(+)-lariciresinol (CHEBI:67246) is a aromatic ether (CHEBI:35618)
(+)-lariciresinol (CHEBI:67246) is a lignan (CHEBI:25036)
(+)-lariciresinol (CHEBI:67246) is a oxolanes (CHEBI:26912)
(+)-lariciresinol (CHEBI:67246) is a phenols (CHEBI:33853)
(+)-lariciresinol (CHEBI:67246) is a primary alcohol (CHEBI:15734)
(+)-lariciresinol (CHEBI:67246) is enantiomer of (−)-lariciresinol (CHEBI:67244)
Incoming (+)-(7S,8R,8'R)-5,5'-dimethoxylariciresinol (CHEBI:67650) has functional parent (+)-lariciresinol (CHEBI:67246)
(+)-5'-methoxylariciresinol (CHEBI:67651) has functional parent (+)-lariciresinol (CHEBI:67246)
(−)-lariciresinol (CHEBI:67244) is enantiomer of (+)-lariciresinol (CHEBI:67246)
IUPAC Name
4-[(2S,3R,4R)-4-(4-hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydrofuran-2-yl]-2-methoxyphenol
Synonyms Sources
(+)-lariciresinol UniProt
Lariciresinol ChemIDplus
Manual Xrefs Databases
C00000602 KNApSAcK
C10646 KEGG COMPOUND
CPD-8907 MetaCyc
Lariciresinol Wikipedia
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Registry Numbers Types Sources
27003-73-2 CAS Registry Number KEGG COMPOUND
83327-19-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
21138310 PubMed citation Europe PMC
21679690 PubMed citation Europe PMC
21973054 PubMed citation Europe PMC
22218086 PubMed citation Europe PMC
8262939 PubMed citation SUBMITTER
Last Modified
26 May 2015