CHEBI:65685 - (−)-3,4-dimethoxy-3,4-desmethylenedioxycubebin

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ChEBI Name (−)-3,4-dimethoxy-3,4-desmethylenedioxycubebin
ChEBI ID CHEBI:65685
ChEBI ASCII Name (-)-3,4-dimethoxy-3,4-desmethylenedioxycubebin
Definition A lignan that consists of tetrahydrofuran-2-ol substituted by a 1,3-benzodioxol-5-ylmethyl group at positions 3 and a 3,4-dimethoxybenzyl group at position 4 (the 3R,4R stereoisomer). It is isolated from the leaves of Piper nigrum and exhibits histamine release inhibitory activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H24O6
Net Charge 0
Average Mass 372.41170
Monoisotopic Mass 372.15729
InChI InChI=1S/C21H24O6/c1-23-17-5-3-13(9-19(17)24-2)7-15-11-25-21(22)16(15)8-14-4-6-18-20(10-14)27-12-26-18/h3-6,9-10,15-16,21-22H,7-8,11-12H2,1-2H3/t15-,16+,21?/m0/s1
InChIKey VHLUROMCVXTWNM-PTHSTZKBSA-N
SMILES [H][C@@]1(COC(O)[C@]1([H])Cc1ccc2OCOc2c1)Cc1ccc(OC)c(OC)c1
Metabolite of Species Details
Piper nigrum (NCBI:txid13216) Found in leaf (BTO:0000713). Mixture of alpha and beta isomer See: PubMed
Roles Classification
Biological Role(s): histamine antagonist
Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): histamine antagonist
Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-3,4-dimethoxy-3,4-desmethylenedioxycubebin (CHEBI:65685) has role histamine antagonist (CHEBI:37956)
(−)-3,4-dimethoxy-3,4-desmethylenedioxycubebin (CHEBI:65685) has role plant metabolite (CHEBI:76924)
(−)-3,4-dimethoxy-3,4-desmethylenedioxycubebin (CHEBI:65685) is a benzodioxoles (CHEBI:38298)
(−)-3,4-dimethoxy-3,4-desmethylenedioxycubebin (CHEBI:65685) is a cyclic acetal (CHEBI:59770)
(−)-3,4-dimethoxy-3,4-desmethylenedioxycubebin (CHEBI:65685) is a lactol (CHEBI:38131)
(−)-3,4-dimethoxy-3,4-desmethylenedioxycubebin (CHEBI:65685) is a lignan (CHEBI:25036)
(−)-3,4-dimethoxy-3,4-desmethylenedioxycubebin (CHEBI:65685) is a secondary alcohol (CHEBI:35681)
IUPAC Name
(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(3,4-dimethoxybenzyl)tetrahydrofuran-2-ol
Synonyms Sources
3-(2H-1,3-benzodioxol-5-ylmethyl)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-ol HMDB
9-hydroxy-3',4'-dimethoxy-3,4-methylenedioxy-9,9'-epoxylignan HMDB
Manual Xref Database
HMDB0032734 HMDB
View more database links
Registry Number Type Source
10028545 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15467205 PubMed citation Europe PMC
18057734 PubMed citation Europe PMC
18827366 PubMed citation Europe PMC
Last Modified
09 November 2021