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

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

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ChEBI ID	CHEBI:65685
ChEBI Name	(−)-3,4-dimethoxy-3,4-desmethylenedioxycubebin
Stars
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.
Last Modified	9 November 2021
Downloads	Molfile

Formula	C21H24O6
Net Charge	0
Average Mass	372.417
Monoisotopic Mass	372.15729
SMILES	[H][C@]1(Cc2ccc(OC)c(OC)c2)COC(O)[C@]1([H])Cc1ccc2c(c1)OCO2
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

Species of Metabolite	Component	Source	Comments
Piper nigrum (ncbitaxon:13216)	leaf (BTO:0000713)	PubMed (15467205)	Mixture of alpha and beta isomer

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. 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.
Application:	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.

ChEBI Ontology

Outgoing Relation(s)
	(−)-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	Source
9-hydroxy-3',4'-dimethoxy-3,4-methylenedioxy-9,9'-epoxylignan	HMDB
3-(2H-1,3-benzodioxol-5-ylmethyl)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-ol	HMDB

Manual Xrefs	Databases
HMDB0032734	HMDB

Registry Numbers	Sources
Reaxys:10028545	Reaxys

Citations