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CHEBI:66613 - negundin B

ChEBI IDCHEBI:66613
ChEBI Namenegundin B
Stars
DefinitionA lignan that consists of 7,8-dihydronaphthalen-2-ol substituted by a 4-hydroxy-3-methoxyphenyl group at position 8, hydroxymethyl groups at positions 6 and 7 and a methoxy group at position 3 (the 7R,8S stereoisomer). Isolated from Vitex negundo, it exhibits inhibitory activity against lipoxygenase.
Last Modified7 April 2017
DownloadsMolfile
FormulaC20H22O6
Net Charge0
Average Mass358.390
Monoisotopic Mass358.14164
SMILES[H][C@]1(c2ccc(O)c(OC)c2)c2cc(O)c(OC)cc2C=C(CO)[C@@H]1CO
InChIInChI=1S/C20H22O6/c1-25-18-6-11(3-4-16(18)23)20-14-8-17(24)19(26-2)7-12(14)5-13(9-21)15(20)10-22/h3-8,15,20-24H,9-10H2,1-2H3/t15-,20-/m0/s1
InChIKeyAKOLXLNVZGAYAV-YWZLYKJASA-N
Species of MetaboliteComponentSourceComments
Vitex negundo (ncbitaxon:361442) root (BTO:0001188) PubMed (15520511)
Roles Classification
Biological Roles:
lipoxygenase inhibitor  A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.
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)
negundin B (CHEBI:66613) has role lipoxygenase inhibitor (CHEBI:35856)
negundin B (CHEBI:66613) has role plant metabolite (CHEBI:76924)
negundin B (CHEBI:66613) is a guaiacols (CHEBI:134251)
negundin B (CHEBI:66613) is a lignan (CHEBI:25036)
negundin B (CHEBI:66613) is a polyphenol (CHEBI:26195)
negundin B (CHEBI:66613) is a primary alcohol (CHEBI:15734)
IUPAC Name 
(7R,8S)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-7,8-dihydronaphthalen-2-ol
Registry NumbersSources
Reaxys:18484753Reaxys
Citations