CHEBI:66613 - negundin B

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ChEBI Name negundin B
ChEBI ID CHEBI:66613
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C20H22O6
Net Charge 0
Average Mass 358.38510
Monoisotopic Mass 358.14164
InChI InChI=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
InChIKey AKOLXLNVZGAYAV-YWZLYKJASA-N
SMILES [H][C@]1([C@@H](CO)C(CO)=Cc2cc(OC)c(O)cc12)c1ccc(O)c(OC)c1
Metabolite of Species Details
Vitex negundo (NCBI:txid361442) Found in root (BTO:0001188). See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
18484753 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15520511 PubMed citation Europe PMC
Last Modified
07 April 2017