beta-sanshool (CHEBI:66166)

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ChEBI Name	β-sanshool

ChEBI ID	CHEBI:66166

ChEBI ASCII Name	beta-sanshool

Definition	An enamide obtained by the fromal condensation of 2-methylpropanamine with dodeca-2,6,8,10-tetraenoic acid (the 2E,6E,8E,10E stereoisomer). Isolated from Zanthoxylum piperitum, it exhibits inhibitory activity against acyl-CoA:cholesterol acyltransferase.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C16H25NO

Net Charge

Average Mass

247.37580

Monoisotopic Mass

247.19361

InChI

InChI=1S/C16H25NO/c1-4-5-6-7-8-9-10-11-12-13-16(18)17-14-15(2)3/h4-9,12-13,15H,10-11,14H2,1-3H3,(H,17,18)/b5-4+,7-6+,9-8+,13-12+

InChIKey

SBXYHCVXUCYYJT-UMYNZBAMSA-N

SMILES

C\C=C\C=C\C=C\CC\C=C\C(=O)NCC(C)C

Metabolite of Species	Details
Zanthoxylum piperitum (NCBI:txid354529)	Found in stem (BTO:0001300). See: PubMed

Roles Classification
Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. EC 2.3.1.26 (sterol O-acyltransferase) inhibitor An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of acyl-CoA:cholesterol acyltransferase (EC 2.3.1.26).

ChEBI Ontology
Outgoing	β-sanshool (CHEBI:66166) has functional parent 2-methylpropanamine (CHEBI:15997) β-sanshool (CHEBI:66166) has role EC 2.3.1.26 (sterol O-acyltransferase) inhibitor (CHEBI:64696) β-sanshool (CHEBI:66166) has role plant metabolite (CHEBI:76924) β-sanshool (CHEBI:66166) is a enamide (CHEBI:51751) β-sanshool (CHEBI:66166) is a secondary carboxamide (CHEBI:140325)

IUPAC Name

(2E,6E,8E,10E)-N-(2-methylpropyl)dodeca-2,6,8,10-tetraenamide

Registry Number	Type	Source
1726183	Reaxys Registry Number	Reaxys

Citation	Type	Source
17202689	PubMed citation	Europe PMC

Last Modified

07 March 2018