CHEBI:66167 - γ-sanshool

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ChEBI Name γ-sanshool
ChEBI ID CHEBI:66167
ChEBI ASCII Name gamma-sanshool
Definition An enamide obtained by the formal condensation of 2-methylpropanamine with tetradeca-2,4,8,10,12-pentaenoic acid (the 2E,4E,8Z,10E,12E 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 C18H27NO
Net Charge 0
Average Mass 273.41310
Monoisotopic Mass 273.20926
InChI InChI=1S/C18H27NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-18(20)19-16-17(2)3/h4-9,12-15,17H,10-11,16H2,1-3H3,(H,19,20)/b5-4+,7-6+,9-8-,13-12+,15-14+
InChIKey KVUKDCFEXVWYBN-JDXPBYPHSA-N
SMILES C\C=C\C=C\C=C/CC\C=C\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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing γ-sanshool (CHEBI:66167) has functional parent 2-methylpropanamine (CHEBI:15997)
γ-sanshool (CHEBI:66167) has role EC 2.3.1.26 (sterol O-acyltransferase) inhibitor (CHEBI:64696)
γ-sanshool (CHEBI:66167) has role plant metabolite (CHEBI:76924)
γ-sanshool (CHEBI:66167) is a enamide (CHEBI:51751)
γ-sanshool (CHEBI:66167) is a secondary carboxamide (CHEBI:140325)
IUPAC Name
(2E,4E,8Z,10E,12E)-N-(2-methylpropyl)tetradeca-2,4,8,10,12-pentaenamide
Registry Number Type Source
4682020 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17202689 PubMed citation Europe PMC
Last Modified
07 March 2018