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CHEBI:66167 - γ-sanshool

ChEBI IDCHEBI:66167
ChEBI Nameγ-sanshool
Stars
ASCII Namegamma-sanshool
DefinitionAn 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.
Last Modified7 March 2018
DownloadsMolfile
FormulaC18H27NO
Net Charge0
Average Mass273.420
Monoisotopic Mass273.20926
SMILESC/C=C/C=C/C=C\CC/C=C/C=C/C(=O)NCC(C)C
InChIInChI=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+
InChIKeyKVUKDCFEXVWYBN-JDXPBYPHSA-N
Species of MetaboliteComponentSourceComments
Zanthoxylum piperitum (ncbitaxon:354529) stem (BTO:0001300) PubMed (17202689)
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.
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 Relation(s)
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 NumbersSources
Reaxys:4682020Reaxys
Citations