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CHEBI:9691 - piperyline

Default Structure
ChEBI IDCHEBI:9691
ChEBI Namepiperyline
Stars
DefinitionA N-acylpyrrolidine that is pyrollidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum.
Last Modified16 August 2022
DownloadsMolfile
FormulaC16H17NO3
Net Charge0
Average Mass271.316
Monoisotopic Mass271.12084
SMILESO=C(/C=C/C=C/c1ccc2c(c1)OCO2)N1CCCC1
InChIInChI=1S/C16H17NO3/c18-16(17-9-3-4-10-17)6-2-1-5-13-7-8-14-15(11-13)20-12-19-14/h1-2,5-8,11H,3-4,9-10,12H2/b5-1+,6-2+
InChIKeyGQIJYUMTOUBHSH-IJIVKGSJSA-N
Species of MetaboliteComponentSourceComments
Piper arboreum (ncbitaxon:130381) leaf (BTO:0000713) DOI (10.5897/AJB09.182)
Piper guineense (ncbitaxon:511543)
fruit (BTO:0000486) PubMed (1271969)
leaf (BTO:0000713) PubMed (30423994)
Piper macropodum (ncbitaxon:2045273) stem (BTO:0001300) PubMed (2618672)
Piper nigrum (ncbitaxon:13216) - PubMed (30073789)
Roles Classification
Biological Roles:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
piperyline (CHEBI:9691) has functional parent (E,E)-piperic acid (CHEBI:37316)
piperyline (CHEBI:9691) has role antifungal agent (CHEBI:35718)
piperyline (CHEBI:9691) has role apoptosis inducer (CHEBI:68495)
piperyline (CHEBI:9691) has role plant metabolite (CHEBI:76924)
piperyline (CHEBI:9691) is a N-acylpyrrolidine (CHEBI:46766)
piperyline (CHEBI:9691) is a benzodioxoles (CHEBI:38298)
piperyline (CHEBI:9691) is a pyrrolidine alkaloid (CHEBI:26456)
piperyline (CHEBI:9691) is a tertiary carboxamide (CHEBI:140326)
IUPAC Name 
(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one
Synonyms  Source
1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]pyrrolidineChEBI
(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(1-pyrrolidinyl)-2,4-pentadien-1-oneChEBI
(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-oneIUPAC
piperilineChemIDplus
piperylinChemIDplus
pyrroperineChemIDplus
UniProt Name  Source
piperylineUniProt
Manual XrefsDatabases
552302ChemSpider
C00002076KNApSAcK
C10174KEGG COMPOUND
FDB000444FooDB
HMDB0029374HMDB
Registry NumbersSources
Reaxys:29164Reaxys
CAS:25924-78-1NIST Chemistry WebBook
CAS:25924-78-1ChemIDplus
Citations