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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:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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