CHEBI:28821 - piperine

ChEBI IDCHEBI:28821
ChEBI Namepiperine
Stars
DefinitionA N-acylpiperidine that is piperidine 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.
Secondary ChEBI IDsCHEBI:7348, CHEBI:12539, CHEBI:21491
Last Modified15 August 2022
DownloadsMolfile
FormulaC17H19NO3
Net Charge0
Average Mass285.343
Monoisotopic Mass285.13649
SMILESO=C(/C=C/C=C/c1ccc2c(c1)OCO2)N1CCCCC1
InChIInChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+
InChIKeyMXXWOMGUGJBKIW-YPCIICBESA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Piper betle (ncbitaxon:13217) - DOI (10.1016/S0031-9422(98)00208-8)
Piper khasianum (ncbitaxon:405331) - DOI (10.1016/S0031-9422(98)00208-8)
Piper nigrum (ncbitaxon:13216) - PubMed (10575373)
Homo sapiens (ncbitaxon:9606) blood serum (BTO:0000133) MetaboLights (MTBLS90)
Roles Classification
Biological Roles:
NF-kappaB inhibitor  An inhibitor of NF-κB (nuclear factor κ-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
human blood serum metabolite  Any metabolite (endogenous or exogenous) found in human blood serum samples.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
food component  A physiological role played by any substance that is distributed in foodstuffs. It includes materials derived from plants or animals, such as vitamins or minerals, as well as environmental contaminants.
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)
piperine (CHEBI:28821) has functional parent (E,E)-piperic acid (CHEBI:37316)
piperine (CHEBI:28821) has role food component (CHEBI:78295)
piperine (CHEBI:28821) has role human blood serum metabolite (CHEBI:85234)
piperine (CHEBI:28821) has role NF-κB inhibitor (CHEBI:73240)
piperine (CHEBI:28821) has role plant metabolite (CHEBI:76924)
piperine (CHEBI:28821) is a N-acylpiperidine (CHEBI:48591)
piperine (CHEBI:28821) is a benzodioxoles (CHEBI:38298)
piperine (CHEBI:28821) is a piperidine alkaloid (CHEBI:26147)
piperine (CHEBI:28821) is a tertiary carboxamide (CHEBI:140326)
IUPAC Name 
1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]piperidine
Synonyms  Source
N-[(E,E)-Piperoyl]piperidineKEGG COMPOUND
PiperineKEGG COMPOUND
1-Piperoyl-piperidineKEGG COMPOUND
1-piperoylpiperidineNIST Chemistry WebBook
1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidineChemIDplus
(E,E)-1-piperoylpiperidineChemIDplus
UniProt Name  Source
piperineUniProt
Manual XrefsDatabases
C03882KEGG COMPOUND
C03882KEGG COMPOUND
HMDB0029377HMDB
PiperineWikipedia
C00002065KNApSAcK
Registry NumbersSources
Gmelin:341351Gmelin
Reaxys:90741Reaxys
CAS:94-62-2KEGG COMPOUND
CAS:94-62-2ChemIDplus
CAS:94-62-2NIST Chemistry WebBook
Citations