CHEBI:28821 - piperine

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ChEBI Name piperine
ChEBI ID CHEBI:28821
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:12539, CHEBI:7348, CHEBI:21491
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Formula C17H19NO3
Net Charge 0
Average Mass 285.33770
Monoisotopic Mass 285.136
InChI InChI=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+
InChIKey MXXWOMGUGJBKIW-YPCIICBESA-N
SMILES O=C(\C=C\C=C\c1ccc2OCOc2c1)N1CCCCC1
Metabolite of Species Details
Piper nigrum (NCBI:txid13216) See: PubMed
Piper betle (NCBI:txid13217) See: DOI
Piper khasianum (NCBI:txid405331) See: DOI
Homo sapiens (NCBI:txid9606) Found in blood serum (BTO:0000133). See: MetaboLights Study
Roles Classification
Biological Role(s): food component
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.
human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
NF-kappaB inhibitor
An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(E,E)-1-piperoylpiperidine ChemIDplus
1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine ChemIDplus
1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-2,4-pentadienoyl]piperidine NIST Chemistry WebBook
1-Piperoyl-piperidine KEGG COMPOUND
1-piperoylpiperidine NIST Chemistry WebBook
N-[(E,E)-Piperoyl]piperidine KEGG COMPOUND
N-[(E,E)-piperoyl]piperidine UniProt
N-[(E,E)-Piperoyl]piperidine KEGG COMPOUND
Piperine KEGG COMPOUND
Manual Xrefs Databases
C00002065 KNApSAcK
C03882 KEGG COMPOUND
HMDB0029377 HMDB
Piperine Wikipedia
View more database links
Registry Numbers Types Sources
341351 Gmelin Registry Number Gmelin
90741 Beilstein Registry Number Beilstein
90741 Reaxys Registry Number Reaxys
94-62-2 CAS Registry Number KEGG COMPOUND
94-62-2 CAS Registry Number NIST Chemistry WebBook
94-62-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10575373 PubMed citation Europe PMC
15531295 PubMed citation Europe PMC
18639606 PubMed citation Europe PMC
19110999 PubMed citation Europe PMC
24272201 PubMed citation Europe PMC
25645812 PubMed citation Europe PMC
8347144 PubMed citation Europe PMC
Last Modified
07 March 2018