Structure via PubChem · Public domain (PubChem)
piperlongumine
Sign in to saveAlso known as piplartine
Piperlongumine (also called piplartine or piperlongumin) is an amide alkaloid constituent of the fruit of the long pepper (Piper longum), a pepper plant found in southern India and southeast Asia. When extracted, piperlongumine may cause skin, eye or respiratory tract irritation.
Chemical data
- Formula
- C17H19NO5
- Molecular weight
- 317.34 g/mol
- IUPAC name
- 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
- SMILES
- COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)N2CCC=CC2=O
- InChIKey
- VABYUUZNAVQNPG-BQYQJAHWSA-N
- XLogP
- 2.1
- Polar surface area
- 65.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
531 papers- Piperlongumine and its derivatives against cancer: A recent update and future prospective.Archiv der Pharmazie · 2024
- Piperlongumine, a potent anticancer phytotherapeutic: Perspectives on contemporary status and future possibilities as an anticancer agent.Pharmacological research · 2020
- Overview of piperlongumine analogues and their therapeutic potential.European journal of medicinal chemistry · 2021
- Piperlongumine: the amazing amide alkaloid from Piper in the treatment of breast cancer.Naunyn-Schmiedeberg's archives of pharmacology · 2024
- Piperlongumine conjugates induce targeted protein degradation.Cell chemical biology · 2023
via PubMed
Wikidata facts
- Mass
- 317.126323
Show 4 more facts
- found in taxon
- Piper lanatum
- chemical formula
- C₁₇H₁₉NO₅
- isomeric SMILES
- COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)N2CCC=CC2=O
- canonical SMILES
- COC1=CC(=CC(=C1OC)OC)C=CC(=O)N2CCC=CC2=O
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Traditional medicine and research
- References
Piperlongumine (also called piplartine or piperlongumin) is an amide alkaloid constituent of the fruit of the long pepper (Piper longum), a pepper plant found in southern India and southeast Asia. When extracted, piperlongumine may cause skin, eye or respiratory tract irritation.
==Traditional medicine and research== Long peppers have been used in Ayurveda and traditional Chinese medicine as a treatment.
Excerpted from Wikipedia’s “piperlongumine” article, available under the CC BY-SA 4.0 licence.