piperlongumine   Click here for help

GtoPdb Ligand ID: 13376

Synonyms: piplartine
PDB Ligand
Compound class: Natural product
Comment: Piperlongumine is a naturally ocurring alkaloid compound that has been isolated from tropical plants of the Piper species. A number of piperlongumine derivatives have been assessed for pharmacological actions with relevance to human diseases [4-5]. The anti-tumour potential of piperlongumine has been widely evaluated. Antiviral activity against SARS-CoV-2 has been examined, but it has a very weak antiviral effect. Senolytic activity (selective clearance of senescent cells) is under investigation [2-3].[1]

piperlongumine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 65.07
Molecular weight 317.34
XLogP 1.1
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)N2CCC=CC2=O
Isomeric SMILES COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)N2CCC=CC2=O
InChI InChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+
InChI Key VABYUUZNAVQNPG-BQYQJAHWSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
IUPAC Name Click here for help
1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
Synonyms Click here for help
piplartine
Database Links Click here for help
BindingDB Ligand 50462013
ChEMBL Ligand CHEMBL465843
GtoPdb PubChem SID 496703346
PubChem CID 637858
RCSB PDB Ligand LQ4
Search Google for chemical match using the InChIKey VABYUUZNAVQNPG-BQYQJAHWSA-N
Search Google for chemicals with the same backbone VABYUUZNAVQNPG
UniChem Compound Search for chemical match using the InChIKey VABYUUZNAVQNPG-BQYQJAHWSA-N
UniChem Connectivity Search for chemical match using the InChIKey VABYUUZNAVQNPG-BQYQJAHWSA-N

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MedChemExpress
Piperlongumine (links to external site)
Cat. No. HY-N2329