PBI-4547   Click here for help

GtoPdb Ligand ID: 12819

Synonyms: PBI4547
Compound class: Synthetic organic
Comment: PBI-4547 is reported to exhibit antagonist activity at G protein-coupled receptor 84 (GPR84) [1], and agonist activity at GPR40 and GPR120 [2]. It is a fatty acid mimetic and is formulated as the sodium salt. PBI-4547 has been used to investigate the therapeutic potential of GPR84 modulation.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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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Click here for structure editor
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 2
Hydrogen bond donors 0
Rotatable bonds 10
Topological polar surface area 40.13
Molecular weight 275.41
XLogP 5.9
No. Lipinski's rules broken 1

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 CCCCCC1=CC(=CC(=C1)CCCCC)CC(=O)[O-]
Isomeric SMILES C(CCCC)C=1C=C(C=C(C1)CCCCC)CC(=O)[O-]
InChI InChI=1S/C18H28O2/c1-3-5-7-9-15-11-16(10-8-6-4-2)13-17(12-15)14-18(19)20/h11-13H,3-10,14H2,1-2H3,(H,19,20)/p-1
InChI Key HFEDEAWUDQDOSS-UHFFFAOYSA-M

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/)
References
1. Chen LH, Zhang Q, Xie X, Nan FJ. (2020)
Modulation of the G-Protein-Coupled Receptor 84 (GPR84) by Agonists and Antagonists.
J Med Chem, 63 (24): 15399-15409. [PMID:33267584]
2. Simard JC, Thibodeau JF, Leduc M, Tremblay M, Laverdure A, Sarra-Bournet F, Gagnon W, Ouboudinar J, Gervais L, Felton A et al.. (2020)
Fatty acid mimetic PBI-4547 restores metabolic homeostasis via GPR84 in mice with non-alcoholic fatty liver disease.
Sci Rep, 10 (1): 12778. [PMID:32728158]