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compound 43 [PMID: 21173551]   Click here for help

GtoPdb Ligand ID: 5831

Synonyms: compound 43 [PMID:16697190] [1] | compound 43 [PMID:23160941] [2] | pyrazolone, 1
PDB Ligand
Compound class: Synthetic organic
Comment: A synthetic small molecule formyl peptide receptor agonist [5].
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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

compound 43 [PMID: 21173551] 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 4
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 67.54
Molecular weight 384.14
XLogP 3.7
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 O=C(Nc1c(C(C)C)n(n(c1=O)c1ccccc1)C)Nc1ccc(cc1)Cl
Isomeric SMILES O=C(Nc1c(C(C)C)n(n(c1=O)c1ccccc1)C)Nc1ccc(cc1)Cl
InChI InChI=1S/C20H21ClN4O2/c1-13(2)18-17(23-20(27)22-15-11-9-14(21)10-12-15)19(26)25(24(18)3)16-7-5-4-6-8-16/h4-13H,1-3H3,(H2,22,23,27)
InChI Key PAEBEUZTAPIOIO-UHFFFAOYSA-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/)
References
1. Bürli RW, Xu H, Zou X, Muller K, Golden J, Frohn M, Adlam M, Plant MH, Wong M, McElvain M et al.. (2006)
Potent hFPRL1 (ALXR) agonists as potential anti-inflammatory agents.
Bioorg Med Chem Lett, 16 (14): 3713-8. [PMID:16697190]
2. He HQ, Liao D, Wang ZG, Wang ZL, Zhou HC, Wang MW, Ye RD. (2013)
Functional characterization of three mouse formyl peptide receptors.
Mol Pharmacol, 83 (2): 389-98. [PMID:23160941]
3. He HQ, Ye RD. (2017)
The Formyl Peptide Receptors: Diversity of Ligands and Mechanism for Recognition.
Molecules, 22 (3). [PMID:28335409]
4. Rabiet MJ, Huet E, Boulay F. (2005)
Human mitochondria-derived N-formylated peptides are novel agonists equally active on FPR and FPRL1, while Listeria monocytogenes-derived peptides preferentially activate FPR.
Eur J Immunol, 35 (8): 2486-95. [PMID:16025565]
5. Sogawa Y, Ohyama T, Maeda H, Hirahara K. (2011)
Formyl peptide receptor 1 and 2 dual agonist inhibits human neutrophil chemotaxis by the induction of chemoattractant receptor cross-desensitization.
J Pharmacol Sci, 115 (1): 63-8. [PMID:21173551]
6. Ye RD, Boulay F, Wang JM, Dahlgren C, Gerard C, Parmentier M, Serhan CN, Murphy PM. (2009)
International Union of Basic and Clinical Pharmacology. LXXIII. Nomenclature for the formyl peptide receptor (FPR) family.
Pharmacol Rev, 61 (2): 119-61. [PMID:19498085]
7. Yi X, Tran E, Odiba JO, Qin CX, Ritchie RH, Baell JB. (2024)
The formyl peptide receptors FPR1 and FPR2 as targets for inflammatory disorders: recent advances in the development of small-molecule agonists.
Eur J Med Chem, 265: 115989. [PMID:38199163]