NF-56-EJ40   Click here for help

GtoPdb Ligand ID: 10519

PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: NF-56-EJ40 is a potent succinate receptor antagonist [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 72.88
Molecular weight 443.22
XLogP 3.75
No. Lipinski's rules broken 0
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Canonical SMILES CN1CCN(CC1)Cc1ccc(cc1)c1cccc(c1)C(=O)Nc1ccccc1CC(=O)O
Isomeric SMILES CN1CCN(CC1)Cc1ccc(cc1)c1cccc(c1)C(=O)Nc1ccccc1CC(=O)O
InChI InChI=1S/C27H29N3O3/c1-29-13-15-30(16-14-29)19-20-9-11-21(12-10-20)22-6-4-7-24(17-22)27(33)28-25-8-3-2-5-23(25)18-26(31)32/h2-12,17H,13-16,18-19H2,1H3,(H,28,33)(H,31,32)
1. Cho EH. (2018)
Succinate as a Regulator of Hepatic Stellate Cells in Liver Fibrosis.
Front Endocrinol (Lausanne), 9: 455. [PMID:30186230]
2. Haffke M, Fehlmann D, Rummel G, Boivineau J, Duckely M, Gommermann N, Cotesta S, Sirockin F, Freuler F, Littlewood-Evans A et al.. (2019)
Structural basis of species-selective antagonist binding to the succinate receptor.
Nature, 574 (7779): 581-585. DOI: 10.1038/s41586-019-1663-8 [PMID:31645725]
3. Littlewood-Evans A, Sarret S, Apfel V, Loesle P, Dawson J, Zhang J, Muller A, Tigani B, Kneuer R, Patel S et al.. (2016)
GPR91 senses extracellular succinate released from inflammatory macrophages and exacerbates rheumatoid arthritis.
J Exp Med, 213 (9): 1655-62. [PMID:27481132]
4. Rubic T, Lametschwandtner G, Jost S, Hinteregger S, Kund J, Carballido-Perrig N, Schwärzler C, Junt T, Voshol H, Meingassner JG et al.. (2008)
Triggering the succinate receptor GPR91 on dendritic cells enhances immunity.
Nat Immunol, 9 (11): 1261-9. [PMID:18820681]