C391   Click here for help

GtoPdb Ligand ID: 9570

Synonyms: compound 5 [PMID: 27994760]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: C391 is a protease activated receptor 2 (PAR2) antagonist [5]. It is a small peptidomimetic derivative of the PAR2 agonist 2-furoyl-LIGRLO-amide [1]. PAR2 antagonists have potential for treating inflammatory, respiratory, gastrointestinal, neurological, and metabolic disorders.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 15
Hydrogen bond donors 6
Rotatable bonds 22
Topological polar surface area 244.92
Molecular weight 767.39
XLogP -0.5
No. Lipinski's rules broken 3
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Canonical SMILES NCCCCC(N1CC2N(CC1=O)C(=O)C(CN2C(=O)c1ccco1)NC(=O)CC(C)C)C(=O)NC(C(=O)NC(C(=O)O)Cc1ccc(cc1)O)CC(C)C
Isomeric SMILES NCCCC[C@H](N1CC2N(CC1=O)C(=O)[C@H](CN2C(=O)c1ccco1)NC(=O)CC(C)C)C(=O)N[C@H](C(=O)N[C@H](C(=O)O)Cc1ccc(cc1)O)CC(C)C
InChI InChI=1S/C38H53N7O10/c1-22(2)16-26(34(49)42-27(38(53)54)18-24-10-12-25(46)13-11-24)41-35(50)29(8-5-6-14-39)43-20-32-44(37(52)30-9-7-15-55-30)19-28(40-31(47)17-23(3)4)36(51)45(32)21-33(43)48/h7,9-13,15,22-23,26-29,32,46H,5-6,8,14,16-21,39H2,1-4H3,(H,40,47)(H,41,50)(H,42,49)(H,53,54)/t26-,27-,28-,29-,32?/m0/s1
Bioactivity Comments
C391 antagonises intracellular calcium mobilisation and MAPK pathway activation induced by peptidomimetic or proteinase activation of human PAR2.
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
PAR2 Hs Antagonist Antagonist 4.8 – 5.9 pIC50 - 1
pIC50 5.9 (IC50 1.3x10-6 M) [1]
Description: Antagonism of peptidomimetic-induced PAR2 Ca2+ signalling in 16HBE14o- cells.
pIC50 4.8 (IC50 1.43x10-5 M) [1]
Description: Antagonism of 2-at-LIGRL-NH2-induced ERK phosphorylation in 16HBE14o- cells.