AZ3451   Click here for help

GtoPdb Ligand ID: 9560

PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: AZ3451 is a negative allosteric modulator of protease-activated receptor 2 (PAR2) that prevents receptor activation and signalling [1]. Substantial evidence indicates that PARs are involved in inflammatory disease, with roles in causing inflammatory reactions in peripheral limb tissue, and modulating arthritic joint inflammation and pain.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 89.17
Molecular weight 570.13
XLogP 7.46
No. Lipinski's rules broken 1
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Canonical SMILES N#Cc1ccc(cc1)NC(=O)c1ccc2c(c1)nc(n2C(C1CCCCC1)C)c1cc2OCOc2cc1Br
Isomeric SMILES N#Cc1ccc(cc1)NC(=O)c1ccc2c(c1)nc(n2[C@H](C1CCCCC1)C)c1cc2OCOc2cc1Br
InChI InChI=1S/C30H27BrN4O3/c1-18(20-5-3-2-4-6-20)35-26-12-9-21(30(36)33-22-10-7-19(16-32)8-11-22)13-25(26)34-29(35)23-14-27-28(15-24(23)31)38-17-37-27/h7-15,18,20H,2-6,17H2,1H3,(H,33,36)/t18-/m0/s1
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
PAR2 Primary target of this compound Hs Allosteric modulator Negative 7.9 pKd - 1
pKd 7.9 (Kd 1.35x10-8 M) [1]
Description: In a BIACORE assay.
PAR2 Hs Allosteric modulator Negative 7.6 – 8.3 pIC50 - 1
pIC50 8.3 (IC50 5.4x10-9 M) [1]
Description: In a FLIPR calcium accumulation assay, vs. SLIGRL activation.
pIC50 7.6 (IC50 2.3x10-8 M) [1]
Description: Antagonism of SLIGRL-NH2-induced IP1 formation.