AZ3451   

GtoPdb Ligand ID: 9560

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.
2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
InChI Key FJAOGFGHTPYADT-SFHVURJKSA-N
Classification
Compound class Synthetic organic
IUPAC Name
2-(6-bromanyl-1,3-benzodioxol-5-yl)-~{N}-(4-cyanophenyl)-1-[(1~{S})-1-cyclohexylethyl]benzimidazole-5-carboxamide
Database Links
GtoPdb PubChem SID 336446946
PubChem CID 126961335
RCSB PDB Ligand 8UN
Search Google for chemical match using the InChIKey FJAOGFGHTPYADT-SFHVURJKSA-N
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SynPHARM 84335 (in complex with PAR2)
84336 (in complex with PAR2)
84445 (in complex with PAR2)

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Tocris
AZ 3451
Cat. No. 6806