pralnacasan   Click here for help

GtoPdb Ligand ID: 6467

Synonyms: VX-740 | VX740
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Pralnacasan (VX-740) is a selective, non-peptide caspase 1 inhibitor that was developed by Vertex for anti-inflammatory potential. Inhibition of caspase 1 is a small molecule strategy developed as an alternative to the use of anti-IL-1β neutralising antibodies, such as canakinumab, or the dimeric fusion protein rilonacept that acts as a IL-1 trap.
Pralnacasan is a prodrug whose active metabolite is VRT-018858 [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 147.24
Molecular weight 523.21
XLogP 0.75
No. Lipinski's rules broken 1
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Canonical SMILES CCOC1OC(=O)CC1NC(=O)C1CCCN2N1C(=O)C(CCC2=O)NC(=O)c1nccc2c1cccc2
Isomeric SMILES CCO[C@@H]1OC(=O)C[C@@H]1NC(=O)[C@@H]1CCCN2N1C(=O)[C@H](CCC2=O)NC(=O)c1nccc2c1cccc2
InChI InChI=1S/C26H29N5O7/c1-2-37-26-18(14-21(33)38-26)29-23(34)19-8-5-13-30-20(32)10-9-17(25(36)31(19)30)28-24(35)22-16-7-4-3-6-15(16)11-12-27-22/h3-4,6-7,11-12,17-19,26H,2,5,8-10,13-14H2,1H3,(H,28,35)(H,29,34)/t17-,18-,19-,26+/m0/s1
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Molecular structure representations generated using Open Babel