talabostat   Click here for help

GtoPdb Ligand ID: 9892

Synonyms: compound 1 [PMID: 18783201] | PT-100 | PT100 | Val-boro-pro | Val-boroPro
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Talabostat (PT-100, or Val-boroPro) is a compound with potent anti-tumour activity. It is a non-selective inhibitor of post-proline-cleaving serine proteases. Talabostat activates macrophages at least in part via inhibition of the serine peptidase, fibroblast activation protein (FAP) , an action that has been examined for anti-cancer utility [2,4-5] and anti-fibrotic potential [3]. More recently talabostat has been reported as an inhibitor of the cytosolic serine dipeptidyl peptidases Dpp8 and Dpp9, and that inhibition of these related enzymes stimulates the immune system via the selective promotion of proinflammatory cell death (pyroptosis) of monocytes and macrophages [6]. This process involves Dpp8/9-induced activation of the NOD-like pattern recognition receptor NLRP1, a protein that acts as an inflammasome sensor, followed by activation of pro-caspase-1 and eventually to pyroptosis [7].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 86.79
Molecular weight 214.15
XLogP -0.57
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC(C(C(=O)N1CCCC1B(O)O)N)C
Isomeric SMILES CC([C@@H](C(=O)N1CCC[C@H]1B(O)O)N)C
InChI InChI=1S/C9H19BN2O3/c1-6(2)8(11)9(13)12-5-3-4-7(12)10(14)15/h6-8,14-15H,3-5,11H2,1-2H3/t7-,8-/m0/s1
InChI Key FKCMADOPPWWGNZ-YUMQZZPRSA-N
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Molecular structure representations generated using Open Babel