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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
[(2R)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid
International Nonproprietary Names Click here for help
INN number INN
8566 talabostat
Synonyms Click here for help
compound 1 [PMID: 18783201] | PT-100 | PT100 | Val-boro-pro | Val-boroPro
Database Links Click here for help
BindingDB Ligand 50050513
CAS Registry No. 149682-77-9 (source: WHO INN record)
ChEMBL Ligand CHEMBL67279
GtoPdb PubChem SID 363894186
PubChem CID 6918572
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