aloxistatin   Click here for help

GtoPdb Ligand ID: 10714

Synonyms: compound 2b [PMID: 8765519] | E-64d | E64d | EP453 | loxistatin
Compound class: Synthetic organic
Comment: Aloxistatin (EP-453) is an irreversible inhibitor of the cysteine protease cathepsin B and calpains 1 and 2 [2]. It acts by alkylating the catalytic cysteine thiol [1]. In cellular assays it inhibits autophagy and lysosomal function.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 13
Topological polar surface area 97.03
Molecular weight 342.22
XLogP 2.31
No. Lipinski's rules broken 1
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Canonical SMILES CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@H](C(=O)NCCC(C)C)CC(C)C
Isomeric SMILES CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@H](C(=O)NCCC(C)C)CC(C)C
InChI InChI=1S/C17H30N2O5/c1-6-23-17(22)14-13(24-14)16(21)19-12(9-11(4)5)15(20)18-8-7-10(2)3/h10-14H,6-9H2,1-5H3,(H,18,20)(H,19,21)/t12-,13-,14-/m0/s1
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Molecular structure representations generated using Open Babel