β-secretase inhibitor IV   Click here for help

GtoPdb Ligand ID: 11713

Synonyms: compound 24 [PMID: 17432843]
PDB Ligand
Compound class: Synthetic organic
Comment: This is a small molecule inhibitor of β-secretase enzymes that is used as a standard tool in biological experiments [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 4
Rotatable bonds 15
Topological polar surface area 136.22
Molecular weight 578.26
XLogP 4.26
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES O[C@@H]([C@@H](NC(=O)c1cc(cc(c1)N(S(=O)(=O)C)C)C(=O)N[C@@H](c1ccccc1)C)Cc1ccccc1)CNC1CC1
Isomeric SMILES C[C@H](c1ccccc1)NC(=O)c1cc(cc(c1)N(C)S(=O)(=O)C)C(=O)N[C@@H](Cc1ccccc1)[C@@H](CNC1CC1)O
InChI InChI=1S/C31H38N4O5S/c1-21(23-12-8-5-9-13-23)33-30(37)24-17-25(19-27(18-24)35(2)41(3,39)40)31(38)34-28(16-22-10-6-4-7-11-22)29(36)20-32-26-14-15-26/h4-13,17-19,21,26,28-29,32,36H,14-16,20H2,1-3H3,(H,33,37)(H,34,38)/t21-,28+,29-/m1/s1
InChI Key VPNIQGRFZCTBEZ-SPTGULJVSA-N
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
beta-secretase 1 Hs Inhibitor Inhibition 6.6 pKi - 1
pKi 6.6 (Ki 2.33x10-7 M) [1]
beta-secretase 2 Hs Inhibitor Inhibition 6.6 pKi - 1
pKi 6.6 (Ki 2.4x10-7 M) [1]
cathepsin D Hs Inhibitor Inhibition 6.3 pKi - 1
pKi 6.3 (Ki 4.48x10-7 M) [1]