compound 3 [PMID: 8410973]   Click here for help

GtoPdb Ligand ID: 8634

Compound class: Synthetic organic
Comment: Compound 3 is reported to inhibit human pepsin, in addition to gastricsin and cathepsins D and E [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 14
Hydrogen bond donors 4
Rotatable bonds 22
Topological polar surface area 183.86
Molecular weight 754.35
XLogP 2.74
No. Lipinski's rules broken 2
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Canonical SMILES C=CCC(C(=O)NC(C(=O)C(C(=O)NCCN1CCOCC1)(F)F)CC1CCCCC1)NC(=O)C(NS(=O)(=O)N1CCOCC1)Cc1ccccc1
Isomeric SMILES C=CC[C@@H](C(=O)N[C@H](C(=O)C(C(=O)NCCN1CCOCC1)(F)F)CC1CCCCC1)NC(=O)[C@@H](NS(=O)(=O)N1CCOCC1)Cc1ccccc1
InChI InChI=1S/C35H52F2N6O8S/c1-2-9-28(39-33(46)30(25-27-12-7-4-8-13-27)41-52(48,49)43-18-22-51-23-19-43)32(45)40-29(24-26-10-5-3-6-11-26)31(44)35(36,37)34(47)38-14-15-42-16-20-50-21-17-42/h2,4,7-8,12-13,26,28-30,41H,1,3,5-6,9-11,14-25H2,(H,38,47)(H,39,46)(H,40,45)/t28-,29-,30-/m0/s1
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
cathepsin E Hs Inhibitor Inhibition 9.3 pKi - 1
pKi 9.3 (Ki 5x10-10 M) [1]
progastricsin Hs Inhibitor Inhibition 9.1 pKi - 1
pKi 9.1 (Ki 9x10-10 M) [1]
pepsinogen A5 Hs Inhibitor Inhibition 8.0 pKi - 1
pKi 8.0 (Ki 1.1x10-8 M) [1]
cathepsin D Hs Inhibitor Inhibition 7.7 pKi - 1
pKi 7.7 (Ki 1.8x10-8 M) [1]