WX-UK1   Click here for help

GtoPdb Ligand ID: 6498

Synonyms: compound 2r-L [2] | UKI-1
Compound class: Synthetic organic
Comment: Drug from the prodrug upamostat. This compound has urokinase-type plasminogen activator inhbitory effect, but also inhibits other trypsin-like enzymes [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 3
Rotatable bonds 14
Topological polar surface area 154.27
Molecular weight 613.33
XLogP 5.58
No. Lipinski's rules broken 2
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Canonical SMILES CCOC(=O)N1CCN(CC1)C(=O)C(NS(=O)(=O)c1c(cc(cc1C(C)C)C(C)C)C(C)C)Cc1cccc(c1)C(=N)N
Isomeric SMILES CCOC(=O)N1CCN(CC1)C(=O)[C@@H](NS(=O)(=O)c1c(cc(cc1C(C)C)C(C)C)C(C)C)Cc1cccc(c1)C(=N)N
InChI InChI=1S/C32H47N5O5S/c1-8-42-32(39)37-14-12-36(13-15-37)31(38)28(17-23-10-9-11-24(16-23)30(33)34)35-43(40,41)29-26(21(4)5)18-25(20(2)3)19-27(29)22(6)7/h9-11,16,18-22,28,35H,8,12-15,17H2,1-7H3,(H3,33,34)/t28-/m0/s1
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
coagulation factor II, thrombin Hs Inhibitor Inhibition 6.3 pKi - 1
pKi 6.3 (Ki 5x10-7 M) [1]
plasminogen activator, urokinase Hs Inhibitor Inhibition 6.2 pKi - 1
pKi 6.2 (Ki 6.5x10-7 M) [1]
plasminogen Hs Inhibitor Inhibition 5.8 pKi - 1
pKi 5.8 (Ki 1.46x10-6 M) [1]
tryptase gamma 1 ? Inhibitor Inhibition 5.2 pKi - 2
pKi 5.2 (Ki 6.3x10-6 M) [2]
plasminogen activator, urokinase Hs Inhibitor Inhibition 6.4 pIC50 - 2
pIC50 6.4 (IC50 4.1x10-7 M) [2]