compound 11 [PMID: 16413183]   Click here for help

GtoPdb Ligand ID: 8493

Compound class: Synthetic organic
Comment: Compound 11 is reported as a small molecule inhibitor of plasma kallikrein (KLKB1) [1]. Compound 11 exhibits favourable pharmacokinetics in rats and may have potential therapeutic uses in inflammatory or coagulation disorders.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 7
Rotatable bonds 7
Topological polar surface area 184.63
Molecular weight 487.15
XLogP 1.38
No. Lipinski's rules broken 1
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Canonical SMILES OC(=O)CC(C1=CC(=c2[nH]c3c([nH]2)ccc(c3)C(=N)N)C(=O)C(=C1)c1cccc(c1)C(=O)N)C(=O)O
Isomeric SMILES OC(=O)CC(C1=C/C(=c/2\[nH]c3c([nH]2)ccc(c3)C(=N)N)/C(=O)C(=C1)c1cccc(c1)C(=O)N)C(=O)O
InChI InChI=1S/C25H21N5O6/c26-22(27)12-4-5-18-19(9-12)30-24(29-18)17-8-14(16(25(35)36)10-20(31)32)7-15(21(17)33)11-2-1-3-13(6-11)23(28)34/h1-9,16,29-30H,10H2,(H3,26,27)(H2,28,34)(H,31,32)(H,35,36)/b24-17+
Bioactivity Comments
Compound 11 shows selectivity for KLKB1 in comparison to related serine proteases (coagulation factors Xa and VIIa, and trypsin) [1].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
kallikrein B1 Primary target of this compound Hs Inhibitor Inhibition 9.3 pKi - 1
pKi 9.3 (Ki 5x10-10 M) [1]
coagulation factor VII Hs Inhibitor Inhibition ~7.0 pKi - 1
pKi ~7.0 (Ki ~1x10-7 M) [1]
Description: Ki calculated from fold selectivity for KLKB1.