compound 11 [PMID: 29442501]   Click here for help

GtoPdb Ligand ID: 9819

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 11 is a peptidyl-diphenyl phosphonate PR3 inhibitor, designed for enhanced inhibitory efficacy [1]. PR3 inhibitors have therapeutic potential for infectious and inflammatory diseases. Its peptide structure is represented as Bt-Val-Tyr-Asp-nValP(O-C6H4-4-Cl)2. Compound 11 is suitable for studies in primate models and human tissues, but is inactive vs. rodent PR3 [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 8
Rotatable bonds 28
Topological polar surface area 285.7
Molecular weight 976.28
XLogP 5.78
No. Lipinski's rules broken 4
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Canonical SMILES CCCC(P(=O)(Oc1ccc(cc1)Cl)Oc1ccc(cc1)Cl)NC(=O)C(NC(=O)C(NC(=O)C(C(C)C)NC(=O)CCCCC1SCC2C1NC(=O)N2)Cc1ccc(cc1)O)CC(=O)O
Isomeric SMILES CCCC(P(=O)(Oc1ccc(cc1)Cl)Oc1ccc(cc1)Cl)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)CCCCC1SC[C@H]2[C@@H]1NC(=O)N2)Cc1ccc(cc1)O)CC(=O)O
InChI InChI=1S/C44H55Cl2N6O11PS/c1-4-7-37(64(61,62-30-18-12-27(45)13-19-30)63-31-20-14-28(46)15-21-31)51-42(58)33(23-38(55)56)47-41(57)32(22-26-10-16-29(53)17-11-26)48-43(59)39(25(2)3)50-36(54)9-6-5-8-35-40-34(24-65-35)49-44(60)52-40/h10-21,25,32-35,37,39-40,53H,4-9,22-24H2,1-3H3,(H,47,57)(H,48,59)(H,50,54)(H,51,58)(H,55,56)(H2,49,52,60)/t32-,33-,34-,35?,37?,39-,40-/m0/s1
1. Guarino C, Gruba N, Grzywa R, Dyguda-Kazimierowicz E, Hamon Y, Łȩgowska M, Skoreński M, Dallet-Choisy S, Marchand-Adam S, Kellenberger C et al.. (2018)
Exploiting the S4-S5 Specificity of Human Neutrophil Proteinase 3 to Improve the Potency of Peptidyl Di(chlorophenyl)-phosphonate Ester Inhibitors: A Kinetic and Molecular Modeling Analysis.
J Med Chem, 61 (5): 1858-1870. [PMID:29442501]