compound 17 [PMID: 23916253]   Click here for help

GtoPdb Ligand ID: 8666

Compound class: Synthetic organic
Comment: Compound 17 is reported from a structure-activity study to identify novel aminopeptidase inhibitors that improve antigen processing [1], principally by inhibiting the endoplasmic reticulum aminopeptidases, ERAP1 and ERAP2, as well as the insulin regulated aminopeptidase IRAP (LNPEP).
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 9
Hydrogen bond donors 6
Rotatable bonds 14
Topological polar surface area 173.56
Molecular weight 441.24
XLogP -1.29
No. Lipinski's rules broken 2
Click here for help
Canonical SMILES NCCCCC(C(=O)O)NC(=O)c1ccc(c(c1)NC(=O)C(CCc1ccccc1)N)N
Isomeric SMILES NCCCC[C@@H](C(=O)O)NC(=O)c1ccc(c(c1)NC(=O)[C@H](CCc1ccccc1)N)N
InChI InChI=1S/C23H31N5O4/c24-13-5-4-8-19(23(31)32)27-21(29)16-10-12-17(25)20(14-16)28-22(30)18(26)11-9-15-6-2-1-3-7-15/h1-3,6-7,10,12,14,18-19H,4-5,8-9,11,13,24-26H2,(H,27,29)(H,28,30)(H,31,32)/t18-,19-/m0/s1
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Endoplasmic reticulum aminopeptidase 1 Hs Inhibitor Inhibition 5.6 pIC50 - 1
pIC50 5.6 (IC50 2.6x10-6 M) [1]
Leucyl-cysteinyl aminopeptidase Hs Inhibitor Inhibition 5.2 pIC50 - 1
pIC50 5.2 (IC50 6x10-6 M) [1]
Endoplasmic reticulum aminopeptidase 2 Hs Inhibitor Inhibition 5.1 pIC50 - 1
pIC50 5.1 (IC50 8.9x10-6 M) [1]