compound 17 [PMID: 23916253]   

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).
2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
InChI Key XPUCDWKMNQBXIH-OALUTQOASA-N
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]