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).
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2D Structure
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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2S)-6-amino-2-[[4-amino-3-[[(2S)-2-amino-4-phenylbutanoyl]amino]benzoyl]amino]hexanoic acid
Database Links Click here for help
ChEMBL Ligand CHEMBL2420382
GtoPdb PubChem SID 252166866
PubChem CID 71817810
Search Google for chemical match using the InChIKey XPUCDWKMNQBXIH-OALUTQOASA-N
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UniChem Connectivity Search for chemical match using the InChIKey XPUCDWKMNQBXIH-OALUTQOASA-N