ONX-0914   Click here for help

GtoPdb Ligand ID: 9031

Synonyms: PR-957
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Proteolix (later Onyx Pharmaceuticals, now Amgen) developed the peptidomimetic inhibitor PR-957 (ONX-0914), which selectively inhibited the chymotrypsin-like activity of LMP7. This blocked presentation of LMP7-specific, MHC-I-restricted antigens and reduced immunoproteasome production of pro-inflammatory cytokines such as IL-6, IFN-γ, TNF-α and IL-23 [1]. Note there are at least 6 isomeric alternatives for this structure including ChEMBL entries and SureChEMBL patent mappings (see "same connectivity" links in the PubChem CID entry).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 3
Rotatable bonds 17
Topological polar surface area 138.6
Molecular weight 580.29
XLogP 0.69
No. Lipinski's rules broken 1
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Canonical SMILES COc1ccc(cc1)CC(C(=O)NC(C(=O)C1(C)CO1)Cc1ccccc1)NC(=O)C(NC(=O)CN1CCOCC1)C
Isomeric SMILES COc1ccc(cc1)C[C@@H](C(=O)N[C@H](C(=O)[C@@]1(C)CO1)Cc1ccccc1)NC(=O)[C@@H](NC(=O)CN1CCOCC1)C
InChI InChI=1S/C31H40N4O7/c1-21(32-27(36)19-35-13-15-41-16-14-35)29(38)34-26(18-23-9-11-24(40-3)12-10-23)30(39)33-25(28(37)31(2)20-42-31)17-22-7-5-4-6-8-22/h4-12,21,25-26H,13-20H2,1-3H3,(H,32,36)(H,33,39)(H,34,38)/t21-,25-,26-,31+/m0/s1
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Molecular structure representations generated using Open Babel