zetomipzomib   Click here for help

GtoPdb Ligand ID: 10409

Synonyms: compound 12 [PMID: 30380863] | KZR-616 | KZR616
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Zetomipzomib (KZR-616) is a first-in-class, selective and irreversible immunoproteasome inhibitor that results in anti-inflammatory activity in vitro and models of inflammatory conditions. It is a tripeptide epoxyketone-based molecule. At the molecular level KZR-616 inhibits the proteolytic activities of the low molecular mass polypeptide-7 (LMP7, a.k.a. proteasome subunit β8) and low molecular mass polypeptide-2 (LMP2, a.k.a. proteasome subunit β9) subunits of the 20S immunoproteasome complex [1-2]. Inhibition of a secondary immunoproteasome subunit, in this case LMP2 is required to achieve a multicytokine inhibitory effect.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 4
Rotatable bonds 17
Topological polar surface area 158.83
Molecular weight 586.3
XLogP -0.35
No. Lipinski's rules broken 2
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Canonical SMILES COc1ccc(cc1)C(C(C(=O)NC(C(=O)C1(C)CO1)CC1=CCCC1)NC(=O)C(NC(=O)CN1CCOCC1)C)O
Isomeric SMILES COc1ccc(cc1)[C@H]([C@@H](C(=O)N[C@H](C(=O)[C@@]1(C)CO1)CC1=CCCC1)NC(=O)[C@@H](NC(=O)CN1CCOCC1)C)O
InChI InChI=1S/C30H42N4O8/c1-19(31-24(35)17-34-12-14-41-15-13-34)28(38)33-25(26(36)21-8-10-22(40-3)11-9-21)29(39)32-23(16-20-6-4-5-7-20)27(37)30(2)18-42-30/h6,8-11,19,23,25-26,36H,4-5,7,12-18H2,1-3H3,(H,31,35)(H,32,39)(H,33,38)/t19-,23-,25-,26+,30+/m0/s1
Classification Click here for help
Compound class Synthetic organic
International Nonproprietary Names Click here for help
INN number INN
11767 zetomipzomib
Synonyms Click here for help
compound 12 [PMID: 30380863] | KZR-616 | KZR616
Database Links Click here for help
CAS Registry No. 1629677-75-3 (source: PubChem)
GtoPdb PubChem SID 385612170
PubChem CID 117607904
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