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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key GHYOCDFICYLMRF-UTIIJYGPSA-N
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
Search Google for chemical match using the InChIKey GHYOCDFICYLMRF-UTIIJYGPSA-N
Search Google for chemicals with the same backbone GHYOCDFICYLMRF
Search PubMed clinical trials zetomipzomib
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Search PubMed titles/abstracts zetomipzomib
UniChem Compound Search for chemical match using the InChIKey GHYOCDFICYLMRF-UTIIJYGPSA-N
UniChem Connectivity Search for chemical match using the InChIKey GHYOCDFICYLMRF-UTIIJYGPSA-N