pevonedistat   Click here for help

GtoPdb Ligand ID: 12117

Synonyms: MLN 4924 | MLN-4924 | MLN4924 | TAK-924 | TAK924
PDB Ligand
Compound class: Synthetic organic
Comment: Pevonedistat (MLN4924) is an inhibitor of the NEDD8 activating enzyme (NAE) [1], which is a heterodimer of NAE1 (NAE1; Q13564) and UBA3 subunits. Pevonedistat is structurally similar to the NAE reaction product adenosine 5′-monophosphate (AMP), and interacts with nucleotide-binding site of NAE. NAE is essential for the NEDD8 conjugation pathway which controls the activity of the cullin-RING ubiquitin E3 ligases. NAE inhibitors are proposed to disrupt cullin-RING ligase-mediated protein turnover and to promote apoptosis in human tumour cells.
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 8
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 140.74
Molecular weight 443.16
XLogP 1.7
No. Lipinski's rules broken 0
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 O[C@H]1C[C@@H](C[C@H]1COS(=O)(=O)N)n1ccc2c1ncnc2N[C@H]1CCc2c1cccc2
Isomeric SMILES C1Cc2ccccc2[C@H]1Nc1c2ccn(c2ncn1)[C@@H]1C[C@H]([C@H](C1)O)COS(=O)(=O)N
InChI InChI=1S/C21H25N5O4S/c22-31(28,29)30-11-14-9-15(10-19(14)27)26-8-7-17-20(23-12-24-21(17)26)25-18-6-5-13-3-1-2-4-16(13)18/h1-4,7-8,12,14-15,18-19,27H,5-6,9-11H2,(H2,22,28,29)(H,23,24,25)/t14-,15+,18-,19-/m0/s1
InChI Key MPUQHZXIXSTTDU-QXGSTGNESA-N
Classification Click here for help
Compound class Synthetic organic
International Nonproprietary Names Click here for help
INN number INN
9605 pevonedistat
Synonyms Click here for help
MLN 4924 | MLN-4924 | MLN4924 | TAK-924 | TAK924
Database Links Click here for help
BindingDB Ligand 50285607
CAS Registry No. 905579-51-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL1231160
DrugBank Ligand DB11759
GtoPdb PubChem SID 472319239
PubChem CID 16720766
RCSB PDB Ligand B39, B39
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UniChem Compound Search for chemical match using the InChIKey MPUQHZXIXSTTDU-QXGSTGNESA-N
UniChem Connectivity Search for chemical match using the InChIKey MPUQHZXIXSTTDU-QXGSTGNESA-N