laduviglusib   Click here for help

GtoPdb Ligand ID: 8014

Synonyms: CHIR 99021 | CHIR-99021 | CHIR99021 | CT-99021 | CT99021
PDB Ligand
Compound class: Synthetic organic
Comment: Laduviglusib (CHIR-99021) is an ATP-competitive inhibitor of glycogen synthase kinase-3α and β (GSK-3α/β), equipotent at both isozymes [8]. The chemical structure of CHIR-99021 matches that submitted to the WHO for the INN laduviglusib. GSK-3β has been implicated in multiple human disorders, by influencing a number of significant cellular pathways (including insulin signalling and glycogen synthesis, neurotrophic factor signalling, Wnt signalling, neurotransmitter signalling and microtubule dynamics) [1]. CHIR-99021 acts as a functional Wnt pathway activator [2,10].
Zaki syndrome, a rare disorder of embryonic organ development in humans, can arise due to homozygous mutations in the Wnt ligand secretion mediator gene (WLS) [4]. CHIR-99021 has been used in a mouse model of Zaki syndrome to demonstrate that activation of Wnt pathway signalling can partially restore embryonic development [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 115.2
Molecular weight 464.1
XLogP 4.16
No. Lipinski's rules broken 0
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Canonical SMILES N#Cc1ccc(nc1)NCCNc1ncc(c(n1)c1ccc(cc1Cl)Cl)c1ncc([nH]1)C
Isomeric SMILES N#Cc1ccc(nc1)NCCNc1ncc(c(n1)c1ccc(cc1Cl)Cl)c1ncc([nH]1)C
InChI InChI=1S/C22H18Cl2N8/c1-13-10-29-21(31-13)17-12-30-22(32-20(17)16-4-3-15(23)8-18(16)24)27-7-6-26-19-5-2-14(9-25)11-28-19/h2-5,8,10-12H,6-7H2,1H3,(H,26,28)(H,29,31)(H,27,30,32)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
11473 laduviglusib
Synonyms Click here for help
CHIR 99021 | CHIR-99021 | CHIR99021 | CT-99021 | CT99021
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9687650
Reactome Reaction Reactome logo R-HSA-9687724
Other databases
CAS Registry No. 252917-06-9
ChEMBL Ligand CHEMBL412142
GtoPdb PubChem SID 249565694
PubChem CID 9956119
RCSB PDB Ligand 65C
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SynPHARM 81001 (in complex with glycogen synthase kinase 3 beta)
UniChem Compound Search for chemical match using the InChIKey AQGNHMOJWBZFQQ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey AQGNHMOJWBZFQQ-UHFFFAOYSA-N

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CHIR 99021 (links to external site)
Cat. No. 4423