6-((2-((4-(2,4-Dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-yl)amino)ethyl)amino)nicotinonitrile

Base Information

• Chemical Name: 6-((2-((4-(2,4-Dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-yl)amino)ethyl)amino)nicotinonitrile
• CAS No.: 252917-06-9
• Deprecated CAS: 1485056-50-5
• Molecular Formula: C22H18Cl2N8
• Molecular Weight: 465.345
• Hs Code.: 29335990
• European Community (EC) Number: 809-015-4
• UNII: 234CMT4GK4
• DSSTox Substance ID: DTXSID90179931
• Nikkaji Number: J2.462.849C
• Wikipedia: CHIR99021
• Wikidata: Q27075965
• NCI Thesaurus Code: C177060
• Pharos Ligand ID: 76PWGN3S2MG4
• ChEMBL ID: CHEMBL412142
• Mol file: 252917-06-9.mol

Synonyms:Chir 99021;Chir-99021;Chir99021;CT 99021;CT-99021;CT99021

Chemical Property of 6-((2-((4-(2,4-Dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-yl)amino)ethyl)amino)nicotinonitrile

Chemical Property:

• Boiling Point: 784.08 °C at 760 mmHg
• PKA: 11.92±0.10(Predicted)
• Flash Point: 427.996 °C
• PSA: 115.20000
• Density: 1.481 g/cm³
• LogP: 5.08558
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble2mg/mL, clear (warmed)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 464.1031480
• Heavy Atom Count: 32
• Complexity: 645

Purity/Quality:

99% ^*data from raw suppliers

CHIR 99021 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(N1)C2=CN=C(N=C2C3=C(C=C(C=C3)Cl)Cl)NCCNC4=NC=C(C=C4)C#N
• Description: CHIR99021 is an aminopyrimidine derivative that is an extremely potent glycogen synthase kinase (GSK) 3 inhibitor, inhibiting both GSK3β (IC?? = 6.7 nM) and GSK3α (IC?? = 10 nM). GSK3 is a serine/threonine kinase that is a key inhibitor of the WNT pathway; therefore CHIR99021 functions as a WNT activator. It shows little activity against a large panel of kinases including CDK2 and other serine/threonine kinases such as MAPK and PKB (Bain et al.).CHIR99021 promotes self-renewal potential of embryonic stem cells (ESCs) of mice by inhibiting glycogen synthase kinase-3 (GSK-3) activity and potentiates the upregulation of β-catenin and c-Myc functions. CHIR99021 promotes self-renewal of ESCs by modulating transforming growth factor β (TGF-β), Notch and mitogen-activated protein kinases (MAPK) signaling pathways. CHIR99021 is an agonist of wingless/integrated (wnt) signalling, upregulates cyclinA expression and promotes cell proliferation in non-small-cell lung cancer (NSCLC) cell lines. Glycogen synthase kinase 3 (GSK3) is a serine/threonine kinase that plays a key inhibitory role in both the insulin and Wnt signaling pathways. CHIR99021 is an aminopyrimidine derivative that inhibits GSK3α and GSK3β with IC50 values of 10 and 6.7 nM, respectively. When tested against twenty different protein kinases, this inhibitor shows greater than 500-fold selectivity for GSK3. CHIR99021 activates glycogen synthesis in CHO-IR cells (EC50 = 0.8 μM) and in isolated type 1 diabetic rat skeletal muscle. A single oral dose (30 mg/kg) of CHIR99021 enhances in vivo glucose metabolism in a rodent model of type 2 diabetes. CHIR99021 has also been shown to induce the reprogramming of murine and human somatic cells into stem cells.
• Uses: Glycogen synthase kinase 3 (GSK3) is a serine/threonine kinase that plays a key inhibitory role in both the insulin and Wnt signaling pathways. CHIR99021 is an aminopyrimidine derivative that inhibits GSK3α and GSK3β with IC50 values of 10 and 6.7 nM, respectively. When tested against twenty different protein kinases, this inhibitor shows greater than 500-fold selectivity for GSK3. CHIR99021 activates glycogen synthesis in CHO-IR cells (EC50 = 0.8 μM) and in isolated type 1 diabetic rat skeletal muscle. A single oral dose (30 mg/kg) of CHIR99021 enhances in vivo glucose metabolism in a rodent model of type 2 diabetes. CHIR99021 has also been shown to induce the reprogramming of murine and human somatic cells into stem cells. A specific GSK-3 inhibitor of GSK-3β and GSK-3α with IC50s of 5 nM and 10 nM, respectively. CHIR99021 has been used:in cocktail with small molecules to convert human lung fibroblast cells into neuronsas a culture medium supplement in potassium supplemented simplex optimization medium (KSOM) for the culture of blastocystsfor chronic inhibition of GSK-3 to investigate its role in corticogenesis