TAK-593

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Synonyms
Status
Molecule Category Free-form
UNII H3I42X8XX7

Structure

InChI Key DZFZXPPHBWCXPQ-UHFFFAOYSA-N
Smiles Cc1cc(C(=O)Nc2cc(Oc3ccc4nc(NC(=O)C5CC5)cn4n3)ccc2C)n(C)n1
InChI
InChI=1S/C23H23N7O3/c1-13-4-7-16(11-17(13)24-23(32)18-10-14(2)27-29(18)3)33-21-9-8-20-25-19(12-30(20)28-21)26-22(31)15-5-6-15/h4,7-12,15H,5-6H2,1-3H3,(H,24,32)(H,26,31)

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H23N7O3
Molecular Weight 445.48
AlogP 3.47
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 6.0
Polar Surface Area 115.44
Molecular species NEUTRAL
Aromatic Rings 4.0
Heavy Atoms 33.0

Bioactivity

Mechanism of Action Action Reference
Platelet-derived growth factor receptor inhibitor INHIBITOR PubMed
Protein: Platelet-derived growth factor receptor
Description: Platelet-derived growth factor receptor beta
Organism : Homo sapiens
P09619 ENSG00000113721
Protein: Platelet-derived growth factor receptor
Description: Platelet-derived growth factor receptor alpha
Organism : Homo sapiens
P16234 ENSG00000134853
Protein: Vascular endothelial growth factor receptor
Description: Vascular endothelial growth factor receptor 1
Organism : Homo sapiens
P17948 ENSG00000102755
Protein: Vascular endothelial growth factor receptor
Description: Vascular endothelial growth factor receptor 3
Organism : Homo sapiens
P35916 ENSG00000037280
Protein: Vascular endothelial growth factor receptor
Description: Vascular endothelial growth factor receptor 2
Organism : Homo sapiens
P35968 ENSG00000128052
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase PDGFR family
- 10 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Ret family
- 18 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase VEGFR family
- 0-1 - - -
Assay Description Organism Bioactivity Reference
Inhibition of VEGFR3 None 1.1 nM
Inhibition of VEGFR2 None 0.95 nM
Inhibition of VEGFR1 None 3.2 nM
Inhibition of human RET Homo sapiens 18.0 nM
Inhibition of human FMS Homo sapiens 10.0 nM
Inhibition of PDGFRbeta (unknown origin) by AlphaScreen assay Homo sapiens 13.0 nM
Inhibition of VEGFR3 (unknown origin) by AlphaScreen assay Homo sapiens 1.1 nM
Inhibition of PDGFRalpha (unknown origin) by AlphaScreen assay Homo sapiens 4.3 nM
Inhibition of VEGFR1 (unknown origin) by AlphaScreen assay Homo sapiens 3.2 nM
Inhibition of VEGFR2 (unknown origin) using biotinylated poly(Glu:Tyr) as substrate after 60 mins by AlphaScreen assay in presence of 1000 uM of ATP Homo sapiens 0.093 nM
Inhibition of VEGFR2 (unknown origin) using biotinylated poly(Glu:Tyr) as substrate after 5 mins by AlphaScreen assay in presence of 1000 uM of ATP Homo sapiens 1.1 nM
Antiproliferative activity against VEGF-stimulated HUVECs after 5 days by WST-8 assay Homo sapiens 0.3 nM
Inhibition of VEGFR2 (unknown origin) using biotinylated poly(Glu:Tyr) as substrate after 5 mins by AlphaScreen assay in presence of 10 uM of ATP Homo sapiens 0.95 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 918.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 35.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 365.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 91.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 869.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 10.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 423.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -11.49 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -13.03 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.15 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.15 %

Cross References

Resources Reference
ChEMBL CHEMBL2180604
DrugBank DB13093
FDA SRS H3I42X8XX7
PubChem 24767976
SureChEMBL SCHEMBL2515478
ZINC ZINC000095579919
CONTENTS