TANZISERTIB

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Synonyms
Status
Molecule Category UNKNOWN
UNII M5O06306UO

Structure

InChI Key IBGLGMOPHJQDJB-IHRRRGAJSA-N
Smiles O[C@H]1CC[C@H](Nc2ncc3nc(Nc4c(F)cc(F)cc4F)n([C@H]4CCOC4)c3n2)CC1
InChI
InChI=1S/C21H23F3N6O2/c22-11-7-15(23)18(16(24)8-11)28-21-27-17-9-25-20(26-12-1-3-14(31)4-2-12)29-19(17)30(21)13-5-6-32-10-13/h7-9,12-14,31H,1-6,10H2,(H,27,28)(H,25,26,29)/t12-,13-,14-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H23F3N6O2
Molecular Weight 448.45
AlogP 3.66
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 5.0
Polar Surface Area 97.12
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 32.0

Bioactivity

Mechanism of Action Action Reference
c-Jun N-terminal kinase 1 inhibitor INHIBITOR PubMed
Protein: c-Jun N-terminal kinase 1
Description: Mitogen-activated protein kinase 8
Organism : Homo sapiens
P45983 ENSG00000107643
Protein: c-Jun N-terminal kinase 2
Description: Mitogen-activated protein kinase 9
Organism : Homo sapiens
P45984 ENSG00000050748
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase MAPK family CMGC protein kinase ERK subfamily
- 480-480 - - -
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase MAPK family CMGC protein kinase JNK subfamily
- 200-1000 - 44 -
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase MAPK family CMGC protein kinase p38 subfamily
- 3400-3400 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase EGFR family
- 380 - - -
Assay Description Organism Bioactivity Reference
Inhibition of hexa-His-tagged JNK1 expressed in baculoviral system using GST-tagged c-Jun as substrate preincubated for 15 mins prior ATP addition measured after 60 mins by scintillation counting None 61.0 nM Inhibition of hexa-His-tagged JNK1 expressed in baculoviral system using GST-tagged c-Jun as substrate preincubated for 15 mins prior ATP addition measured after 60 mins by scintillation counting None 44.0 nM
Inhibition of hexa-His-tagged JNK2 expressed in baculoviral system using GST-tagged cJun as substrate preincubated for 15 mins prior ATP addition measured after 60 mins by scintillation counting None 7.0 nM Inhibition of hexa-His-tagged JNK2 expressed in baculoviral system using GST-tagged cJun as substrate preincubated for 15 mins prior ATP addition measured after 60 mins by scintillation counting None 6.2 nM
Inhibition of hexa-His-tagged JNK3 expressed in baculoviral system using GST-tagged cJun as substrate preincubated for 15 mins prior ATP addition measured after 60 mins by scintillation counting None 6.0 nM
Inhibition of JNK-mediated GST tagged c-Jun phosphorylation in human Jurkat T cells compound treated for 30 mins prior anisomycin stimulation measured after 40 mins by fluorescence spectrophotometry Homo sapiens 200.0 nM
Antiinflammatory activity in CD rat assessed as inhibition of LPS-stimulated TNFalpha production at 30 mg/kg, po administered 1 hr prior LPS challenge measured after 90 mins by ELISA Rattus norvegicus 77.0 %
Inhibition of ERK1 None 480.0 nM
Inhibition of EGFR None 380.0 nM
Inhibition of EGFR at 3 uM None 50.0 %
Antiinflammatory activity in CD rat assessed as inhibition of LPS-stimulated TNFalpha production at 10 mg/kg, po administered 1 hr prior LPS challenge measured after 90 mins by ELISA Rattus norvegicus 23.0 %
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 156.0 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 1.0 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 729.0 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 17.0 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 2.0 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 934.0 nM
Inhibition of JNK1 (unknown origin) Homo sapiens 61.0 nM
Inhibition of JNK2 (unknown origin) Homo sapiens 7.0 nM
Inhibition of JNK3 (unknown origin) Homo sapiens 6.0 nM
Inhibition of ERK1 (unknown origin) Homo sapiens 480.0 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 -10.95 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 36.58 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -8.837 %
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 0.04 % 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 -0.04 % 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 0.04 % 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 -0.04 %
Inhibition of JNK1 (unknown origin) assessed as reduction in phosphorylated ULight-labeled 4EBP1 peptide measured after 1 hr by time-resolved fluorescence assay Homo sapiens 133.0 nM
Inhibition of JNK2 (unknown origin) assessed as reduction in phosphorylated ULight-labeled 4EBP1 peptide measured after 1 hr by time-resolved fluorescence assay Homo sapiens 5.0 nM

Cross References

Resources Reference
ChEMBL CHEMBL1950289
DrugBank DB11798
FDA SRS M5O06306UO
PDB KBI
PubChem 11597537
SureChEMBL SCHEMBL2133055
ZINC ZINC000102930548
CONTENTS