BARASERTIB

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Synonyms
Status
Molecule Category UNKNOWN
UNII 16XC2U7W8N
EPA CompTox DTXSID00222583

Structure

InChI Key GBJVVSCPOBPEIT-UHFFFAOYSA-N
Smiles CCN(CCCOc1ccc2c(Nc3cc(CC(=O)Nc4cccc(F)c4)[nH]n3)ncnc2c1)CCOP(=O)(O)O
InChI
InChI=1S/C26H31FN7O6P/c1-2-34(10-12-40-41(36,37)38)9-4-11-39-21-7-8-22-23(16-21)28-17-29-26(22)31-24-14-20(32-33-24)15-25(35)30-19-6-3-5-18(27)13-19/h3,5-8,13-14,16-17H,2,4,9-12,15H2,1H3,(H,30,35)(H2,36,37,38)(H2,28,29,31,32,33)

Physicochemical Descriptors

Property Name Value
Molecular Formula C26H31FN7O6P
Molecular Weight 587.55
AlogP 3.62
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 5.0
Number of Rotational Bond 15.0
Polar Surface Area 174.82
Molecular species ZWITTERION
Aromatic Rings 4.0
Heavy Atoms 41.0

Bioactivity

Mechanism of Action Action Reference
Serine/threonine-protein kinase Aurora-B inhibitor INHIBITOR PubMed
Protein: Serine/threonine-protein kinase Aurora-B
Description: Aurora kinase B
Organism : Homo sapiens
Q96GD4 ENSG00000178999
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase AUR family
- 0 - 0 -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase PDGFR family
- - 17 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Ret family
- - 80 - -
Assay Description Organism Bioactivity Reference
Inhibition of Flt3 None 8.0 nM
Binding affinity to Ret None 80.0 nM
Binding affinity to Kit None 17.0 nM
Binding affinity to PDGFRA None 38.0 nM
Binding affinity to PDGFRB None 41.0 nM
Competitive inhibition of Aurora B ATP binding site None 1.0 nM
Competitive inhibition of Aurora C ATP binding site None 17.0 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: RET None 158.49 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: STK6 None 39.81 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: KIT None 19.95 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: PDGFRB None 316.23 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: KDR None 316.23 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: STK12 None 5.012 nM
Inhibition of aurora B (unknown origin) Homo sapiens 0.37 nM
Inhibition of Aurora B (unknown origin) Homo sapiens 0.37 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 49.0 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 257.0 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 82.0 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 33.0 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 209.0 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 -1.4 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 19.03 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 14.44 %
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 -0.13 % 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 -0.13 % 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 %
Inhibition of recombinant GST-tagged N-terminal truncated human Aurora A (123 to 401 residues) expressed in Sf9 insect cell using tetra-LRRASLG peptide as substrate incubated for 20 mins by Kinase-Glo plus luminescent kinase assay Homo sapiens 0.37 nM
Growth inhibition of human NCI-H82 cells assessed as reduction in cell viability after 72 hrs by PrestoBlue Cell Viability assay Homo sapiens 1.0 nM
Growth inhibition of human SKNBE2 cells assessed as reduction in cell viability after 72 hrs by PrestoBlue Cell Viability assay Homo sapiens 1.0 nM

Cross References

Resources Reference
ChEBI 167636
ChEMBL CHEMBL415049
DrugBank DB11747
FDA SRS 16XC2U7W8N
Guide to Pharmacology 7332
PubChem 11497983
SureChEMBL SCHEMBL16671950
ZINC ZINC000043129461
CONTENTS