VOLASERTIB

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Synonyms
Status
Molecule Category UNKNOWN
UNII 6EM57086EA

Structure

InChI Key SXNJFOWDRLKDSF-STROYTFGSA-N
Smiles CC[C@@H]1C(=O)N(C)c2cnc(Nc3ccc(C(=O)N[C@H]4CC[C@H](N5CCN(CC6CC6)CC5)CC4)cc3OC)nc2N1C(C)C
InChI
InChI=1S/C34H50N8O3/c1-6-28-33(44)39(4)29-20-35-34(38-31(29)42(28)22(2)3)37-27-14-9-24(19-30(27)45-5)32(43)36-25-10-12-26(13-11-25)41-17-15-40(16-18-41)21-23-7-8-23/h9,14,19-20,22-23,25-26,28H,6-8,10-13,15-18,21H2,1-5H3,(H,36,43)(H,35,37,38)/t25-,26-,28-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C34H50N8O3
Molecular Weight 618.83
AlogP 4.27
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 10.0
Polar Surface Area 106.17
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 45.0

Bioactivity

Mechanism of Action Action Reference
Serine/threonine-protein kinase PLK1 inhibitor INHIBITOR PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase PLK family
- 1-2 - - 98
Epigenetic regulator Reader Bromodomain
- 1070 79-255 - -
Assay Description Organism Bioactivity Reference
Competitive inhibition of human PLK1 in presence of ATP Homo sapiens 0.87 nM
Binding affinity to BRD4 (unknown origin) by isothermal titration calorimetric assay Homo sapiens 255.0 nM
Inhibition of NH2-terminal GST-tagged recombinant human Plk1 (1 to 603 residues) expressed in baculovirus expression system using casein as substrate after 45 mins in presence of [gamma32P]-ATP by radiometric assay Homo sapiens 0.87 nM
Binding affinity to recombinant human His6-TEV protease-tagged BRD4 bromodomain 1 expressed in bacteria by isothermal titration calorimetric method Homo sapiens 79.0 nM
Inhibition of N-terminal GST-tagged recombinant human PLK1 (1 to 603 residues) expressed in baculovirus expression system using bovine milk casein as substrate after 45 mins in presence of [gamma-33P]-ATP by radiometric assay Homo sapiens 0.87 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 195.0 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 286.0 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 601.0 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 -6.81 %
Cytotoxicity against human A549 cells assessed as reduction in cell viability after 72 hrs by MTT assay Homo sapiens 80.0 nM
Cytotoxicity against human HCT116 cells assessed as reduction in cell viability after 72 hrs by MTT assay Homo sapiens 110.0 nM
Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by MTT assay Homo sapiens 90.0 nM
Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 72 hrs by MTT assay Homo sapiens 110.0 nM
Cytotoxicity against human PC3 cells assessed as reduction in cell viability after 72 hrs by MTT assay Homo sapiens 90.0 nM
Inhibition of recombinant human N-terminal His6-tagged PLK1 expressed in baculovirus infected Sf21 insect cells at 1 uM using FAM-labelled peptide as substrate preincubated for 10 mins followed by substrate addition measured after 1 hr relative to control Homo sapiens 97.7 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 16.45 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -5.691 %
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 -0.32 % 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 -0.33 % 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 -0.33 % 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 -0.32 %
Inhibition of recombinant human N-terminal GST-tagged PLK1 (1 to 603 residues) expressed in baculovirus expression system using casein as substrate incubated for 45 mins by radiometric assay Homo sapiens 0.87 nM
Inhibition of human PLK1 using casein as substrate in presence of [gamma-33P]ATP by radiometric assay Homo sapiens 2.36 nM
Antiproliferative activity against human HepG2 cells assessed as inhibition of cell growth incubated for 48 hrs by MTS assay Homo sapiens 4.0 nM
Antiproliferative activity against human SMMC-7721 cells assessed as inhibition of cell growth incubated for 48 hrs by MTS assay Homo sapiens 77.2 nM
Antiproliferative activity against human HCT-116 cells assessed as inhibition of cell growth incubated for 48 hrs by MTS assay Homo sapiens 602.4 nM
Antiproliferative activity against human A549 cells assessed as inhibition of cell growth incubated for 48 hrs by MTS assay Homo sapiens 206.4 nM
Antiproliferative activity against human JeKo-1 cells assessed as inhibition of cell growth incubated for 48 hrs by MTS assay Homo sapiens 4.0 nM
Antiproliferative activity against human K562 cells assessed as inhibition of cell growth incubated for 48 hrs by MTS assay Homo sapiens 4.0 nM
Antiproliferative activity against human KARPAS-299 cells assessed as inhibition of cell growth incubated for 48 hrs by MTS assay Homo sapiens 4.0 nM
Antiproliferative activity against human DU-145 cells assessed as inhibition of cell growth incubated for 48 hrs by MTS assay Homo sapiens 4.0 nM
Antiproliferative activity against human LO2 cells assessed as inhibition of cell growth incubated for 48 hrs by MTS assay Homo sapiens 4.0 nM
Binding affinity to recombinant human N-terminal hexaHis-tagged BRD4 expressed in Escherichia coli BL21 (DE3) cells by MST assay Homo sapiens 169.0 nM
Binding affinity to recombinant human N-terminal hexaHis-tagged BRD4 expressed in Escherichia coli BL21 (DE3) cells by qPCR assay Homo sapiens 77.0 nM
Binding affinity to recombinant human N-terminal hexaHis-tagged BRD4 expressed in Escherichia coli BL21 (DE3) cells by ITC analysis Homo sapiens 317.0 nM
Binding affinity to recombinant human N-terminal hexaHis-tagged BRDT expressed in Escherichia coli BL21 (DE3) cells by qPCR assay Homo sapiens 113.0 nM
Inhibition of cell growth in human MM1.S cells incubated for 72 hrs by CellTiter-blue reagent based assay Homo sapiens 4.5 nM
Inhibition of cell growth in HEK293T cells incubated for 72 hrs by CellTiter-blue reagent based assay Homo sapiens 1.1 nM

Related Entries

Cross References

Resources Reference
ChEMBL CHEMBL1233528
DrugBank DB12062
FDA SRS 6EM57086EA
Guide to Pharmacology 7947
PDB IBI
SureChEMBL SCHEMBL738946
CONTENTS