SARACATINIB

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Synonyms
Status
Molecule Category Free-form
UNII 9KD24QGH76
EPA CompTox DTXSID90191355

Structure

InChI Key OUKYUETWWIPKQR-UHFFFAOYSA-N
Smiles CN1CCN(CCOc2cc(OC3CCOCC3)c3c(Nc4c(Cl)ccc5c4OCO5)ncnc3c2)CC1
InChI
InChI=1S/C27H32ClN5O5/c1-32-6-8-33(9-7-32)10-13-35-19-14-21-24(23(15-19)38-18-4-11-34-12-5-18)27(30-16-29-21)31-25-20(28)2-3-22-26(25)37-17-36-22/h2-3,14-16,18H,4-13,17H2,1H3,(H,29,30,31)

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H32ClN5O5
Molecular Weight 542.04
AlogP 3.94
Hydrogen Bond Acceptor 10.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 8.0
Polar Surface Area 90.44
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 38.0

Bioactivity

Mechanism of Action Action Reference
Tyrosine-protein kinase ABL inhibitor INHIBITOR PubMed
Protein: Tyrosine-protein kinase ABL
Description: Tyrosine-protein kinase ABL1
Organism : Homo sapiens
P00519 ENSG00000097007
Protein: Tyrosine-protein kinase SRC
Description: Proto-oncogene tyrosine-protein kinase Src
Organism : Homo sapiens
P12931 ENSG00000197122
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase CDK family CMGC protein kinase CDC2 subfamily
- 10000 - - -
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase WEE family
- 418-10000 2817 40-5200 -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE7 family
- 14000 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Abl family
- 30-30 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Csk family
- 840-840 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase EGFR family
- 66-2600 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase PDGFR family
- 200-200 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Src family
- 1-76 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase VEGFR family
- 20900-21000 - - -
Assay Description Organism Bioactivity Reference
Inhibition of human c-Src in NIH3T3 cells Homo sapiens 2.7 nM
Antiproliferative activity against mouse NIH3T3 cell line transfected with c-SRC Homo sapiens 76.0 nM
Inhibition of A549 cell migration by microdroplet migration assay Homo sapiens 140.0 nM
Antiproliferative activity against huamn K562 cell line Homo sapiens 220.0 nM
Inhibition of recombinant CSK by ELISA Homo sapiens 840.0 nM
Inhibition of recombinant C-YES by ELISA Homo sapiens 4.0 nM
Inhibition of recombinant LCK by ELISA Homo sapiens 4.0 nM
Inhibition of C-KIT by ELISA Homo sapiens 200.0 nM
Inhibition of recombinant v-Abl by ELISA Agrobacterium sp. 30.0 nM
Antiproliferative activity against NIH 3T3 cells xenografted in athymic rat measured as inhibition of tumor volume at 6 mg/kg/day after 18 days None 95.0 %
Inhibition of paxillin phosphorylation in Calu-6 xenograft tumor model at 20 mg/kg/day, po None 80.0 %
Inhibition of paxillin phosphorylation in A549 cells by Western blotting at 1 uM Homo sapiens 70.0 %
Inhibition of FAK phosphorylation in Calu-6 xenograft tumor model at 20 mg/kg/day, po None 80.0 %
Inhibition of Src kinase None 1.0 nM
Inhibition of Src None 3.0 nM
Inhibition of c-Kit by cellular assay None 200.0 nM
Inhibition of Lck by cellular assay None 4.0 nM
Inhibition of c-Abl None 30.0 nM
Inhibition of Csk None 840.0 nM
Inhibition of c-Yes None 4.0 nM
Inhibition of Src kinase None 3.0 nM Inhibition of Src kinase None 10.0 nM
Inhibition of SRC None 2.7 nM
Inhibition of LCK None 4.0 nM
Inhibition of YES None 4.0 nM
Inhibition of ABL1 None 30.0 nM
Inhibition of KIT None 200.0 nM
Inhibition of CSK None 840.0 nM
Antiosteoporotic activity in men with osteoporosis assessed as decrease in bone resorption-associated serum CTX-1 level at 250 mg/kg after 10 to 14 days Homo sapiens 88.0 %
Antiosteoporotic activity in men with osteoporosis assessed as decrease in bone resorption-associated urinary CTX-1 level at 250 mg/kg after 10 to 14 days Homo sapiens 67.0 %
Inhibition of c-SRC None 2.7 nM
SANGER: Inhibition of human NCI-H1648 cell growth in a cell viability assay. Homo sapiens 281.16 nM
SANGER: Inhibition of human NOS-1 cell growth in a cell viability assay. Homo sapiens 605.29 nM
SANGER: Inhibition of human A704 cell growth in a cell viability assay. Homo sapiens 892.1 nM
SANGER: Inhibition of human BB30-HNC cell growth in a cell viability assay. Homo sapiens 862.03 nM
SANGER: Inhibition of human BV-173 cell growth in a cell viability assay. Homo sapiens 652.49 nM
SANGER: Inhibition of human TE-12 cell growth in a cell viability assay. Homo sapiens 326.8 nM
SANGER: Inhibition of human TE-15 cell growth in a cell viability assay. Homo sapiens 274.12 nM
SANGER: Inhibition of human TE-8 cell growth in a cell viability assay. Homo sapiens 872.75 nM
SANGER: Inhibition of human TK10 cell growth in a cell viability assay. Homo sapiens 906.69 nM
SANGER: Inhibition of human CTV-1 cell growth in a cell viability assay. Homo sapiens 61.43 nM
SANGER: Inhibition of human D-336MG cell growth in a cell viability assay. Homo sapiens 503.04 nM
SANGER: Inhibition of human EM-2 cell growth in a cell viability assay. Homo sapiens 265.0 nM
SANGER: Inhibition of human EW-24 cell growth in a cell viability assay. Homo sapiens 626.93 nM
SANGER: Inhibition of human K-562 cell growth in a cell viability assay. Homo sapiens 449.67 nM
SANGER: Inhibition of human LAMA-84 cell growth in a cell viability assay. Homo sapiens 159.9 nM
SANGER: Inhibition of human LB996-RCC cell growth in a cell viability assay. Homo sapiens 441.96 nM
SANGER: Inhibition of human MEG-01 cell growth in a cell viability assay. Homo sapiens 236.88 nM
SANGER: Inhibition of human NCCIT cell growth in a cell viability assay. Homo sapiens 732.18 nM
SANGER: Inhibition of human NCI-H1436 cell growth in a cell viability assay. Homo sapiens 790.49 nM
Inhibition of Yes1 (unknown origin) by [gamma-33P]-ATP radiolabeled enzyme activity assay Homo sapiens 0.7 nM
Inhibition of Yes1 (unknown origin) assessed as kinase-dependent enzymatic production of ADP from ATP using coupled luminescence-based reaction by ADP-Glo kinase assay Homo sapiens 6.2 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 53.0 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 4.0 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 142.0 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 275.0 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 16.0 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 60.0 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 29.0 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 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 917.0 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 956.0 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 140.0 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 98.0 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 108.0 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 100.0 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 9.0 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 113.0 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 631.0 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 566.0 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 178.0 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 132.0 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 197.0 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 95.0 nM
Inhibition of human full length PKMYT1 expressed in HEK293 cells using EFS (247 to 259 residues) as substrate after 1 hr by fluorescence polarization immunoasay Homo sapiens 418.0 nM Inhibition of human full length PKMYT1 expressed in HEK293 cells using EFS (247 to 259 residues) as substrate after 1 hr by fluorescence polarization immunoasay Homo sapiens 39.8 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 -8.56 %
Inhibition of SRC (unknown origin) Homo sapiens 2.7 nM
Inhibition of EGFR in human A431 cells assessed as reduction in EGF-stimulated EGFR autophosphorylation preincuabted for 90 mins followed by EGF-stimulation by sandwich-ELISA Homo sapiens 66.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -4.163 %
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 -0.02 % 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 -0.02 %

Cross References

Resources Reference
ChEMBL CHEMBL217092
DrugBank DB11805
FDA SRS 9KD24QGH76
Guide to Pharmacology 7731
PDB H8H
PubChem 10302451
SureChEMBL SCHEMBL41547
ZINC ZINC000024811973
CONTENTS