ORANTINIB

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Synonyms
Status
Molecule Category UNKNOWN
UNII 9RL37ZZ665

Structure

InChI Key NHFDRBXTEDBWCZ-ZROIWOOFSA-N
Smiles Cc1[nH]c(/C=C2\C(=O)Nc3ccccc32)c(C)c1CCC(=O)O
InChI
InChI=1S/C18H18N2O3/c1-10-12(7-8-17(21)22)11(2)19-16(10)9-14-13-5-3-4-6-15(13)20-18(14)23/h3-6,9,19H,7-8H2,1-2H3,(H,20,23)(H,21,22)/b14-9-

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H18N2O3
Molecular Weight 310.35
AlogP 3.14
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 4.0
Polar Surface Area 82.19
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 23.0

Bioactivity

Mechanism of Action Action Reference
Fibroblast 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: Fibroblast growth factor receptor
Description: Fibroblast growth factor receptor 1
Organism : Homo sapiens
P11362 ENSG00000077782
Protein: Platelet-derived growth factor receptor
Description: Platelet-derived growth factor receptor alpha
Organism : Homo sapiens
P16234 ENSG00000134853
Protein: Fibroblast growth factor receptor
Description: Fibroblast growth factor receptor 2
Organism : Homo sapiens
P21802 ENSG00000066468
Protein: Fibroblast growth factor receptor
Description: Fibroblast growth factor receptor 4
Organism : Homo sapiens
P22455 ENSG00000160867
Protein: Fibroblast growth factor receptor
Description: Fibroblast growth factor receptor 3
Organism : Homo sapiens
P22607 ENSG00000068078
Protein: Vascular endothelial growth factor receptor 2
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 Other protein kinase group Other protein kinase AUR family
- 35-47 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase FGFR family
- 1810-9300 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase PDGFR family
- 300-49000 - - 77
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Syk family
- 28400 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase VEGFR family
- 135-3900 - - -
Assay Description Organism Bioactivity Reference
Inhibitory activity of compound against VEGF induced cell proliferation None 410.0 nM
Inhibition of PDGF-induced BrdU incorporation in 3T3 cells without bovine serum albumin Mus musculus 300.0 nM
Inhibition of Platelet-derived growth factor receptor beta (PDGF-Rbeta) Homo sapiens 60.0 nM
Inhibitory activity against Platelet-derived growth factor receptor beta None 60.0 nM
Inhibition of VEGFR2 None 680.0 nM
Inhibition of PDGFRbeta None 50.0 nM
Inhibition of Aurora B in the presence of 20uM ATP Homo sapiens 35.0 nM
Inhibition of Aurora C in the presence of 5uM ATP Homo sapiens 210.0 nM
Inhibition of PDGF-stimulated PDGFRbeta phosphorylation expressed in mouse NIH/3T3 cells by chemiluminescence assay None 100.0 nM
Inhibition of N-terminal GST-tagged Flt1 using poly(Glu,Tyr) as substrate after 60 mins by alphascreen assay None 28.0 nM
Inhibition of N-terminal GST-tagged KDR after 4 hrs by luciferase-luciferin coupled chemiluminescence assay None 135.0 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 933.0 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 303.0 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 19.0 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 0.3 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 0.8 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 744.0 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 637.0 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 316.0 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 12.0 nM
Inhibition of FLT3 ITD mutant (unknown origin) using TAMRA-Src- tide as substrate at 12.5 uM after 1 hr by fluorescence polarization assay relative to control Homo sapiens 100.0 %
Inhibition of FLT3 ITD mutant (unknown origin) using TAMRA-Src- tide as substrate at 1.25 uM after 1 hr by fluorescence polarization assay relative to control Homo sapiens 76.7 %
Inhibition of recombinant aurora B (unknown origin) Homo sapiens 47.0 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 20.41 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 16.06 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 31.75 %
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 -0.28 % 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 -0.39 % 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 -0.39 % 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 -0.28 %

Related Entries

Cross References

Resources Reference
ChEMBL CHEMBL274654
DrugBank DB12072
FDA SRS 9RL37ZZ665
Guide to Pharmacology 7816
PDB SU6
PubChem 5329099
SureChEMBL SCHEMBL134661
ZINC ZINC000003834032
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