BindingDB PrimarySearch

BDBM291522 1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)piperidin-1-yl)prop-2-en-1-one ::US10413562, Compound A250::US9580449, Example A250::US9580449, Example A39

SMILES: Nc1ncnc(NCC2CCN(CC2)C(=O)C=C)c1-c1ccc(Oc2ccccc2)cc1

InChI Key: InChIKey=QUIWHXQETADMGN-UHFFFAOYSA-N

Data: 1 KI 14 IC50 8 Kd

PDB links: 1 PDB ID matches this monomer.

Activity Spreadsheet -- Enzyme Inhibition Constant Data from BindingDB

Found 24 hits for monomerid = 291522
Target/Host (Institution)	Ligand	Target/Host Links	Ligand Links	Trg + Lig Links	Ki nM	ΔG° kcal/mole	IC50 nM	Kd nM	EC50/IC50 nM	k_off s^-1	k_on M^-1s^-1	pH	Temp °C
1,3-beta-glucan synthase component GLS2 (Saccharomyces cerevisiae)	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	KEGG UniProtKB/SwissProt GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	Article PubMed	3.10E+3	n/a	n/a	n/a	n/a	n/a	n/a	n/a	n/a
Merck KGaA Curated by ChEMBL					Assay Description Inhibition of human ERG expressed in HEK293 cells at -80 mV holding potential by HPLC analysis				J Med Chem 62: 7643-7655 (2019) Article DOI: 10.1021/acs.jmedchem.9b00794
Merck KGaA Curated by ChEMBL					More data for this Ligand-Target Pair
Platelet glycoprotein VI (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB UniProtKB/SwissProt GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem		n/a	n/a	5.84E+3	n/a	n/a	n/a	n/a	n/a	n/a
TBA									Citation and Details
TBA					More data for this Ligand-Target Pair
Cytoplasmic tyrosine-protein kinase BMX (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB NCI pathway Reactome pathway KEGG UniProtKB/SwissProt B.MOAD antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	Article PubMed	n/a	n/a	38	n/a	n/a	n/a	n/a	n/a	n/a
Genentech Curated by ChEMBL					Assay Description Inhibition of cytoplasmic recombinant human full length His-tagged BMX expressed in baculovirus by Z'-LYTE assay				J Med Chem 61: 2227-2245 (2018) Article DOI: 10.1021/acs.jmedchem.7b01712 BindingDB Entry DOI: 10.7270/Q2H134F7
Genentech Curated by ChEMBL					More data for this Ligand-Target Pair
Tyrosine-protein kinase TEC (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB Reactome pathway KEGG UniProtKB/SwissProt B.MOAD antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	Article PubMed	n/a	n/a	38	n/a	n/a	n/a	n/a	n/a	n/a
Genentech Curated by ChEMBL					Assay Description Inhibition of recombinant human cytoplasmic full length His-tagged TEC expressed in baculovirus by Z'-LYTE assay				J Med Chem 61: 2227-2245 (2018) Article DOI: 10.1021/acs.jmedchem.7b01712 BindingDB Entry DOI: 10.7270/Q2H134F7
Genentech Curated by ChEMBL					More data for this Ligand-Target Pair
Receptor protein-tyrosine kinase erbB-4 (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB UniProtKB/SwissProt B.MOAD antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	Article PubMed	n/a	n/a	38	n/a	n/a	n/a	n/a	n/a	n/a
Genentech Curated by ChEMBL					Assay Description Inhibition of recombinant human cytoplasmic GST-tagged ERBB4 expressed in baculovirus by Z'-LYTE assay				J Med Chem 61: 2227-2245 (2018) Article DOI: 10.1021/acs.jmedchem.7b01712 BindingDB Entry DOI: 10.7270/Q2H134F7
Genentech Curated by ChEMBL					More data for this Ligand-Target Pair
Tyrosine-protein kinase BTK (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB NCI pathway Reactome pathway KEGG UniProtKB/SwissProt B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	PDB US Patent	n/a	n/a	<100	n/a	n/a	n/a	n/a	n/a	n/a
Merck Patent GmbH US Patent					Assay Description 2.5� stocks of full-length human BTK (08-080) from CarnaBio USA, Inc., Natick, Mass., 1.6�ATP and appropriate kinKDR peptide substrate (FITC-AHA-EEPL...				US Patent US10413562 (2019) BindingDB Entry DOI: 10.7270/Q27M0B95
Merck Patent GmbH US Patent					More data for this Ligand-Target Pair				3D Structure (crystal)
Tyrosine-protein kinase BTK (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB NCI pathway Reactome pathway KEGG UniProtKB/SwissProt B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	PDB Article PubMed	n/a	n/a	8.90	n/a	n/a	n/a	n/a	n/a	n/a
Merck KGaA Curated by ChEMBL					Assay Description Covalent inhibition of N-terminal GST-fused human BTK (2-659(end) amino acids) expressed in baculovirus expression system using FITC-AHA-EEPLYWSFPAKK...				J Med Chem 62: 7643-7655 (2019) Article DOI: 10.1021/acs.jmedchem.9b00794
Merck KGaA Curated by ChEMBL					More data for this Ligand-Target Pair				3D Structure (crystal)
Epidermal growth factor receptor (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB KEGG UniProtKB/SwissProt B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	Article PubMed	n/a	n/a	5.80E+3	n/a	n/a	n/a	n/a	n/a	n/a
Merck KGaA Curated by ChEMBL					Assay Description Inhibition of N-terminal GST-tagged human EGFR (696 to end aminoacids) expressed in baculovirus infected Sf21 cells				J Med Chem 62: 7643-7655 (2019) Article DOI: 10.1021/acs.jmedchem.9b00794
Merck KGaA Curated by ChEMBL					More data for this Ligand-Target Pair
Tyrosine-protein kinase BTK (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB NCI pathway Reactome pathway KEGG UniProtKB/SwissProt B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	PDB Article PubMed	n/a	n/a	61	n/a	n/a	n/a	n/a	n/a	n/a
Merck KGaA Curated by ChEMBL					Assay Description Inhibition of BTK in human PBMC cells assessed as reduction in anti-IgM-stimulated CD69 expression on B cells preincubated for 60 mins followed by go...				J Med Chem 62: 7643-7655 (2019) Article DOI: 10.1021/acs.jmedchem.9b00794
Merck KGaA Curated by ChEMBL					More data for this Ligand-Target Pair				3D Structure (crystal)
Tyrosine-protein kinase BTK (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB NCI pathway Reactome pathway KEGG UniProtKB/SwissProt B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	PDB Article PubMed	n/a	n/a	8.60E+3	n/a	n/a	n/a	n/a	n/a	n/a
Merck KGaA Curated by ChEMBL					Assay Description Inhibition of BTK Cys481S mutant (unknown origin)				J Med Chem 62: 7643-7655 (2019) Article DOI: 10.1021/acs.jmedchem.9b00794
Merck KGaA Curated by ChEMBL					More data for this Ligand-Target Pair				3D Structure (crystal)
Tyrosine-protein kinase ITK/TSK (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB Reactome pathway KEGG UniProtKB/SwissProt B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	Article PubMed	n/a	n/a	n/a	3.70E+3	n/a	n/a	n/a	n/a	n/a
TBA Curated by ChEMBL					Assay Description Binding affinity to DNA-tagged recombinant ITK (unknown origin) measured after 1 hr by biotinylated-ligand affinity bead-based qPCR analysis				J Med Chem 63: 5102-5118 (2020) Article DOI: 10.1021/acs.jmedchem.9b01916
TBA Curated by ChEMBL					More data for this Ligand-Target Pair
Tyrosine-protein kinase BTK (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB NCI pathway Reactome pathway KEGG UniProtKB/SwissProt B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	PDB Article PubMed	n/a	n/a	62	n/a	n/a	n/a	n/a	n/a	n/a
TBA Curated by ChEMBL					Assay Description Inhibition of full-length human recombinant BTK using FITC-Ahx-TSELKKVVALYDYMPMNAND-NH2 as substrate measured after 60 mins by caliper assay				J Med Chem 63: 5102-5118 (2020) Article DOI: 10.1021/acs.jmedchem.9b01916
TBA Curated by ChEMBL					More data for this Ligand-Target Pair				3D Structure (crystal)
Tyrosine-protein kinase BTK (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB NCI pathway Reactome pathway KEGG UniProtKB/SwissProt B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	PDB Article PubMed	n/a	n/a	61	n/a	n/a	n/a	n/a	n/a	n/a
TBA Curated by ChEMBL					Assay Description Inhibition of BTK in vitamin D3 differentiated human THP1 cells assessed as inhibition of FCgammaR-induced IL8 production measured after 24 hrs by HT...				J Med Chem 63: 5102-5118 (2020) Article DOI: 10.1021/acs.jmedchem.9b01916
TBA Curated by ChEMBL					More data for this Ligand-Target Pair				3D Structure (crystal)
Tyrosine-protein kinase BTK (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB NCI pathway Reactome pathway KEGG UniProtKB/SwissProt B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	PDB Article PubMed	n/a	n/a	320	n/a	n/a	n/a	n/a	n/a	n/a
TBA Curated by ChEMBL					Assay Description Inhibition of BTK in human B cells assessed as reduction in anti-IgM/IL4-stimulated CD69 expression on B cells preincubated for 60 mins followed by a...				J Med Chem 63: 5102-5118 (2020) Article DOI: 10.1021/acs.jmedchem.9b01916
TBA Curated by ChEMBL					More data for this Ligand-Target Pair				3D Structure (crystal)
Tyrosine-protein kinase BTK (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB NCI pathway Reactome pathway KEGG UniProtKB/SwissProt B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	PDB Article PubMed	n/a	n/a	n/a	16	n/a	n/a	n/a	n/a	n/a
TBA Curated by ChEMBL					Assay Description Binding affinity to DNA-tagged recombinant BTK (unknown origin) measured after 1 hr by biotinylated-ligand affinity bead-based qPCR analysis				J Med Chem 63: 5102-5118 (2020) Article DOI: 10.1021/acs.jmedchem.9b01916
TBA Curated by ChEMBL					More data for this Ligand-Target Pair				3D Structure (crystal)
Epidermal growth factor receptor (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB KEGG UniProtKB/SwissProt B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	Article PubMed	n/a	n/a	n/a	7.10E+3	n/a	n/a	n/a	n/a	n/a
TBA Curated by ChEMBL					Assay Description Binding affinity to DNA-tagged recombinant EGFR (unknown origin) measured after 1 hr by biotinylated-ligand affinity bead-based qPCR analysis				J Med Chem 63: 5102-5118 (2020) Article DOI: 10.1021/acs.jmedchem.9b01916
TBA Curated by ChEMBL					More data for this Ligand-Target Pair
Receptor protein-tyrosine kinase erbB-4 (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB UniProtKB/SwissProt B.MOAD antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	Article PubMed	n/a	n/a	n/a	5.60E+3	n/a	n/a	n/a	n/a	n/a
TBA Curated by ChEMBL					Assay Description Binding affinity to DNA-tagged recombinant ERBB4 (unknown origin) measured after 1 hr by biotinylated-ligand affinity bead-based qPCR analysis				J Med Chem 63: 5102-5118 (2020) Article DOI: 10.1021/acs.jmedchem.9b01916
TBA Curated by ChEMBL					More data for this Ligand-Target Pair
Cytoplasmic tyrosine-protein kinase BMX (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB NCI pathway Reactome pathway KEGG UniProtKB/SwissProt B.MOAD antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	Article PubMed	n/a	n/a	n/a	31	n/a	n/a	n/a	n/a	n/a
TBA Curated by ChEMBL					Assay Description Binding affinity to DNA-tagged recombinant BMX (unknown origin) measured after 1 hr by biotinylated-ligand affinity bead-based qPCR analysis				J Med Chem 63: 5102-5118 (2020) Article DOI: 10.1021/acs.jmedchem.9b01916
TBA Curated by ChEMBL					More data for this Ligand-Target Pair
Tyrosine-protein kinase TEC (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB Reactome pathway KEGG UniProtKB/SwissProt B.MOAD antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	Article PubMed	n/a	n/a	n/a	4.5	n/a	n/a	n/a	n/a	n/a
TBA Curated by ChEMBL					Assay Description Binding affinity to DNA-tagged recombinant TEC (unknown origin) measured after 1 hr by biotinylated-ligand affinity bead-based qPCR analysis				J Med Chem 63: 5102-5118 (2020) Article DOI: 10.1021/acs.jmedchem.9b01916
TBA Curated by ChEMBL					More data for this Ligand-Target Pair
Tyrosine-protein kinase JAK3 (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB Reactome pathway KEGG UniProtKB/SwissProt UniProtKB/TrEMBL B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	Article PubMed	n/a	n/a	n/a	>1.00E+4	n/a	n/a	n/a	n/a	n/a
TBA Curated by ChEMBL					Assay Description Binding affinity to DNA-tagged recombinant JAK3 (unknown origin) measured after 1 hr by biotinylated-ligand affinity bead-based qPCR analysis				J Med Chem 63: 5102-5118 (2020) Article DOI: 10.1021/acs.jmedchem.9b01916
TBA Curated by ChEMBL					More data for this Ligand-Target Pair
Receptor tyrosine-protein kinase erbB-2 (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB UniProtKB/SwissProt UniProtKB/TrEMBL B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	Article PubMed	n/a	n/a	n/a	>1.00E+4	n/a	n/a	n/a	n/a	n/a
TBA Curated by ChEMBL					Assay Description Binding affinity to DNA-tagged recombinant ERBB2 (unknown origin) measured after 1 hr by biotinylated-ligand affinity bead-based qPCR analysis				J Med Chem 63: 5102-5118 (2020) Article DOI: 10.1021/acs.jmedchem.9b01916
TBA Curated by ChEMBL					More data for this Ligand-Target Pair
Tyrosine-protein kinase BTK (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB NCI pathway Reactome pathway KEGG UniProtKB/SwissProt B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	PDB Article PubMed	n/a	n/a	1.18E+3	n/a	n/a	n/a	n/a	n/a	n/a
TBA Curated by ChEMBL					Assay Description Inhibition of BTK in human basophils assessed as reduction in anti-IgE mouse IgG1 antibody Le2-stimulated CD63 expression on basophil preincubated fo...				J Med Chem 63: 5102-5118 (2020) Article DOI: 10.1021/acs.jmedchem.9b01916
TBA Curated by ChEMBL					More data for this Ligand-Target Pair				3D Structure (crystal)
Tyrosine-protein kinase BTK (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB NCI pathway Reactome pathway KEGG UniProtKB/SwissProt B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	PDB US Patent	n/a	n/a	<1.00E+3	n/a	n/a	n/a	n/a	7.5	27
Merck Patent GmbH US Patent					Assay Description The following describes a microfluidic, off-chip mobility shift kinase assay used to measure inherent potency of compounds against BTK enzyme. Compou...				US Patent US9580449 (2017) BindingDB Entry DOI: 10.7270/Q28K7C4Z
Merck Patent GmbH US Patent					More data for this Ligand-Target Pair				3D Structure (crystal)
Tyrosine-protein kinase BTK (Homo sapiens (Human))	BDBM291522 (1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)...) Show SMILES Show InChI	PDB MMDB NCI pathway Reactome pathway KEGG UniProtKB/SwissProt B.MOAD DrugBank antibodypedia GoogleScholar AffyNet	Purchase PC cid PC sid PDB UniChem	PDB US Patent	n/a	n/a	<100	n/a	n/a	n/a	n/a	7.5	27
Merck Patent GmbH US Patent					Assay Description The following describes a microfluidic, off-chip mobility shift kinase assay used to measure inherent potency of compounds against BTK enzyme. Compou...				US Patent US9580449 (2017) BindingDB Entry DOI: 10.7270/Q28K7C4Z
Merck Patent GmbH US Patent					More data for this Ligand-Target Pair				3D Structure (crystal)