6MNY
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2GE9
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5KUP
| Bruton's tyrosine kinase (BTK) with pyridazinone compound 9 | Descriptor: | 2-(2-METHOXYETHOXY)ETHANOL, 6-~{tert}-butyl-8-fluoranyl-2-[3-(hydroxymethyl)-4-[1-methyl-6-oxidanylidene-5-(pyrimidin-4-ylamino)pyridin-3-yl]pyridin-2-yl]phthalazin-1-one, GLYCEROL, ... | Authors: | Eigenbrot, C, Yu, C. | Deposit date: | 2016-07-13 | Release date: | 2016-09-14 | Last modified: | 2023-10-04 | Method: | X-RAY DIFFRACTION (1.389 Å) | Cite: | Battling Btk Mutants With Noncovalent Inhibitors That Overcome Cys481 and Thr474 Mutations. Acs Chem.Biol., 11, 2016
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1AWX
| SH3 DOMAIN FROM BRUTON'S TYROSINE KINASE, NMR, MINIMIZED AVERAGE STRUCTURE | Descriptor: | BRUTON'S TYROSINE KINASE | Authors: | Hansson, H, Mattsson, P.T, Allard, P, Haapaniemi, P, Vihinen, M, Smith, C.I.E, Hard, T. | Deposit date: | 1997-10-06 | Release date: | 1998-04-08 | Last modified: | 2024-05-22 | Method: | SOLUTION NMR | Cite: | Solution structure of the SH3 domain from Bruton's tyrosine kinase. Biochemistry, 37, 1998
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1AWW
| SH3 DOMAIN FROM BRUTON'S TYROSINE KINASE, NMR, 42 STRUCTURES | Descriptor: | BRUTON'S TYROSINE KINASE | Authors: | Hansson, H, Mattsson, P.T, Allard, P, Haapaniemi, P, Vihinen, M, Smith, C.I.E, Hard, T. | Deposit date: | 1997-10-06 | Release date: | 1998-04-08 | Last modified: | 2024-05-22 | Method: | SOLUTION NMR | Cite: | Solution structure of the SH3 domain from Bruton's tyrosine kinase. Biochemistry, 37, 1998
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4OTF
| Crystal structure of the kinase domain of Bruton's Tyrosine kinase with GDC0834 | Descriptor: | N-{3-[6-({4-[(2R)-1,4-dimethyl-3-oxopiperazin-2-yl]phenyl}amino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl]-2-methylphenyl }-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide, SULFATE ION, Tyrosine-protein kinase BTK | Authors: | Hymowitz, S.G, Maurer, B. | Deposit date: | 2014-02-13 | Release date: | 2015-01-28 | Last modified: | 2023-12-06 | Method: | X-RAY DIFFRACTION (1.95 Å) | Cite: | Potent and selective Bruton's tyrosine kinase inhibitors: Discovery of GDC-0834. Bioorg.Med.Chem.Lett., 25, 2015
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6BKW
| BTK complex with compound 12 | Descriptor: | GLYCEROL, N-(3-{5-[(1,5-dimethyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxo-1,6-dihydropyridazin-3-yl}-2,6-difluorophenyl)-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide, SULFATE ION, ... | Authors: | Kiefer, J.R, Eigenbrot, C, Yu, C.L. | Deposit date: | 2017-11-09 | Release date: | 2018-11-07 | Last modified: | 2019-03-27 | Method: | X-RAY DIFFRACTION (1.499 Å) | Cite: | Water molecules in protein-ligand interfaces. Evaluation of software tools and SAR comparison. J. Comput. Aided Mol. Des., 33, 2019
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6BKH
| BTK complex with compound 11 | Descriptor: | N-[2-(hydroxymethyl)-3-{5-[(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-yl)amino]-6-oxo-1,6-dihydropyridazin-3-yl}phenyl]-1-benzothiophene-2-carboxamide, SULFATE ION, Tyrosine-protein kinase BTK | Authors: | Kiefer, J.R, Eigenbrot, C, Yu, C.L. | Deposit date: | 2017-11-08 | Release date: | 2018-11-07 | Last modified: | 2019-03-27 | Method: | X-RAY DIFFRACTION (1.792 Å) | Cite: | Water molecules in protein-ligand interfaces. Evaluation of software tools and SAR comparison. J. Comput. Aided Mol. Des., 33, 2019
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6BLN
| BTK complex with compound 13 | Descriptor: | GLYCEROL, N-(3-{5-[(1,5-dimethyl-1H-pyrazol-3-yl)amino]-6-oxo-1,6-dihydropyridazin-3-yl}-2,6-difluorophenyl)-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide, SULFATE ION, ... | Authors: | Kiefer, J.R, Eigenbrot, C, Yu, C.L. | Deposit date: | 2017-11-10 | Release date: | 2018-11-07 | Last modified: | 2019-03-27 | Method: | X-RAY DIFFRACTION (1.3 Å) | Cite: | Water molecules in protein-ligand interfaces. Evaluation of software tools and SAR comparison. J. Comput. Aided Mol. Des., 33, 2019
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6BKE
| BTK complex with compound 10 | Descriptor: | N-[2-(2-hydroxyethyl)-3-{5-[(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-yl)amino]-6-oxo-1,6-dihydropyridazin-3-yl}phenyl]-1-benzothiophene-2-carboxamide, SULFATE ION, Tyrosine-protein kinase BTK | Authors: | Kiefer, J.R, Eigenbrot, C, Yu, C.L, Wang, G.X. | Deposit date: | 2017-11-08 | Release date: | 2018-11-07 | Last modified: | 2019-03-27 | Method: | X-RAY DIFFRACTION (1.95 Å) | Cite: | Water molecules in protein-ligand interfaces. Evaluation of software tools and SAR comparison. J. Comput. Aided Mol. Des., 33, 2019
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6BIK
| BTK complex with compound 7 | Descriptor: | 4-tert-butyl-N-[2-(hydroxymethyl)-3-(1-methyl-5-{[5-(morpholine-4-carbonyl)pyridin-2-yl]amino}-6-oxo-1,6-dihydropyridazin-3-yl)phenyl]benzamide, GLYCEROL, SULFATE ION, ... | Authors: | Kiefer, J.R, Eigenbrot, C, Yu, C.L. | Deposit date: | 2017-11-02 | Release date: | 2018-11-07 | Last modified: | 2019-03-27 | Method: | X-RAY DIFFRACTION (1.901 Å) | Cite: | Water molecules in protein-ligand interfaces. Evaluation of software tools and SAR comparison. J. Comput. Aided Mol. Des., 33, 2019
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4XI2
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6EP9
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4RX5
| Bruton's tyrosine kinase (BTK) with pyridazinone compound 23 | Descriptor: | 2-(2-METHOXYETHOXY)ETHANOL, GLYCEROL, N-(6-fluoro-2-methyl-3-{5-[(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-yl)amino]-6-oxo-1,6-dihydropyridazin-3-yl}phenyl)-1-benzothiophene-2-carboxamide, ... | Authors: | Eigenbrot, C, Yu, C. | Deposit date: | 2014-12-08 | Release date: | 2015-12-02 | Last modified: | 2023-09-20 | Method: | X-RAY DIFFRACTION (1.356 Å) | Cite: | Discovery of highly potent and selective Bruton's tyrosine kinase inhibitors: Pyridazinone analogs with improved metabolic stability. Bioorg.Med.Chem.Lett., 26, 2016
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5J87
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2Z0P
| Crystal structure of PH domain of Bruton's tyrosine kinase | Descriptor: | (2R)-3-{[(S)-{[(2S,3R,5S,6S)-2,6-DIHYDROXY-3,4,5-TRIS(PHOSPHONOOXY)CYCLOHEXYL]OXY}(HYDROXY)PHOSPHORYL]OXY}-2-(1-HYDROXY BUTOXY)PROPYL BUTYRATE, Tyrosine-protein kinase BTK, ZINC ION | Authors: | Murayama, K, Kato-Murayama, M, Mishima, C, Shirouzu, M, Yokoyama, S, RIKEN Structural Genomics/Proteomics Initiative (RSGI) | Deposit date: | 2007-05-07 | Release date: | 2008-05-13 | Last modified: | 2023-11-01 | Method: | X-RAY DIFFRACTION (2.58 Å) | Cite: | Crystal structure of the Bruton's tyrosine kinase PH domain with phosphatidylinositol Biochem.Biophys.Res.Commun., 377, 2008
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6XE4
| BTK Fluorocyclopropyl amide inhibitor, Compound 25 | Descriptor: | (1S,2S)-N-[2'-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-3'-(hydroxymethyl)-1-methyl-6-oxo[1,6-dihydro[3,4'-bipyridine]]-5-yl]-2-fluorocyclopropane-1-carboxamide, SULFATE ION, Tyrosine-protein kinase BTK | Authors: | Kiefer, J.R, Crawford, J.J, Lee, W, Eigenbrot, C, Yu, C. | Deposit date: | 2020-06-11 | Release date: | 2020-07-22 | Last modified: | 2024-03-06 | Method: | X-RAY DIFFRACTION (1.6 Å) | Cite: | Stereochemical Differences in Fluorocyclopropyl Amides Enable Tuning of Btk Inhibition and Off-Target Activity. Acs Med.Chem.Lett., 11, 2020
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5FBO
| BTK-inhibitor co-structure | Descriptor: | 4-[8-azanyl-3-[(2~{S})-1-[4-(dimethylamino)butanoyl]pyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-~{N}-(1,3-thiazol-2-yl)benzamide, 4-[8-azanyl-3-[(3~{R},6~{S})-1-cyclopropylcarbonyl-6-methyl-piperidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-3-fluoranyl-~{N}-[4-(trifluoromethyl)pyridin-2-yl]benzamide, Tyrosine-protein kinase BTK | Authors: | Fischmann, T.O. | Deposit date: | 2015-12-14 | Release date: | 2016-03-23 | Last modified: | 2024-03-06 | Method: | X-RAY DIFFRACTION (1.894 Å) | Cite: | Discovery of 8-Amino-imidazo[1,5-a]pyrazines as Reversible BTK Inhibitors for the Treatment of Rheumatoid Arthritis. ACS Med Chem Lett, 7, 2016
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3K54
| Structures of human Bruton's tyrosine kinase in active and inactive conformations suggests a mechanism of activation for TEC family kinases. | Descriptor: | N-(2-CHLORO-6-METHYLPHENYL)-2-({6-[4-(2-HYDROXYETHYL)PIPERAZIN-1-YL]-2-METHYLPYRIMIDIN-4-YL}AMINO)-1,3-THIAZOLE-5-CARBOXAMIDE, Tyrosine-protein kinase BTK | Authors: | Marcotte, D.J, Liu, Y.-T, Arduini, R.M, Hession, C.A, Miatkowski, K, Wildes, C.P, Cullen, P.F, Hopkins, B.T, Mertsching, E, Jenkins, T.J, Romanowski, M.J, Baker, D.P, Silvian, L.F. | Deposit date: | 2009-10-06 | Release date: | 2010-01-19 | Last modified: | 2023-09-06 | Method: | X-RAY DIFFRACTION (1.94 Å) | Cite: | Structures of human Bruton's tyrosine kinase in active and inactive conformations suggest a mechanism of activation for TEC family kinases. Protein Sci., 19, 2010
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5FBN
| BTK kinase domain with inhibitor 1 | Descriptor: | 1,2-ETHANEDIOL, 4-[8-azanyl-3-[(2~{S})-1-[4-(dimethylamino)butanoyl]pyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-~{N}-(1,3-thiazol-2-yl)benzamide, 4-[8-azanyl-3-[(3~{R})-1-(3-methyloxetan-3-yl)carbonylpiperidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-~{N}-[4-(trifluoromethyl)pyridin-2-yl]benzamide, ... | Authors: | Raaijmakers, H.C.A, Vu-Pham, D. | Deposit date: | 2015-12-14 | Release date: | 2016-02-03 | Last modified: | 2024-05-01 | Method: | X-RAY DIFFRACTION (1.8 Å) | Cite: | Discovery of 8-Amino-imidazo[1,5-a]pyrazines as Reversible BTK Inhibitors for the Treatment of Rheumatoid Arthritis. Acs Med.Chem.Lett., 7, 2016
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1K2P
| Crystal structure of Bruton's tyrosine kinase domain | Descriptor: | Tyrosine-protein kinase BTK | Authors: | Mao, C, Zhou, M, Uckun, F.M. | Deposit date: | 2001-09-28 | Release date: | 2002-06-26 | Last modified: | 2024-02-07 | Method: | X-RAY DIFFRACTION (2.1 Å) | Cite: | Crystal structure of Bruton's tyrosine kinase domain suggests a novel pathway for activation and provides insights into the molecular basis of X-linked agammaglobulinemia. J.Biol.Chem., 276, 2001
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7YC9
| Co-crystal structure of BTK kinase domain with inhibitor | Descriptor: | (7~{S})-2-(4-bromanyl-3,5-dimethoxy-phenyl)-7-(1-propanoylpiperidin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide, 1,2-ETHANEDIOL, Tyrosine-protein kinase BTK | Authors: | Zhou, X. | Deposit date: | 2022-07-01 | Release date: | 2023-05-17 | Last modified: | 2023-11-29 | Method: | X-RAY DIFFRACTION (1.4 Å) | Cite: | Discovery of BGB-8035, a Highly Selective Covalent Inhibitor of Bruton's Tyrosine Kinase for B-Cell Malignancies and Autoimmune Diseases. J.Med.Chem., 66, 2023
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5T18
| Crystal structure of Bruton agammabulinemia tyrosine kinase complexed with BMS-986142 aka (2s)-6-fluoro-5-[3-(8-fluoro-1-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-3-yl)-2-methylphenyl]-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1h-carbazole-8-carboxamide | Descriptor: | 6-Fluoro-5-(R)-(3-(S)-(8-fluoro-1-methyl-2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl)-2-methylphenyl)-2-(S)-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide, Tyrosine-protein kinase BTK | Authors: | Muckelbauer, J.K. | Deposit date: | 2016-08-18 | Release date: | 2017-03-08 | Last modified: | 2024-03-06 | Method: | X-RAY DIFFRACTION (1.5 Å) | Cite: | Discovery of 6-Fluoro-5-(R)-(3-(S)-(8-fluoro-1-methyl-2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl)-2-methylphenyl)-2-(S)-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (BMS-986142): A Reversible Inhibitor of Bruton's Tyrosine Kinase (BTK) Conformationally Constrained by Two Locked Atropisomers. J. Med. Chem., 59, 2016
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1QLY
| NMR Study of the SH3 Domain From Bruton's Tyrosine Kinase, 20 Structures | Descriptor: | TYROSINE-PROTEIN KINASE BTK | Authors: | Tzeng, S.R, Lou, Y.C, Pai, M.T, Chen, C, Chen, S.H, Cheng, J.Y. | Deposit date: | 1999-09-20 | Release date: | 1999-12-14 | Last modified: | 2024-05-15 | Method: | SOLUTION NMR | Cite: | Solution Structure of the Human Btk SH3 Domain Complexed with a Proline-Rich Peptide from P120Cbl J.Biomol.NMR, 16, 2000
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3GEN
| The 1.6 A crystal structure of human bruton's tyrosine kinase bound to a pyrrolopyrimidine-containing compound | Descriptor: | 4-Amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl-cyclopentane, Tyrosine-protein kinase BTK | Authors: | Marcotte, D.J, Liu, Y.T, Arduini, R.M, Hession, C.A, Miatkowski, K, Wildes, C.P, Cullen, P.F, Hopkins, B, Mertsching, E, Jenkins, T.J, Romanowski, M.J, Baker, D.P, Silvian, L.F. | Deposit date: | 2009-02-25 | Release date: | 2010-01-19 | Last modified: | 2024-03-13 | Method: | X-RAY DIFFRACTION (1.6 Å) | Cite: | Structures of human Bruton's tyrosine kinase in active and inactive conformations suggest a mechanism of activation for TEC family kinases. Protein Sci., 19, 2010
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