data_72F # _chem_comp.id 72F _chem_comp.name "N-[3-({6-[(2S)-2-cyano-3-(methylamino)-3-oxopropyl]-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethynyl)-4-methylphenyl]-3-(trifluoromethyl)benzamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C31 H27 F3 N6 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "N-[3-({6-[(1E)-2-cyano-3-(methylamino)-3-oxoprop-1-en-1-yl]-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethynyl)-4-methylphenyl]-3-(trifluoromethyl)benzamide inhibitor, bound form" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2016-08-15 _chem_comp.pdbx_modified_date 2021-03-13 _chem_comp.pdbx_ambiguous_flag N _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 588.580 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 72F _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 5SYS _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site RCSB # # loop_ _chem_comp_atom.comp_id _chem_comp_atom.atom_id _chem_comp_atom.alt_atom_id _chem_comp_atom.type_symbol _chem_comp_atom.charge _chem_comp_atom.pdbx_align _chem_comp_atom.pdbx_aromatic_flag _chem_comp_atom.pdbx_leaving_atom_flag _chem_comp_atom.pdbx_stereo_config _chem_comp_atom.model_Cartn_x _chem_comp_atom.model_Cartn_y _chem_comp_atom.model_Cartn_z _chem_comp_atom.pdbx_model_Cartn_x_ideal _chem_comp_atom.pdbx_model_Cartn_y_ideal _chem_comp_atom.pdbx_model_Cartn_z_ideal _chem_comp_atom.pdbx_component_atom_id _chem_comp_atom.pdbx_component_comp_id _chem_comp_atom.pdbx_ordinal 72F C7 C1 C 0 1 Y N N 6.072 37.283 5.737 -2.502 1.007 0.372 C7 72F 1 72F C10 C2 C 0 1 Y N N 3.064 35.149 7.415 0.275 -1.923 0.268 C10 72F 2 72F C6 C3 C 0 1 Y N N 7.328 36.676 5.446 -2.289 2.434 0.082 C6 72F 3 72F C4 C4 C 0 1 Y N N 9.861 36.311 4.579 -2.569 5.062 -0.306 C4 72F 4 72F C5 C5 C 0 1 Y N N 8.081 35.533 5.730 -1.197 3.211 -0.289 C5 72F 5 72F C9 C6 C 0 1 N N N 4.155 35.931 6.908 -0.710 -0.884 0.305 C9 72F 6 72F C1 C7 C 0 1 N N N 6.680 39.627 2.178 -6.658 2.163 -0.411 C1 72F 7 72F N1 N1 N 0 1 Y N N 9.283 37.449 4.188 -3.630 4.368 0.045 N1 72F 8 72F C2 C8 C 0 1 N N N 7.482 39.804 3.460 -5.859 2.319 0.883 C2 72F 9 72F O1 O1 O 0 1 N N N -1.521 32.408 6.927 3.733 -0.330 0.511 O1 72F 10 72F N2 N2 N 0 1 Y N N 9.338 35.336 5.318 -1.380 4.510 -0.471 N2 72F 11 72F C3 C9 C 0 1 Y N N 8.029 37.599 4.640 -3.542 3.057 0.249 C3 72F 12 72F C11 C10 C 0 1 Y N N 2.345 34.292 6.579 1.598 -1.624 -0.064 C11 72F 13 72F C13 C11 C 0 1 N N N -0.514 31.918 6.417 4.417 -1.166 -0.045 C13 72F 14 72F C12 C12 C 0 1 Y N N 1.218 33.626 7.066 2.545 -2.634 -0.092 C12 72F 15 72F N3 N3 N 0 1 N N N 0.652 32.603 6.253 3.872 -2.339 -0.424 N3 72F 16 72F C8 C13 C 0 1 N N N 5.036 36.565 6.407 -1.518 -0.032 0.335 C8 72F 17 72F N5 N4 N 0 1 N N N 2.382 38.417 7.061 -3.034 -1.784 -1.734 N5 72F 18 72F C30 C14 C 0 1 N N N 2.902 38.846 6.143 -3.903 -1.488 -1.065 C30 72F 19 72F C27 C15 C 0 1 N N S 3.625 39.374 4.984 -5.029 -1.104 -0.198 C27 72F 20 72F C28 C16 C 0 1 N N N 2.899 40.609 4.443 -5.808 -2.335 0.188 C28 72F 21 72F O2 O2 O 0 1 N N N 2.551 41.519 5.195 -5.923 -2.638 1.356 O2 72F 22 72F N4 N5 N 0 1 N N N 2.662 40.617 3.136 -6.377 -3.099 -0.766 N4 72F 23 72F C29 C17 C 0 1 N N N 1.661 41.479 2.533 -7.135 -4.295 -0.391 C29 72F 24 72F C26 C18 C 0 1 N N N 5.080 39.675 5.422 -4.493 -0.424 1.063 C26 72F 25 72F C25 C19 C 0 1 Y N N 6.066 38.530 5.166 -3.819 0.871 0.688 C25 72F 26 72F N N6 N 0 1 Y N N 7.226 38.719 4.428 -4.438 2.086 0.611 N 72F 27 72F O O3 O 0 1 N N N 7.471 40.073 1.072 -8.044 2.391 -0.146 O 72F 28 72F C C20 C 0 1 N N N 7.491 41.484 0.843 -8.884 2.269 -1.295 C 72F 29 72F C23 C21 C 0 1 Y N N 2.689 35.327 8.754 -0.083 -3.240 0.571 C23 72F 30 72F C24 C22 C 0 1 N N N 3.601 36.023 9.731 -1.508 -3.569 0.936 C24 72F 31 72F C22 C23 C 0 1 Y N N 1.519 34.710 9.190 0.868 -4.239 0.534 C22 72F 32 72F C21 C24 C 0 1 Y N N 0.782 33.882 8.364 2.178 -3.941 0.211 C21 72F 33 72F C14 C25 C 0 1 Y N N -0.528 30.510 5.903 5.847 -0.897 -0.306 C14 72F 34 72F C20 C26 C 0 1 Y N N 0.638 29.756 5.758 6.635 -1.856 -0.945 C20 72F 35 72F C19 C27 C 0 1 Y N N 0.582 28.472 5.238 7.969 -1.599 -1.185 C19 72F 36 72F C18 C28 C 0 1 Y N N -0.631 27.930 4.859 8.526 -0.394 -0.794 C18 72F 37 72F C16 C29 C 0 1 Y N N -1.801 28.666 4.995 7.750 0.561 -0.161 C16 72F 38 72F C15 C30 C 0 1 Y N N -1.746 29.949 5.530 6.413 0.318 0.080 C15 72F 39 72F C17 C31 C 0 1 N N N -3.101 28.125 4.510 8.365 1.870 0.262 C17 72F 40 72F F F1 F 0 1 N N N -3.634 28.886 3.561 8.242 2.017 1.648 F 72F 41 72F F1 F2 F 0 1 N N N -4.026 28.077 5.463 9.718 1.885 -0.091 F1 72F 42 72F F2 F3 F 0 1 N N N -2.987 26.891 4.011 7.704 2.924 -0.379 F2 72F 43 72F H1 H1 H 0 1 N N N 10.881 36.163 4.255 -2.673 6.125 -0.465 H1 72F 44 72F H2 H2 H 0 1 N N N 7.617 34.758 6.321 -0.223 2.766 -0.425 H2 72F 45 72F H3 H3 H 0 1 N N N 5.756 40.222 2.235 -6.306 2.888 -1.146 H3 72F 46 72F H4 H4 H 0 1 N N N 6.425 38.565 2.045 -6.524 1.155 -0.802 H4 72F 47 72F H5 H5 H 0 1 N N N 8.553 39.811 3.210 -5.993 3.328 1.274 H5 72F 48 72F H6 H6 H 0 1 N N N 7.206 40.764 3.921 -6.211 1.595 1.618 H6 72F 49 72F H7 H7 H 0 1 N N N 2.660 34.144 5.557 1.881 -0.608 -0.299 H7 72F 50 72F H8 H8 H 0 1 N N N 1.187 32.352 5.446 4.399 -2.979 -0.927 H8 72F 51 72F H9 H9 H 0 1 N N N 3.653 38.611 4.192 -5.681 -0.414 -0.734 H9 72F 52 72F H10 H10 H 0 1 N N N 3.192 40.008 2.546 -6.285 -2.856 -1.701 H10 72F 53 72F H11 H11 H 0 1 N N N 1.642 41.314 1.446 -6.482 -4.985 0.145 H11 72F 54 72F H12 H12 H 0 1 N N N 0.673 41.246 2.957 -7.968 -4.011 0.251 H12 72F 55 72F H13 H13 H 0 1 N N N 1.910 42.530 2.740 -7.516 -4.780 -1.290 H13 72F 56 72F H14 H14 H 0 1 N N N 5.430 40.560 4.870 -5.319 -0.220 1.745 H14 72F 57 72F H15 H15 H 0 1 N N N 5.077 39.892 6.500 -3.772 -1.080 1.551 H15 72F 58 72F H16 H16 H 0 1 N N N 8.127 41.706 -0.027 -9.919 2.456 -1.010 H16 72F 59 72F H17 H17 H 0 1 N N N 6.468 41.838 0.649 -8.577 2.995 -2.048 H17 72F 60 72F H18 H18 H 0 1 N N N 7.893 41.994 1.731 -8.796 1.262 -1.705 H18 72F 61 72F H19 H19 H 0 1 N N N 3.344 37.092 9.775 -2.066 -3.817 0.034 H19 72F 62 72F H20 H20 H 0 1 N N N 3.480 35.575 10.728 -1.521 -4.420 1.617 H20 72F 63 72F H21 H21 H 0 1 N N N 4.645 35.910 9.403 -1.967 -2.708 1.422 H21 72F 64 72F H22 H22 H 0 1 N N N 1.178 34.883 10.200 0.589 -5.256 0.768 H22 72F 65 72F H23 H23 H 0 1 N N N -0.132 33.434 8.725 2.919 -4.726 0.188 H23 72F 66 72F H24 H24 H 0 1 N N N 1.589 30.175 6.052 6.202 -2.797 -1.249 H24 72F 67 72F H25 H25 H 0 1 N N N 1.488 27.895 5.129 8.580 -2.339 -1.679 H25 72F 68 72F H26 H26 H 0 1 N N N -0.670 26.929 4.455 9.571 -0.199 -0.980 H26 72F 69 72F H27 H27 H 0 1 N N N -2.657 30.515 5.657 5.808 1.064 0.574 H27 72F 70 # # loop_ _chem_comp_bond.comp_id _chem_comp_bond.atom_id_1 _chem_comp_bond.atom_id_2 _chem_comp_bond.value_order _chem_comp_bond.pdbx_aromatic_flag _chem_comp_bond.pdbx_stereo_config _chem_comp_bond.pdbx_ordinal 72F C O SING N N 1 72F O C1 SING N N 2 72F C1 C2 SING N N 3 72F C29 N4 SING N N 4 72F N4 C28 SING N N 5 72F C2 N SING N N 6 72F F C17 SING N N 7 72F F2 C17 SING N N 8 72F N1 C4 DOUB Y N 9 72F N1 C3 SING Y N 10 72F N C3 SING Y N 11 72F N C25 SING Y N 12 72F C28 C27 SING N N 13 72F C28 O2 DOUB N N 14 72F C17 C16 SING N N 15 72F C17 F1 SING N N 16 72F C4 N2 SING Y N 17 72F C3 C6 DOUB Y N 18 72F C18 C16 DOUB Y N 19 72F C18 C19 SING Y N 20 72F C27 C26 SING N N 21 72F C27 C30 SING N N 22 72F C16 C15 SING Y N 23 72F C25 C26 SING N N 24 72F C25 C7 DOUB Y N 25 72F C19 C20 DOUB Y N 26 72F N2 C5 DOUB Y N 27 72F C6 C5 SING Y N 28 72F C6 C7 SING Y N 29 72F C15 C14 DOUB Y N 30 72F C7 C8 SING N N 31 72F C20 C14 SING Y N 32 72F C14 C13 SING N N 33 72F C30 N5 TRIP N N 34 72F N3 C13 SING N N 35 72F N3 C12 SING N N 36 72F C8 C9 TRIP N N 37 72F C13 O1 DOUB N N 38 72F C11 C12 DOUB Y N 39 72F C11 C10 SING Y N 40 72F C9 C10 SING N N 41 72F C12 C21 SING Y N 42 72F C10 C23 DOUB Y N 43 72F C21 C22 DOUB Y N 44 72F C23 C22 SING Y N 45 72F C23 C24 SING N N 46 72F C4 H1 SING N N 47 72F C5 H2 SING N N 48 72F C1 H3 SING N N 49 72F C1 H4 SING N N 50 72F C2 H5 SING N N 51 72F C2 H6 SING N N 52 72F C11 H7 SING N N 53 72F N3 H8 SING N N 54 72F C27 H9 SING N N 55 72F N4 H10 SING N N 56 72F C29 H11 SING N N 57 72F C29 H12 SING N N 58 72F C29 H13 SING N N 59 72F C26 H14 SING N N 60 72F C26 H15 SING N N 61 72F C H16 SING N N 62 72F C H17 SING N N 63 72F C H18 SING N N 64 72F C24 H19 SING N N 65 72F C24 H20 SING N N 66 72F C24 H21 SING N N 67 72F C22 H22 SING N N 68 72F C21 H23 SING N N 69 72F C20 H24 SING N N 70 72F C19 H25 SING N N 71 72F C18 H26 SING N N 72 72F C15 H27 SING N N 73 # # loop_ _pdbx_chem_comp_descriptor.comp_id _pdbx_chem_comp_descriptor.type _pdbx_chem_comp_descriptor.program _pdbx_chem_comp_descriptor.program_version _pdbx_chem_comp_descriptor.descriptor 72F SMILES ACDLabs 12.01 "c4(C#Cc1c(ccc(c1)NC(=O)c2cccc(c2)C(F)(F)F)C)c3cncnc3n(CCOC)c4CC(C#N)C(=O)NC" 72F InChI InChI 1.03 "InChI=1S/C31H27F3N6O3/c1-19-7-9-24(39-30(42)21-5-4-6-23(13-21)31(32,33)34)14-20(19)8-10-25-26-17-37-18-38-28(26)40(11-12-43-3)27(25)15-22(16-35)29(41)36-2/h4-7,9,13-14,17-18,22H,11-12,15H2,1-3H3,(H,36,41)(H,39,42)/t22-/m0/s1" 72F InChIKey InChI 1.03 JDCJZTAGQPRSAO-QFIPXVFZSA-N 72F SMILES_CANONICAL CACTVS 3.385 "CNC(=O)[C@@H](Cc1n(CCOC)c2ncncc2c1C#Cc3cc(NC(=O)c4cccc(c4)C(F)(F)F)ccc3C)C#N" 72F SMILES CACTVS 3.385 "CNC(=O)[CH](Cc1n(CCOC)c2ncncc2c1C#Cc3cc(NC(=O)c4cccc(c4)C(F)(F)F)ccc3C)C#N" 72F SMILES_CANONICAL "OpenEye OEToolkits" 2.0.5 "Cc1ccc(cc1C#Cc2c3cncnc3n(c2C[C@@H](C#N)C(=O)NC)CCOC)NC(=O)c4cccc(c4)C(F)(F)F" 72F SMILES "OpenEye OEToolkits" 2.0.5 "Cc1ccc(cc1C#Cc2c3cncnc3n(c2CC(C#N)C(=O)NC)CCOC)NC(=O)c4cccc(c4)C(F)(F)F" # # loop_ _pdbx_chem_comp_identifier.comp_id _pdbx_chem_comp_identifier.type _pdbx_chem_comp_identifier.program _pdbx_chem_comp_identifier.program_version _pdbx_chem_comp_identifier.identifier 72F "SYSTEMATIC NAME" ACDLabs 12.01 "N-[3-({6-[(2S)-2-cyano-3-(methylamino)-3-oxopropyl]-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethynyl)-4-methylphenyl]-3-(trifluoromethyl)benzamide" 72F "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.5 "~{N}-[3-[2-[6-[(2~{S})-2-cyano-3-(methylamino)-3-oxidanylidene-propyl]-7-(2-methoxyethyl)pyrrolo[2,3-d]pyrimidin-5-yl]ethynyl]-4-methyl-phenyl]-3-(trifluoromethyl)benzamide" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 72F "Create component" 2016-08-15 RCSB 72F "Initial release" 2017-08-16 RCSB 72F "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 72F _pdbx_chem_comp_synonyms.name "N-[3-({6-[(1E)-2-cyano-3-(methylamino)-3-oxoprop-1-en-1-yl]-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethynyl)-4-methylphenyl]-3-(trifluoromethyl)benzamide inhibitor, bound form" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##