data_0WN # _chem_comp.id 0WN _chem_comp.name "N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[(3S)-tetrahydrofuran-3-yloxy]quinazolin-6-yl}-4-(dimethylamino)butanamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C24 H27 Cl F N5 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "Afatinib, bound form" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-07-27 _chem_comp.pdbx_modified_date 2020-06-17 _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 487.954 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 0WN _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 4G5J _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 0WN C1 C1 C 0 1 Y N N 53.179 -1.616 -21.729 2.395 2.933 -0.958 C1 0WN 1 0WN N2 N2 N 0 1 Y N N 52.841 -0.626 -22.609 2.754 1.685 -0.704 N2 0WN 2 0WN N3 N3 N 0 1 Y N N 52.705 -1.567 -20.443 1.154 3.351 -0.869 N3 0WN 3 0WN C4 C4 C 0 1 Y N N 52.030 0.428 -22.238 1.866 0.769 -0.339 C4 0WN 4 0WN C5 C5 C 0 1 Y N N 51.903 -0.523 -20.053 0.175 2.505 -0.513 C5 0WN 5 0WN C6 C6 C 0 1 Y N N 51.541 0.500 -20.927 0.510 1.159 -0.225 C6 0WN 6 0WN C7 C7 C 0 1 Y N N 50.245 1.523 -19.135 -1.794 0.687 0.251 C7 0WN 7 0WN C8 C8 C 0 1 Y N N 50.709 1.535 -20.453 -0.489 0.256 0.155 C8 0WN 8 0WN C9 C9 C 0 1 Y N N 50.649 0.493 -18.285 -2.128 2.018 -0.040 C9 0WN 9 0WN C10 C10 C 0 1 Y N N 51.466 -0.523 -18.756 -1.158 2.922 -0.409 C10 0WN 10 0WN N11 N11 N 0 1 N N N 51.626 1.325 -23.267 2.255 -0.529 -0.077 N11 0WN 11 0WN C12 C12 C 0 1 Y N N 51.771 -0.562 -26.542 5.899 -0.279 0.348 C12 0WN 12 0WN C13 C13 C 0 1 Y N N 51.725 0.522 -27.405 6.299 -1.536 -0.079 C13 0WN 13 0WN C14 C14 C 0 1 Y N N 51.699 -0.342 -25.166 4.558 0.056 0.350 C14 0WN 14 0WN C15 C15 C 0 1 Y N N 51.609 1.813 -26.914 5.357 -2.457 -0.504 C15 0WN 15 0WN C16 C16 C 0 1 Y N N 51.590 0.965 -24.656 3.612 -0.867 -0.077 C16 0WN 16 0WN C17 C17 C 0 1 Y N N 51.543 2.030 -25.551 4.016 -2.125 -0.505 C17 0WN 17 0WN F18 F18 F 0 1 N N N 51.788 0.322 -28.712 7.610 -1.863 -0.079 F18 0WN 18 0WN CL1 CL1 CL 0 0 N N N 51.905 -2.162 -27.204 7.082 0.871 0.889 CL1 0WN 19 0WN O20 O20 O 0 1 N N N 50.214 0.487 -16.992 -3.424 2.420 0.044 O20 0WN 20 0WN C21 C21 C 0 1 N N S 50.725 -0.345 -15.942 -3.715 3.759 -0.359 C21 0WN 21 0WN C22 C22 C 0 1 N N N 50.327 -1.827 -16.047 -3.596 4.724 0.842 C22 0WN 22 0WN O23 O23 O 0 1 N N N 49.723 -2.243 -14.826 -4.660 5.682 0.652 O23 0WN 23 0WN C24 C24 C 0 1 N N N 49.197 -1.053 -14.252 -5.790 4.909 0.192 C24 0WN 24 0WN C25 C25 C 0 1 N N N 50.146 0.072 -14.615 -5.192 3.884 -0.796 C25 0WN 25 0WN N26 N26 N 0 1 N N N 49.457 2.563 -18.547 -2.798 -0.216 0.625 N26 0WN 26 0WN C27 C27 C 0 1 N N N 49.568 3.957 -18.748 -2.680 -1.522 0.315 C27 0WN 27 0WN C28 C28 C 0 1 N N N 48.675 4.884 -17.968 -3.803 -2.476 0.630 C28 0WN 28 0WN O29 O29 O 0 1 N N N 50.361 4.417 -19.549 -1.669 -1.929 -0.217 O29 0WN 29 0WN C30 C30 C 0 1 N N N 49.026 6.397 -18.154 -3.416 -3.886 0.179 C30 0WN 30 0WN C31 C31 C 0 1 N N N 47.902 7.464 -18.167 -4.556 -4.854 0.499 C31 0WN 31 0WN N32 N32 N 0 1 N N N 47.949 8.415 -19.312 -4.185 -6.208 0.066 N32 0WN 32 0WN C33 C33 C 0 1 N N N 47.478 7.801 -20.584 -5.144 -7.202 0.565 C33 0WN 33 0WN C34 C34 C 0 1 N N N 47.187 9.659 -19.029 -4.065 -6.279 -1.396 C34 0WN 34 0WN H1 H1 H 0 1 N N N 53.814 -2.430 -22.044 3.158 3.641 -1.248 H1 0WN 35 0WN H2 H2 H 0 1 N N N 50.428 2.342 -21.113 -0.239 -0.772 0.371 H2 0WN 36 0WN H3 H3 H 0 1 N N N 51.761 -1.323 -18.093 -1.423 3.948 -0.618 H3 0WN 37 0WN H4 H4 H 0 1 N N N 51.354 2.252 -23.009 1.586 -1.208 0.107 H4 0WN 38 0WN H5 H5 H 0 1 N N N 51.727 -1.181 -24.487 4.247 1.035 0.683 H5 0WN 39 0WN H6 H6 H 0 1 N N N 51.570 2.649 -27.597 5.671 -3.435 -0.837 H6 0WN 40 0WN H7 H7 H 0 1 N N N 51.454 3.039 -25.175 3.282 -2.843 -0.837 H7 0WN 41 0WN H8 H8 H 0 1 N N N 51.822 -0.274 -15.898 -3.050 4.067 -1.167 H8 0WN 42 0WN H9 H9 H 0 1 N N N 49.612 -1.957 -16.873 -3.734 4.183 1.778 H9 0WN 43 0WN H10 H10 H 0 1 N N N 51.223 -2.435 -16.239 -2.628 5.225 0.831 H10 0WN 44 0WN H11 H11 H 0 1 N N N 48.196 -0.848 -14.658 -6.265 4.397 1.029 H11 0WN 45 0WN H12 H12 H 0 1 N N N 49.135 -1.157 -13.159 -6.509 5.553 -0.315 H12 0WN 46 0WN H13 H13 H 0 1 N N N 50.938 0.173 -13.859 -5.257 4.256 -1.819 H13 0WN 47 0WN H14 H14 H 0 1 N N N 49.604 1.025 -14.708 -5.700 2.924 -0.705 H14 0WN 48 0WN H15 H15 H 0 1 N N N 48.740 2.267 -17.916 -3.578 0.100 1.108 H15 0WN 49 0WN H16 H16 H 0 1 N N N 47.637 4.725 -18.296 -3.989 -2.476 1.704 H16 0WN 50 0WN H17 H17 H 0 1 N N N 48.764 4.635 -16.900 -4.705 -2.161 0.105 H17 0WN 51 0WN H18 H18 H 0 1 N N N 49.555 6.483 -19.115 -3.230 -3.886 -0.895 H18 0WN 52 0WN H19 H19 H 0 1 N Y N 49.708 6.666 -17.334 -2.514 -4.200 0.704 H19 0WN 53 0WN H20 H20 H 0 1 N N N 47.974 8.047 -17.237 -4.743 -4.855 1.573 H20 0WN 54 0WN H21 H21 H 0 1 N N N 46.935 6.940 -18.198 -5.458 -4.540 -0.026 H21 0WN 55 0WN H23 H23 H 0 1 N N N 48.049 6.882 -20.782 -4.846 -8.196 0.230 H23 0WN 56 0WN H24 H24 H 0 1 N N N 46.409 7.557 -20.499 -5.162 -7.176 1.654 H24 0WN 57 0WN H25 H25 H 0 1 N N N 47.628 8.511 -21.411 -6.138 -6.973 0.180 H25 0WN 58 0WN H26 H26 H 0 1 N N N 47.544 10.102 -18.088 -3.298 -5.582 -1.733 H26 0WN 59 0WN H27 H27 H 0 1 N N N 47.336 10.375 -19.851 -3.790 -7.292 -1.690 H27 0WN 60 0WN H28 H28 H 0 1 N N N 46.117 9.421 -18.939 -5.020 -6.016 -1.852 H28 0WN 61 # # 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 0WN F18 C13 SING N N 1 0WN C13 C15 DOUB Y N 2 0WN C13 C12 SING Y N 3 0WN CL1 C12 SING N N 4 0WN C15 C17 SING Y N 5 0WN C12 C14 DOUB Y N 6 0WN C17 C16 DOUB Y N 7 0WN C14 C16 SING Y N 8 0WN C16 N11 SING N N 9 0WN N11 C4 SING N N 10 0WN N2 C4 DOUB Y N 11 0WN N2 C1 SING Y N 12 0WN C4 C6 SING Y N 13 0WN C1 N3 DOUB Y N 14 0WN C6 C8 DOUB Y N 15 0WN C6 C5 SING Y N 16 0WN C33 N32 SING N N 17 0WN C8 C7 SING Y N 18 0WN N3 C5 SING Y N 19 0WN C5 C10 DOUB Y N 20 0WN O29 C27 DOUB N N 21 0WN N32 C34 SING N N 22 0WN N32 C31 SING N N 23 0WN C7 N26 SING N N 24 0WN C7 C9 DOUB Y N 25 0WN C10 C9 SING Y N 26 0WN C27 N26 SING N N 27 0WN C27 C28 SING N N 28 0WN C9 O20 SING N N 29 0WN C31 C30 SING N N 30 0WN C30 C28 SING N N 31 0WN O20 C21 SING N N 32 0WN C22 C21 SING N N 33 0WN C22 O23 SING N N 34 0WN C21 C25 SING N N 35 0WN O23 C24 SING N N 36 0WN C25 C24 SING N N 37 0WN C1 H1 SING N N 38 0WN C8 H2 SING N N 39 0WN C10 H3 SING N N 40 0WN N11 H4 SING N N 41 0WN C14 H5 SING N N 42 0WN C15 H6 SING N N 43 0WN C17 H7 SING N N 44 0WN C21 H8 SING N N 45 0WN C22 H9 SING N N 46 0WN C22 H10 SING N N 47 0WN C24 H11 SING N N 48 0WN C24 H12 SING N N 49 0WN C25 H13 SING N N 50 0WN C25 H14 SING N N 51 0WN N26 H15 SING N N 52 0WN C28 H16 SING N N 53 0WN C28 H17 SING N N 54 0WN C30 H18 SING N N 55 0WN C30 H19 SING N N 56 0WN C31 H20 SING N N 57 0WN C31 H21 SING N N 58 0WN C33 H23 SING N N 59 0WN C33 H24 SING N N 60 0WN C33 H25 SING N N 61 0WN C34 H26 SING N N 62 0WN C34 H27 SING N N 63 0WN C34 H28 SING N N 64 # # 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 0WN SMILES ACDLabs 12.01 "Fc1ccc(cc1Cl)Nc4ncnc3cc(OC2CCOC2)c(cc34)NC(=O)CCCN(C)C" 0WN InChI InChI 1.03 "InChI=1S/C24H27ClFN5O3/c1-31(2)8-3-4-23(32)30-21-11-17-20(12-22(21)34-16-7-9-33-13-16)27-14-28-24(17)29-15-5-6-19(26)18(25)10-15/h5-6,10-12,14,16H,3-4,7-9,13H2,1-2H3,(H,30,32)(H,27,28,29)/t16-/m0/s1" 0WN InChIKey InChI 1.03 JSENTLOBWVHLNR-INIZCTEOSA-N 0WN SMILES_CANONICAL CACTVS 3.370 "CN(C)CCCC(=O)Nc1cc2c(Nc3ccc(F)c(Cl)c3)ncnc2cc1O[C@H]4CCOC4" 0WN SMILES CACTVS 3.370 "CN(C)CCCC(=O)Nc1cc2c(Nc3ccc(F)c(Cl)c3)ncnc2cc1O[CH]4CCOC4" 0WN SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CN(C)CCCC(=O)Nc1cc2c(cc1O[C@H]3CCOC3)ncnc2Nc4ccc(c(c4)Cl)F" 0WN SMILES "OpenEye OEToolkits" 1.7.6 "CN(C)CCCC(=O)Nc1cc2c(cc1OC3CCOC3)ncnc2Nc4ccc(c(c4)Cl)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 0WN "SYSTEMATIC NAME" ACDLabs 12.01 "N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[(3S)-tetrahydrofuran-3-yloxy]quinazolin-6-yl}-4-(dimethylamino)butanamide" 0WN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "N-[4-[(3-chloranyl-4-fluoranyl-phenyl)amino]-7-[(3S)-oxolan-3-yl]oxy-quinazolin-6-yl]-4-(dimethylamino)butanamide" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 0WN "Create component" 2012-07-27 RCSB 0WN "Initial release" 2012-08-24 RCSB 0WN "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 0WN _pdbx_chem_comp_synonyms.name "Afatinib, bound form" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##