data_YY3 # _chem_comp.id YY3 _chem_comp.name "N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)prop-2-enamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C28 H33 N7 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "Osimertinib; AZD 9291" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2015-04-14 _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 499.607 _chem_comp.one_letter_code ? _chem_comp.three_letter_code YY3 _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 4ZAU _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 YY3 C13 C1 C 0 1 N N N -3.219 -49.797 11.090 -7.402 -0.752 2.495 C13 YY3 1 YY3 N2 N1 N 0 1 N N N -2.436 -49.043 12.078 -7.838 -1.157 1.153 N2 YY3 2 YY3 C12 C2 C 0 1 N N N -3.194 -48.214 13.048 -9.280 -0.937 0.979 C12 YY3 3 YY3 C11 C3 C 0 1 N N N -1.879 -50.142 12.917 -7.070 -0.456 0.115 C11 YY3 4 YY3 C10 C4 C 0 1 N N N -0.345 -50.272 12.750 -5.608 -0.903 0.173 C10 YY3 5 YY3 N1 N2 N 0 1 N N N 0.254 -49.422 13.827 -4.840 -0.202 -0.865 N1 YY3 6 YY3 C28 C5 C 0 1 N N N 1.286 -48.486 13.305 -5.277 -0.608 -2.207 C28 YY3 7 YY3 C3 C6 C 0 1 Y N N 1.827 -50.988 14.792 -2.949 -1.699 -0.745 C3 YY3 8 YY3 C4 C7 C 0 1 Y N N 2.257 -51.756 15.883 -1.588 -1.906 -0.582 C4 YY3 9 YY3 O1 O1 O 0 1 N N N 3.384 -52.563 15.797 -1.083 -3.168 -0.628 O1 YY3 10 YY3 C14 C8 C 0 1 N N N 4.256 -52.214 14.743 -2.012 -4.232 -0.847 C14 YY3 11 YY3 C2 C9 C 0 1 Y N N 0.689 -50.202 14.923 -3.465 -0.412 -0.699 C2 YY3 12 YY3 C1 C10 C 0 1 Y N N -0.087 -50.180 16.114 -2.614 0.673 -0.489 C1 YY3 13 YY3 N N3 N 0 1 N N N -1.189 -49.383 16.261 -3.135 1.974 -0.442 N YY3 14 YY3 C7 C11 C 0 1 N N N -2.231 -49.678 17.060 -2.592 2.887 0.387 C7 YY3 15 YY3 O O2 O 0 1 N N N -2.274 -50.745 17.661 -1.598 2.610 1.031 O YY3 16 YY3 C8 C12 C 0 1 N N N -3.397 -48.677 17.218 -3.201 4.220 0.512 C8 YY3 17 YY3 C9 C13 C 0 1 N N N -4.596 -48.925 18.068 -2.665 5.122 1.330 C9 YY3 18 YY3 C6 C14 C 0 1 Y N N 0.377 -50.964 17.204 -1.253 0.464 -0.326 C6 YY3 19 YY3 C5 C15 C 0 1 Y N N 1.539 -51.745 17.102 -0.738 -0.823 -0.372 C5 YY3 20 YY3 N3 N4 N 0 1 N N N 2.039 -52.582 18.130 0.639 -1.035 -0.207 N3 YY3 21 YY3 C15 C16 C 0 1 Y N N 1.698 -52.593 19.485 1.536 -0.024 -0.508 C15 YY3 22 YY3 N5 N5 N 0 1 Y N N 0.969 -51.651 20.069 2.819 -0.198 -0.235 N5 YY3 23 YY3 N4 N6 N 0 1 Y N N 2.165 -53.615 20.209 1.087 1.091 -1.069 N4 YY3 24 YY3 C16 C17 C 0 1 Y N N 1.887 -53.718 21.568 1.913 2.081 -1.373 C16 YY3 25 YY3 C17 C18 C 0 1 Y N N 1.137 -52.743 22.189 3.261 1.946 -1.101 C17 YY3 26 YY3 C18 C19 C 0 1 Y N N 0.675 -51.686 21.396 3.707 0.756 -0.514 C18 YY3 27 YY3 C19 C20 C 0 1 Y N N -0.146 -50.602 22.012 5.140 0.561 -0.208 C19 YY3 28 YY3 C26 C21 C 0 1 Y N N -0.411 -49.394 21.476 5.756 -0.631 0.399 C26 YY3 29 YY3 C25 C22 C 0 1 Y N N -0.056 -48.818 20.307 5.261 -1.854 0.848 C25 YY3 30 YY3 C24 C23 C 0 1 Y N N -0.467 -47.530 19.965 6.117 -2.779 1.378 C24 YY3 31 YY3 C23 C24 C 0 1 Y N N -1.266 -46.834 20.866 7.475 -2.509 1.473 C23 YY3 32 YY3 C22 C25 C 0 1 Y N N -1.616 -47.437 22.071 7.983 -1.306 1.036 C22 YY3 33 YY3 C21 C26 C 0 1 Y N N -1.172 -48.726 22.353 7.130 -0.351 0.492 C21 YY3 34 YY3 N6 N7 N 0 1 Y N N -1.374 -49.508 23.404 7.329 0.913 -0.020 N6 YY3 35 YY3 C27 C27 C 0 1 N N N -2.158 -49.137 24.586 8.627 1.587 -0.109 C27 YY3 36 YY3 C20 C28 C 0 1 Y N N -0.751 -50.661 23.205 6.147 1.444 -0.438 C20 YY3 37 YY3 H1 H1 H 0 1 N N N -3.698 -49.097 10.389 -7.549 0.321 2.617 H1 YY3 38 YY3 H2 H2 H 0 1 N N N -2.554 -50.474 10.534 -7.986 -1.286 3.244 H2 YY3 39 YY3 H3 H3 H 0 1 N N N -3.992 -50.385 11.606 -6.345 -0.990 2.621 H3 YY3 40 YY3 H5 H5 H 0 1 N N N -2.491 -47.707 13.725 -9.496 0.129 1.046 H5 YY3 41 YY3 H6 H6 H 0 1 N N N -3.786 -47.463 12.504 -9.590 -1.311 0.003 H6 YY3 42 YY3 H7 H7 H 0 1 N N N -3.867 -48.858 13.633 -9.825 -1.467 1.760 H7 YY3 43 YY3 H8 H8 H 0 1 N N N -2.106 -49.934 13.973 -7.484 -0.692 -0.865 H8 YY3 44 YY3 H9 H9 H 0 1 N N N -2.351 -51.090 12.621 -7.128 0.619 0.284 H9 YY3 45 YY3 H10 H10 H 0 1 N N N -0.034 -51.320 12.871 -5.194 -0.667 1.153 H10 YY3 46 YY3 H11 H11 H 0 1 N N N -0.035 -49.910 11.759 -5.550 -1.979 0.004 H11 YY3 47 YY3 H12 H12 H 0 1 N N N 1.692 -47.888 14.134 -6.333 -0.369 -2.333 H12 YY3 48 YY3 H13 H13 H 0 1 N N N 2.098 -49.061 12.835 -4.692 -0.074 -2.956 H13 YY3 49 YY3 H14 H14 H 0 1 N N N 0.831 -47.818 12.559 -5.130 -1.681 -2.329 H14 YY3 50 YY3 H15 H15 H 0 1 N N N 2.374 -51.007 13.861 -3.607 -2.538 -0.913 H15 YY3 51 YY3 H16 H16 H 0 1 N N N 5.120 -52.895 14.740 -2.750 -4.240 -0.045 H16 YY3 52 YY3 H17 H17 H 0 1 N N N 3.723 -52.295 13.784 -2.516 -4.083 -1.802 H17 YY3 53 YY3 H18 H18 H 0 1 N N N 4.605 -51.180 14.883 -1.480 -5.183 -0.861 H18 YY3 54 YY3 H19 H19 H 0 1 N N N -1.222 -48.528 15.743 -3.886 2.216 -1.006 H19 YY3 55 YY3 H20 H20 H 0 1 N N N -3.340 -47.742 16.681 -4.083 4.467 -0.060 H20 YY3 56 YY3 H22 H22 H 0 1 N N N -5.375 -48.180 18.133 -1.783 4.875 1.903 H22 YY3 57 YY3 H23 H23 H 0 1 N N N -4.685 -49.850 18.619 -3.112 6.101 1.423 H23 YY3 58 YY3 H25 H25 H 0 1 N N N -0.176 -50.959 18.131 -0.593 1.304 -0.163 H25 YY3 59 YY3 H26 H26 H 0 1 N N N 2.726 -53.253 17.849 0.963 -1.889 0.119 H26 YY3 60 YY3 H27 H27 H 0 1 N N N 2.258 -54.559 22.135 1.536 2.984 -1.829 H27 YY3 61 YY3 H28 H28 H 0 1 N N N 0.915 -52.792 23.245 3.954 2.739 -1.339 H28 YY3 62 YY3 H29 H29 H 0 1 N N N 0.564 -49.371 19.617 4.205 -2.070 0.778 H29 YY3 63 YY3 H30 H30 H 0 1 N N N -0.173 -47.085 19.026 5.733 -3.727 1.726 H30 YY3 64 YY3 H31 H31 H 0 1 N N N -1.611 -45.837 20.633 8.139 -3.249 1.895 H31 YY3 65 YY3 H32 H32 H 0 1 N N N -2.230 -46.907 22.784 9.042 -1.105 1.114 H32 YY3 66 YY3 H33 H33 H 0 1 N N N -2.161 -49.972 25.302 9.093 1.352 -1.065 H33 YY3 67 YY3 H34 H34 H 0 1 N N N -1.711 -48.250 25.059 8.483 2.664 -0.029 H34 YY3 68 YY3 H35 H35 H 0 1 N N N -3.191 -48.910 24.284 9.269 1.244 0.702 H35 YY3 69 YY3 H36 H36 H 0 1 N N N -0.734 -51.500 23.885 6.027 2.421 -0.883 H36 YY3 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 YY3 C13 N2 SING N N 1 YY3 N2 C11 SING N N 2 YY3 N2 C12 SING N N 3 YY3 C10 C11 SING N N 4 YY3 C10 N1 SING N N 5 YY3 C28 N1 SING N N 6 YY3 N1 C2 SING N N 7 YY3 C14 O1 SING N N 8 YY3 C3 C2 DOUB Y N 9 YY3 C3 C4 SING Y N 10 YY3 C2 C1 SING Y N 11 YY3 O1 C4 SING N N 12 YY3 C4 C5 DOUB Y N 13 YY3 C1 N SING N N 14 YY3 C1 C6 DOUB Y N 15 YY3 N C7 SING N N 16 YY3 C7 C8 SING N N 17 YY3 C7 O DOUB N N 18 YY3 C5 C6 SING Y N 19 YY3 C5 N3 SING N N 20 YY3 C8 C9 DOUB N N 21 YY3 N3 C15 SING N N 22 YY3 C15 N5 DOUB Y N 23 YY3 C15 N4 SING Y N 24 YY3 C24 C25 DOUB Y N 25 YY3 C24 C23 SING Y N 26 YY3 N5 C18 SING Y N 27 YY3 N4 C16 DOUB Y N 28 YY3 C25 C26 SING Y N 29 YY3 C23 C22 DOUB Y N 30 YY3 C18 C19 SING N N 31 YY3 C18 C17 DOUB Y N 32 YY3 C26 C19 SING Y N 33 YY3 C26 C21 DOUB Y N 34 YY3 C16 C17 SING Y N 35 YY3 C19 C20 DOUB Y N 36 YY3 C22 C21 SING Y N 37 YY3 C21 N6 SING Y N 38 YY3 C20 N6 SING Y N 39 YY3 N6 C27 SING N N 40 YY3 C13 H1 SING N N 41 YY3 C13 H2 SING N N 42 YY3 C13 H3 SING N N 43 YY3 C12 H5 SING N N 44 YY3 C12 H6 SING N N 45 YY3 C12 H7 SING N N 46 YY3 C11 H8 SING N N 47 YY3 C11 H9 SING N N 48 YY3 C10 H10 SING N N 49 YY3 C10 H11 SING N N 50 YY3 C28 H12 SING N N 51 YY3 C28 H13 SING N N 52 YY3 C28 H14 SING N N 53 YY3 C3 H15 SING N N 54 YY3 C14 H16 SING N N 55 YY3 C14 H17 SING N N 56 YY3 C14 H18 SING N N 57 YY3 N H19 SING N N 58 YY3 C8 H20 SING N N 59 YY3 C9 H22 SING N N 60 YY3 C9 H23 SING N N 61 YY3 C6 H25 SING N N 62 YY3 N3 H26 SING N N 63 YY3 C16 H27 SING N N 64 YY3 C17 H28 SING N N 65 YY3 C25 H29 SING N N 66 YY3 C24 H30 SING N N 67 YY3 C23 H31 SING N N 68 YY3 C22 H32 SING N N 69 YY3 C27 H33 SING N N 70 YY3 C27 H34 SING N N 71 YY3 C27 H35 SING N N 72 YY3 C20 H36 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 YY3 SMILES ACDLabs 12.01 "CN(CCN(c1cc(c(cc1NC(\C=C)=O)Nc2nc(ccn2)c3cn(c4c3cccc4)C)OC)C)C" YY3 InChI InChI 1.03 "InChI=1S/C28H33N7O2/c1-7-27(36)30-22-16-23(26(37-6)17-25(22)34(4)15-14-33(2)3)32-28-29-13-12-21(31-28)20-18-35(5)24-11-9-8-10-19(20)24/h7-13,16-18H,1,14-15H2,2-6H3,(H,30,36)(H,29,31,32)" YY3 InChIKey InChI 1.03 DUYJMQONPNNFPI-UHFFFAOYSA-N YY3 SMILES_CANONICAL CACTVS 3.385 "COc1cc(N(C)CCN(C)C)c(NC(=O)C=C)cc1Nc2nccc(n2)c3cn(C)c4ccccc34" YY3 SMILES CACTVS 3.385 "COc1cc(N(C)CCN(C)C)c(NC(=O)C=C)cc1Nc2nccc(n2)c3cn(C)c4ccccc34" YY3 SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "Cn1cc(c2c1cccc2)c3ccnc(n3)Nc4cc(c(cc4OC)N(C)CCN(C)C)NC(=O)C=C" YY3 SMILES "OpenEye OEToolkits" 1.9.2 "Cn1cc(c2c1cccc2)c3ccnc(n3)Nc4cc(c(cc4OC)N(C)CCN(C)C)NC(=O)C=C" # # 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 YY3 "SYSTEMATIC NAME" ACDLabs 12.01 "N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)prop-2-enamide" YY3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "N-[2-[2-(dimethylamino)ethyl-methyl-amino]-4-methoxy-5-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]phenyl]prop-2-enamide" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site YY3 "Create component" 2015-04-14 RCSB YY3 "Modify formula" 2015-04-14 RCSB YY3 "Initial release" 2015-11-11 RCSB YY3 "Modify synonyms" 2020-08-31 RCSB YY3 "Modify synonyms" 2021-03-13 RCSB # # loop_ _pdbx_chem_comp_synonyms.ordinal _pdbx_chem_comp_synonyms.comp_id _pdbx_chem_comp_synonyms.name _pdbx_chem_comp_synonyms.provenance _pdbx_chem_comp_synonyms.type 1 YY3 Osimertinib PDB ? 2 YY3 "AZD 9291" PDB ? ##