data_GS3 # _chem_comp.id GS3 _chem_comp.name "2-fluoro-6-{[2-({2-methoxy-4-[4-(1-methylethyl)piperazin-1-yl]phenyl}amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}benzamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C27 H31 F N8 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2008-09-24 _chem_comp.pdbx_modified_date 2011-06-04 _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 518.586 _chem_comp.one_letter_code ? _chem_comp.three_letter_code GS3 _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 3EKN _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 GS3 C1 C1 C 0 1 N N N -0.116 19.872 20.551 -2.253 3.773 -1.756 C1 GS3 1 GS3 O1 O1 O 0 1 N N N 1.132 19.669 19.898 -1.364 2.794 -1.213 O1 GS3 2 GS3 C2 C2 C 0 1 Y N N 2.162 19.955 20.796 -1.923 1.650 -0.736 C2 GS3 3 GS3 C3 C3 C 0 1 Y N N 1.938 20.089 22.150 -3.295 1.474 -0.790 C3 GS3 4 GS3 C4 C4 C 0 1 Y N N 2.977 20.393 23.006 -3.864 0.305 -0.303 C4 GS3 5 GS3 C5 C5 C 0 1 Y N N 4.239 20.537 22.459 -3.057 -0.687 0.238 C5 GS3 6 GS3 C6 C6 C 0 1 Y N N 4.471 20.387 21.108 -1.687 -0.513 0.293 C6 GS3 7 GS3 C7 C7 C 0 1 Y N N 3.424 20.098 20.255 -1.115 0.651 -0.198 C7 GS3 8 GS3 N1 N1 N 0 1 N N N 3.546 19.938 18.854 0.276 0.825 -0.147 N1 GS3 9 GS3 C8 C8 C 0 1 Y N N 4.596 20.336 18.013 1.112 -0.280 -0.113 C8 GS3 10 GS3 N2 N2 N 0 1 Y N N 5.563 21.119 18.505 2.414 -0.091 0.056 N2 GS3 11 GS3 C9 C9 C 0 1 Y N N 6.587 21.497 17.727 3.256 -1.119 0.095 C9 GS3 12 GS3 N3 N3 N 0 1 N N N 7.638 22.317 18.172 4.614 -0.917 0.272 N3 GS3 13 GS3 C10 C10 C 0 1 Y N N 7.822 22.810 19.474 5.098 0.361 0.532 C10 GS3 14 GS3 C11 C11 C 0 1 Y N N 6.766 23.165 20.289 4.274 1.315 1.111 C11 GS3 15 GS3 C12 C12 C 0 1 Y N N 6.993 23.653 21.557 4.756 2.583 1.369 C12 GS3 16 GS3 C13 C13 C 0 1 Y N N 8.276 23.799 22.041 6.062 2.915 1.053 C13 GS3 17 GS3 C14 C14 C 0 1 Y N N 9.338 23.452 21.234 6.899 1.980 0.476 C14 GS3 18 GS3 F1 F1 F 0 1 N N N 10.618 23.578 21.659 8.173 2.309 0.170 F1 GS3 19 GS3 C15 C15 C 0 1 Y N N 9.101 22.968 19.966 6.426 0.689 0.214 C15 GS3 20 GS3 C16 C16 C 0 1 N N N 10.274 22.607 19.156 7.314 -0.316 -0.396 C16 GS3 21 GS3 O2 O2 O 0 1 N N N 10.376 22.948 17.988 7.373 -0.420 -1.606 O2 GS3 22 GS3 N4 N4 N 0 1 N N N 11.190 21.869 19.861 8.059 -1.121 0.387 N4 GS3 23 GS3 C17 C17 C 0 1 Y N N 6.600 21.056 16.415 2.735 -2.415 -0.046 C17 GS3 24 GS3 C18 C18 C 0 1 Y N N 7.466 21.228 15.305 3.304 -3.762 -0.059 C18 GS3 25 GS3 C19 C19 C 0 1 Y N N 6.924 20.533 14.252 2.281 -4.614 -0.235 C19 GS3 26 GS3 N5 N5 N 0 1 Y N N 5.770 19.949 14.684 1.105 -3.913 -0.335 N5 GS3 27 GS3 C20 C20 C 0 1 Y N N 5.561 20.259 16.001 1.348 -2.572 -0.224 C20 GS3 28 GS3 N6 N6 N 0 1 Y N N 4.536 19.865 16.757 0.580 -1.484 -0.246 N6 GS3 29 GS3 N7 N7 N 0 1 N N N 2.747 20.531 24.395 -5.251 0.126 -0.357 N7 GS3 30 GS3 C21 C21 C 0 1 N N N 3.997 20.454 25.127 -5.637 -1.174 0.208 C21 GS3 31 GS3 C22 C22 C 0 1 N N N 3.658 20.165 26.566 -7.148 -1.365 0.058 C22 GS3 32 GS3 N8 N8 N 0 1 N N N 2.842 21.304 27.063 -7.848 -0.268 0.741 N8 GS3 33 GS3 C23 C23 C 0 1 N N N 1.621 21.586 26.231 -7.462 1.033 0.176 C23 GS3 34 GS3 C24 C24 C 0 1 N N N 1.985 21.725 24.759 -5.950 1.223 0.326 C24 GS3 35 GS3 C25 C25 C 0 1 N N N 2.596 21.203 28.541 -9.303 -0.455 0.684 C25 GS3 36 GS3 C26 C26 C 0 1 N N N 3.910 21.389 29.275 -9.991 0.635 1.509 C26 GS3 37 GS3 C27 C27 C 0 1 N N N 1.714 22.351 28.962 -9.773 -0.367 -0.769 C27 GS3 38 GS3 H1 H1 H 0 1 N N N 0.043 19.924 21.638 -1.679 4.634 -2.100 H1 GS3 39 GS3 H1A H1A H 0 1 N N N -0.564 20.813 20.200 -2.799 3.342 -2.596 H1A GS3 40 GS3 H1B H1B H 0 1 N N N -0.791 19.035 20.319 -2.958 4.090 -0.988 H1B GS3 41 GS3 H3 H3 H 0 1 N N N 0.941 19.955 22.544 -3.923 2.246 -1.211 H3 GS3 42 GS3 H5 H5 H 0 1 N N N 5.068 20.774 23.110 -3.501 -1.596 0.617 H5 GS3 43 GS3 H6 H6 H 0 1 N N N 5.472 20.496 20.717 -1.061 -1.285 0.715 H6 GS3 44 GS3 HN1 HN1 H 0 1 N N N 2.780 19.479 18.403 0.654 1.718 -0.136 HN1 GS3 45 GS3 HN3 HN3 H 0 1 N N N 8.325 22.576 17.492 5.227 -1.666 0.216 HN3 GS3 46 GS3 H11 H11 H 0 1 N N N 5.753 23.059 19.929 3.253 1.066 1.361 H11 GS3 47 GS3 H12 H12 H 0 1 N N N 6.154 23.925 22.181 4.109 3.322 1.819 H12 GS3 48 GS3 H13 H13 H 0 1 N N N 8.446 24.179 23.037 6.428 3.910 1.258 H13 GS3 49 GS3 HN4 HN4 H 0 1 N N N 10.877 21.720 20.799 8.011 -1.038 1.352 HN4 GS3 50 GS3 HN4A HN4A H 0 0 N N N 12.053 21.527 19.488 8.643 -1.783 -0.014 HN4A GS3 51 GS3 H18 H18 H 0 1 N N N 8.382 21.800 15.291 4.346 -4.022 0.051 H18 GS3 52 GS3 H19 H19 H 0 1 N N N 7.339 20.462 13.257 2.370 -5.688 -0.289 H19 GS3 53 GS3 HN5 HN5 H 0 1 N N N 5.168 19.380 14.124 0.230 -4.311 -0.464 HN5 GS3 54 GS3 H21 H21 H 0 1 N N N 4.628 19.652 24.717 -5.115 -1.971 -0.322 H21 GS3 55 GS3 H21A H21A H 0 0 N N N 4.555 21.398 25.042 -5.370 -1.205 1.265 H21A GS3 56 GS3 H22 H22 H 0 1 N N N 3.088 19.227 26.642 -7.412 -1.361 -0.999 H22 GS3 57 GS3 H22A H22A H 0 0 N N N 4.573 20.050 27.166 -7.441 -2.316 0.503 H22A GS3 58 GS3 H23 H23 H 0 1 N N N 0.910 20.755 26.347 -7.729 1.063 -0.881 H23 GS3 59 GS3 H23A H23A H 0 0 N N N 1.173 22.531 26.573 -7.983 1.829 0.706 H23A GS3 60 GS3 H24 H24 H 0 1 N N N 2.591 22.629 24.599 -5.687 1.220 1.383 H24 GS3 61 GS3 H24A H24A H 0 0 N N N 1.082 21.818 24.138 -5.657 2.174 -0.119 H24A GS3 62 GS3 H25 H25 H 0 1 N N N 2.140 20.228 28.767 -9.560 -1.434 1.090 H25 GS3 63 GS3 H26 H26 H 0 1 N N N 4.734 21.434 28.547 -11.071 0.496 1.467 H26 GS3 64 GS3 H26A H26A H 0 0 N N N 3.878 22.325 29.851 -9.657 0.572 2.545 H26A GS3 65 GS3 H26B H26B H 0 0 N N N 4.071 20.542 29.959 -9.734 1.613 1.104 H26B GS3 66 GS3 H27 H27 H 0 1 N N N 1.499 22.274 30.038 -9.283 -1.143 -1.357 H27 GS3 67 GS3 H27A H27A H 0 0 N N N 2.228 23.302 28.758 -10.853 -0.506 -0.812 H27A GS3 68 GS3 H27B H27B H 0 0 N N N 0.771 22.315 28.397 -9.516 0.612 -1.175 H27B GS3 69 # 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 GS3 C1 O1 SING N N 1 GS3 O1 C2 SING N N 2 GS3 C2 C3 DOUB Y N 3 GS3 C2 C7 SING Y N 4 GS3 C3 C4 SING Y N 5 GS3 C4 C5 DOUB Y N 6 GS3 C4 N7 SING N N 7 GS3 C5 C6 SING Y N 8 GS3 C6 C7 DOUB Y N 9 GS3 C7 N1 SING N N 10 GS3 N1 C8 SING N N 11 GS3 C8 N2 DOUB Y N 12 GS3 C8 N6 SING Y N 13 GS3 N2 C9 SING Y N 14 GS3 C9 N3 SING N N 15 GS3 C9 C17 DOUB Y N 16 GS3 N3 C10 SING N N 17 GS3 C10 C11 DOUB Y N 18 GS3 C10 C15 SING Y N 19 GS3 C11 C12 SING Y N 20 GS3 C12 C13 DOUB Y N 21 GS3 C13 C14 SING Y N 22 GS3 C14 F1 SING N N 23 GS3 C14 C15 DOUB Y N 24 GS3 C15 C16 SING N N 25 GS3 C16 O2 DOUB N N 26 GS3 C16 N4 SING N N 27 GS3 C17 C18 SING Y N 28 GS3 C17 C20 SING Y N 29 GS3 C18 C19 DOUB Y N 30 GS3 C19 N5 SING Y N 31 GS3 N5 C20 SING Y N 32 GS3 C20 N6 DOUB Y N 33 GS3 N7 C21 SING N N 34 GS3 N7 C24 SING N N 35 GS3 C21 C22 SING N N 36 GS3 C22 N8 SING N N 37 GS3 N8 C23 SING N N 38 GS3 N8 C25 SING N N 39 GS3 C23 C24 SING N N 40 GS3 C25 C26 SING N N 41 GS3 C25 C27 SING N N 42 GS3 C1 H1 SING N N 43 GS3 C1 H1A SING N N 44 GS3 C1 H1B SING N N 45 GS3 C3 H3 SING N N 46 GS3 C5 H5 SING N N 47 GS3 C6 H6 SING N N 48 GS3 N1 HN1 SING N N 49 GS3 N3 HN3 SING N N 50 GS3 C11 H11 SING N N 51 GS3 C12 H12 SING N N 52 GS3 C13 H13 SING N N 53 GS3 N4 HN4 SING N N 54 GS3 N4 HN4A SING N N 55 GS3 C18 H18 SING N N 56 GS3 C19 H19 SING N N 57 GS3 N5 HN5 SING N N 58 GS3 C21 H21 SING N N 59 GS3 C21 H21A SING N N 60 GS3 C22 H22 SING N N 61 GS3 C22 H22A SING N N 62 GS3 C23 H23 SING N N 63 GS3 C23 H23A SING N N 64 GS3 C24 H24 SING N N 65 GS3 C24 H24A SING N N 66 GS3 C25 H25 SING N N 67 GS3 C26 H26 SING N N 68 GS3 C26 H26A SING N N 69 GS3 C26 H26B SING N N 70 GS3 C27 H27 SING N N 71 GS3 C27 H27A SING N N 72 GS3 C27 H27B 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 GS3 SMILES ACDLabs 10.04 "Fc1cccc(c1C(=O)N)Nc3nc(nc2nccc23)Nc5ccc(N4CCN(C(C)C)CC4)cc5OC" GS3 SMILES_CANONICAL CACTVS 3.341 "COc1cc(ccc1Nc2nc3[nH]ccc3c(Nc4cccc(F)c4C(N)=O)n2)N5CCN(CC5)C(C)C" GS3 SMILES CACTVS 3.341 "COc1cc(ccc1Nc2nc3[nH]ccc3c(Nc4cccc(F)c4C(N)=O)n2)N5CCN(CC5)C(C)C" GS3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CC(C)N1CCN(CC1)c2ccc(c(c2)OC)Nc3nc4c(cc[nH]4)c(n3)Nc5cccc(c5C(=O)N)F" GS3 SMILES "OpenEye OEToolkits" 1.5.0 "CC(C)N1CCN(CC1)c2ccc(c(c2)OC)Nc3nc4c(cc[nH]4)c(n3)Nc5cccc(c5C(=O)N)F" GS3 InChI InChI 1.03 "InChI=1S/C27H31FN8O2/c1-16(2)35-11-13-36(14-12-35)17-7-8-20(22(15-17)38-3)32-27-33-25-18(9-10-30-25)26(34-27)31-21-6-4-5-19(28)23(21)24(29)37/h4-10,15-16H,11-14H2,1-3H3,(H2,29,37)(H3,30,31,32,33,34)" GS3 InChIKey InChI 1.03 HXZDICYKFAOZLE-UHFFFAOYSA-N # 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 GS3 "SYSTEMATIC NAME" ACDLabs 10.04 "2-fluoro-6-{[2-({2-methoxy-4-[4-(1-methylethyl)piperazin-1-yl]phenyl}amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}benzamide" GS3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-fluoro-6-[[2-[[2-methoxy-4-(4-propan-2-ylpiperazin-1-yl)phenyl]amino]-7H-pyrrolo[3,2-e]pyrimidin-4-yl]amino]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 GS3 "Create component" 2008-09-24 RCSB GS3 "Modify aromatic_flag" 2011-06-04 RCSB GS3 "Modify descriptor" 2011-06-04 RCSB #