data_STI # _chem_comp.id STI _chem_comp.name "4-(4-METHYL-PIPERAZIN-1-YLMETHYL)-N-[4-METHYL-3-(4-PYRIDIN-3-YL-PYRIMIDIN-2-YLAMINO)-PHENYL]-BENZAMIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C29 H31 N7 O" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "STI-571; IMATINIB" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2001-04-11 _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 493.603 _chem_comp.one_letter_code ? _chem_comp.three_letter_code STI _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details ? _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 1IEP _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 STI C1 C1 C 0 1 Y N N 16.356 100.406 50.614 2.740 -0.022 8.889 C1 STI 1 STI C6 C6 C 0 1 Y N N 15.218 100.012 51.414 1.914 0.207 7.802 C6 STI 2 STI C5 C5 C 0 1 Y N N 15.089 100.453 52.798 2.435 0.009 6.520 C5 STI 3 STI C4 C4 C 0 1 Y N N 16.138 101.298 53.339 3.755 -0.413 6.387 C4 STI 4 STI N3 N3 N 0 1 Y N N 17.220 101.660 52.543 4.505 -0.614 7.452 N3 STI 5 STI C2 C2 C 0 1 Y N N 17.356 101.243 51.215 4.042 -0.436 8.674 C2 STI 6 STI C7 C7 C 0 1 Y N N 13.928 100.078 53.673 1.593 0.241 5.321 C7 STI 7 STI C12 C12 C 0 1 Y N N 12.723 99.470 53.173 2.131 0.848 4.183 C12 STI 8 STI C11 C11 C 0 1 Y N N 11.704 99.172 54.114 1.308 1.042 3.088 C11 STI 9 STI N10 N10 N 0 1 Y N N 11.881 99.464 55.456 0.045 0.651 3.150 N10 STI 10 STI C9 C9 C 0 1 Y N N 13.053 100.050 55.907 -0.438 0.077 4.242 C9 STI 11 STI N8 N8 N 0 1 Y N N 14.046 100.345 55.023 0.313 -0.122 5.314 N8 STI 12 STI N13 N13 N 0 1 N N N 13.263 100.362 57.253 -1.765 -0.317 4.266 N13 STI 13 STI C14 C14 C 0 1 Y N N 12.302 100.109 58.246 -2.541 -0.230 3.106 C14 STI 14 STI C19 C19 C 0 1 Y N N 11.195 101.040 58.488 -3.901 0.040 3.198 C19 STI 15 STI C18 C18 C 0 1 Y N N 10.251 100.722 59.524 -4.669 0.126 2.052 C18 STI 16 STI C17 C17 C 0 1 Y N N 10.386 99.520 60.309 -4.087 -0.056 0.812 C17 STI 17 STI C16 C16 C 0 1 Y N N 11.456 98.610 60.086 -2.728 -0.327 0.714 C16 STI 18 STI C15 C15 C 0 1 Y N N 12.424 98.921 59.032 -1.955 -0.419 1.862 C15 STI 19 STI N21 N21 N 0 1 N N N 11.516 97.436 60.923 -2.140 -0.512 -0.541 N21 STI 20 STI C22 C22 C 0 1 N N N 12.446 96.415 60.910 -2.547 0.228 -1.591 C22 STI 21 STI C23 C23 C 0 1 Y N N 12.472 95.442 62.042 -1.994 -0.031 -2.937 C23 STI 22 STI C25 C25 C 0 1 Y N N 13.689 94.696 62.364 -2.413 0.734 -4.027 C25 STI 23 STI C26 C26 C 0 1 Y N N 13.682 93.749 63.449 -1.892 0.486 -5.280 C26 STI 24 STI C27 C27 C 0 1 Y N N 12.463 93.546 64.214 -0.957 -0.517 -5.458 C27 STI 25 STI C28 C28 C 0 1 Y N N 11.274 94.301 63.879 -0.542 -1.283 -4.384 C28 STI 26 STI C29 C29 C 0 1 Y N N 11.272 95.230 62.817 -1.050 -1.042 -3.124 C29 STI 27 STI C46 C46 C 0 1 N N N 12.371 92.542 65.368 -0.393 -0.781 -6.830 C46 STI 28 STI N48 N48 N 0 1 N N N 11.230 91.579 65.364 0.809 0.038 -7.032 N48 STI 29 STI C53 C53 C 0 1 N N N 11.214 90.778 64.093 1.306 -0.264 -8.379 C53 STI 30 STI C52 C52 C 0 1 N N N 10.031 89.776 64.067 2.629 0.463 -8.615 C52 STI 31 STI N51 N51 N 0 1 N N N 10.081 88.858 65.278 3.638 -0.027 -7.668 N51 STI 32 STI C54 C54 C 0 1 N N N 8.985 87.875 65.306 4.840 0.792 -7.870 C54 STI 33 STI C50 C50 C 0 1 N N N 10.070 89.659 66.572 3.141 0.276 -6.321 C50 STI 34 STI C49 C49 C 0 1 N N N 11.273 90.652 66.574 1.817 -0.452 -6.085 C49 STI 35 STI O29 O29 O 0 1 N N N 13.258 96.231 60.024 -3.368 1.110 -1.431 O29 STI 36 STI C20 C20 C 0 1 N N N 10.986 102.351 57.694 -4.539 0.240 4.548 C20 STI 37 STI H11 1H1 H 0 1 N N N 16.459 100.074 49.566 2.371 0.120 9.894 H11 STI 38 STI H61 1H6 H 0 1 N N N 14.441 99.369 50.964 0.893 0.532 7.941 H61 STI 39 STI H41 1H4 H 0 1 N N N 16.112 101.672 54.376 4.171 -0.570 5.403 H41 STI 40 STI H21 1H2 H 0 1 N N N 18.243 101.570 50.647 4.689 -0.616 9.519 H21 STI 41 STI H121 1H12 H 0 0 N N N 12.584 99.239 52.103 3.166 1.157 4.159 H121 STI 42 STI H111 1H11 H 0 0 N N N 10.756 98.704 53.796 1.692 1.508 2.193 H111 STI 43 STI H131 1H13 H 0 0 N N N 13.506 101.351 57.305 -2.157 -0.654 5.087 H131 STI 44 STI H181 1H18 H 0 0 N N N 9.411 101.410 59.719 -5.725 0.336 2.126 H181 STI 45 STI H171 1H17 H 0 0 N N N 9.652 99.290 61.100 -4.690 0.011 -0.080 H171 STI 46 STI H151 1H15 H 0 0 N N N 13.268 98.241 58.824 -0.899 -0.630 1.788 H151 STI 47 STI H211 1H21 H 0 0 N N N 10.792 97.308 61.630 -1.440 -1.173 -0.656 H211 STI 48 STI H251 1H25 H 0 0 N N N 14.616 94.848 61.786 -3.142 1.518 -3.889 H251 STI 49 STI H261 1H26 H 0 0 N N N 14.599 93.186 63.691 -2.216 1.077 -6.124 H261 STI 50 STI H281 1H28 H 0 0 N N N 10.340 94.164 64.450 0.187 -2.065 -4.530 H281 STI 51 STI H291 1H29 H 0 0 N N N 10.344 95.783 62.595 -0.722 -1.638 -2.285 H291 STI 52 STI H461 1H46 H 0 0 N N N 13.328 91.975 65.438 -1.137 -0.526 -7.585 H461 STI 53 STI H462 2H46 H 0 0 N N N 12.381 93.094 66.336 -0.132 -1.836 -6.919 H462 STI 54 STI H531 1H53 H 0 0 N N N 11.208 91.438 63.194 0.574 0.063 -9.118 H531 STI 55 STI H532 2H53 H 0 0 N N N 12.188 90.263 63.923 1.460 -1.339 -8.475 H532 STI 56 STI H521 1H52 H 0 0 N N N 9.048 90.297 63.982 2.486 1.533 -8.470 H521 STI 57 STI H522 2H52 H 0 0 N N N 9.996 89.200 63.112 2.968 0.278 -9.635 H522 STI 58 STI H541 1H54 H 0 0 N N N 9.021 87.201 66.194 5.623 0.464 -7.185 H541 STI 59 STI H542 2H54 H 0 0 N N N 7.994 88.382 65.233 5.187 0.682 -8.897 H542 STI 60 STI H543 3H54 H 0 0 N N N 8.957 87.284 64.360 4.603 1.838 -7.676 H543 STI 61 STI H501 1H50 H 0 0 N N N 9.096 90.174 66.741 3.872 -0.052 -5.582 H501 STI 62 STI H502 2H50 H 0 0 N N N 10.061 89.004 67.474 2.986 1.350 -6.225 H502 STI 63 STI H491 1H49 H 0 0 N N N 12.247 90.113 66.642 1.478 -0.267 -5.065 H491 STI 64 STI H492 2H49 H 0 0 N N N 11.327 91.226 67.527 1.961 -1.522 -6.230 H492 STI 65 STI H201 1H20 H 0 0 N N N 10.144 103.058 57.878 -4.890 -0.718 4.930 H201 STI 66 STI H202 2H20 H 0 0 N N N 11.931 102.936 57.771 -3.807 0.661 5.237 H202 STI 67 STI H203 3H20 H 0 0 N N N 10.957 102.079 56.612 -5.383 0.924 4.453 H203 STI 68 # # 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 STI C1 C6 DOUB Y N 1 STI C1 C2 SING Y N 2 STI C1 H11 SING N N 3 STI C6 C5 SING Y N 4 STI C6 H61 SING N N 5 STI C5 C4 DOUB Y N 6 STI C5 C7 SING Y N 7 STI C4 N3 SING Y N 8 STI C4 H41 SING N N 9 STI N3 C2 DOUB Y N 10 STI C2 H21 SING N N 11 STI C7 C12 DOUB Y N 12 STI C7 N8 SING Y N 13 STI C12 C11 SING Y N 14 STI C12 H121 SING N N 15 STI C11 N10 DOUB Y N 16 STI C11 H111 SING N N 17 STI N10 C9 SING Y N 18 STI C9 N8 DOUB Y N 19 STI C9 N13 SING N N 20 STI N13 C14 SING N N 21 STI N13 H131 SING N N 22 STI C14 C19 DOUB Y N 23 STI C14 C15 SING Y N 24 STI C19 C18 SING Y N 25 STI C19 C20 SING N N 26 STI C18 C17 DOUB Y N 27 STI C18 H181 SING N N 28 STI C17 C16 SING Y N 29 STI C17 H171 SING N N 30 STI C16 C15 DOUB Y N 31 STI C16 N21 SING N N 32 STI C15 H151 SING N N 33 STI N21 C22 SING N N 34 STI N21 H211 SING N N 35 STI C22 C23 SING N N 36 STI C22 O29 DOUB N N 37 STI C23 C25 DOUB Y N 38 STI C23 C29 SING Y N 39 STI C25 C26 SING Y N 40 STI C25 H251 SING N N 41 STI C26 C27 DOUB Y N 42 STI C26 H261 SING N N 43 STI C27 C28 SING Y N 44 STI C27 C46 SING N N 45 STI C28 C29 DOUB Y N 46 STI C28 H281 SING N N 47 STI C29 H291 SING N N 48 STI C46 N48 SING N N 49 STI C46 H461 SING N N 50 STI C46 H462 SING N N 51 STI N48 C53 SING N N 52 STI N48 C49 SING N N 53 STI C53 C52 SING N N 54 STI C53 H531 SING N N 55 STI C53 H532 SING N N 56 STI C52 N51 SING N N 57 STI C52 H521 SING N N 58 STI C52 H522 SING N N 59 STI N51 C54 SING N N 60 STI N51 C50 SING N N 61 STI C54 H541 SING N N 62 STI C54 H542 SING N N 63 STI C54 H543 SING N N 64 STI C50 C49 SING N N 65 STI C50 H501 SING N N 66 STI C50 H502 SING N N 67 STI C49 H491 SING N N 68 STI C49 H492 SING N N 69 STI C20 H201 SING N N 70 STI C20 H202 SING N N 71 STI C20 H203 SING N N 72 # # 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 STI SMILES ACDLabs 10.04 "O=C(Nc3ccc(c(Nc2nc(c1cccnc1)ccn2)c3)C)c4ccc(cc4)CN5CCN(CC5)C" STI SMILES_CANONICAL CACTVS 3.341 "CN1CCN(CC1)Cc2ccc(cc2)C(=O)Nc3ccc(C)c(Nc4nccc(n4)c5cccnc5)c3" STI SMILES CACTVS 3.341 "CN1CCN(CC1)Cc2ccc(cc2)C(=O)Nc3ccc(C)c(Nc4nccc(n4)c5cccnc5)c3" STI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "Cc1ccc(cc1Nc2nccc(n2)c3cccnc3)NC(=O)c4ccc(cc4)CN5CCN(CC5)C" STI SMILES "OpenEye OEToolkits" 1.5.0 "Cc1ccc(cc1Nc2nccc(n2)c3cccnc3)NC(=O)c4ccc(cc4)CN5CCN(CC5)C" STI InChI InChI 1.03 "InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)" STI InChIKey InChI 1.03 KTUFNOKKBVMGRW-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 STI "SYSTEMATIC NAME" ACDLabs 10.04 "4-[(4-methylpiperazin-1-yl)methyl]-N-{4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl}benzamide" STI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "4-[(4-methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]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 STI "Create component" 2001-04-11 RCSB STI "Modify aromatic_flag" 2011-06-04 RCSB STI "Modify descriptor" 2011-06-04 RCSB STI "Modify synonyms" 2020-06-05 PDBE # # 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 STI STI-571 ? ? 2 STI IMATINIB ? ? ##