data_38O # _chem_comp.id 38O _chem_comp.name "4-amino-5-fluoro-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H21 F N6 O" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms Dovitinib _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2014-07-09 _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 392.429 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 38O _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 4TYI _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # # 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 38O C1 C1 C 0 1 N N N -3.399 -5.392 5.855 8.683 1.536 0.419 C1 38O 1 38O C3 C2 C 0 1 N N N -2.708 -7.655 5.251 7.170 -0.059 -0.597 C3 38O 2 38O C4 C3 C 0 1 N N N -1.488 -8.437 4.743 5.827 -0.772 -0.421 C4 38O 3 38O C6 C4 C 0 1 N N N -0.045 -7.104 6.231 4.947 1.168 0.727 C6 38O 4 38O C7 C5 C 0 1 N N N -1.268 -6.257 6.615 6.289 1.882 0.551 C7 38O 5 38O C8 C6 C 0 1 Y N N 0.057 -9.672 6.398 3.496 -0.396 -0.294 C8 38O 6 38O C12 C7 C 0 1 Y N N 0.358 -14.149 7.461 -1.013 -0.782 -0.041 C12 38O 7 38O N13 N1 N 0 1 Y N N 1.346 -13.360 7.875 -0.322 -1.965 -0.051 N13 38O 8 38O C15 C8 C 0 1 Y N N 1.796 -10.860 7.640 2.186 -2.409 -0.170 C15 38O 9 38O C16 C9 C 0 1 Y N N 1.285 -9.699 7.103 3.413 -1.786 -0.256 C16 38O 10 38O C17 C10 C 0 1 N N N 0.271 -15.629 7.679 -2.478 -0.657 0.035 C17 38O 11 38O C18 C11 C 0 1 N N N -0.538 -16.505 6.893 -3.084 0.596 -0.093 C18 38O 12 38O C21 C12 C 0 1 Y N N -1.306 -18.901 6.485 -5.216 1.892 -0.131 C21 38O 13 38O C23 C13 C 0 1 Y N N -1.258 -20.248 6.810 -6.593 1.926 -0.048 C23 38O 14 38O C24 C14 C 0 1 Y N N -0.444 -20.696 7.846 -7.312 0.757 0.153 C24 38O 15 38O O29 O1 O 0 1 N N N 1.757 -15.527 9.418 -2.744 -2.894 0.340 O29 38O 16 38O N2 N2 N 0 1 N N N -2.271 -6.279 5.538 7.369 0.885 0.512 N2 38O 17 38O N5 N3 N 0 1 N N N -0.475 -8.470 5.832 4.748 0.224 -0.382 N5 38O 18 38O C9 C15 C 0 1 Y N N -0.619 -10.894 6.264 2.349 0.374 -0.250 C9 38O 19 38O C10 C16 C 0 1 Y N N -0.098 -12.067 6.794 1.099 -0.248 -0.169 C10 38O 20 38O N11 N4 N 0 1 Y N N -0.552 -13.362 6.792 -0.171 0.224 -0.111 N11 38O 21 38O C14 C17 C 0 1 Y N N 1.115 -12.076 7.491 1.025 -1.651 -0.131 C14 38O 22 38O N19 N5 N 0 1 N N N -1.326 -16.080 5.839 -2.331 1.728 -0.292 N19 38O 23 38O C20 C18 C 0 1 Y N N -0.528 -17.960 7.204 -4.547 0.668 -0.010 C20 38O 24 38O F22 F1 F 0 1 N N N -2.106 -18.504 5.471 -4.519 3.032 -0.328 F22 38O 25 38O C25 C19 C 0 1 Y N N 0.328 -19.800 8.567 -6.666 -0.455 0.275 C25 38O 26 38O C26 C20 C 0 1 Y N N 0.295 -18.436 8.256 -5.279 -0.516 0.194 C26 38O 27 38O N27 N6 N 0 1 N N N 1.058 -17.543 8.980 -4.619 -1.723 0.313 N27 38O 28 38O C28 C21 C 0 1 N N N 1.051 -16.222 8.720 -3.281 -1.804 0.233 C28 38O 29 38O H1 H1 H 0 1 N N N -3.023 -4.379 6.061 8.753 2.082 -0.521 H1 38O 30 38O H2 H2 H 0 1 N N N -4.091 -5.359 5.000 8.804 2.229 1.252 H2 38O 31 38O H3 H3 H 0 1 N N N -3.928 -5.774 6.741 9.467 0.780 0.460 H3 38O 32 38O H4 H4 H 0 1 N N N -3.494 -7.645 4.481 7.975 -0.794 -0.598 H4 38O 33 38O H5 H5 H 0 1 N N N -3.098 -8.123 6.167 7.173 0.484 -1.542 H5 38O 34 38O H6 H6 H 0 1 N N N -1.786 -9.463 4.479 5.665 -1.452 -1.258 H6 38O 35 38O H7 H7 H 0 1 N N N -1.067 -7.938 3.857 5.835 -1.337 0.511 H7 38O 36 38O H8 H8 H 0 1 N N N 0.635 -7.174 7.093 4.944 0.625 1.672 H8 38O 37 38O H9 H9 H 0 1 N N N 0.478 -6.627 5.389 4.142 1.903 0.728 H9 38O 38 38O H10 H10 H 0 1 N N N -0.948 -5.219 6.791 6.282 2.447 -0.381 H10 38O 39 38O H11 H11 H 0 1 N N N -1.715 -6.663 7.534 6.452 2.561 1.388 H11 38O 40 38O H12 H12 H 0 1 N N N 2.144 -13.667 8.394 -0.704 -2.855 -0.009 H12 38O 41 38O H13 H13 H 0 1 N N N 2.730 -10.833 8.181 2.128 -3.487 -0.141 H13 38O 42 38O H14 H14 H 0 1 N N N 1.839 -8.780 7.223 4.315 -2.379 -0.295 H14 38O 43 38O H15 H15 H 0 1 N N N -1.857 -20.955 6.255 -7.114 2.867 -0.140 H15 38O 44 38O H16 H16 H 0 1 N N N -0.414 -21.748 8.089 -8.389 0.796 0.216 H16 38O 45 38O H18 H18 H 0 1 N N N -1.562 -10.923 5.739 2.418 1.452 -0.279 H18 38O 46 38O H20 H20 H 0 1 N N N -1.242 -15.089 5.738 -2.703 2.600 -0.087 H20 38O 47 38O H21 H21 H 0 1 N N N -1.025 -16.527 4.997 -1.428 1.655 -0.639 H21 38O 48 38O H22 H22 H 0 1 N N N 0.956 -20.155 9.371 -7.237 -1.358 0.431 H22 38O 49 38O H23 H23 H 0 1 N N N 1.634 -17.888 9.721 -5.135 -2.532 0.454 H23 38O 50 # # 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 38O C4 C3 SING N N 1 38O C4 N5 SING N N 2 38O C3 N2 SING N N 3 38O F22 C21 SING N N 4 38O N2 C1 SING N N 5 38O N2 C7 SING N N 6 38O N5 C6 SING N N 7 38O N5 C8 SING N N 8 38O N19 C18 SING N N 9 38O C6 C7 SING N N 10 38O C9 C8 DOUB Y N 11 38O C9 C10 SING Y N 12 38O C8 C16 SING Y N 13 38O C21 C23 DOUB Y N 14 38O C21 C20 SING Y N 15 38O N11 C10 SING Y N 16 38O N11 C12 DOUB Y N 17 38O C10 C14 DOUB Y N 18 38O C23 C24 SING Y N 19 38O C18 C20 SING N N 20 38O C18 C17 DOUB N N 21 38O C16 C15 DOUB Y N 22 38O C20 C26 DOUB Y N 23 38O C12 C17 SING N N 24 38O C12 N13 SING Y N 25 38O C14 C15 SING Y N 26 38O C14 N13 SING Y N 27 38O C17 C28 SING N N 28 38O C24 C25 DOUB Y N 29 38O C26 C25 SING Y N 30 38O C26 N27 SING N N 31 38O C28 N27 SING N N 32 38O C28 O29 DOUB N N 33 38O C1 H1 SING N N 34 38O C1 H2 SING N N 35 38O C1 H3 SING N N 36 38O C3 H4 SING N N 37 38O C3 H5 SING N N 38 38O C4 H6 SING N N 39 38O C4 H7 SING N N 40 38O C6 H8 SING N N 41 38O C6 H9 SING N N 42 38O C7 H10 SING N N 43 38O C7 H11 SING N N 44 38O N13 H12 SING N N 45 38O C15 H13 SING N N 46 38O C16 H14 SING N N 47 38O C23 H15 SING N N 48 38O C24 H16 SING N N 49 38O C9 H18 SING N N 50 38O N19 H20 SING N N 51 38O N19 H21 SING N N 52 38O C25 H22 SING N N 53 38O N27 H23 SING N N 54 # # 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 38O SMILES ACDLabs 12.01 "Fc1cccc2c1C(N)=C(C(=O)N2)c4nc5cc(N3CCN(C)CC3)ccc5n4" 38O InChI InChI 1.03 "InChI=1S/C21H21FN6O/c1-27-7-9-28(10-8-27)12-5-6-14-16(11-12)25-20(24-14)18-19(23)17-13(22)3-2-4-15(17)26-21(18)29/h2-6,11H,7-10H2,1H3,(H,24,25)(H3,23,26,29)" 38O InChIKey InChI 1.03 PIQCTGMSNWUMAF-UHFFFAOYSA-N 38O SMILES_CANONICAL CACTVS 3.385 "CN1CCN(CC1)c2ccc3[nH]c(nc3c2)C4=C(N)c5c(F)cccc5NC4=O" 38O SMILES CACTVS 3.385 "CN1CCN(CC1)c2ccc3[nH]c(nc3c2)C4=C(N)c5c(F)cccc5NC4=O" 38O SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "CN1CCN(CC1)c2ccc3c(c2)nc([nH]3)C4=C(c5c(cccc5F)NC4=O)N" 38O SMILES "OpenEye OEToolkits" 1.9.2 "CN1CCN(CC1)c2ccc3c(c2)nc([nH]3)C4=C(c5c(cccc5F)NC4=O)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 38O "SYSTEMATIC NAME" ACDLabs 12.01 "4-amino-5-fluoro-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one" 38O "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "4-azanyl-5-fluoranyl-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-quinolin-2-one" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 38O "Create component" 2014-07-09 EBI 38O "Modify descriptor" 2014-09-05 RCSB 38O "Initial release" 2014-09-24 RCSB 38O "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 38O _pdbx_chem_comp_synonyms.name Dovitinib _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##