data_1S9 # _chem_comp.id 1S9 _chem_comp.name "[(4-{[4-(benzoylamino)phenyl]amino}-6-methoxyquinazolin-7-yl)oxy]acetic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C24 H20 N4 O5" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-05-17 _chem_comp.pdbx_modified_date 2014-10-10 _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 444.439 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 1S9 _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 4KNX _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 1S9 C1 C1 C 0 1 N N N -12.030 89.429 131.492 -4.187 3.575 -0.615 C1 1S9 1 1S9 O2 O2 O 0 1 N N N -11.795 90.767 131.073 -5.031 2.433 -0.450 O2 1S9 2 1S9 C3 C3 C 0 1 Y N N -12.033 90.809 129.709 -4.418 1.240 -0.226 C3 1S9 3 1S9 C4 C4 C 0 1 Y N N -11.383 89.966 128.831 -3.055 1.181 -0.170 C4 1S9 4 1S9 C5 C5 C 0 1 Y N N -11.648 90.044 127.477 -2.423 -0.047 0.061 C5 1S9 5 1S9 C6 C6 C 0 1 Y N N -12.558 90.965 126.986 -3.200 -1.220 0.234 C6 1S9 6 1S9 C7 C7 C 0 1 Y N N -13.193 91.799 127.878 -4.596 -1.136 0.172 C7 1S9 7 1S9 C8 C8 C 0 1 Y N N -12.934 91.729 129.229 -5.194 0.085 -0.051 C8 1S9 8 1S9 O9 O9 O 0 1 N N N -13.575 92.568 130.124 -6.548 0.169 -0.111 O9 1S9 9 1S9 C10 C10 C 0 1 N N N -13.571 93.869 129.547 -7.282 -1.044 0.065 C10 1S9 10 1S9 C11 C11 C 0 1 N N N -15.002 94.186 129.168 -8.758 -0.757 -0.033 C11 1S9 11 1S9 O12 O12 O 0 1 N N N -15.844 93.281 129.430 -9.646 -1.755 0.102 O12 1S9 12 1S9 O13 O13 O 0 1 N N N -15.161 95.316 128.634 -9.142 0.371 -0.233 O13 1S9 13 1S9 N14 N14 N 0 1 Y N N -12.830 91.062 125.681 -2.569 -2.384 0.453 N14 1S9 14 1S9 C15 C15 C 0 1 Y N N -12.167 90.213 124.895 -1.259 -2.432 0.505 C15 1S9 15 1S9 N16 N16 N 0 1 Y N N -11.276 89.292 125.264 -0.494 -1.364 0.349 N16 1S9 16 1S9 C17 C17 C 0 1 Y N N -11.016 89.211 126.573 -1.015 -0.164 0.128 C17 1S9 17 1S9 N18 N18 N 0 1 N N N -10.081 88.262 127.035 -0.204 0.942 -0.034 N18 1S9 18 1S9 C19 C19 C 0 1 Y N N -9.343 87.433 126.165 1.181 0.823 0.124 C19 1S9 19 1S9 C20 C20 C 0 1 Y N N -9.106 86.118 126.504 1.828 -0.341 -0.272 C20 1S9 20 1S9 C21 C21 C 0 1 Y N N -8.389 85.289 125.668 3.195 -0.458 -0.116 C21 1S9 21 1S9 C22 C22 C 0 1 Y N N -7.899 85.773 124.476 3.923 0.587 0.437 C22 1S9 22 1S9 C23 C23 C 0 1 Y N N -8.121 87.087 124.125 3.276 1.751 0.833 C23 1S9 23 1S9 C24 C24 C 0 1 Y N N -8.839 87.906 124.970 1.911 1.870 0.672 C24 1S9 24 1S9 N25 N25 N 0 1 N N N -7.168 84.928 123.624 5.309 0.468 0.596 N25 1S9 25 1S9 C26 C26 C 0 1 N N N -7.661 84.584 122.383 6.036 -0.206 -0.318 C26 1S9 26 1S9 O27 O27 O 0 1 N N N -8.625 85.073 121.810 5.481 -0.776 -1.237 O27 1S9 27 1S9 C28 C28 C 0 1 Y N N -6.912 83.518 121.713 7.509 -0.251 -0.202 C28 1S9 28 1S9 C29 C29 C 0 1 Y N N -6.423 83.750 120.447 8.150 0.397 0.855 C29 1S9 29 1S9 C30 C30 C 0 1 Y N N -5.720 82.755 119.806 9.524 0.346 0.961 C30 1S9 30 1S9 C31 C31 C 0 1 Y N N -5.517 81.545 120.434 10.268 -0.346 0.022 C31 1S9 31 1S9 C32 C32 C 0 1 Y N N -6.013 81.323 121.701 9.639 -0.991 -1.029 C32 1S9 32 1S9 C33 C33 C 0 1 Y N N -6.718 82.313 122.350 8.266 -0.948 -1.146 C33 1S9 33 1S9 H1 H1 H 0 1 N N N -11.853 89.347 132.574 -3.588 3.717 0.284 H1 1S9 34 1S9 H2 H2 H 0 1 N N N -13.071 89.153 131.269 -3.529 3.419 -1.469 H2 1S9 35 1S9 H3 H3 H 0 1 N N N -11.348 88.752 130.956 -4.801 4.459 -0.786 H3 1S9 36 1S9 H4 H4 H 0 1 N N N -10.668 89.246 129.201 -2.467 2.077 -0.303 H4 1S9 37 1S9 H5 H5 H 0 1 N N N -13.907 92.522 127.512 -5.201 -2.021 0.302 H5 1S9 38 1S9 H6 H6 H 0 1 N N N -12.931 93.884 128.653 -6.998 -1.756 -0.710 H6 1S9 39 1S9 H7 H7 H 0 1 N N N -13.201 94.605 130.276 -7.058 -1.465 1.045 H7 1S9 40 1S9 H8 H8 H 0 1 N N N -16.709 93.563 129.156 -10.582 -1.522 0.031 H8 1S9 41 1S9 H9 H9 H 0 1 N N N -12.376 90.279 123.837 -0.784 -3.385 0.683 H9 1S9 42 1S9 H10 H10 H 0 1 N N N -9.935 88.173 128.020 -0.595 1.801 -0.257 H10 1S9 43 1S9 H11 H11 H 0 1 N N N -9.487 85.732 127.438 1.262 -1.154 -0.701 H11 1S9 44 1S9 H12 H12 H 0 1 N N N -8.212 84.261 125.948 3.698 -1.363 -0.424 H12 1S9 45 1S9 H13 H13 H 0 1 N N N -7.735 87.473 123.193 3.843 2.563 1.263 H13 1S9 46 1S9 H14 H14 H 0 1 N N N -9.010 88.936 124.692 1.408 2.775 0.980 H14 1S9 47 1S9 H15 H15 H 0 1 N N N -6.282 84.573 123.921 5.746 0.869 1.363 H15 1S9 48 1S9 H16 H16 H 0 1 N N N -6.589 84.701 119.963 7.570 0.938 1.589 H16 1S9 49 1S9 H17 H17 H 0 1 N N N -5.328 82.922 118.813 10.021 0.848 1.778 H17 1S9 50 1S9 H18 H18 H 0 1 N N N -4.965 80.765 119.930 11.344 -0.383 0.109 H18 1S9 51 1S9 H19 H19 H 0 1 N N N -5.849 80.372 122.185 10.226 -1.529 -1.759 H19 1S9 52 1S9 H20 H20 H 0 1 N N N -7.112 82.147 123.342 7.776 -1.455 -1.964 H20 1S9 53 # 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 1S9 C30 C31 DOUB Y N 1 1S9 C30 C29 SING Y N 2 1S9 C31 C32 SING Y N 3 1S9 C29 C28 DOUB Y N 4 1S9 C32 C33 DOUB Y N 5 1S9 C28 C33 SING Y N 6 1S9 C28 C26 SING N N 7 1S9 O27 C26 DOUB N N 8 1S9 C26 N25 SING N N 9 1S9 N25 C22 SING N N 10 1S9 C23 C22 DOUB Y N 11 1S9 C23 C24 SING Y N 12 1S9 C22 C21 SING Y N 13 1S9 C15 N16 DOUB Y N 14 1S9 C15 N14 SING Y N 15 1S9 C24 C19 DOUB Y N 16 1S9 N16 C17 SING Y N 17 1S9 C21 C20 DOUB Y N 18 1S9 N14 C6 DOUB Y N 19 1S9 C19 C20 SING Y N 20 1S9 C19 N18 SING N N 21 1S9 C17 N18 SING N N 22 1S9 C17 C5 DOUB Y N 23 1S9 C6 C5 SING Y N 24 1S9 C6 C7 SING Y N 25 1S9 C5 C4 SING Y N 26 1S9 C7 C8 DOUB Y N 27 1S9 O13 C11 DOUB N N 28 1S9 C4 C3 DOUB Y N 29 1S9 C11 O12 SING N N 30 1S9 C11 C10 SING N N 31 1S9 C8 C3 SING Y N 32 1S9 C8 O9 SING N N 33 1S9 C10 O9 SING N N 34 1S9 C3 O2 SING N N 35 1S9 O2 C1 SING N N 36 1S9 C1 H1 SING N N 37 1S9 C1 H2 SING N N 38 1S9 C1 H3 SING N N 39 1S9 C4 H4 SING N N 40 1S9 C7 H5 SING N N 41 1S9 C10 H6 SING N N 42 1S9 C10 H7 SING N N 43 1S9 O12 H8 SING N N 44 1S9 C15 H9 SING N N 45 1S9 N18 H10 SING N N 46 1S9 C20 H11 SING N N 47 1S9 C21 H12 SING N N 48 1S9 C23 H13 SING N N 49 1S9 C24 H14 SING N N 50 1S9 N25 H15 SING N N 51 1S9 C29 H16 SING N N 52 1S9 C30 H17 SING N N 53 1S9 C31 H18 SING N N 54 1S9 C32 H19 SING N N 55 1S9 C33 H20 SING N N 56 # 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 1S9 SMILES ACDLabs 12.01 "O=C(c1ccccc1)Nc2ccc(cc2)Nc4ncnc3c4cc(OC)c(OCC(=O)O)c3" 1S9 InChI InChI 1.03 "InChI=1S/C24H20N4O5/c1-32-20-11-18-19(12-21(20)33-13-22(29)30)25-14-26-23(18)27-16-7-9-17(10-8-16)28-24(31)15-5-3-2-4-6-15/h2-12,14H,13H2,1H3,(H,28,31)(H,29,30)(H,25,26,27)" 1S9 InChIKey InChI 1.03 VAJKCEBFUQHYLC-UHFFFAOYSA-N 1S9 SMILES_CANONICAL CACTVS 3.370 "COc1cc2c(Nc3ccc(NC(=O)c4ccccc4)cc3)ncnc2cc1OCC(O)=O" 1S9 SMILES CACTVS 3.370 "COc1cc2c(Nc3ccc(NC(=O)c4ccccc4)cc3)ncnc2cc1OCC(O)=O" 1S9 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "COc1cc2c(cc1OCC(=O)O)ncnc2Nc3ccc(cc3)NC(=O)c4ccccc4" 1S9 SMILES "OpenEye OEToolkits" 1.7.6 "COc1cc2c(cc1OCC(=O)O)ncnc2Nc3ccc(cc3)NC(=O)c4ccccc4" # 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 1S9 "SYSTEMATIC NAME" ACDLabs 12.01 "[(4-{[4-(benzoylamino)phenyl]amino}-6-methoxyquinazolin-7-yl)oxy]acetic acid" 1S9 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "2-[4-[(4-benzamidophenyl)amino]-6-methoxy-quinazolin-7-yl]oxyethanoic acid" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 1S9 "Create component" 2013-05-17 RCSB 1S9 "Initial release" 2014-10-15 RCSB #