data_B5S # _chem_comp.id B5S _chem_comp.name "3-{5-[(3-hydroxy-5-methoxyphenyl)amino]-2-(phenylcarbamoyl)phenoxy}propan-1-aminium" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C23 H26 N3 O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 1 _chem_comp.pdbx_initial_date 2014-05-21 _chem_comp.pdbx_modified_date 2014-10-03 _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 408.470 _chem_comp.one_letter_code ? _chem_comp.three_letter_code B5S _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 4umq _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 B5S C1 C1 C 0 1 N N N 34.418 20.428 19.413 5.800 -2.904 -2.270 C1 B5S 1 B5S O2 O2 O 0 1 N N N 33.571 19.520 18.717 4.646 -2.136 -1.923 O2 B5S 2 B5S C3 C3 C 0 1 Y N N 32.283 19.913 18.462 4.793 -1.212 -0.937 C3 B5S 3 B5S C4 C4 C 0 1 Y N N 31.779 21.177 18.730 6.023 -1.050 -0.317 C4 B5S 4 B5S C5 C5 C 0 1 Y N N 30.455 21.469 18.432 6.174 -0.107 0.689 C5 B5S 5 B5S O6 O6 O 0 1 N N N 29.948 22.710 18.692 7.379 0.052 1.296 O6 B5S 6 B5S C7 C7 C 0 1 Y N N 29.637 20.498 17.866 5.095 0.673 1.076 C7 B5S 7 B5S C8 C8 C 0 1 Y N N 30.131 19.224 17.592 3.864 0.511 0.455 C8 B5S 8 B5S N9 N9 N 0 1 N N N 29.256 18.269 17.015 2.776 1.298 0.844 N9 B5S 9 B5S C10 C10 C 0 1 Y N N 29.456 17.097 16.250 1.481 0.808 0.712 C10 B5S 10 B5S C11 C11 C 0 1 Y N N 30.662 16.792 15.623 1.236 -0.556 0.863 C11 B5S 11 B5S C12 C12 C 0 1 Y N N 30.798 15.629 14.886 -0.032 -1.047 0.735 C12 B5S 12 B5S C13 C13 C 0 1 Y N N 29.729 14.741 14.756 -1.094 -0.182 0.452 C13 B5S 13 B5S C14 C14 C 0 1 N N N 29.938 13.493 13.941 -2.461 -0.712 0.315 C14 B5S 14 B5S O15 O15 O 0 1 N N N 31.022 13.261 13.402 -3.383 0.042 0.069 O15 B5S 15 B5S N16 N16 N 0 1 N N N 28.860 12.665 13.851 -2.690 -2.032 0.462 N16 B5S 16 B5S C17 C17 C 0 1 Y N N 28.617 11.529 13.038 -3.967 -2.550 0.226 C17 B5S 17 B5S C18 C18 C 0 1 Y N N 27.396 10.890 13.227 -4.777 -1.988 -0.752 C18 B5S 18 B5S C19 C19 C 0 1 Y N N 27.069 9.777 12.482 -6.038 -2.502 -0.982 C19 B5S 19 B5S C20 C20 C 0 1 Y N N 27.948 9.290 11.547 -6.495 -3.576 -0.240 C20 B5S 20 B5S C21 C21 C 0 1 Y N N 29.162 9.912 11.348 -5.691 -4.137 0.736 C21 B5S 21 B5S C22 C22 C 0 1 Y N N 29.502 11.029 12.089 -4.427 -3.632 0.967 C22 B5S 22 B5S C23 C23 C 0 1 Y N N 28.512 15.049 15.388 -0.852 1.192 0.300 C23 B5S 23 B5S O24 O24 O 0 1 N N N 27.510 14.127 15.213 -1.877 2.039 0.025 O24 B5S 24 B5S C25 C25 C 0 1 N N N 26.151 14.515 15.483 -1.554 3.423 -0.116 C25 B5S 25 B5S C26 C26 C 0 1 N N N 25.812 14.152 16.920 -2.827 4.215 -0.421 C26 B5S 26 B5S C27 C27 C 0 1 N N N 25.111 15.266 17.685 -2.482 5.698 -0.573 C27 B5S 27 B5S N28 N28 N 1 1 N N N 23.969 15.825 16.919 -3.704 6.458 -0.866 N28 B5S 28 B5S C32 C32 C 0 1 Y N N 28.388 16.216 16.123 0.435 1.681 0.437 C32 B5S 29 B5S C33 C33 C 0 1 Y N N 31.462 18.945 17.896 3.715 -0.429 -0.555 C33 B5S 30 B5S HN28 HN28 H 0 0 N N N 23.534 16.552 17.451 -4.114 6.119 -1.724 HN28 B5S 31 B5S HN2A HN2A H 0 0 N N N 24.300 16.199 16.052 -4.363 6.341 -0.110 HN2A B5S 32 B5S HN2B HN2B H 0 0 N N N 23.303 15.101 16.737 -3.477 7.436 -0.966 HN2B B5S 33 B5S H1 H1 H 0 1 N N N 35.413 19.976 19.543 6.593 -2.237 -2.609 H1 B5S 34 B5S H1A H1A H 0 1 N N N 34.511 21.359 18.835 6.143 -3.460 -1.397 H1A B5S 35 B5S H1B H1B H 0 1 N N N 33.985 20.651 20.399 5.547 -3.602 -3.068 H1B B5S 36 B5S H4 H4 H 0 1 N N N 32.415 21.932 19.169 6.863 -1.658 -0.618 H4 B5S 37 B5S HO6 HO6 H 0 1 N N N 29.035 22.741 18.430 7.951 0.704 0.870 HO6 B5S 38 B5S H7 H7 H 0 1 N N N 28.608 20.733 17.636 5.213 1.407 1.859 H7 B5S 39 B5S HN9 HN9 H 0 1 N N N 28.291 18.467 17.186 2.924 2.185 1.206 HN9 B5S 40 B5S H11 H11 H 0 1 N N N 31.498 17.469 15.713 2.053 -1.228 1.081 H11 B5S 41 B5S H12 H12 H 0 1 N N N 31.740 15.406 14.407 -0.214 -2.105 0.853 H12 B5S 42 B5S HN16 HN16 H 0 0 N N N 28.108 12.900 14.467 -1.969 -2.622 0.732 HN16 B5S 43 B5S H18 H18 H 0 1 N N N 26.700 11.268 13.962 -4.421 -1.149 -1.332 H18 B5S 44 B5S H19 H19 H 0 1 N N N 26.119 9.287 12.634 -6.668 -2.065 -1.743 H19 B5S 45 B5S H20 H20 H 0 1 N N N 27.688 8.418 10.966 -7.481 -3.976 -0.422 H20 B5S 46 B5S H21 H21 H 0 1 N N N 29.850 9.526 10.611 -6.051 -4.975 1.314 H21 B5S 47 B5S H22 H22 H 0 1 N N N 30.454 11.513 11.931 -3.798 -4.074 1.725 H22 B5S 48 B5S H25 H25 H 0 1 N N N 26.041 15.600 15.341 -1.112 3.790 0.811 H25 B5S 49 B5S H25A H25A H 0 0 N N N 25.473 13.985 14.798 -0.843 3.549 -0.933 H25A B5S 50 B5S H26 H26 H 0 1 N N N 25.154 13.271 16.909 -3.270 3.849 -1.348 H26 B5S 51 B5S H26A H26A H 0 0 N N N 26.746 13.905 17.445 -3.538 4.089 0.395 H26A B5S 52 B5S H27 H27 H 0 1 N N N 24.738 14.863 18.638 -2.040 6.064 0.354 H27 B5S 53 B5S H27A H27A H 0 0 N N N 25.834 16.071 17.885 -1.771 5.824 -1.389 H27A B5S 54 B5S H32 H32 H 0 1 N N N 27.449 16.445 16.604 0.627 2.737 0.326 H32 B5S 55 B5S H33 H33 H 0 1 N N N 31.861 17.963 17.689 2.758 -0.553 -1.041 H33 B5S 56 # 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 B5S C1 O2 SING N N 1 B5S C1 H1 SING N N 2 B5S C1 H1A SING N N 3 B5S C1 H1B SING N N 4 B5S O2 C3 SING N N 5 B5S C3 C4 DOUB Y N 6 B5S C3 C33 SING Y N 7 B5S C4 C5 SING Y N 8 B5S C4 H4 SING N N 9 B5S C5 O6 SING N N 10 B5S C5 C7 DOUB Y N 11 B5S O6 HO6 SING N N 12 B5S C7 C8 SING Y N 13 B5S C7 H7 SING N N 14 B5S C8 N9 SING N N 15 B5S C8 C33 DOUB Y N 16 B5S N9 C10 SING N N 17 B5S N9 HN9 SING N N 18 B5S C10 C11 DOUB Y N 19 B5S C10 C32 SING Y N 20 B5S C11 C12 SING Y N 21 B5S C11 H11 SING N N 22 B5S C12 C13 DOUB Y N 23 B5S C12 H12 SING N N 24 B5S C13 C14 SING N N 25 B5S C13 C23 SING Y N 26 B5S C14 O15 DOUB N N 27 B5S C14 N16 SING N N 28 B5S N16 C17 SING N N 29 B5S N16 HN16 SING N N 30 B5S C17 C18 DOUB Y N 31 B5S C17 C22 SING Y N 32 B5S C18 C19 SING Y N 33 B5S C18 H18 SING N N 34 B5S C19 C20 DOUB Y N 35 B5S C19 H19 SING N N 36 B5S C20 C21 SING Y N 37 B5S C20 H20 SING N N 38 B5S C21 C22 DOUB Y N 39 B5S C21 H21 SING N N 40 B5S C22 H22 SING N N 41 B5S C23 O24 SING N N 42 B5S C23 C32 DOUB Y N 43 B5S O24 C25 SING N N 44 B5S C25 C26 SING N N 45 B5S C25 H25 SING N N 46 B5S C25 H25A SING N N 47 B5S C26 C27 SING N N 48 B5S C26 H26 SING N N 49 B5S C26 H26A SING N N 50 B5S C27 N28 SING N N 51 B5S C27 H27 SING N N 52 B5S C27 H27A SING N N 53 B5S N28 HN28 SING N N 54 B5S N28 HN2A SING N N 55 B5S N28 HN2B SING N N 56 B5S C32 H32 SING N N 57 B5S C33 H33 SING N N 58 # 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 B5S SMILES ACDLabs 12.01 "O=C(Nc1ccccc1)c2ccc(cc2OCCC[NH3+])Nc3cc(O)cc(OC)c3" B5S InChI InChI 1.03 "InChI=1S/C23H25N3O4/c1-29-20-13-18(12-19(27)15-20)25-17-8-9-21(22(14-17)30-11-5-10-24)23(28)26-16-6-3-2-4-7-16/h2-4,6-9,12-15,25,27H,5,10-11,24H2,1H3,(H,26,28)/p+1" B5S InChIKey InChI 1.03 TUABKEMVLJKHPG-UHFFFAOYSA-O B5S SMILES_CANONICAL CACTVS 3.385 "COc1cc(O)cc(Nc2ccc(C(=O)Nc3ccccc3)c(OCCC[NH3+])c2)c1" B5S SMILES CACTVS 3.385 "COc1cc(O)cc(Nc2ccc(C(=O)Nc3ccccc3)c(OCCC[NH3+])c2)c1" B5S SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "COc1cc(cc(c1)O)Nc2ccc(c(c2)OCCC[NH3+])C(=O)Nc3ccccc3" B5S SMILES "OpenEye OEToolkits" 1.7.6 "COc1cc(cc(c1)O)Nc2ccc(c(c2)OCCC[NH3+])C(=O)Nc3ccccc3" # 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 B5S "SYSTEMATIC NAME" ACDLabs 12.01 "3-{5-[(3-hydroxy-5-methoxyphenyl)amino]-2-(phenylcarbamoyl)phenoxy}propan-1-aminium" B5S "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "3-[5-[(3-methoxy-5-oxidanyl-phenyl)amino]-2-(phenylcarbamoyl)phenoxy]propylazanium" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site B5S "Create component" 2014-05-21 EBI B5S "Initial release" 2014-10-08 RCSB #