data_442 # _chem_comp.id 442 _chem_comp.name "2-[3,5-DIBROMO-4-(4-HYDROXY-3-{HYDROXY[(2-PHENYLETHYL)AMINO]METHYL}PHENOXY)PHENYL]ETHANE-1,1-DIOL" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C23 H23 Br2 N O5" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "[3,5-DIBROMO-4-(4-HYDROXY-3-PHENETHYLCARBAMOYL-PHENOXY)-PHENYL]-ACETIC ACID" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2003-11-21 _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 553.240 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 442 _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 1R6G _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 442 O3 O3 O 0 1 N N N 44.122 2.728 17.556 1.173 -0.301 8.516 O3 442 1 442 C8 C8 C 0 1 N N N 45.306 3.158 17.604 0.987 0.188 7.187 C8 442 2 442 O2 O2 O 0 1 N N N 46.268 2.489 18.055 2.209 0.757 6.713 O2 442 3 442 C7 C7 C 0 1 N N N 45.501 4.566 17.071 0.572 -0.964 6.271 C7 442 4 442 C5 C5 C 0 1 Y N N 46.900 4.597 16.462 0.375 -0.447 4.870 C5 442 5 442 C6 C6 C 0 1 Y N N 47.047 4.048 15.191 -0.868 0.004 4.470 C6 442 6 442 C4 C4 C 0 1 Y N N 48.036 5.012 17.177 1.437 -0.431 3.984 C4 442 7 442 C3 C3 C 0 1 Y N N 49.318 4.920 16.627 1.260 0.042 2.698 C3 442 8 442 BR2 BR2 BR 0 0 N N N 50.926 5.435 17.448 2.713 0.063 1.488 BR2 442 9 442 C2 C2 C 0 1 Y N N 49.504 4.353 15.294 0.013 0.502 2.295 C2 442 10 442 C1 C1 C 0 1 Y N N 48.295 3.920 14.588 -1.050 0.484 3.186 C1 442 11 442 BR1 BR1 BR 0 0 N N N 48.483 3.190 12.876 -2.750 1.110 2.642 BR1 442 12 442 O4 O4 O 0 1 N N N 50.759 4.280 14.733 -0.164 0.968 1.031 O4 442 13 442 C11 C11 C 0 1 Y N N 51.140 5.274 13.850 -0.529 -0.095 0.268 C11 442 14 442 C12 C12 C 0 1 Y N N 52.096 5.016 12.860 -0.788 0.076 -1.083 C12 442 15 442 C13 C13 C 0 1 Y N N 52.482 6.023 11.981 -1.154 -1.005 -1.860 C13 442 16 442 C14 C14 C 0 1 Y N N 51.856 7.364 12.116 -1.273 -2.262 -1.285 C14 442 17 442 C15 C15 C 0 1 Y N N 50.913 7.583 13.101 -1.020 -2.433 0.067 C15 442 18 442 C16 C16 C 0 1 Y N N 50.556 6.549 13.956 -0.649 -1.353 0.842 C16 442 19 442 O O O 0 1 N N N 52.166 8.359 11.299 -1.639 -3.326 -2.049 O 442 20 442 C17 C17 C 0 1 N N R 53.491 5.769 10.887 -1.430 -0.819 -3.329 C17 442 21 442 O1 O1 O 0 1 N N N 54.353 4.887 10.963 -2.812 -0.512 -3.520 O1 442 22 442 N28 N28 N 0 1 N N N 53.430 6.534 9.809 -0.608 0.282 -3.846 N28 442 23 442 C29 C29 C 0 1 N N N 54.685 6.970 9.253 -0.335 -0.019 -5.257 C29 442 24 442 C30 C30 C 0 1 N N N 54.622 7.945 8.069 0.521 1.095 -5.861 C30 442 25 442 C31 C31 C 0 1 Y N N 54.772 9.235 8.812 0.801 0.785 -7.309 C31 442 26 442 C36 C36 C 0 1 Y N N 56.037 9.602 9.227 1.924 0.057 -7.656 C36 442 27 442 C35 C35 C 0 1 Y N N 56.199 10.718 10.029 2.178 -0.230 -8.984 C35 442 28 442 C32 C32 C 0 1 Y N N 53.654 9.936 9.229 -0.061 1.233 -8.291 C32 442 29 442 C33 C33 C 0 1 Y N N 53.818 11.050 10.045 0.194 0.949 -9.619 C33 442 30 442 C34 C34 C 0 1 Y N N 55.095 11.444 10.443 1.315 0.216 -9.966 C34 442 31 442 HO3 HO3 H 0 1 N N N 43.394 3.234 17.215 1.433 0.454 9.059 HO3 442 32 442 H8 H8 H 0 1 N N N 45.962 2.371 18.045 0.207 0.950 7.187 H8 442 33 442 HO2 HO2 H 0 1 N N N 47.160 2.813 18.091 2.870 0.052 6.729 HO2 442 34 442 H71 1H7 H 0 1 N N N 45.332 5.359 17.837 1.352 -1.726 6.271 H71 442 35 442 H72 2H7 H 0 1 N N N 44.701 4.888 16.364 -0.359 -1.398 6.633 H72 442 36 442 H6 H6 H 0 1 N N N 46.151 3.705 14.647 -1.695 -0.009 5.163 H6 442 37 442 H4 H4 H 0 1 N N N 47.919 5.420 18.195 2.407 -0.789 4.299 H4 442 38 442 H12 H12 H 0 1 N N N 52.548 4.014 12.772 -0.695 1.055 -1.530 H12 442 39 442 H15 H15 H 0 1 N N N 50.448 8.578 13.204 -1.114 -3.412 0.514 H15 442 40 442 H16 H16 H 0 1 N N N 49.796 6.744 14.732 -0.451 -1.486 1.895 H16 442 41 442 HO HO H 0 1 N N N 51.766 9.216 11.385 -2.604 -3.374 -2.018 HO 442 42 442 H17 H17 H 0 1 N N N 53.894 4.987 11.573 -1.184 -1.737 -3.864 H17 442 43 442 HO1 HO1 H 0 1 N N N 54.988 4.727 10.275 -2.987 0.303 -3.032 HO1 442 44 442 H28 H28 H 0 1 N N N 52.840 7.344 9.998 -1.188 1.108 -3.833 H28 442 45 442 H291 1H29 H 0 0 N N N 55.295 6.081 8.970 0.197 -0.967 -5.330 H291 442 46 442 H292 2H29 H 0 0 N N N 55.318 7.406 10.061 -1.276 -0.089 -5.802 H292 442 47 442 H301 1H30 H 0 0 N N N 53.728 7.859 7.409 -0.011 2.043 -5.789 H301 442 48 442 H302 2H30 H 0 0 N N N 55.351 7.765 7.245 1.463 1.165 -5.316 H302 442 49 442 H36 H36 H 0 1 N N N 56.913 9.007 8.920 2.599 -0.292 -6.888 H36 442 50 442 H35 H35 H 0 1 N N N 57.211 11.030 10.339 3.053 -0.803 -9.254 H35 442 51 442 H32 H32 H 0 1 N N N 52.647 9.612 8.916 -0.937 1.805 -8.021 H32 442 52 442 H33 H33 H 0 1 N N N 52.935 11.621 10.377 -0.480 1.298 -10.387 H33 442 53 442 H34 H34 H 0 1 N N N 55.232 12.330 11.085 1.515 -0.005 -11.003 H34 442 54 # # 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 442 O3 C8 SING N N 1 442 O3 HO3 SING N N 2 442 C8 O2 SING N N 3 442 C8 C7 SING N N 4 442 C8 H8 SING N N 5 442 O2 HO2 SING N N 6 442 C7 C5 SING N N 7 442 C7 H71 SING N N 8 442 C7 H72 SING N N 9 442 C5 C6 SING Y N 10 442 C5 C4 DOUB Y N 11 442 C6 C1 DOUB Y N 12 442 C6 H6 SING N N 13 442 C4 C3 SING Y N 14 442 C4 H4 SING N N 15 442 C3 BR2 SING N N 16 442 C3 C2 DOUB Y N 17 442 C2 C1 SING Y N 18 442 C2 O4 SING N N 19 442 C1 BR1 SING N N 20 442 O4 C11 SING N N 21 442 C11 C12 DOUB Y N 22 442 C11 C16 SING Y N 23 442 C12 C13 SING Y N 24 442 C12 H12 SING N N 25 442 C13 C14 DOUB Y N 26 442 C13 C17 SING N N 27 442 C14 C15 SING Y N 28 442 C14 O SING N N 29 442 C15 C16 DOUB Y N 30 442 C15 H15 SING N N 31 442 C16 H16 SING N N 32 442 O HO SING N N 33 442 C17 O1 SING N N 34 442 C17 N28 SING N N 35 442 C17 H17 SING N N 36 442 O1 HO1 SING N N 37 442 N28 C29 SING N N 38 442 N28 H28 SING N N 39 442 C29 C30 SING N N 40 442 C29 H291 SING N N 41 442 C29 H292 SING N N 42 442 C30 C31 SING N N 43 442 C30 H301 SING N N 44 442 C30 H302 SING N N 45 442 C31 C36 SING Y N 46 442 C31 C32 DOUB Y N 47 442 C36 C35 DOUB Y N 48 442 C36 H36 SING N N 49 442 C35 C34 SING Y N 50 442 C35 H35 SING N N 51 442 C32 C33 SING Y N 52 442 C32 H32 SING N N 53 442 C33 C34 DOUB Y N 54 442 C33 H33 SING N N 55 442 C34 H34 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 442 SMILES ACDLabs 10.04 "Brc3cc(cc(Br)c3Oc1cc(c(O)cc1)C(O)NCCc2ccccc2)CC(O)O" 442 SMILES_CANONICAL CACTVS 3.341 "OC(O)Cc1cc(Br)c(Oc2ccc(O)c(c2)[C@@H](O)NCCc3ccccc3)c(Br)c1" 442 SMILES CACTVS 3.341 "OC(O)Cc1cc(Br)c(Oc2ccc(O)c(c2)[CH](O)NCCc3ccccc3)c(Br)c1" 442 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1ccc(cc1)CCNC(c2cc(ccc2O)Oc3c(cc(cc3Br)CC(O)O)Br)O" 442 SMILES "OpenEye OEToolkits" 1.5.0 "c1ccc(cc1)CCNC(c2cc(ccc2O)Oc3c(cc(cc3Br)CC(O)O)Br)O" 442 InChI InChI 1.03 "InChI=1S/C23H23Br2NO5/c24-18-10-15(12-21(28)29)11-19(25)22(18)31-16-6-7-20(27)17(13-16)23(30)26-9-8-14-4-2-1-3-5-14/h1-7,10-11,13,21,23,26-30H,8-9,12H2" 442 InChIKey InChI 1.03 KIRQJXNQGZAKGR-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 442 "SYSTEMATIC NAME" ACDLabs 10.04 "2-[3,5-dibromo-4-(4-hydroxy-3-{(R)-hydroxy[(2-phenylethyl)amino]methyl}phenoxy)phenyl]ethane-1,1-diol" 442 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[3,5-dibromo-4-[4-hydroxy-3-[hydroxy-(phenethylamino)methyl]phenoxy]phenyl]ethane-1,1-diol" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 442 "Create component" 2003-11-21 RCSB 442 "Modify descriptor" 2011-06-04 RCSB 442 "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 442 _pdbx_chem_comp_synonyms.name "[3,5-DIBROMO-4-(4-HYDROXY-3-PHENETHYLCARBAMOYL-PHENOXY)-PHENYL]-ACETIC ACID" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##