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                    2008-10-14 
_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 InChI            InChI                1.02b InChI=1/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                1.02b KIRQJXNQGZAKGR-UHFFFAOYAR                                                                                                                              
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                                                                                                    
# 
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          
# 
