data_BRL
# 
_chem_comp.id                                    BRL 
_chem_comp.name                                  "2,4-THIAZOLIDIINEDIONE, 5-[[4-[2-(METHYL-2-PYRIDINYLAMINO)ETHOXY]PHENYL]METHYL]-(9CL)" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H19 N3 O3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "BRL49653; ROSIGLITAZONE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        357.427 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     BRL 
_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        2PRG 
_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 
BRL S1   S1   S 0 1 N N N 58.576 -9.122  42.375 -1.069 -0.616 4.021  S1   BRL 1  
BRL O2   O2   O 0 1 N N N 58.355 -11.658 42.966 -2.612 -0.429 6.243  O2   BRL 2  
BRL O4   O4   O 0 1 N N N 54.844 -9.349  41.615 1.772  0.669  6.138  O4   BRL 3  
BRL O13  O13  O 0 1 N N N 60.511 -3.002  39.875 0.394  -0.497 -2.144 O13  BRL 4  
BRL N3   N3   N 0 1 N N N 56.450 -10.574 42.575 -0.383 0.153  6.278  N3   BRL 5  
BRL N16  N16  N 0 1 N N N 61.670 -0.597  41.280 1.174  -0.291 -4.871 N16  BRL 6  
BRL N18  N18  N 0 1 Y N N 61.550 -0.496  43.886 -1.094 -0.813 -4.574 N18  BRL 7  
BRL C2   C2   C 0 1 N N N 57.754 -10.606 42.700 -1.525 -0.287 5.717  C2   BRL 8  
BRL C4   C4   C 0 1 N N N 56.028 -9.511  41.910 0.755  0.270  5.614  C4   BRL 9  
BRL C5   C5   C 0 1 N N S 57.088 -8.480  41.631 0.697  -0.129 4.147  C5   BRL 10 
BRL C6   C6   C 0 1 N N N 57.265 -7.861  40.174 1.013  1.056  3.233  C6   BRL 11 
BRL C7   C7   C 0 1 Y N N 58.147 -6.594  40.030 0.847  0.640  1.794  C7   BRL 12 
BRL C8   C8   C 0 1 Y N N 57.672 -5.283  40.439 -0.378 0.784  1.171  C8   BRL 13 
BRL C9   C9   C 0 1 Y N N 58.537 -4.149  40.368 -0.532 0.403  -0.147 C9   BRL 14 
BRL C10  C10  C 0 1 Y N N 59.877 -4.266  39.865 0.544  -0.122 -0.846 C10  BRL 15 
BRL C11  C11  C 0 1 Y N N 60.345 -5.585  39.415 1.771  -0.270 -0.217 C11  BRL 16 
BRL C12  C12  C 0 1 Y N N 59.489 -6.735  39.505 1.922  0.116  1.100  C12  BRL 17 
BRL C14  C14  C 0 1 N N N 61.929 -2.644  39.573 1.662  -0.992 -2.579 C14  BRL 18 
BRL C15  C15  C 0 1 N N N 62.178 -1.158  39.955 1.563  -1.434 -4.041 C15  BRL 19 
BRL C16  C16  C 0 1 N N N 60.598 0.444   40.959 2.203  0.571  -5.457 C16  BRL 20 
BRL C17  C17  C 0 1 Y N N 62.224 -0.914  42.737 -0.170 -0.026 -5.102 C17  BRL 21 
BRL C19  C19  C 0 1 Y N N 61.987 -0.714  45.160 -2.381 -0.593 -4.764 C19  BRL 22 
BRL C20  C20  C 0 1 Y N N 63.229 -1.421  45.397 -2.812 0.467  -5.536 C20  BRL 23 
BRL C21  C21  C 0 1 Y N N 63.985 -1.897  44.269 -1.874 1.313  -6.113 C21  BRL 24 
BRL C22  C22  C 0 1 Y N N 63.482 -1.655  42.945 -0.532 1.060  -5.891 C22  BRL 25 
BRL HN3  HN3  H 0 1 N N N 55.833 -11.294 42.952 -0.396 0.397  7.217  HN3  BRL 26 
BRL H5   H5   H 0 1 N N N 56.736 -7.524  42.085 1.356  -0.972 3.939  H5   BRL 27 
BRL H61  1H6  H 0 1 N N N 57.641 -8.650  39.483 2.040  1.381  3.402  H61  BRL 28 
BRL H62  2H6  H 0 1 N N N 56.259 -7.660  39.736 0.331  1.877  3.455  H62  BRL 29 
BRL H8   H8   H 0 1 N N N 56.641 -5.146  40.808 -1.215 1.194  1.716  H8   BRL 30 
BRL H9   H9   H 0 1 N N N 58.164 -3.167  40.706 -1.489 0.516  -0.634 H9   BRL 31 
BRL H11  H11  H 0 1 N N N 61.359 -5.714  39.001 2.610  -0.680 -0.759 H11  BRL 32 
BRL H12  H12  H 0 1 N N N 59.859 -7.719  39.173 2.878  0.004  1.589  H12  BRL 33 
BRL H141 1H14 H 0 0 N N N 62.652 -3.333  40.066 1.952  -1.843 -1.962 H141 BRL 34 
BRL H142 2H14 H 0 0 N N N 62.202 -2.859  38.513 2.411  -0.205 -2.487 H142 BRL 35 
BRL H151 1H15 H 0 0 N N N 61.784 -0.516  39.132 0.814  -2.221 -4.132 H151 BRL 36 
BRL H152 2H15 H 0 0 N N N 63.273 -0.961  39.891 2.530  -1.812 -4.373 H152 BRL 37 
BRL H161 1H16 H 0 0 N N N 60.226 0.853   41.927 3.189  0.209  -5.168 H161 BRL 38 
BRL H162 2H16 H 0 0 N N N 60.956 1.236   40.261 2.114  0.555  -6.543 H162 BRL 39 
BRL H163 3H16 H 0 0 N N N 59.780 0.041   40.315 2.070  1.591  -5.096 H163 BRL 40 
BRL H19  H19  H 0 1 N N N 61.353 -0.329  45.976 -3.107 -1.253 -4.314 H19  BRL 41 
BRL H20  H20  H 0 1 N N N 63.594 -1.594  46.423 -3.867 0.636  -5.690 H20  BRL 42 
BRL H21  H21  H 0 1 N N N 64.934 -2.438  44.416 -2.185 2.149  -6.721 H21  BRL 43 
BRL H22  H22  H 0 1 N N N 64.061 -2.038  42.088 0.223  1.699  -6.325 H22  BRL 44 
# 
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 
BRL S1  C2   SING N N 1  
BRL S1  C5   SING N N 2  
BRL O2  C2   DOUB N N 3  
BRL O4  C4   DOUB N N 4  
BRL O13 C10  SING N N 5  
BRL O13 C14  SING N N 6  
BRL N3  C2   SING N N 7  
BRL N3  C4   SING N N 8  
BRL N3  HN3  SING N N 9  
BRL N16 C15  SING N N 10 
BRL N16 C16  SING N N 11 
BRL N16 C17  SING N N 12 
BRL N18 C17  DOUB Y N 13 
BRL N18 C19  SING Y N 14 
BRL C4  C5   SING N N 15 
BRL C5  C6   SING N N 16 
BRL C5  H5   SING N N 17 
BRL C6  C7   SING N N 18 
BRL C6  H61  SING N N 19 
BRL C6  H62  SING N N 20 
BRL C7  C8   DOUB Y N 21 
BRL C7  C12  SING Y N 22 
BRL C8  C9   SING Y N 23 
BRL C8  H8   SING N N 24 
BRL C9  C10  DOUB Y N 25 
BRL C9  H9   SING N N 26 
BRL C10 C11  SING Y N 27 
BRL C11 C12  DOUB Y N 28 
BRL C11 H11  SING N N 29 
BRL C12 H12  SING N N 30 
BRL C14 C15  SING N N 31 
BRL C14 H141 SING N N 32 
BRL C14 H142 SING N N 33 
BRL C15 H151 SING N N 34 
BRL C15 H152 SING N N 35 
BRL C16 H161 SING N N 36 
BRL C16 H162 SING N N 37 
BRL C16 H163 SING N N 38 
BRL C17 C22  SING Y N 39 
BRL C19 C20  DOUB Y N 40 
BRL C19 H19  SING N N 41 
BRL C20 C21  SING Y N 42 
BRL C20 H20  SING N N 43 
BRL C21 C22  DOUB Y N 44 
BRL C21 H21  SING N N 45 
BRL C22 H22  SING N N 46 
# 
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 
BRL SMILES           ACDLabs              10.04 O=C1NC(=O)SC1Cc3ccc(OCCN(c2ncccc2)C)cc3                                                                                                             
BRL InChI            InChI                1.02b InChI=1/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)/t15-/m0/s1/f/h20H 
BRL InChIKey         InChI                1.02b YASAKCUCGLMORW-QTNNGFIUDE                                                                                                                           
BRL SMILES_CANONICAL CACTVS               3.341 CN(CCOc1ccc(C[C@@H]2SC(=O)NC2=O)cc1)c3ccccn3                                                                                                        
BRL SMILES           CACTVS               3.341 CN(CCOc1ccc(C[CH]2SC(=O)NC2=O)cc1)c3ccccn3                                                                                                          
BRL SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CN(CCOc1ccc(cc1)C[C@H]2C(=O)NC(=O)S2)c3ccccn3                                                                                                       
BRL SMILES           "OpenEye OEToolkits" 1.5.0 CN(CCOc1ccc(cc1)CC2C(=O)NC(=O)S2)c3ccccn3                                                                                                           
# 
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 
BRL "SYSTEMATIC NAME" ACDLabs              10.04 (5S)-5-(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione         
BRL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (5S)-5-[[4-[2-(methyl-pyridin-2-yl-amino)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione 
# 
