data_IMN
# 
_chem_comp.id                                    IMN 
_chem_comp.name                                  INDOMETHACIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H16 Cl N O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_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                        357.788 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     IMN 
_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        4COX 
_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 
IMN C    C    C  0 1 Y N N 60.214 43.705 74.033 0.797  0.741  1.060  C    IMN 1  
IMN C1   C1   C  0 1 Y N N 60.167 44.692 75.051 0.149  0.305  2.229  C1   IMN 2  
IMN C2   C2   C  0 1 Y N N 61.370 45.200 75.611 0.884  -0.292 3.253  C2   IMN 3  
IMN C3   C3   C  0 1 Y N N 62.642 44.731 75.152 2.251  -0.441 3.114  C3   IMN 4  
IMN C4   C4   C  0 1 Y N N 62.704 43.719 74.114 2.889  -0.009 1.956  C4   IMN 5  
IMN C5   C5   C  0 1 Y N N 61.484 43.213 73.556 2.171  0.577  0.937  C5   IMN 6  
IMN C6   C6   C  0 1 N N N 65.098 44.712 75.330 4.335  -1.036 3.677  C6   IMN 7  
IMN C7   C7   C  0 1 Y N N 58.705 44.960 75.282 -1.272 0.617  2.048  C7   IMN 8  
IMN C8   C8   C  0 1 Y N N 58.020 44.170 74.448 -1.401 1.194  0.845  C8   IMN 9  
IMN C9   C9   C  0 1 N N N 58.435 42.451 72.857 0.051  1.807  -0.985 C9   IMN 10 
IMN C10  C10  C  0 1 Y N N 58.848 42.389 71.382 0.094  0.931  -2.173 C10  IMN 11 
IMN C11  C11  C  0 1 Y N N 58.673 41.182 70.661 0.433  1.458  -3.421 C11  IMN 12 
IMN C12  C12  C  0 1 Y N N 59.039 41.088 69.295 0.473  0.634  -4.526 C12  IMN 13 
IMN C13  C13  C  0 1 Y N N 59.564 42.162 68.654 0.177  -0.712 -4.400 C13  IMN 14 
IMN C14  C14  C  0 1 Y N N 59.751 43.348 69.337 -0.159 -1.241 -3.165 C14  IMN 15 
IMN C15  C15  C  0 1 Y N N 59.390 43.476 70.721 -0.196 -0.429 -2.051 C15  IMN 16 
IMN C16  C16  C  0 1 N N N 56.509 44.131 74.368 -2.699 1.677  0.250  C16  IMN 17 
IMN C17  C17  C  0 1 N N N 58.056 45.941 76.310 -2.381 0.341  3.030  C17  IMN 18 
IMN C18  C18  C  0 1 N N N 58.801 47.270 76.422 -2.956 -1.026 2.767  C18  IMN 19 
IMN N    N    N  0 1 Y N N 58.855 43.404 73.694 -0.173 1.279  0.233  N    IMN 20 
IMN O    O    O  0 1 N N N 63.805 45.271 75.699 2.974  -1.018 4.111  O    IMN 21 
IMN O1   O1   O  0 1 N N N 57.679 41.588 73.314 0.217  3.005  -1.107 O1   IMN 22 
IMN O2   O2   O  0 1 N N N 59.697 47.562 75.647 -2.512 -1.707 1.874  O2   IMN 23 
IMN O3   O3   O  0 1 N N N 58.474 48.117 77.354 -3.963 -1.488 3.526  O3   IMN 24 
IMN CL   CL   CL 0 0 N N N 59.924 42.053 66.997 0.229  -1.743 -5.796 CL   IMN 25 
IMN H2   H2   H  0 1 N N N 61.316 45.962 76.406 0.389  -0.633 4.150  H2   IMN 26 
IMN H4   H4   H  0 1 N N N 63.672 43.336 73.751 3.957  -0.134 1.855  H4   IMN 27 
IMN H5   H5   H  0 1 N N N 61.522 42.447 72.762 2.676  0.910  0.042  H5   IMN 28 
IMN H61  1H6  H  0 1 N N N 66.028 45.143 75.767 4.957  -1.492 4.447  H61  IMN 29 
IMN H62  2H6  H  0 1 N N N 65.083 43.616 75.535 4.415  -1.614 2.756  H62  IMN 30 
IMN H63  3H6  H  0 1 N N N 65.187 44.726 74.218 4.672  -0.015 3.495  H63  IMN 31 
IMN H11  H11  H  0 1 N N N 58.245 40.302 71.170 0.664  2.508  -3.520 H11  IMN 32 
IMN H12  H12  H  0 1 N N N 58.912 40.157 68.717 0.734  1.041  -5.492 H12  IMN 33 
IMN H14  H14  H  0 1 N N N 60.188 44.192 68.777 -0.389 -2.292 -3.073 H14  IMN 34 
IMN H15  H15  H  0 1 N N N 59.530 44.416 71.280 -0.459 -0.842 -1.089 H15  IMN 35 
IMN H161 1H16 H  0 0 N N N 55.937 43.472 73.672 -3.160 0.870  -0.319 H161 IMN 36 
IMN H162 2H16 H  0 0 N N N 56.132 43.925 75.397 -3.371 1.987  1.050  H162 IMN 37 
IMN H163 3H16 H  0 0 N N N 56.164 45.175 74.186 -2.504 2.523  -0.408 H163 IMN 38 
IMN H171 1H17 H  0 0 N N N 56.978 46.107 76.075 -1.985 0.380  4.045  H171 IMN 39 
IMN H172 2H17 H  0 0 N N N 57.952 45.458 77.309 -3.163 1.092  2.916  H172 IMN 40 
IMN HO3  HO3  H  0 1 N N N 58.937 48.943 77.423 -4.332 -2.365 3.357  HO3  IMN 41 
# 
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 
IMN C   C1   DOUB Y N 1  
IMN C   C5   SING Y N 2  
IMN C   N    SING Y N 3  
IMN C1  C2   SING Y N 4  
IMN C1  C7   SING Y N 5  
IMN C2  C3   DOUB Y N 6  
IMN C2  H2   SING N N 7  
IMN C3  C4   SING Y N 8  
IMN C3  O    SING N N 9  
IMN C4  C5   DOUB Y N 10 
IMN C4  H4   SING N N 11 
IMN C5  H5   SING N N 12 
IMN C6  O    SING N N 13 
IMN C6  H61  SING N N 14 
IMN C6  H62  SING N N 15 
IMN C6  H63  SING N N 16 
IMN C7  C8   DOUB Y N 17 
IMN C7  C17  SING N N 18 
IMN C8  C16  SING N N 19 
IMN C8  N    SING Y N 20 
IMN C9  C10  SING N N 21 
IMN C9  N    SING N N 22 
IMN C9  O1   DOUB N N 23 
IMN C10 C11  DOUB Y N 24 
IMN C10 C15  SING Y N 25 
IMN C11 C12  SING Y N 26 
IMN C11 H11  SING N N 27 
IMN C12 C13  DOUB Y N 28 
IMN C12 H12  SING N N 29 
IMN C13 C14  SING Y N 30 
IMN C13 CL   SING N N 31 
IMN C14 C15  DOUB Y N 32 
IMN C14 H14  SING N N 33 
IMN C15 H15  SING N N 34 
IMN C16 H161 SING N N 35 
IMN C16 H162 SING N N 36 
IMN C16 H163 SING N N 37 
IMN C17 C18  SING N N 38 
IMN C17 H171 SING N N 39 
IMN C17 H172 SING N N 40 
IMN C18 O2   DOUB N N 41 
IMN C18 O3   SING N N 42 
IMN O3  HO3  SING N N 43 
# 
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 
IMN SMILES           ACDLabs              10.04 Clc1ccc(cc1)C(=O)n3c2ccc(OC)cc2c(c3C)CC(=O)O                                                                                      
IMN InChI            InChI                1.02b InChI=1/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)/f/h22H 
IMN InChIKey         InChI                1.02b CGIGDMFJXJATDK-QWOVJGMICU                                                                                                         
IMN SMILES_CANONICAL CACTVS               3.341 COc1ccc2n(c(C)c(CC(O)=O)c2c1)C(=O)c3ccc(Cl)cc3                                                                                    
IMN SMILES           CACTVS               3.341 COc1ccc2n(c(C)c(CC(O)=O)c2c1)C(=O)c3ccc(Cl)cc3                                                                                    
IMN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c(c2cc(ccc2n1C(=O)c3ccc(cc3)Cl)OC)CC(=O)O                                                                                      
IMN SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c(c2cc(ccc2n1C(=O)c3ccc(cc3)Cl)OC)CC(=O)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 
IMN "SYSTEMATIC NAME" ACDLabs              10.04 "{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid" 
IMN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[1-(4-chlorophenyl)carbonyl-5-methoxy-2-methyl-indol-3-yl]ethanoic acid"  
# 
