data_IMS
# 
_chem_comp.id                                    IMS 
_chem_comp.name                                  2-[1-(4-CHLOROBENZOYL)-5-METHOXY-2-METHYL-1H-INDOL-3-YL]-N-[(1S)-1-(HYDROXYMETHYL)PROPYL]ACETAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H25 Cl N2 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-02-08 
_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                        428.909 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     IMS 
_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        ? 
_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 
IMS C2   C2   C  0 1 Y N N 249.721 105.722 -40.507 1.148  2.591  0.601  C2   IMS 1  
IMS C3   C3   C  0 1 Y N N 248.817 105.236 -39.557 0.557  3.784  0.229  C3   IMS 2  
IMS C4   C4   C  0 1 Y N N 248.818 105.798 -38.291 -0.615 3.782  -0.522 C4   IMS 3  
IMS C5   C5   C  0 1 Y N N 249.695 106.832 -37.972 -1.201 2.594  -0.904 C5   IMS 4  
IMS C6   C6   C  0 1 N N N 246.644 104.036 -39.319 0.292  6.002  0.073  C6   IMS 5  
IMS C7   C7   C  0 1 Y N N 251.607 107.400 -40.956 0.908  -0.026 0.433  C7   IMS 6  
IMS C8   C8   C  0 1 Y N N 252.158 108.355 -40.100 -0.034 -0.761 -0.174 C8   IMS 7  
IMS C9   C9   C  0 1 N N N 251.829 109.084 -37.878 -2.040 -0.355 -1.456 C9   IMS 8  
IMS O2   O2   O  0 1 N N N 251.466 109.424 -42.609 3.138  -0.439 -0.922 O2   IMS 9  
IMS C18  C18  C  0 1 N N N 251.994 108.481 -43.154 3.263  -0.717 0.251  C18  IMS 10 
IMS N2   N2   N  0 1 N N N 252.503 108.719 -44.368 4.443  -1.176 0.713  N2   IMS 11 
IMS C19  C19  C  0 1 N N S 253.205 107.932 -45.367 5.575  -1.340 -0.203 C19  IMS 12 
IMS C21  C21  C  0 1 N N N 252.118 107.374 -46.264 6.884  -1.255 0.583  C21  IMS 13 
IMS C22  C22  C  0 1 N N N 251.034 108.389 -46.534 7.037  0.150  1.169  C22  IMS 14 
IMS C20  C20  C  0 1 N N N 253.981 109.029 -46.119 5.480  -2.703 -0.892 C20  IMS 15 
IMS O3   O3   O  0 1 N N N 254.859 108.599 -47.178 5.629  -3.739 0.081  O3   IMS 16 
IMS C17  C17  C  0 1 N N N 252.017 107.156 -42.411 2.099  -0.549 1.194  C17  IMS 17 
IMS C1   C1   C  0 1 Y N N 250.610 106.758 -40.191 0.559  1.384  0.224  C1   IMS 18 
IMS C16  C16  C  0 1 N N N 253.250 109.325 -40.412 -0.070 -2.267 -0.204 C16  IMS 19 
IMS N    N    N  0 1 Y N N 251.542 108.241 -38.931 -0.962 0.062  -0.764 N    IMS 20 
IMS C    C    C  0 1 Y N N 250.589 107.316 -38.917 -0.621 1.385  -0.539 C    IMS 21 
IMS O    O    O  0 1 N N N 247.953 104.203 -39.874 1.122  4.964  0.598  O    IMS 22 
IMS O1   O1   O  0 1 N N N 251.072 109.982 -37.544 -1.983 -0.460 -2.666 O1   IMS 23 
IMS C10  C10  C  0 1 Y N N 253.064 109.042 -37.075 -3.292 -0.684 -0.745 C10  IMS 24 
IMS C15  C15  C  0 1 Y N N 254.254 108.561 -37.581 -3.396 -0.462 0.630  C15  IMS 25 
IMS C14  C14  C  0 1 Y N N 255.375 108.559 -36.781 -4.569 -0.767 1.287  C14  IMS 26 
IMS C13  C13  C  0 1 Y N N 255.279 109.054 -35.490 -5.639 -1.301 0.588  C13  IMS 27 
IMS CL   CL   CL 0 0 N N N 256.482 109.070 -34.588 -7.111 -1.688 1.424  CL   IMS 28 
IMS C12  C12  C  0 1 Y N N 254.075 109.545 -35.003 -5.540 -1.529 -0.775 C12  IMS 29 
IMS C11  C11  C  0 1 Y N N 252.958 109.553 -35.803 -4.374 -1.223 -1.444 C11  IMS 30 
IMS H2   H2   H  0 1 N N N 249.734 105.293 -41.498 2.057  2.594  1.183  H2   IMS 31 
IMS H4   H4   H  0 1 N N N 248.131 105.430 -37.543 -1.069 4.719  -0.808 H4   IMS 32 
IMS H5   H5   H  0 1 N N N 249.679 107.261 -36.981 -2.110 2.603  -1.486 H5   IMS 33 
IMS H61  1H6  H  0 1 N N N 246.203 103.101 -39.695 0.708  6.972  0.345  H61  IMS 34 
IMS H62  2H6  H  0 1 N N N 246.010 104.885 -39.613 0.248  5.917  -1.013 H62  IMS 35 
IMS H63  3H6  H  0 1 N N N 246.713 103.993 -38.222 -0.712 5.908  0.486  H63  IMS 36 
IMS HN2  HN2  H  0 1 N N N 252.368 109.667 -44.657 4.543  -1.398 1.652  HN2  IMS 37 
IMS H19  H19  H  0 1 N N N 253.847 107.115 -45.005 5.550  -0.551 -0.955 H19  IMS 38 
IMS H211 1H21 H  0 0 N N N 251.661 106.514 -45.753 7.722  -1.465 -0.082 H211 IMS 39 
IMS H212 2H21 H  0 0 N N N 252.570 107.078 -47.222 6.871  -1.986 1.392  H212 IMS 40 
IMS H221 1H22 H  0 0 N N N 250.310 107.970 -47.249 7.970  0.211  1.729  H221 IMS 41 
IMS H222 2H22 H  0 0 N N N 251.482 109.300 -46.957 7.051  0.881  0.360  H222 IMS 42 
IMS H223 3H22 H  0 0 N N N 250.520 108.636 -45.594 6.200  0.360  1.834  H223 IMS 43 
IMS H201 1H20 H  0 0 N N N 254.638 109.489 -45.366 4.510  -2.798 -1.378 H201 IMS 44 
IMS H202 2H20 H  0 0 N N N 253.235 109.700 -46.571 6.271  -2.789 -1.638 H202 IMS 45 
IMS HO3  HO3  H  0 1 N N N 254.363 108.504 -47.983 5.564  -4.579 -0.393 HO3  IMS 46 
IMS H171 1H17 H  0 0 N N N 251.317 106.451 -42.883 1.851  -1.512 1.640  H171 IMS 47 
IMS H172 2H17 H  0 0 N N N 253.030 106.730 -42.444 2.367  0.157  1.980  H172 IMS 48 
IMS H161 1H16 H  0 0 N N N 254.221 108.880 -40.150 -0.633 -2.635 0.654  H161 IMS 49 
IMS H162 2H16 H  0 0 N N N 253.100 110.246 -39.830 -0.550 -2.601 -1.124 H162 IMS 50 
IMS H163 3H16 H  0 0 N N N 253.234 109.563 -41.486 0.948  -2.656 -0.164 H163 IMS 51 
IMS H15  H15  H  0 1 N N N 254.306 108.190 -38.594 -2.563 -0.046 1.176  H15  IMS 52 
IMS H14  H14  H  0 1 N N N 256.314 108.178 -37.154 -4.653 -0.592 2.350  H14  IMS 53 
IMS H12  H12  H  0 1 N N N 254.016 109.922 -33.993 -6.378 -1.946 -1.314 H12  IMS 54 
IMS H11  H11  H  0 1 N N N 252.021 109.950 -35.442 -4.298 -1.400 -2.507 H11  IMS 55 
# 
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 
IMS C2  C3   DOUB Y N 1  
IMS C2  C1   SING Y N 2  
IMS C2  H2   SING N N 3  
IMS C3  C4   SING Y N 4  
IMS C3  O    SING N N 5  
IMS C4  C5   DOUB Y N 6  
IMS C4  H4   SING N N 7  
IMS C5  C    SING Y N 8  
IMS C5  H5   SING N N 9  
IMS C6  O    SING N N 10 
IMS C6  H61  SING N N 11 
IMS C6  H62  SING N N 12 
IMS C6  H63  SING N N 13 
IMS C7  C8   DOUB Y N 14 
IMS C7  C17  SING N N 15 
IMS C7  C1   SING Y N 16 
IMS C8  C16  SING N N 17 
IMS C8  N    SING Y N 18 
IMS C9  N    SING N N 19 
IMS C9  O1   DOUB N N 20 
IMS C9  C10  SING N N 21 
IMS O2  C18  DOUB N N 22 
IMS C18 N2   SING N N 23 
IMS C18 C17  SING N N 24 
IMS N2  C19  SING N N 25 
IMS N2  HN2  SING N N 26 
IMS C19 C21  SING N N 27 
IMS C19 C20  SING N N 28 
IMS C19 H19  SING N N 29 
IMS C21 C22  SING N N 30 
IMS C21 H211 SING N N 31 
IMS C21 H212 SING N N 32 
IMS C22 H221 SING N N 33 
IMS C22 H222 SING N N 34 
IMS C22 H223 SING N N 35 
IMS C20 O3   SING N N 36 
IMS C20 H201 SING N N 37 
IMS C20 H202 SING N N 38 
IMS O3  HO3  SING N N 39 
IMS C17 H171 SING N N 40 
IMS C17 H172 SING N N 41 
IMS C1  C    DOUB Y N 42 
IMS C16 H161 SING N N 43 
IMS C16 H162 SING N N 44 
IMS C16 H163 SING N N 45 
IMS N   C    SING Y N 46 
IMS C10 C15  SING Y N 47 
IMS C10 C11  DOUB Y N 48 
IMS C15 C14  DOUB Y N 49 
IMS C15 H15  SING N N 50 
IMS C14 C13  SING Y N 51 
IMS C14 H14  SING N N 52 
IMS C13 CL   SING N N 53 
IMS C13 C12  DOUB Y N 54 
IMS C12 C11  SING Y N 55 
IMS C12 H12  SING N N 56 
IMS C11 H11  SING N N 57 
# 
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 
IMS SMILES           ACDLabs              10.04 Clc1ccc(cc1)C(=O)n3c2ccc(OC)cc2c(c3C)CC(=O)NC(CC)CO                                                                                                                      
IMS InChI            InChI                1.02b InChI=1/C23H25ClN2O4/c1-4-17(13-27)25-22(28)12-19-14(2)26(21-10-9-18(30-3)11-20(19)21)23(29)15-5-7-16(24)8-6-15/h5-11,17,27H,4,12-13H2,1-3H3,(H,25,28)/t17-/m0/s1/f/h25H 
IMS InChIKey         InChI                1.02b GKJWXEORYGBJFS-BDWLMLNDDO                                                                                                                                                
IMS SMILES_CANONICAL CACTVS               3.341 CC[C@@H](CO)NC(=O)Cc1c(C)n(C(=O)c2ccc(Cl)cc2)c3ccc(OC)cc13                                                                                                               
IMS SMILES           CACTVS               3.341 CC[CH](CO)NC(=O)Cc1c(C)n(C(=O)c2ccc(Cl)cc2)c3ccc(OC)cc13                                                                                                                 
IMS SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@@H](CO)NC(=O)Cc1c(n(c2c1cc(cc2)OC)C(=O)c3ccc(cc3)Cl)C                                                                                                               
IMS SMILES           "OpenEye OEToolkits" 1.5.0 CCC(CO)NC(=O)Cc1c(n(c2c1cc(cc2)OC)C(=O)c3ccc(cc3)Cl)C                                                                                                                    
# 
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 
IMS "SYSTEMATIC NAME" ACDLabs              10.04 2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}-N-[(1S)-1-(hydroxymethyl)propyl]acetamide 
IMS "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-[1-(4-chlorophenyl)carbonyl-5-methoxy-2-methyl-indol-3-yl]-N-[(2S)-1-hydroxybutan-2-yl]ethanamide         
# 
