data_IM8
# 
_chem_comp.id                                    IM8 
_chem_comp.name                                  2-[1-(4-CHLOROBENZOYL)-5-METHOXY-2-METHYL-1H-INDOL-3-YL]-N-[(1R)-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                     2006-02-06 
_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                     IM8 
_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 
IM8 C2   C2   C  0 1 Y N N 252.823 108.812 -41.305 1.209  -2.456 -0.657 C2   IM8 1  
IM8 C3   C3   C  0 1 Y N N 252.542 108.203 -42.591 0.657  -3.679 -0.325 C3   IM8 2  
IM8 C4   C4   C  0 1 Y N N 251.799 106.957 -42.653 -0.516 -3.738 0.421  C4   IM8 3  
IM8 C5   C5   C  0 1 Y N N 251.337 106.314 -41.499 -1.142 -2.583 0.837  C5   IM8 4  
IM8 C6   C6   C  0 1 N N N 252.927 108.220 -45.030 0.467  -5.908 -0.238 C6   IM8 5  
IM8 C7   C7   C  0 1 Y N N 252.550 108.592 -38.854 0.882  0.145  -0.411 C7   IM8 6  
IM8 C8   C8   C  0 1 Y N N 251.892 107.592 -38.117 -0.086 0.830  0.215  C8   IM8 7  
IM8 C9   C9   C  0 1 N N N 250.682 105.522 -38.509 -2.082 0.317  1.476  C9   IM8 8  
IM8 C    C    C  0 1 Y N N 251.625 106.936 -40.256 -0.603 -1.345 0.512  C    IM8 9  
IM8 C1   C1   C  0 1 Y N N 252.336 108.126 -40.186 0.579  -1.281 -0.246 C1   IM8 10 
IM8 C10  C10  C  0 1 Y N N 249.315 105.114 -39.012 -3.342 0.626  0.771  C10  IM8 11 
IM8 C11  C11  C  0 1 Y N N 248.466 106.005 -39.728 -4.444 1.107  1.482  C11  IM8 12 
IM8 C12  C12  C  0 1 Y N N 247.197 105.559 -40.197 -5.617 1.395  0.817  C12  IM8 13 
IM8 C13  C13  C  0 1 Y N N 246.759 104.227 -39.950 -5.705 1.206  -0.552 C13  IM8 14 
IM8 C14  C14  C  0 1 Y N N 247.591 103.332 -39.230 -4.615 0.730  -1.263 C14  IM8 15 
IM8 C15  C15  C  0 1 Y N N 248.857 103.772 -38.768 -3.435 0.444  -0.611 C15  IM8 16 
IM8 C16  C16  C  0 1 N N N 251.835 107.551 -36.631 -0.173 2.332  0.292  C16  IM8 17 
IM8 C17  C17  C  0 1 N N N 253.443 109.783 -38.381 2.057  0.731  -1.150 C17  IM8 18 
IM8 C18  C18  C  0 1 N N N 253.039 110.634 -37.312 3.211  0.909  -0.198 C18  IM8 19 
IM8 N    N    N  0 1 Y N N 251.346 106.619 -38.945 -0.988 -0.042 0.776  N    IM8 20 
IM8 O    O    O  0 1 N N N 253.026 108.840 -43.768 1.263  -4.827 -0.728 O    IM8 21 
IM8 O1   O1   O  0 1 N N N 251.205 104.810 -37.661 -2.031 0.387  2.689  O1   IM8 22 
IM8 O2   O2   O  0 1 N N N 253.018 110.177 -36.159 3.092  0.591  0.966  O2   IM8 23 
IM8 O3   O3   O  0 1 N N N 250.642 113.553 -39.316 6.878  -0.015 -0.878 O3   IM8 24 
IM8 CL   CL   CL 0 0 N N N 245.235 103.680 -40.515 -7.186 1.569  -1.382 CL   IM8 25 
IM8 N2   N2   N  0 1 N N N 252.772 111.927 -37.544 4.377  1.421  -0.641 N2   IM8 26 
IM8 C19  C19  C  0 1 N N R 252.894 112.653 -38.822 5.499  1.594  0.285  C19  IM8 27 
IM8 C20  C20  C  0 1 N N N 251.577 112.528 -39.619 6.283  0.284  0.386  C20  IM8 28 
IM8 C21  C21  C  0 1 N N N 253.313 114.084 -38.474 6.421  2.700  -0.233 C21  IM8 29 
IM8 C22  C22  C  0 1 N N N 253.071 115.150 -39.464 5.674  4.035  -0.216 C22  IM8 30 
IM8 H2   H2   H  0 1 N N N 253.374 109.737 -41.216 2.120  -2.410 -1.236 H2   IM8 31 
IM8 H4   H4   H  0 1 N N N 251.597 106.514 -43.617 -0.940 -4.698 0.676  H4   IM8 32 
IM8 H5   H5   H  0 1 N N N 250.786 105.386 -41.552 -2.052 -2.640 1.415  H5   IM8 33 
IM8 H61  1H6  H  0 1 N N N 252.005 107.621 -45.073 0.915  -6.855 -0.538 H61  IM8 34 
IM8 H62  2H6  H  0 1 N N N 253.797 107.566 -45.186 0.416  -5.858 0.850  H62  IM8 35 
IM8 H63  3H6  H  0 1 N N N 252.901 108.989 -45.816 -0.539 -5.835 -0.652 H63  IM8 36 
IM8 H11  H11  H  0 1 N N N 248.784 107.020 -39.916 -4.377 1.254  2.550  H11  IM8 37 
IM8 H12  H12  H  0 1 N N N 246.561 106.238 -40.745 -6.470 1.767  1.366  H12  IM8 38 
IM8 H14  H14  H  0 1 N N N 247.262 102.322 -39.035 -4.690 0.585  -2.331 H14  IM8 39 
IM8 H15  H15  H  0 1 N N N 249.489 103.087 -38.223 -2.586 0.073  -1.166 H15  IM8 40 
IM8 H161 1H16 H  0 0 N N N 251.304 106.643 -36.310 -0.745 2.707  -0.557 H161 IM8 41 
IM8 H162 2H16 H  0 0 N N N 251.302 108.439 -36.260 -0.667 2.621  1.219  H162 IM8 42 
IM8 H163 3H16 H  0 0 N N N 252.857 107.541 -36.224 0.831  2.756  0.268  H163 IM8 43 
IM8 H171 1H17 H  0 0 N N N 253.432 110.458 -39.250 1.778  1.699  -1.567 H171 IM8 44 
IM8 H172 2H17 H  0 0 N N N 254.394 109.333 -38.059 2.351  0.059  -1.956 H172 IM8 45 
IM8 HO3  HO3  H  0 1 N N N 250.433 113.528 -38.390 7.361  -0.846 -0.771 HO3  IM8 46 
IM8 HN2  HN2  H  0 1 N N N 252.454 112.461 -36.761 4.472  1.675  -1.572 HN2  IM8 47 
IM8 H19  H19  H  0 1 N N N 253.660 112.234 -39.491 5.120  1.868  1.269  H19  IM8 48 
IM8 H201 1H20 H  0 0 N N N 251.828 112.616 -40.686 7.063  0.385  1.140  H201 IM8 49 
IM8 H202 2H20 H  0 0 N N N 251.117 111.559 -39.375 5.607  -0.523 0.669  H202 IM8 50 
IM8 H211 1H21 H  0 0 N N N 254.408 114.035 -38.386 6.730  2.469  -1.252 H211 IM8 51 
IM8 H212 2H21 H  0 0 N N N 252.753 114.363 -37.570 7.301  2.769  0.407  H212 IM8 52 
IM8 H221 1H22 H  0 0 N N N 252.125 114.954 -39.989 6.331  4.824  -0.585 H221 IM8 53 
IM8 H222 2H22 H  0 0 N N N 253.897 115.170 -40.190 4.794  3.967  -0.856 H222 IM8 54 
IM8 H223 3H22 H  0 0 N N N 253.011 116.121 -38.951 5.365  4.267  0.803  H223 IM8 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 
IM8 C2  C3   SING Y N 1  
IM8 C2  C1   DOUB Y N 2  
IM8 C2  H2   SING N N 3  
IM8 C3  C4   DOUB Y N 4  
IM8 C3  O    SING N N 5  
IM8 C4  C5   SING Y N 6  
IM8 C4  H4   SING N N 7  
IM8 C5  C    DOUB Y N 8  
IM8 C5  H5   SING N N 9  
IM8 C6  O    SING N N 10 
IM8 C6  H61  SING N N 11 
IM8 C6  H62  SING N N 12 
IM8 C6  H63  SING N N 13 
IM8 C7  C8   DOUB Y N 14 
IM8 C7  C1   SING Y N 15 
IM8 C7  C17  SING N N 16 
IM8 C8  C16  SING N N 17 
IM8 C8  N    SING Y N 18 
IM8 C9  C10  SING N N 19 
IM8 C9  N    SING N N 20 
IM8 C9  O1   DOUB N N 21 
IM8 C   C1   SING Y N 22 
IM8 C   N    SING Y N 23 
IM8 C10 C11  SING Y N 24 
IM8 C10 C15  DOUB Y N 25 
IM8 C11 C12  DOUB Y N 26 
IM8 C11 H11  SING N N 27 
IM8 C12 C13  SING Y N 28 
IM8 C12 H12  SING N N 29 
IM8 C13 C14  DOUB Y N 30 
IM8 C13 CL   SING N N 31 
IM8 C14 C15  SING Y N 32 
IM8 C14 H14  SING N N 33 
IM8 C15 H15  SING N N 34 
IM8 C16 H161 SING N N 35 
IM8 C16 H162 SING N N 36 
IM8 C16 H163 SING N N 37 
IM8 C17 C18  SING N N 38 
IM8 C17 H171 SING N N 39 
IM8 C17 H172 SING N N 40 
IM8 C18 O2   DOUB N N 41 
IM8 C18 N2   SING N N 42 
IM8 O3  C20  SING N N 43 
IM8 O3  HO3  SING N N 44 
IM8 N2  C19  SING N N 45 
IM8 N2  HN2  SING N N 46 
IM8 C19 C20  SING N N 47 
IM8 C19 C21  SING N N 48 
IM8 C19 H19  SING N N 49 
IM8 C20 H201 SING N N 50 
IM8 C20 H202 SING N N 51 
IM8 C21 C22  SING N N 52 
IM8 C21 H211 SING N N 53 
IM8 C21 H212 SING N N 54 
IM8 C22 H221 SING N N 55 
IM8 C22 H222 SING N N 56 
IM8 C22 H223 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 
IM8 SMILES           ACDLabs              10.04 Clc1ccc(cc1)C(=O)n3c2ccc(OC)cc2c(c3C)CC(=O)NC(CC)CO                                                                                                                      
IM8 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-/m1/s1/f/h25H 
IM8 InChIKey         InChI                1.02b GKJWXEORYGBJFS-UPJBZSFKDP                                                                                                                                                
IM8 SMILES_CANONICAL CACTVS               3.341 CC[C@H](CO)NC(=O)Cc1c(C)n(C(=O)c2ccc(Cl)cc2)c3ccc(OC)cc13                                                                                                                
IM8 SMILES           CACTVS               3.341 CC[CH](CO)NC(=O)Cc1c(C)n(C(=O)c2ccc(Cl)cc2)c3ccc(OC)cc13                                                                                                                 
IM8 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@H](CO)NC(=O)Cc1c(n(c2c1cc(cc2)OC)C(=O)c3ccc(cc3)Cl)C                                                                                                                
IM8 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 
IM8 "SYSTEMATIC NAME" ACDLabs              10.04 2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}-N-[(1R)-1-(hydroxymethyl)propyl]acetamide 
IM8 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-[1-(4-chlorophenyl)carbonyl-5-methoxy-2-methyl-indol-3-yl]-N-[(2R)-1-hydroxybutan-2-yl]ethanamide         
# 
