data_CHI
# 
_chem_comp.id                                    CHI 
_chem_comp.name                                  "5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID [1-(4-FLUOROBENZYL)-2-(4-HYDROXYPIPERIDIN-1YL)-2-OXOETHYL]AMIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H23 Cl F N3 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-10-18 
_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                        443.898 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CHI 
_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        1C50 
_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 
CHI CL1  CL1  CL 0 0 N N N 17.496 7.685  49.605 -1.326 -0.868 -7.822 CL1  CHI 1  
CHI C1   C1   C  0 1 Y N N 17.962 8.986  50.559 -1.375 -0.319 -6.175 C1   CHI 2  
CHI C2   C2   C  0 1 Y N N 18.584 10.027 49.905 -2.197 0.745  -5.828 C2   CHI 3  
CHI C3   C3   C  0 1 Y N N 18.996 11.208 50.635 -2.250 1.196  -4.528 C3   CHI 4  
CHI C4   C4   C  0 1 Y N N 18.716 11.157 52.092 -1.474 0.581  -3.550 C4   CHI 5  
CHI N1   N1   N  0 1 Y N N 18.997 12.126 52.952 -1.315 0.797  -2.201 N1   CHI 6  
CHI C5   C5   C  0 1 Y N N 18.110 10.113 52.696 -0.641 -0.498 -3.904 C5   CHI 7  
CHI C6   C6   C  0 1 Y N N 17.668 8.962  51.994 -0.604 -0.938 -5.233 C6   CHI 8  
CHI C7   C7   C  0 1 Y N N 18.015 10.430 54.104 0.021  -0.912 -2.723 C7   CHI 9  
CHI C8   C8   C  0 1 Y N N 18.659 11.793 54.170 -0.406 -0.118 -1.707 C8   CHI 10 
CHI C9   C9   C  0 1 N N N 18.849 12.548 55.436 0.032  -0.213 -0.307 C9   CHI 11 
CHI O1   O1   O  0 1 N N N 19.355 13.632 55.253 0.841  -1.061 0.019  O1   CHI 12 
CHI N2   N2   N  0 1 N N N 18.478 12.082 56.683 -0.461 0.638  0.612  N2   CHI 13 
CHI C10  C10  C  0 1 N N S 18.742 12.910 57.908 -0.023 0.542  2.007  C10  CHI 14 
CHI C11  C11  C  0 1 N N N 20.262 13.089 58.133 -1.136 1.001  2.915  C11  CHI 15 
CHI O2   O2   O  0 1 N N N 21.001 11.968 58.317 -2.008 1.726  2.487  O2   CHI 16 
CHI N3   N3   N  0 1 N N N 20.890 14.286 58.174 -1.161 0.604  4.203  N3   CHI 17 
CHI C12  C12  C  0 1 N N N 19.924 15.397 58.474 -0.095 -0.249 4.745  C12  CHI 18 
CHI C13  C13  C  0 1 N N N 20.669 16.752 58.552 -0.731 -1.484 5.390  C13  CHI 19 
CHI C14  C14  C  0 1 N N N 21.785 16.690 59.643 -1.766 -1.037 6.425  C14  CHI 20 
CHI O3   O3   O  0 1 N N N 22.508 17.930 59.751 -2.339 -2.187 7.052  O3   CHI 21 
CHI C15  C15  C  0 1 N N N 22.775 15.555 59.310 -2.868 -0.232 5.733  C15  CHI 22 
CHI C16  C16  C  0 1 N N N 22.016 14.197 59.175 -2.256 1.017  5.092  C16  CHI 23 
CHI C17  C17  C  0 1 N N N 18.155 12.217 59.229 1.204  1.430  2.218  C17  CHI 24 
CHI C18  C18  C  0 1 Y N N 18.393 13.072 60.504 2.359  0.889  1.415  C18  CHI 25 
CHI C19  C19  C  0 1 Y N N 17.586 14.197 60.874 2.558  1.318  0.116  C19  CHI 26 
CHI C20  C20  C  0 1 Y N N 17.887 14.917 62.045 3.616  0.823  -0.621 C20  CHI 27 
CHI C21  C21  C  0 1 Y N N 19.010 14.519 62.847 4.477  -0.104 -0.059 C21  CHI 28 
CHI F1   F1   F  0 1 N N N 19.328 15.194 63.946 5.512  -0.589 -0.779 F1   CHI 29 
CHI C22  C22  C  0 1 Y N N 19.801 13.402 62.476 4.277  -0.533 1.241  C22  CHI 30 
CHI C23  C23  C  0 1 Y N N 19.495 12.704 61.327 3.221  -0.032 1.979  C23  CHI 31 
CHI H21  1H2  H  0 1 N N N 18.748 9.917  48.819 -2.800 1.224  -6.585 H21  CHI 32 
CHI H31  1H3  H  0 1 N N N 19.476 12.063 50.130 -2.893 2.024  -4.268 H31  CHI 33 
CHI HN1  HN1  H  0 1 N N N 19.422 13.020 52.706 -1.767 1.481  -1.681 HN1  CHI 34 
CHI H61  1H6  H  0 1 N N N 17.150 8.135  52.509 0.031  -1.766 -5.511 H61  CHI 35 
CHI H7   H7   H  0 1 N N N 17.575 9.808  54.901 0.737  -1.716 -2.644 H7   CHI 36 
CHI HN2  HN2  H  0 1 N N N 18.028 11.166 56.698 -1.105 1.314  0.351  HN2  CHI 37 
CHI H101 1H10 H  0 0 N N N 18.243 13.892 57.733 0.231  -0.491 2.238  H101 CHI 38 
CHI H121 1H12 H  0 0 N N N 19.083 15.426 57.741 0.470  0.304  5.494  H121 CHI 39 
CHI H122 2H12 H  0 0 N N N 19.331 15.194 59.396 0.569  -0.559 3.938  H122 CHI 40 
CHI H131 1H13 H  0 0 N N N 21.072 17.063 57.560 0.040  -2.077 5.879  H131 CHI 41 
CHI H132 2H13 H  0 0 N N N 19.969 17.603 58.719 -1.220 -2.084 4.622  H132 CHI 42 
CHI H14  H14  H  0 1 N N N 21.284 16.497 60.620 -1.282 -0.417 7.178  H14  CHI 43 
CHI HO3  HO3  H  0 1 N N N 23.186 17.892 60.414 -2.983 -1.862 7.695  HO3  CHI 44 
CHI H151 1H15 H  0 0 N N N 23.381 15.784 58.402 -3.337 -0.844 4.962  H151 CHI 45 
CHI H152 2H15 H  0 0 N N N 23.604 15.495 60.052 -3.617 0.065  6.467  H152 CHI 46 
CHI H161 1H16 H  0 0 N N N 21.653 13.833 60.164 -1.867 1.673  5.870  H161 CHI 47 
CHI H162 2H16 H  0 0 N N N 22.714 13.363 58.929 -3.017 1.542  4.515  H162 CHI 48 
CHI H171 1H17 H  0 0 N N N 17.074 11.970 59.106 0.979  2.445  1.893  H171 CHI 49 
CHI H172 2H17 H  0 0 N N N 18.560 11.186 59.355 1.470  1.438  3.276  H172 CHI 50 
CHI H191 1H19 H  0 0 N N N 16.728 14.510 60.254 1.886  2.042  -0.321 H191 CHI 51 
CHI H201 1H20 H  0 0 N N N 17.255 15.775 62.328 3.771  1.158  -1.636 H201 CHI 52 
CHI H221 1H22 H  0 0 N N N 20.660 13.073 63.085 4.947  -1.257 1.681  H221 CHI 53 
CHI H231 1H23 H  0 0 N N N 20.136 11.845 61.064 3.065  -0.367 2.994  H231 CHI 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 
CHI CL1 C1   SING N N 1  
CHI C1  C2   SING Y N 2  
CHI C1  C6   DOUB Y N 3  
CHI C2  C3   DOUB Y N 4  
CHI C2  H21  SING N N 5  
CHI C3  C4   SING Y N 6  
CHI C3  H31  SING N N 7  
CHI C4  N1   SING Y N 8  
CHI C4  C5   DOUB Y N 9  
CHI N1  C8   SING Y N 10 
CHI N1  HN1  SING N N 11 
CHI C5  C6   SING Y N 12 
CHI C5  C7   SING Y N 13 
CHI C6  H61  SING N N 14 
CHI C7  C8   DOUB Y N 15 
CHI C7  H7   SING N N 16 
CHI C8  C9   SING N N 17 
CHI C9  O1   DOUB N N 18 
CHI C9  N2   SING N N 19 
CHI N2  C10  SING N N 20 
CHI N2  HN2  SING N N 21 
CHI C10 C11  SING N N 22 
CHI C10 C17  SING N N 23 
CHI C10 H101 SING N N 24 
CHI C11 O2   DOUB N N 25 
CHI C11 N3   SING N N 26 
CHI N3  C12  SING N N 27 
CHI N3  C16  SING N N 28 
CHI C12 C13  SING N N 29 
CHI C12 H121 SING N N 30 
CHI C12 H122 SING N N 31 
CHI C13 C14  SING N N 32 
CHI C13 H131 SING N N 33 
CHI C13 H132 SING N N 34 
CHI C14 O3   SING N N 35 
CHI C14 C15  SING N N 36 
CHI C14 H14  SING N N 37 
CHI O3  HO3  SING N N 38 
CHI C15 C16  SING N N 39 
CHI C15 H151 SING N N 40 
CHI C15 H152 SING N N 41 
CHI C16 H161 SING N N 42 
CHI C16 H162 SING N N 43 
CHI C17 C18  SING N N 44 
CHI C17 H171 SING N N 45 
CHI C17 H172 SING N N 46 
CHI C18 C19  DOUB Y N 47 
CHI C18 C23  SING Y N 48 
CHI C19 C20  SING Y N 49 
CHI C19 H191 SING N N 50 
CHI C20 C21  DOUB Y N 51 
CHI C20 H201 SING N N 52 
CHI C21 F1   SING N N 53 
CHI C21 C22  SING Y N 54 
CHI C22 C23  DOUB Y N 55 
CHI C22 H221 SING N N 56 
CHI C23 H231 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 
CHI SMILES           ACDLabs              10.04 O=C(N1CCC(O)CC1)C(NC(=O)c3cc2cc(Cl)ccc2n3)Cc4ccc(F)cc4                                                                                                                            
CHI InChI            InChI                1.02b InChI=1/C23H23ClFN3O3/c24-16-3-6-19-15(12-16)13-20(26-19)22(30)27-21(11-14-1-4-17(25)5-2-14)23(31)28-9-7-18(29)8-10-28/h1-6,12-13,18,21,26,29H,7-11H2,(H,27,30)/t21-/m0/s1/f/h27H 
CHI InChIKey         InChI                1.02b YDCGVASFVACWKF-VJKGTFNXDJ                                                                                                                                                         
CHI SMILES_CANONICAL CACTVS               3.341 O[C@H]1CCN(CC1)C(=O)[C@H](Cc2ccc(F)cc2)NC(=O)c3[nH]c4ccc(Cl)cc4c3                                                                                                                 
CHI SMILES           CACTVS               3.341 O[CH]1CCN(CC1)C(=O)[CH](Cc2ccc(F)cc2)NC(=O)c3[nH]c4ccc(Cl)cc4c3                                                                                                                   
CHI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C[C@@H](C(=O)N2CCC(CC2)O)NC(=O)c3cc4cc(ccc4[nH]3)Cl)F                                                                                                                    
CHI SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1CC(C(=O)N2CCC(CC2)O)NC(=O)c3cc4cc(ccc4[nH]3)Cl)F                                                                                                                         
# 
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 
CHI "SYSTEMATIC NAME" ACDLabs              10.04 5-chloro-N-[(1S)-1-(4-fluorobenzyl)-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-1H-indole-2-carboxamide        
CHI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 5-chloro-N-[(2S)-3-(4-fluorophenyl)-1-(4-hydroxypiperidin-1-yl)-1-oxo-propan-2-yl]-1H-indole-2-carboxamide 
# 
