data_288
# 
_chem_comp.id                                    288 
_chem_comp.name                                  "5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID{[CYCLOPENTYL-(2-HYDROXY-ETHYL)-CARBAMOYL]-METHYL}-AMIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H24 Cl N3 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-10-21 
_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                        365.854 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     288 
_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 
288 C1   C1   C  0 1 Y N N 68.181 -71.099 81.724 3.624  -0.155 -0.568 C1   288 1  
288 C2   C2   C  0 1 Y N N 66.912 -70.745 82.280 3.031  -0.302 0.702  C2   288 2  
288 C3   C3   C  0 1 Y N N 67.916 -71.698 80.465 2.593  -0.314 -1.526 C3   288 3  
288 C4   C4   C  0 1 Y N N 69.376 -70.809 82.460 4.998  0.095  -0.667 C4   288 4  
288 N5   N5   N  0 1 Y N N 65.969 -71.119 81.390 1.690  -0.536 0.504  N5   288 5  
288 C6   C6   C  0 1 Y N N 66.845 -70.122 83.551 3.822  -0.197 1.842  C6   288 6  
288 C7   C7   C  0 1 Y N N 66.569 -71.693 80.291 1.434  -0.538 -0.853 C7   288 7  
288 C8   C8   C  0 1 Y N N 69.285 -70.189 83.714 5.754  0.194  0.466  C8   288 8  
288 C9   C9   C  0 1 Y N N 68.025 -69.847 84.255 5.171  0.048  1.720  C9   288 9  
288 C10  C10  C  0 1 N N N 65.811 -72.204 79.128 0.117  -0.754 -1.471 C10  288 10 
288 CL11 CL11 CL 0 0 N N N 70.710 -69.826 84.608 7.457  0.504  0.340  CL11 288 11 
288 N12  N12  N  0 1 N N N 66.418 -72.774 78.039 -0.964 -0.973 -0.697 N12  288 12 
288 O13  O13  O  0 1 N N N 64.591 -72.104 79.151 0.004  -0.735 -2.682 O13  288 13 
288 C14  C14  C  0 1 N N N 65.546 -73.233 76.933 -2.275 -1.188 -1.313 C14  288 14 
288 C15  C15  C  0 1 N N R 64.943 -74.620 77.195 -3.340 -1.297 -0.220 C15  288 15 
288 N16  N16  N  0 1 N N N 64.061 -75.185 76.264 -3.282 -0.108 0.641  N16  288 16 
288 O17  O17  O  0 1 N N N 65.233 -75.213 78.224 -3.099 -2.466 0.566  O17  288 17 
288 C18  C18  C  0 1 N N N 63.730 -74.409 75.022 -3.927 0.983  -0.102 C18  288 18 
288 C19  C19  C  0 1 N N N 63.459 -76.536 76.500 -4.134 -0.387 1.804  C19  288 19 
288 C20  C20  C  0 1 N N N 64.324 -75.017 73.735 -4.308 2.123  0.859  C20  288 20 
288 C21  C21  C  0 1 N N N 62.211 -74.254 74.787 -2.940 1.582  -1.125 C21  288 21 
288 C22  C22  C  0 1 N N N 62.498 -76.523 77.713 -5.595 -0.476 1.358  C22  288 22 
288 C23  C23  C  0 1 N N N 63.146 -75.190 72.759 -3.539 3.374  0.387  C23  288 23 
288 C24  C24  C  0 1 N N N 62.102 -74.148 73.244 -3.250 3.099  -1.110 C24  288 24 
288 O25  O25  O  0 1 N N N 61.948 -77.823 77.911 -5.773 -1.635 0.541  O25  288 25 
288 H3   H3   H  0 1 N N N 68.641 -72.102 79.738 2.707  -0.266 -2.598 H3   288 26 
288 H4   H4   H  0 1 N N N 70.371 -71.064 82.059 5.459  0.209  -1.637 H4   288 27 
288 HN5  HN5  H  0 1 N N N 64.967 -70.989 81.526 1.033  -0.677 1.204  HN5  288 28 
288 H6   H6   H  0 1 N N N 65.872 -69.850 83.994 3.378  -0.308 2.821  H6   288 29 
288 H9   H9   H  0 1 N N N 67.962 -69.358 85.242 5.783  0.129  2.606  H9   288 30 
288 H12  H12  H  0 1 N N N 67.435 -72.850 78.051 -0.873 -0.988 0.269  H12  288 31 
288 H141 1H14 H  0 0 N N N 66.088 -73.209 75.959 -2.256 -2.109 -1.895 H141 288 32 
288 H142 2H14 H  0 0 N N N 64.749 -72.484 76.714 -2.511 -0.349 -1.968 H142 288 33 
288 H15  H15  H  0 1 N N N 64.897 -75.642 76.753 -4.326 -1.365 -0.679 H15  288 34 
288 H17  H17  H  0 1 N N N 64.860 -76.071 78.386 -2.256 -2.328 1.020  H17  288 35 
288 H18  H18  H  0 1 N N N 64.194 -73.414 75.218 -4.816 0.612  -0.613 H18  288 36 
288 H191 1H19 H  0 0 N N N 64.245 -77.320 76.610 -4.026 0.415  2.535  H191 288 37 
288 H192 2H19 H  0 0 N N N 62.955 -76.924 75.584 -3.834 -1.332 2.256  H192 288 38 
288 H201 1H20 H  0 0 N N N 64.896 -75.958 73.912 -5.382 2.305  0.814  H201 288 39 
288 H202 2H20 H  0 0 N N N 65.167 -74.423 73.312 -4.015 1.866  1.877  H202 288 40 
288 H211 1H21 H  0 0 N N N 61.738 -73.412 75.345 -1.911 1.400  -0.814 H211 288 41 
288 H212 2H21 H  0 0 N N N 61.586 -75.057 75.243 -3.119 1.166  -2.117 H212 288 42 
288 H221 1H22 H  0 0 N N N 61.706 -75.745 77.611 -5.855 0.415  0.786  H221 288 43 
288 H222 2H22 H  0 0 N N N 62.992 -76.133 78.634 -6.239 -0.546 2.234  H222 288 44 
288 H231 1H23 H  0 0 N N N 62.756 -76.232 72.691 -4.156 4.265  0.499  H231 288 45 
288 H232 2H23 H  0 0 N N N 63.424 -75.095 71.683 -2.608 3.481  0.942  H232 288 46 
288 H241 1H24 H  0 0 N N N 62.241 -73.120 72.834 -4.126 3.320  -1.720 H241 288 47 
288 H242 2H24 H  0 0 N N N 61.074 -74.290 72.836 -2.387 3.673  -1.448 H242 288 48 
288 H25  H25  H  0 1 N N N 61.358 -77.815 78.656 -6.705 -1.653 0.282  H25  288 49 
# 
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 
288 C1  C2   SING Y N 1  
288 C1  C3   SING Y N 2  
288 C1  C4   DOUB Y N 3  
288 C2  N5   SING Y N 4  
288 C2  C6   DOUB Y N 5  
288 C3  C7   DOUB Y N 6  
288 C3  H3   SING N N 7  
288 C4  C8   SING Y N 8  
288 C4  H4   SING N N 9  
288 N5  C7   SING Y N 10 
288 N5  HN5  SING N N 11 
288 C6  C9   SING Y N 12 
288 C6  H6   SING N N 13 
288 C7  C10  SING N N 14 
288 C8  C9   DOUB Y N 15 
288 C8  CL11 SING N N 16 
288 C9  H9   SING N N 17 
288 C10 N12  SING N N 18 
288 C10 O13  DOUB N N 19 
288 N12 C14  SING N N 20 
288 N12 H12  SING N N 21 
288 C14 C15  SING N N 22 
288 C14 H141 SING N N 23 
288 C14 H142 SING N N 24 
288 C15 N16  SING N N 25 
288 C15 O17  SING N N 26 
288 C15 H15  SING N N 27 
288 N16 C18  SING N N 28 
288 N16 C19  SING N N 29 
288 O17 H17  SING N N 30 
288 C18 C20  SING N N 31 
288 C18 C21  SING N N 32 
288 C18 H18  SING N N 33 
288 C19 C22  SING N N 34 
288 C19 H191 SING N N 35 
288 C19 H192 SING N N 36 
288 C20 C23  SING N N 37 
288 C20 H201 SING N N 38 
288 C20 H202 SING N N 39 
288 C21 C24  SING N N 40 
288 C21 H211 SING N N 41 
288 C21 H212 SING N N 42 
288 C22 O25  SING N N 43 
288 C22 H221 SING N N 44 
288 C22 H222 SING N N 45 
288 C23 C24  SING N N 46 
288 C23 H231 SING N N 47 
288 C23 H232 SING N N 48 
288 C24 H241 SING N N 49 
288 C24 H242 SING N N 50 
288 O25 H25  SING N N 51 
# 
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 
288 SMILES           ACDLabs              10.04 Clc1cc2c(cc1)nc(c2)C(=O)NCC(O)N(C3CCCC3)CCO                                                                                                                         
288 InChI            InChI                1.02b InChI=1/C18H24ClN3O3/c19-13-5-6-15-12(9-13)10-16(21-15)18(25)20-11-17(24)22(7-8-23)14-3-1-2-4-14/h5-6,9-10,14,17,21,23-24H,1-4,7-8,11H2,(H,20,25)/t17-/m1/s1/f/h20H 
288 InChIKey         InChI                1.02b VXABTOCIIZSEPD-JEBMTRRRDZ                                                                                                                                           
288 SMILES_CANONICAL CACTVS               3.341 OCCN([C@H](O)CNC(=O)c1[nH]c2ccc(Cl)cc2c1)C3CCCC3                                                                                                                    
288 SMILES           CACTVS               3.341 OCCN([CH](O)CNC(=O)c1[nH]c2ccc(Cl)cc2c1)C3CCCC3                                                                                                                     
288 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc2c(cc1Cl)cc([nH]2)C(=O)NCC(N(CCO)C3CCCC3)O                                                                                                                      
288 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc2c(cc1Cl)cc([nH]2)C(=O)NCC(N(CCO)C3CCCC3)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 
288 "SYSTEMATIC NAME" ACDLabs              10.04 5-chloro-N-{(2R)-2-[cyclopentyl(2-hydroxyethyl)amino]-2-hydroxyethyl}-1H-indole-2-carboxamide 
288 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 5-chloro-N-[2-(cyclopentyl-(2-hydroxyethyl)amino)-2-hydroxy-ethyl]-1H-indole-2-carboxamide    
# 
