data_GSI
# 
_chem_comp.id                                    GSI 
_chem_comp.name                                  2-(5-chlorothiophen-2-yl)-N-[(3S)-1-(4-{2-[(dimethylamino)methyl]-1H-imidazol-1-yl}-2-fluorophenyl)-2-oxopyrrolidin-3-yl]ethanesulfonamide 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             ? 
_chem_comp.formula                               "C22 H25 CL F N5 O3 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-11-16 
_chem_comp.pdbx_modified_date                    2008-11-21 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        526.047 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GSI 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2VH0 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
GSI CL1  CL1  CL 0 0 N N N 13.822 7.275  26.215 13.822 7.275  26.215 CL1  GSI 1  
GSI C1   C1   C  0 1 Y N N 12.099 7.504  26.229 12.099 7.504  26.229 C1   GSI 2  
GSI C2   C2   C  0 1 Y N N 11.250 7.032  27.294 11.250 7.032  27.294 C2   GSI 3  
GSI C3   C3   C  0 1 Y N N 9.887  7.357  26.987 9.887  7.357  26.987 C3   GSI 4  
GSI S2   S2   S  0 1 Y N N 11.277 8.277  24.955 11.277 8.277  24.955 S2   GSI 5  
GSI C4   C4   C  0 1 Y N N 9.759  8.039  25.729 9.759  8.039  25.729 C4   GSI 6  
GSI C5   C5   C  0 1 N N N 8.456  8.451  25.212 8.456  8.451  25.212 C5   GSI 7  
GSI C6   C6   C  0 1 N N N 8.234  8.908  23.962 8.234  8.908  23.962 C6   GSI 8  
GSI S1   S1   S  0 1 N N N 6.570  9.320  23.664 6.570  9.320  23.664 S1   GSI 9  
GSI O2   O2   O  0 1 N N N 6.574  10.581 23.002 6.574  10.581 23.002 O2   GSI 10 
GSI O1   O1   O  0 1 N N N 5.852  9.025  24.849 5.852  9.025  24.849 O1   GSI 11 
GSI N1   N1   N  0 1 N N N 6.010  8.386  22.476 6.010  8.386  22.476 N1   GSI 12 
GSI C12  C12  C  0 1 N N S 5.927  6.952  22.602 5.927  6.952  22.602 C12  GSI 13 
GSI C13  C13  C  0 1 N N N 4.583  6.459  22.064 4.583  6.459  22.064 C13  GSI 14 
GSI C14  C14  C  0 1 N N N 4.973  5.114  21.443 4.973  5.114  21.443 C14  GSI 15 
GSI C50  C50  C  0 1 N N N 6.965  6.258  21.738 6.965  6.258  21.738 C50  GSI 16 
GSI O3   O3   O  0 1 N N N 8.133  6.598  21.595 8.133  6.598  21.595 O3   GSI 17 
GSI N2   N2   N  0 1 N N N 6.393  5.208  21.139 6.393  5.208  21.139 N2   GSI 18 
GSI C15  C15  C  0 1 Y N N 7.057  4.315  20.345 7.057  4.315  20.345 C15  GSI 19 
GSI C21  C21  C  0 1 Y N N 6.965  2.929  20.635 6.965  2.929  20.635 C21  GSI 20 
GSI C24  C24  C  0 1 Y N N 7.661  2.026  19.805 7.661  2.026  19.805 C24  GSI 21 
GSI C27  C27  C  0 1 Y N N 8.411  2.481  18.705 8.411  2.481  18.705 C27  GSI 22 
GSI C26  C26  C  0 1 Y N N 8.505  3.865  18.423 8.505  3.865  18.423 C26  GSI 23 
GSI C22  C22  C  0 1 Y N N 7.825  4.756  19.261 7.825  4.756  19.261 C22  GSI 24 
GSI F1   F1   F  0 1 N N N 7.887  6.078  19.015 7.887  6.078  19.015 F1   GSI 25 
GSI N4   N4   N  0 1 Y N N 9.100  1.592  17.868 9.100  1.592  17.868 N4   GSI 26 
GSI C9   C9   C  0 1 Y N N 10.205 0.897  18.284 10.205 0.897  18.284 C9   GSI 27 
GSI C7   C7   C  0 1 Y N N 10.652 0.120  17.188 10.652 0.120  17.188 C7   GSI 28 
GSI N3   N3   N  0 1 Y N N 9.791  0.376  16.167 9.791  0.376  16.167 N3   GSI 29 
GSI C8   C8   C  0 1 Y N N 8.854  1.263  16.575 8.854  1.263  16.575 C8   GSI 30 
GSI C10  C10  C  0 1 N N N 7.737  1.794  15.687 7.737  1.794  15.687 C10  GSI 31 
GSI N5   N5   N  0 1 N N N 7.111  0.745  14.851 7.111  0.745  14.851 N5   GSI 32 
GSI C11  C11  C  0 1 N N N 6.414  -0.254 15.679 6.414  -0.254 15.679 C11  GSI 33 
GSI C16  C16  C  0 1 N N N 6.170  1.371  13.911 6.170  1.371  13.911 C16  GSI 34 
GSI H2   H2   H  0 1 N N N 11.586 6.516  28.181 11.586 6.516  28.181 H2   GSI 35 
GSI H3   H3   H  0 1 N N N 9.052  7.116  27.628 9.052  7.116  27.628 H3   GSI 36 
GSI H5C1 1H5C H  0 0 N N N 7.826  7.553  25.296 7.826  7.553  25.296 H5C1 GSI 37 
GSI H5C2 2H5C H  0 0 N N N 8.271  9.359  25.805 8.271  9.359  25.805 H5C2 GSI 38 
GSI H6C1 1H6C H  0 0 N N N 8.844  9.811  23.813 8.844  9.811  23.813 H6C1 GSI 39 
GSI H6C2 2H6C H  0 0 N N N 8.501  8.100  23.265 8.501  8.100  23.265 H6C2 GSI 40 
GSI H1   H1   H  0 1 N N N 5.072  8.694  22.314 5.072  8.694  22.315 H1   GSI 41 
GSI H12  H12  H  0 1 N N N 6.073  6.725  23.668 6.073  6.725  23.668 H12  GSI 42 
GSI H131 1H13 H  0 0 N N N 3.833  6.346  22.861 3.833  6.346  22.861 H131 GSI 43 
GSI H132 2H13 H  0 0 N N N 4.106  7.153  21.356 4.107  7.153  21.356 H132 GSI 44 
GSI H141 1H14 H  0 0 N N N 4.781  4.292  22.148 4.781  4.292  22.148 H141 GSI 45 
GSI H142 2H14 H  0 0 N N N 4.383  4.904  20.539 4.383  4.904  20.539 H142 GSI 46 
GSI H21  H21  H  0 1 N N N 6.378  2.575  21.469 6.378  2.575  21.469 H21  GSI 47 
GSI H24  H24  H  0 1 N N N 7.618  0.968  20.017 7.618  0.968  20.017 H24  GSI 48 
GSI H26  H26  H  0 1 N N N 9.085  4.223  17.585 9.085  4.223  17.585 H26  GSI 49 
GSI H9   H9   H  0 1 N N N 10.652 0.935  19.266 10.652 0.935  19.266 H9   GSI 50 
GSI H7   H7   H  0 1 N N N 11.505 -0.542 17.167 11.505 -0.542 17.167 H7   GSI 51 
GSI H101 1H10 H  0 0 N N N 6.960  2.230  16.333 6.960  2.230  16.333 H101 GSI 52 
GSI H102 2H10 H  0 0 N N N 8.181  2.536  15.007 8.181  2.536  15.007 H102 GSI 53 
GSI H111 1H11 H  0 0 N N N 6.240  -1.165 15.087 6.240  -1.165 15.087 H111 GSI 54 
GSI H112 2H11 H  0 0 N N N 7.032  -0.499 16.556 7.032  -0.499 16.556 H112 GSI 55 
GSI H113 3H11 H  0 0 N N N 5.449  0.156  16.013 5.449  0.156  16.013 H113 GSI 56 
GSI H161 1H16 H  0 0 N N N 5.202  1.527  14.410 5.202  1.527  14.410 H161 GSI 57 
GSI H162 2H16 H  0 0 N N N 6.572  2.340  13.580 6.573  2.340  13.580 H162 GSI 58 
GSI H163 3H16 H  0 0 N N N 6.031  0.714  13.040 6.031  0.714  13.040 H163 GSI 59 
# 
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 
GSI CL1 C1   SING N N 1  
GSI C1  C2   DOUB Y N 2  
GSI C1  S2   SING Y N 3  
GSI C2  C3   SING Y N 4  
GSI C3  C4   DOUB N N 5  
GSI S2  C4   SING Y N 6  
GSI C4  C5   SING N N 7  
GSI C5  C6   SING Y N 8  
GSI C6  S1   SING N N 9  
GSI S1  O2   DOUB N N 10 
GSI S1  O1   DOUB N N 11 
GSI S1  N1   SING N N 12 
GSI N1  C12  SING N N 13 
GSI C12 C13  SING N N 14 
GSI C12 C50  SING N N 15 
GSI C13 C14  SING N N 16 
GSI C14 N2   SING N N 17 
GSI C50 O3   DOUB N N 18 
GSI C50 N2   SING N N 19 
GSI N2  C15  SING N N 20 
GSI C15 C21  SING N N 21 
GSI C15 C22  DOUB N N 22 
GSI C21 C24  DOUB N N 23 
GSI C24 C27  SING N N 24 
GSI C27 C26  DOUB N N 25 
GSI C27 N4   SING N N 26 
GSI C26 C22  SING N N 27 
GSI C22 F1   SING N N 28 
GSI N4  C9   SING N N 29 
GSI N4  C8   SING N N 30 
GSI C9  C7   DOUB N N 31 
GSI C7  N3   SING N N 32 
GSI N3  C8   DOUB Y N 33 
GSI C8  C10  SING Y N 34 
GSI C10 N5   SING Y N 35 
GSI N5  C11  SING N N 36 
GSI N5  C16  SING Y N 37 
GSI C2  H2   SING N N 38 
GSI C3  H3   SING Y N 39 
GSI C5  H5C1 SING N N 40 
GSI C5  H5C2 SING Y N 41 
GSI C6  H6C1 SING N N 42 
GSI C6  H6C2 SING N N 43 
GSI N1  H1   SING Y N 44 
GSI C12 H12  SING Y N 45 
GSI C13 H131 SING Y N 46 
GSI C13 H132 SING N N 47 
GSI C14 H141 SING Y N 48 
GSI C14 H142 SING N N 49 
GSI C21 H21  SING Y N 50 
GSI C24 H24  SING N N 51 
GSI C26 H26  SING N N 52 
GSI C9  H9   SING N N 53 
GSI C7  H7   SING N N 54 
GSI C10 H101 SING N N 55 
GSI C10 H102 SING N N 56 
GSI C11 H111 SING N N 57 
GSI C11 H112 SING N N 58 
GSI C11 H113 SING N N 59 
GSI C16 H161 SING N N 60 
GSI C16 H162 SING N N 61 
GSI C16 H163 SING N N 62 
# 
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 
GSI SMILES           ACDLabs              10.04 Clc1sc(cc1)CCS(=O)(=O)NC4C(=O)N(c3ccc(n2ccnc2CN(C)C)cc3F)CC4                                                                                                                          
GSI InChI            InChI                1.02b InChI=1/C22H25ClFN5O3S2/c1-27(2)14-21-25-9-11-28(21)15-3-5-19(17(24)13-15)29-10-7-18(22(29)30)26-34(31,32)12-8-16-4-6-20(23)33-16/h3-6,9,11,13,18,26H,7-8,10,12,14H2,1-2H3/t18-/m0/s1 
GSI InChIKey         InChI                1.02b JENHCPNBBPPGMN-SFHVURJKBB                                                                                                                                                             
GSI SMILES_CANONICAL CACTVS               3.341 CN(C)Cc1nccn1c2ccc(N3CC[C@H](N[S](=O)(=O)CCc4sc(Cl)cc4)C3=O)c(F)c2                                                                                                                    
GSI SMILES           CACTVS               3.341 CN(C)Cc1nccn1c2ccc(N3CC[CH](N[S](=O)(=O)CCc4sc(Cl)cc4)C3=O)c(F)c2                                                                                                                     
GSI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CN(C)Cc1nccn1c2ccc(c(c2)F)N3CC[C@@H](C3=O)NS(=O)(=O)CCc4ccc(s4)Cl                                                                                                                     
GSI SMILES           "OpenEye OEToolkits" 1.5.0 CN(C)Cc1nccn1c2ccc(c(c2)F)N3CCC(C3=O)NS(=O)(=O)CCc4ccc(s4)Cl                                                                                                                          
# 
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 
GSI "SYSTEMATIC NAME" ACDLabs              10.04 2-(5-chlorothiophen-2-yl)-N-[(3S)-1-(4-{2-[(dimethylamino)methyl]-1H-imidazol-1-yl}-2-fluorophenyl)-2-oxopyrrolidin-3-yl]ethanesulfonamide 
GSI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-(5-chlorothiophen-2-yl)-N-[(3S)-1-[4-[2-(dimethylaminomethyl)imidazol-1-yl]-2-fluoro-phenyl]-2-oxo-pyrrolidin-3-yl]ethanesulfonamide     
# 
