data_FRX
# 
_chem_comp.id                                    FRX 
_chem_comp.name                                  (S)-2-CHLORO-N-(1-(2-(2-HYDROXYETHYLAMINO)-2-OXOETHYL)-2-OXO-1,2,3,4-TETRAHYDROQUINOLIN-3-YL)-6H-THIENO[2,3-B]PYRROLE-5-CARBOXAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H19 Cl N4 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-11-02 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        446.907 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FRX 
_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        2IEI 
_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 
FRX O26  O26  O  0 1 N N N 75.235 20.444 24.082 -2.048 -4.422  -1.913 O26  FRX 1  
FRX C22  C22  C  0 1 N N N 75.183 19.582 23.217 -0.956 -4.474  -2.472 C22  FRX 2  
FRX N22  N22  N  0 1 N N N 74.888 18.300 23.459 -0.757 -4.439  -3.845 N22  FRX 3  
FRX C24  C24  C  0 1 N N N 74.565 17.625 24.714 -1.837 -4.336  -4.800 C24  FRX 4  
FRX C25  C25  C  0 1 N N N 74.138 16.222 24.273 -2.310 -5.725  -5.186 C25  FRX 5  
FRX O25  O25  O  0 1 N N N 74.238 15.289 25.347 -1.241 -6.435  -5.799 O25  FRX 6  
FRX C21  C21  C  0 1 N N N 75.473 19.968 21.783 0.351  -4.588  -1.730 C21  FRX 7  
FRX N17  N17  N  0 1 N N N 74.634 19.298 20.783 0.097  -4.625  -0.292 N17  FRX 8  
FRX C19  C19  C  0 1 N N N 73.366 19.665 20.484 -0.089 -5.869  0.334  C19  FRX 9  
FRX O19  O19  O  0 1 N N N 72.828 20.625 21.005 0.013  -6.952  -0.246 O19  FRX 10 
FRX C17  C17  C  0 1 Y N N 75.250 18.257 20.057 0.055  -3.389  0.436  C17  FRX 11 
FRX C31  C31  C  0 1 Y N N 76.394 17.613 20.544 0.040  -2.144  -0.213 C31  FRX 12 
FRX C30  C30  C  0 1 Y N N 77.001 16.596 19.801 0.017  -0.954  0.519  C30  FRX 13 
FRX C29  C29  C  0 1 Y N N 76.468 16.216 18.574 0.020  -0.988  1.909  C29  FRX 14 
FRX C16  C16  C  0 1 Y N N 74.730 17.877 18.822 0.056  -3.412  1.841  C16  FRX 15 
FRX C28  C28  C  0 1 Y N N 75.331 16.857 18.082 0.047  -2.213  2.569  C28  FRX 16 
FRX C15  C15  C  0 1 N N N 73.495 18.575 18.287 0.159  -4.723  2.565  C15  FRX 17 
FRX C13  C13  C  0 1 N N S 72.570 18.907 19.450 -0.571 -5.795  1.779  C13  FRX 18 
FRX N11  N11  N  0 1 N N N 71.381 19.633 18.993 -0.397 -7.087  2.390  N11  FRX 19 
FRX C11  C11  C  0 1 N N N 70.139 19.146 19.127 -1.274 -7.590  3.342  C11  FRX 20 
FRX O13  O13  O  0 1 N N N 69.955 17.995 19.499 -2.269 -7.001  3.756  O13  FRX 21 
FRX C7   C7   C  0 1 Y N N 68.917 19.926 18.849 -0.940 -8.927  3.895  C7   FRX 22 
FRX N8   N8   N  0 1 Y N N 67.662 19.578 19.262 -1.726 -9.519  4.832  N8   FRX 23 
FRX C3   C3   C  0 1 Y N N 66.797 20.517 18.776 -1.132 -10.705 5.103  C3   FRX 24 
FRX C4   C4   C  0 1 Y N N 67.465 21.421 18.097 -0.030 -10.812 4.349  C4   FRX 25 
FRX C6   C6   C  0 1 Y N N 68.597 20.954 18.241 0.133  -9.686  3.553  C6   FRX 26 
FRX C5   C5   C  0 1 Y N N 66.742 22.412 17.577 0.695  -11.989 4.517  C5   FRX 27 
FRX S2   S2   S  0 1 Y N N 65.151 20.757 18.868 -1.404 -12.014 6.090  S2   FRX 28 
FRX C1   C1   C  0 1 Y N N 65.457 22.149 17.952 0.045  -12.772 5.468  C1   FRX 29 
FRX CL   CL   CL 0 0 N N N 64.092 23.187 17.521 0.506  -14.317 6.051  CL   FRX 30 
FRX HN22 HN22 H  0 0 N N N 74.889 17.709 22.652 0.195  -4.489  -4.196 HN22 FRX 31 
FRX H241 1H24 H  0 0 N N N 75.435 17.588 25.386 -1.471 -3.785  -5.672 H241 FRX 32 
FRX H242 2H24 H  0 0 N N N 73.783 18.146 25.286 -2.651 -3.772  -4.335 H242 FRX 33 
FRX H251 1H25 H  0 0 N N N 73.093 16.259 23.930 -3.128 -5.655  -5.910 H251 FRX 34 
FRX H252 2H25 H  0 0 N N N 74.805 15.893 23.463 -2.653 -6.291  -4.313 H252 FRX 35 
FRX HO25 HO25 H  0 0 N N N 74.260 14.406 24.999 -0.588 -5.772  -6.077 HO25 FRX 36 
FRX H211 1H21 H  0 0 N N N 76.520 19.706 21.571 0.865  -5.507  -2.028 H211 FRX 37 
FRX H212 2H21 H  0 0 N N N 75.259 21.044 21.700 0.985  -3.727  -1.960 H212 FRX 38 
FRX H31  H31  H  0 1 N N N 76.809 17.903 21.498 0.040  -2.075  -1.298 H31  FRX 39 
FRX H30  H30  H  0 1 N N N 77.885 16.105 20.180 0.001  -0.000  -0.000 H30  FRX 40 
FRX H29  H29  H  0 1 N N N 76.933 15.426 18.003 0.010  -0.063  2.477  H29  FRX 41 
FRX H28  H28  H  0 1 N N N 74.916 16.564 17.129 0.067  -2.230  3.656  H28  FRX 42 
FRX H151 1H15 H  0 0 N N N 73.788 19.502 17.772 1.221  -4.974  2.684  H151 FRX 43 
FRX H152 2H15 H  0 0 N N N 72.975 17.917 17.575 -0.274 -4.647  3.570  H152 FRX 44 
FRX H13  H13  H  0 1 N N N 72.187 17.985 19.912 -1.650 -5.597  1.757  H13  FRX 45 
FRX HN11 HN11 H  0 0 N N N 71.501 20.528 18.564 0.441  -7.610  2.145  HN11 FRX 46 
FRX HN8  HN8  H  0 1 N N N 67.421 18.782 19.818 -2.576 -9.158  5.244  HN8  FRX 47 
FRX H6   H6   H  0 1 N N N 69.403 21.507 17.783 0.913  -9.460  2.840  H6   FRX 48 
FRX H5   H5   H  0 1 N N N 67.097 23.244 16.986 1.608  -12.273 4.011  H5   FRX 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 
FRX O26 C22  DOUB N N 1  
FRX C22 C21  SING N N 2  
FRX C22 N22  SING N N 3  
FRX N22 C24  SING N N 4  
FRX N22 HN22 SING N N 5  
FRX C24 C25  SING N N 6  
FRX C24 H241 SING N N 7  
FRX C24 H242 SING N N 8  
FRX C25 O25  SING N N 9  
FRX C25 H251 SING N N 10 
FRX C25 H252 SING N N 11 
FRX O25 HO25 SING N N 12 
FRX C21 N17  SING N N 13 
FRX C21 H211 SING N N 14 
FRX C21 H212 SING N N 15 
FRX N17 C17  SING N N 16 
FRX N17 C19  SING N N 17 
FRX C19 C13  SING N N 18 
FRX C19 O19  DOUB N N 19 
FRX C17 C16  DOUB Y N 20 
FRX C17 C31  SING Y N 21 
FRX C31 C30  DOUB Y N 22 
FRX C31 H31  SING N N 23 
FRX C30 C29  SING Y N 24 
FRX C30 H30  SING N N 25 
FRX C29 C28  DOUB Y N 26 
FRX C29 H29  SING N N 27 
FRX C16 C28  SING Y N 28 
FRX C16 C15  SING N N 29 
FRX C28 H28  SING N N 30 
FRX C15 C13  SING N N 31 
FRX C15 H151 SING N N 32 
FRX C15 H152 SING N N 33 
FRX C13 N11  SING N N 34 
FRX C13 H13  SING N N 35 
FRX N11 C11  SING N N 36 
FRX N11 HN11 SING N N 37 
FRX C11 C7   SING N N 38 
FRX C11 O13  DOUB N N 39 
FRX C7  C6   DOUB Y N 40 
FRX C7  N8   SING Y N 41 
FRX N8  C3   SING Y N 42 
FRX N8  HN8  SING N N 43 
FRX C3  C4   DOUB Y N 44 
FRX C3  S2   SING Y N 45 
FRX C4  C5   SING Y N 46 
FRX C4  C6   SING Y N 47 
FRX C6  H6   SING N N 48 
FRX C5  C1   DOUB Y N 49 
FRX C5  H5   SING N N 50 
FRX S2  C1   SING Y N 51 
FRX C1  CL   SING N N 52 
# 
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 
FRX SMILES           ACDLabs              10.04 Clc2sc1nc(cc1c2)C(=O)NC4C(=O)N(c3ccccc3C4)CC(=O)NCCO                                                                                                                                    
FRX InChI            InChI                1.02b InChI=1/C20H19ClN4O4S/c21-16-9-12-8-13(24-19(12)30-16)18(28)23-14-7-11-3-1-2-4-15(11)25(20(14)29)10-17(27)22-5-6-26/h1-4,8-9,14,24,26H,5-7,10H2,(H,22,27)(H,23,28)/t14-/m0/s1/f/h22-23H 
FRX InChIKey         InChI                1.02b VUKPNWLGSLOHIF-PLMDPJFHDM                                                                                                                                                               
FRX SMILES_CANONICAL CACTVS               3.341 OCCNC(=O)CN1C(=O)[C@H](Cc2ccccc12)NC(=O)c3[nH]c4sc(Cl)cc4c3                                                                                                                             
FRX SMILES           CACTVS               3.341 OCCNC(=O)CN1C(=O)[CH](Cc2ccccc12)NC(=O)c3[nH]c4sc(Cl)cc4c3                                                                                                                              
FRX SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)C[C@@H](C(=O)N2CC(=O)NCCO)NC(=O)c3cc4cc(sc4[nH]3)Cl                                                                                                                          
FRX SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)CC(C(=O)N2CC(=O)NCCO)NC(=O)c3cc4cc(sc4[nH]3)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 
FRX "SYSTEMATIC NAME" ACDLabs              10.04 2-chloro-N-[(3S)-1-{2-[(2-hydroxyethyl)amino]-2-oxoethyl}-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide 
FRX "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-chloro-N-[(3S)-1-[2-(2-hydroxyethylamino)-2-oxo-ethyl]-2-oxo-3,4-dihydroquinolin-3-yl]-6H-thieno[3,2-d]pyrrole-5-carboxamide         
# 
