data_598
# 
_chem_comp.id                                    598 
_chem_comp.name                                  "6-{[1-(BENZYLSULFONYL)PIPERIDIN-4-YL]AMINO}-3-(CARBOXYMETHOXY)THIENO[3,2-B][1]BENZOTHIOPHENE-2-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H24 N2 O7 S3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-09-30 
_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                        560.662 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     598 
_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   Y 
_chem_comp.pdbx_model_coordinates_db_code        2B07 
_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 
598 S1   S1   S 0 1 Y N N 44.362 14.118 0.520  -5.037 -2.135 0.691  S1   598 1  
598 C2   C2   C 0 1 Y N N 44.683 15.334 1.685  -6.596 -1.290 0.507  C2   598 2  
598 C3   C3   C 0 1 Y N N 45.591 14.969 2.649  -6.221 -0.109 -0.115 C3   598 3  
598 C4   C4   C 0 1 Y N N 46.014 13.629 2.437  -4.877 0.096  -0.413 C4   598 4  
598 C5   C5   C 0 1 Y N N 45.439 13.049 1.343  -3.977 -0.902 -0.055 C5   598 5  
598 C6   C6   C 0 1 N N N 43.967 16.716 1.523  -7.886 -1.715 0.897  C6   598 6  
598 O7   O7   O 0 1 N N N 44.037 17.562 2.467  -8.049 -2.913 1.498  O7   598 7  
598 O8   O8   O 0 1 N N N 43.380 16.841 0.412  -8.850 -1.001 0.692  O8   598 8  
598 O9   O9   O 0 1 N N N 46.022 15.741 3.679  -7.149 0.828  -0.435 O9   598 9  
598 C10  C10  C 0 1 N N N 47.268 16.415 3.451  -7.257 1.703  0.690  C10  598 10 
598 C11  C11  C 0 1 N N N 47.572 17.199 4.727  -8.278 2.773  0.399  C11  598 11 
598 O14  O14  O 0 1 N N N 46.696 17.160 5.632  -8.854 2.785  -0.663 O14  598 12 
598 O15  O15  O 0 1 N N N 48.673 17.786 4.744  -8.547 3.712  1.320  O15  598 13 
598 S18  S18  S 0 1 Y N N 47.117 12.555 3.231  -3.828 1.337  -1.161 S18  598 14 
598 C19  C19  C 0 1 Y N N 46.762 11.325 2.064  -2.258 0.532  -0.991 C19  598 15 
598 C20  C20  C 0 1 Y N N 45.840 11.711 1.093  -2.561 -0.690 -0.360 C20  598 16 
598 C21  C21  C 0 1 Y N N 47.310 10.027 2.014  -0.969 0.877  -1.339 C21  598 17 
598 C22  C22  C 0 1 Y N N 46.934 9.110  1.005  0.072  0.001  -1.060 C22  598 18 
598 C23  C23  C 0 1 Y N N 46.013 9.523  0.036  -0.206 -1.213 -0.432 C23  598 19 
598 C24  C24  C 0 1 Y N N 45.459 10.814 0.065  -1.475 -1.557 -0.088 C24  598 20 
598 N28  N28  N 0 1 N N N 47.516 7.851  1.030  1.383  0.333  -1.404 N28  598 21 
598 C29  C29  C 0 1 N N N 48.572 7.451  1.944  2.476  -0.597 -1.106 C29  598 22 
598 C30  C30  C 0 1 N N N 47.941 6.952  3.265  3.636  -0.346 -2.073 C30  598 23 
598 C31  C31  C 0 1 N N N 49.019 6.484  4.237  4.762  -1.343 -1.781 C31  598 24 
598 N32  N32  N 0 1 N N N 49.840 5.430  3.540  5.127  -1.242 -0.361 N32  598 25 
598 C33  C33  C 0 1 N N N 50.537 5.932  2.297  4.071  -1.377 0.651  C33  598 26 
598 C34  C34  C 0 1 N N N 49.468 6.381  1.303  2.952  -0.380 0.332  C34  598 27 
598 S44  S44  S 0 1 N N N 50.672 4.294  4.548  6.699  -0.981 0.089  S44  598 28 
598 C45  C45  C 0 1 N N N 49.658 2.830  4.310  6.818  0.828  0.148  C45  598 29 
598 C46  C46  C 0 1 Y N N 49.315 2.674  2.849  8.214  1.227  0.551  C46  598 30 
598 C49  C49  C 0 1 Y N N 48.025 2.994  2.382  9.182  1.426  -0.416 C49  598 31 
598 C50  C50  C 0 1 Y N N 47.695 2.855  1.024  10.463 1.792  -0.047 C50  598 32 
598 C51  C51  C 0 1 Y N N 48.657 2.398  0.119  10.776 1.959  1.289  C51  598 33 
598 C52  C52  C 0 1 Y N N 49.948 2.076  0.567  9.808  1.761  2.256  C52  598 34 
598 C53  C53  C 0 1 Y N N 50.276 2.212  1.925  8.526  1.399  1.887  C53  598 35 
598 O59  O59  O 0 1 N N N 50.568 4.726  5.928  6.753  -1.552 1.390  O59  598 36 
598 O60  O60  O 0 1 N N N 51.981 4.069  3.954  7.433  -1.519 -1.002 O60  598 37 
598 HO7  HO7  H 0 1 N N N 43.566 18.350 2.223  -8.994 -3.008 1.680  HO7  598 38 
598 H101 1H10 H 0 0 N N N 47.206 17.083 2.579  -6.290 2.167  0.884  H101 598 39 
598 H102 2H10 H 0 0 N N N 48.068 15.688 3.245  -7.568 1.133  1.566  H102 598 40 
598 H14  H14  H 0 1 N N N 46.991 17.664 6.381  ?      ?      ?      H14  598 41 
598 H21  H21  H 0 1 N N N 48.031 9.727  2.760  -0.770 1.821  -1.825 H21  598 42 
598 H23  H23  H 0 1 N N N 45.723 8.838  -0.747 0.604  -1.894 -0.216 H23  598 43 
598 H24  H24  H 0 1 N N N 44.749 11.120 -0.690 -1.658 -2.504 0.396  H24  598 44 
598 H28  H28  H 0 1 N N N 46.761 7.225  1.224  1.571  1.178  -1.840 H28  598 45 
598 H29  H29  H 0 1 N N N 49.213 8.316  2.168  2.123  -1.622 -1.221 H29  598 46 
598 H301 1H30 H 0 0 N N N 47.275 6.105  3.041  3.290  -0.478 -3.098 H301 598 47 
598 H302 2H30 H 0 0 N N N 47.375 7.775  3.726  4.006  0.670  -1.941 H302 598 48 
598 H311 1H31 H 0 0 N N N 48.561 6.073  5.149  4.421  -2.355 -1.999 H311 598 49 
598 H312 2H31 H 0 0 N N N 49.659 7.330  4.526  5.629  -1.106 -2.399 H312 598 50 
598 H331 1H33 H 0 0 N N N 51.154 5.134  1.858  3.673  -2.391 0.631  H331 598 51 
598 H332 2H33 H 0 0 N N N 51.193 6.778  2.550  4.481  -1.162 1.638  H332 598 52 
598 H341 1H34 H 0 0 N N N 49.957 6.804  0.413  3.329  0.637  0.441  H341 598 53 
598 H342 2H34 H 0 0 N N N 48.852 5.516  1.015  2.120  -0.536 1.018  H342 598 54 
598 H451 1H45 H 0 0 N N N 48.730 2.934  4.891  6.592  1.239  -0.836 H451 598 55 
598 H452 2H45 H 0 0 N N N 50.213 1.943  4.650  6.105  1.215  0.876  H452 598 56 
598 H49  H49  H 0 1 N N N 47.280 3.351  3.078  8.938  1.295  -1.460 H49  598 57 
598 H50  H50  H 0 1 N N N 46.701 3.100  0.680  11.219 1.946  -0.802 H50  598 58 
598 H51  H51  H 0 1 N N N 48.407 2.292  -0.926 11.777 2.244  1.578  H51  598 59 
598 H52  H52  H 0 1 N N N 50.690 1.723  -0.134 10.052 1.892  3.300  H52  598 60 
598 H53  H53  H 0 1 N N N 51.270 1.961  2.265  7.770  1.245  2.642  H53  598 61 
# 
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 
598 S1  C2   SING Y N 1  
598 S1  C5   SING Y N 2  
598 C2  C3   DOUB Y N 3  
598 C2  C6   SING N N 4  
598 C3  C4   SING Y N 5  
598 C3  O9   SING N N 6  
598 C4  C5   DOUB Y N 7  
598 C4  S18  SING Y N 8  
598 C5  C20  SING Y N 9  
598 C6  O7   SING N N 10 
598 C6  O8   DOUB N N 11 
598 O7  HO7  SING N N 12 
598 O9  C10  SING N N 13 
598 C10 C11  SING N N 14 
598 C10 H101 SING N N 15 
598 C10 H102 SING N N 16 
598 C11 O14  SING N N 17 
598 C11 O15  DOUB N N 18 
598 O14 H14  SING N N 19 
598 S18 C19  SING Y N 20 
598 C19 C20  DOUB Y N 21 
598 C19 C21  SING Y N 22 
598 C20 C24  SING Y N 23 
598 C21 C22  DOUB Y N 24 
598 C21 H21  SING N N 25 
598 C22 C23  SING Y N 26 
598 C22 N28  SING N N 27 
598 C23 C24  DOUB Y N 28 
598 C23 H23  SING N N 29 
598 C24 H24  SING N N 30 
598 N28 C29  SING N N 31 
598 N28 H28  SING N N 32 
598 C29 C30  SING N N 33 
598 C29 C34  SING N N 34 
598 C29 H29  SING N N 35 
598 C30 C31  SING N N 36 
598 C30 H301 SING N N 37 
598 C30 H302 SING N N 38 
598 C31 N32  SING N N 39 
598 C31 H311 SING N N 40 
598 C31 H312 SING N N 41 
598 N32 C33  SING N N 42 
598 N32 S44  SING N N 43 
598 C33 C34  SING N N 44 
598 C33 H331 SING N N 45 
598 C33 H332 SING N N 46 
598 C34 H341 SING N N 47 
598 C34 H342 SING N N 48 
598 S44 C45  SING N N 49 
598 S44 O59  DOUB N N 50 
598 S44 O60  DOUB N N 51 
598 C45 C46  SING N N 52 
598 C45 H451 SING N N 53 
598 C45 H452 SING N N 54 
598 C46 C49  DOUB Y N 55 
598 C46 C53  SING Y N 56 
598 C49 C50  SING Y N 57 
598 C49 H49  SING N N 58 
598 C50 C51  DOUB Y N 59 
598 C50 H50  SING N N 60 
598 C51 C52  SING Y N 61 
598 C51 H51  SING N N 62 
598 C52 C53  DOUB Y N 63 
598 C52 H52  SING N N 64 
598 C53 H53  SING N N 65 
# 
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 
598 SMILES           ACDLabs              10.04 O=S(=O)(N4CCC(Nc1cc2sc3c(OCC(=O)O)c(sc3c2cc1)C(=O)O)CC4)Cc5ccccc5                                                                                                                                   
598 InChI            InChI                1.02b InChI=1/C25H24N2O7S3/c28-20(29)13-34-21-23-22(36-24(21)25(30)31)18-7-6-17(12-19(18)35-23)26-16-8-10-27(11-9-16)37(32,33)14-15-4-2-1-3-5-15/h1-7,12,16,26H,8-11,13-14H2,(H,28,29)(H,30,31)/f/h28,30H 
598 InChIKey         InChI                1.02b UEELPALQXUYKFT-XYULLFFJCL                                                                                                                                                                           
598 SMILES_CANONICAL CACTVS               3.341 OC(=O)COc1c(sc2c1sc3cc(NC4CCN(CC4)[S](=O)(=O)Cc5ccccc5)ccc23)C(O)=O                                                                                                                                 
598 SMILES           CACTVS               3.341 OC(=O)COc1c(sc2c1sc3cc(NC4CCN(CC4)[S](=O)(=O)Cc5ccccc5)ccc23)C(O)=O                                                                                                                                 
598 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CS(=O)(=O)N2CCC(CC2)Nc3ccc4c(c3)sc5c4sc(c5OCC(=O)O)C(=O)O                                                                                                                                 
598 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CS(=O)(=O)N2CCC(CC2)Nc3ccc4c(c3)sc5c4sc(c5OCC(=O)O)C(=O)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 
598 "SYSTEMATIC NAME" ACDLabs              10.04 "6-{[1-(benzylsulfonyl)piperidin-4-yl]amino}-3-(carboxymethoxy)thieno[3,2-b][1]benzothiophene-2-carboxylic acid"      
598 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "3-(carboxymethyloxy)-6-[[1-(phenylmethylsulfonyl)piperidin-4-yl]amino]thieno[4,5-b][1]benzothiole-2-carboxylic acid" 
# 
