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 2011-06-04 _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 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" 598 InChI InChI 1.03 "InChI=1S/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)" 598 InChIKey InChI 1.03 UEELPALQXUYKFT-UHFFFAOYSA-N # 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" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 598 "Create component" 2005-09-30 RCSB 598 "Modify descriptor" 2011-06-04 RCSB #