data_H6S # _chem_comp.id H6S _chem_comp.name "2-[(R)-(2-chlorophenyl){2-[(2S)-1-methylpyrrolidin-2-yl]ethoxy}methyl]thieno[3,2-b]pyridine-7-carboxylic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H23 Cl N2 O3 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2018-06-11 _chem_comp.pdbx_modified_date 2018-11-16 _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 430.948 _chem_comp.one_letter_code ? _chem_comp.three_letter_code H6S _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 6DQ8 _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 H6S C02 C1 C 0 1 Y N N -27.817 23.148 5.195 -0.427 -3.011 0.235 C02 H6S 1 H6S C03 C2 C 0 1 Y N N -29.154 23.147 5.539 -0.567 -4.022 1.170 C03 H6S 2 H6S C04 C3 C 0 1 Y N N -30.098 22.587 4.706 -0.885 -3.713 2.478 C04 H6S 3 H6S C05 C4 C 0 1 Y N N -29.699 22.022 3.515 -1.064 -2.394 2.854 C05 H6S 4 H6S C06 C5 C 0 1 Y N N -28.365 22.020 3.163 -0.924 -1.385 1.921 C06 H6S 5 H6S C07 C6 C 0 1 Y N N -27.392 22.584 3.983 -0.600 -1.692 0.612 C07 H6S 6 H6S C08 C7 C 0 1 N N R -25.948 22.529 3.521 -0.447 -0.591 -0.405 C08 H6S 7 H6S C10 C8 C 0 1 N N N -25.584 24.867 3.127 -2.555 0.548 -0.482 C10 H6S 8 H6S C11 C9 C 0 1 N N N -24.393 25.779 3.095 -3.275 1.803 0.016 C11 H6S 9 H6S C12 C10 C 0 1 N N S -23.087 25.047 2.889 -4.667 1.875 -0.614 C12 H6S 10 H6S C14 C11 C 0 1 N N N -22.709 23.928 0.718 -5.537 -0.373 -0.909 C14 H6S 11 H6S C15 C12 C 0 1 N N N -21.260 25.652 1.485 -6.904 1.367 0.085 C15 H6S 12 H6S C16 C13 C 0 1 N N N -21.066 26.345 2.809 -6.860 2.835 -0.390 C16 H6S 13 H6S C17 C14 C 0 1 N N N -21.944 25.573 3.758 -5.361 3.207 -0.235 C17 H6S 14 H6S C18 C15 C 0 1 Y N N -25.225 21.336 4.094 1.006 -0.206 -0.515 C18 H6S 15 H6S C20 C16 C 0 1 Y N N -24.843 20.209 3.423 1.813 -0.615 -1.475 C20 H6S 16 H6S C21 C17 C 0 1 Y N N -24.189 19.228 4.185 3.176 -0.120 -1.383 C21 H6S 17 H6S C22 C18 C 0 1 Y N N -24.032 19.562 5.530 3.351 0.708 -0.268 C22 H6S 18 H6S C23 C19 C 0 1 Y N N -23.363 18.605 6.402 4.617 1.279 -0.024 C23 H6S 19 H6S C24 C20 C 0 1 N N N -23.144 18.866 7.850 4.840 2.157 1.143 C24 H6S 20 H6S C27 C21 C 0 1 Y N N -22.924 17.420 5.835 5.654 0.993 -0.912 C27 H6S 21 H6S C28 C22 C 0 1 Y N N -23.131 17.179 4.479 5.404 0.165 -1.992 C28 H6S 22 H6S N13 N1 N 0 1 N N N -22.641 25.172 1.478 -5.541 0.822 -0.055 N13 H6S 23 H6S N29 N2 N 0 1 Y N N -23.747 18.057 3.662 4.218 -0.353 -2.198 N29 H6S 24 H6S O09 O1 O 0 1 N N N -25.234 23.716 3.880 -1.211 0.545 0.004 O09 H6S 25 H6S O25 O2 O 0 1 N N N -22.393 18.165 8.522 6.057 2.693 1.361 O25 H6S 26 H6S O26 O3 O 0 1 N N N -23.766 19.879 8.419 3.926 2.396 1.907 O26 H6S 27 H6S S19 S1 S 0 1 Y N N -24.756 21.184 5.787 1.836 0.848 0.613 S19 H6S 28 H6S CL CL1 CL 0 0 N N N -26.707 23.876 6.307 -0.026 -3.399 -1.409 CL H6S 29 H6S H1 H1 H 0 1 N N N -29.464 23.591 6.473 -0.428 -5.052 0.876 H1 H6S 30 H6S H2 H2 H 0 1 N N N -31.141 22.591 4.985 -0.994 -4.502 3.208 H2 H6S 31 H6S H3 H3 H 0 1 N N N -30.431 21.580 2.856 -1.313 -2.153 3.877 H3 H6S 32 H6S H4 H4 H 0 1 N N N -28.068 21.569 2.227 -1.063 -0.355 2.214 H4 H6S 33 H6S H5 H5 H 0 1 N N N -25.949 22.430 2.425 -0.805 -0.939 -1.374 H5 H6S 34 H6S H6 H6 H 0 1 N N N -26.434 25.379 3.601 -3.075 -0.338 -0.117 H6 H6S 35 H6S H7 H7 H 0 1 N N N -25.858 24.574 2.103 -2.547 0.541 -1.572 H7 H6S 36 H6S H8 H8 H 0 1 N N N -24.343 26.322 4.051 -3.368 1.762 1.101 H8 H6S 37 H6S H9 H9 H 0 1 N N N -24.525 26.497 2.272 -2.702 2.686 -0.267 H9 H6S 38 H6S H10 H10 H 0 1 N N N -23.240 23.983 3.123 -4.598 1.778 -1.698 H10 H6S 39 H6S H11 H11 H 0 1 N N N -23.746 23.560 0.708 -5.824 -0.097 -1.923 H11 H6S 40 H6S H12 H12 H 0 1 N N N -22.375 24.110 -0.314 -4.537 -0.808 -0.920 H12 H6S 41 H6S H13 H13 H 0 1 N N N -22.058 23.176 1.187 -6.245 -1.103 -0.516 H13 H6S 42 H6S H14 H14 H 0 1 N N N -20.562 24.807 1.390 -7.215 1.324 1.128 H14 H6S 43 H6S H15 H15 H 0 1 N N N -21.097 26.358 0.657 -7.598 0.798 -0.533 H15 H6S 44 H6S H16 H16 H 0 1 N N N -20.013 26.298 3.124 -7.171 2.912 -1.432 H16 H6S 45 H6S H17 H17 H 0 1 N N N -21.384 27.396 2.750 -7.481 3.464 0.247 H17 H6S 46 H6S H18 H18 H 0 1 N N N -21.387 24.740 4.212 -5.133 3.488 0.793 H18 H6S 47 H6S H19 H19 H 0 1 N N N -22.330 26.230 4.551 -5.084 4.003 -0.927 H19 H6S 48 H6S H20 H20 H 0 1 N N N -25.033 20.080 2.368 1.485 -1.270 -2.269 H20 H6S 49 H6S H21 H21 H 0 1 N N N -22.421 16.683 6.444 6.638 1.411 -0.759 H21 H6S 50 H6S H22 H22 H 0 1 N N N -22.782 16.246 4.063 6.204 -0.059 -2.682 H22 H6S 51 H6S H24 H24 H 0 1 N N N -22.375 18.486 9.416 6.154 3.261 2.137 H24 H6S 52 # 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 H6S C14 N13 SING N N 1 H6S N13 C15 SING N N 2 H6S N13 C12 SING N N 3 H6S C15 C16 SING N N 4 H6S C16 C17 SING N N 5 H6S C12 C11 SING N N 6 H6S C12 C17 SING N N 7 H6S C11 C10 SING N N 8 H6S C10 O09 SING N N 9 H6S C06 C05 DOUB Y N 10 H6S C06 C07 SING Y N 11 H6S C20 C18 DOUB Y N 12 H6S C20 C21 SING Y N 13 H6S C05 C04 SING Y N 14 H6S C08 O09 SING N N 15 H6S C08 C07 SING N N 16 H6S C08 C18 SING N N 17 H6S N29 C21 DOUB Y N 18 H6S N29 C28 SING Y N 19 H6S C07 C02 DOUB Y N 20 H6S C18 S19 SING Y N 21 H6S C21 C22 SING Y N 22 H6S C28 C27 DOUB Y N 23 H6S C04 C03 DOUB Y N 24 H6S C02 C03 SING Y N 25 H6S C02 CL SING N N 26 H6S C22 S19 SING Y N 27 H6S C22 C23 DOUB Y N 28 H6S C27 C23 SING Y N 29 H6S C23 C24 SING N N 30 H6S C24 O26 DOUB N N 31 H6S C24 O25 SING N N 32 H6S C03 H1 SING N N 33 H6S C04 H2 SING N N 34 H6S C05 H3 SING N N 35 H6S C06 H4 SING N N 36 H6S C08 H5 SING N N 37 H6S C10 H6 SING N N 38 H6S C10 H7 SING N N 39 H6S C11 H8 SING N N 40 H6S C11 H9 SING N N 41 H6S C12 H10 SING N N 42 H6S C14 H11 SING N N 43 H6S C14 H12 SING N N 44 H6S C14 H13 SING N N 45 H6S C15 H14 SING N N 46 H6S C15 H15 SING N N 47 H6S C16 H16 SING N N 48 H6S C16 H17 SING N N 49 H6S C17 H18 SING N N 50 H6S C17 H19 SING N N 51 H6S C20 H20 SING N N 52 H6S C27 H21 SING N N 53 H6S C28 H22 SING N N 54 H6S O25 H24 SING N N 55 # 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 H6S SMILES ACDLabs 12.01 "c1(ccccc1C(OCCC2CCCN2C)c3sc4c(c3)nccc4C(=O)O)Cl" H6S InChI InChI 1.03 "InChI=1S/C22H23ClN2O3S/c1-25-11-4-5-14(25)9-12-28-20(15-6-2-3-7-17(15)23)19-13-18-21(29-19)16(22(26)27)8-10-24-18/h2-3,6-8,10,13-14,20H,4-5,9,11-12H2,1H3,(H,26,27)/t14-,20+/m0/s1" H6S InChIKey InChI 1.03 CKHGFLIUOABPPV-VBKZILBWSA-N H6S SMILES_CANONICAL CACTVS 3.385 "CN1CCC[C@H]1CCO[C@@H](c2sc3c(c2)nccc3C(O)=O)c4ccccc4Cl" H6S SMILES CACTVS 3.385 "CN1CCC[CH]1CCO[CH](c2sc3c(c2)nccc3C(O)=O)c4ccccc4Cl" H6S SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "CN1CCC[C@H]1CCO[C@H](c2ccccc2Cl)c3cc4c(s3)c(ccn4)C(=O)O" H6S SMILES "OpenEye OEToolkits" 2.0.6 "CN1CCCC1CCOC(c2ccccc2Cl)c3cc4c(s3)c(ccn4)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 H6S "SYSTEMATIC NAME" ACDLabs 12.01 "2-[(R)-(2-chlorophenyl){2-[(2S)-1-methylpyrrolidin-2-yl]ethoxy}methyl]thieno[3,2-b]pyridine-7-carboxylic acid" H6S "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "2-[(~{R})-(2-chlorophenyl)-[2-[(2~{S})-1-methylpyrrolidin-2-yl]ethoxy]methyl]thieno[3,2-b]pyridine-7-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 H6S "Create component" 2018-06-11 RCSB H6S "Initial release" 2018-11-21 RCSB #