data_I66 # _chem_comp.id I66 _chem_comp.name "ethyl 5-hydroxy-2-phenyl-4-(pyrrolidin-1-ylmethyl)-1-benzofuran-3-carboxylate" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H23 N O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2014-01-17 _chem_comp.pdbx_modified_date 2017-06-30 _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 365.422 _chem_comp.one_letter_code ? _chem_comp.three_letter_code I66 _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 4O9Q _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 I66 O1 O1 O 0 1 N N N 6.261 27.635 6.443 -0.448 -1.780 -0.906 O1 I66 1 I66 C2 C2 C 0 1 N N N 5.690 26.555 6.322 -0.678 -1.179 0.126 C2 I66 2 I66 O3 O3 O 0 1 N N N 6.098 25.711 5.336 -0.891 -1.861 1.270 O3 I66 3 I66 C4 C4 C 0 1 N N N 7.374 26.014 4.714 -0.831 -3.309 1.195 C4 I66 4 I66 C5 C5 C 0 1 N N N 7.602 24.993 3.601 -1.095 -3.903 2.580 C5 I66 5 I66 C6 C6 C 0 1 Y N N 4.450 26.249 7.098 -0.717 0.286 0.128 C6 I66 6 I66 C7 C7 C 0 1 Y N N 3.412 27.190 7.626 0.410 1.210 0.361 C7 I66 7 I66 C8 C8 C 0 1 Y N N 3.176 28.578 7.614 1.764 1.033 0.632 C8 I66 8 I66 C9 C9 C 0 1 Y N N 2.030 29.092 8.239 2.576 2.139 0.803 C9 I66 9 I66 O10 O10 O 0 1 N N N 1.803 30.436 8.225 3.900 1.975 1.068 O10 I66 10 I66 C11 C11 C 0 1 Y N N 1.129 28.255 8.893 2.041 3.419 0.703 C11 I66 11 I66 C12 C12 C 0 1 Y N N 1.356 26.899 8.918 0.701 3.601 0.435 C12 I66 12 I66 C13 C13 C 0 1 Y N N 2.479 26.369 8.290 -0.130 2.501 0.260 C13 I66 13 I66 O14 O14 O 0 1 Y N N 2.895 25.097 8.177 -1.449 2.384 -0.006 O14 I66 14 I66 C15 C15 C 0 1 Y N N 4.028 24.976 7.496 -1.819 1.097 -0.095 C15 I66 15 I66 C16 C16 C 0 1 Y N N 4.668 23.646 7.296 -3.185 0.620 -0.381 C16 I66 16 I66 C17 C17 C 0 1 Y N N 6.069 23.501 7.272 -4.220 1.536 -0.589 C17 I66 17 I66 C18 C18 C 0 1 Y N N 6.656 22.257 7.116 -5.494 1.083 -0.856 C18 I66 18 I66 C19 C19 C 0 1 Y N N 5.846 21.134 7.007 -5.751 -0.276 -0.918 C19 I66 19 I66 C20 C20 C 0 1 Y N N 4.461 21.257 7.063 -4.731 -1.189 -0.713 C20 I66 20 I66 C21 C21 C 0 1 Y N N 3.859 22.496 7.212 -3.450 -0.751 -0.451 C21 I66 21 I66 C22 C22 C 0 1 N N N 4.109 29.577 6.935 2.340 -0.355 0.739 C22 I66 22 I66 N23 N23 N 0 1 N N N 5.270 29.938 7.792 2.801 -0.798 -0.583 N23 I66 23 I66 C24 C24 C 0 1 N N N 6.280 30.769 7.083 4.040 -0.082 -0.983 C24 I66 24 I66 C25 C25 C 0 1 N N N 6.779 31.828 8.106 4.646 -1.003 -2.071 C25 I66 25 I66 C26 C26 C 0 1 N N N 6.160 31.397 9.479 4.334 -2.421 -1.538 C26 I66 26 I66 C27 C27 C 0 1 N N N 4.899 30.638 9.035 3.152 -2.235 -0.569 C27 I66 27 I66 H1 H1 H 0 1 N N N 8.180 25.943 5.459 -1.586 -3.669 0.496 H1 I66 28 I66 H2 H2 H 0 1 N N N 7.353 27.030 4.292 0.158 -3.615 0.852 H2 I66 29 I66 H3 H3 H 0 1 N N N 8.564 25.196 3.108 -1.051 -4.991 2.524 H3 I66 30 I66 H4 H4 H 0 1 N N N 7.616 23.980 4.030 -0.341 -3.544 3.280 H4 I66 31 I66 H5 H5 H 0 1 N N N 6.789 25.067 2.863 -2.084 -3.598 2.924 H5 I66 32 I66 H6 H6 H 0 1 N N N 0.994 30.626 8.685 4.457 1.934 0.279 H6 I66 33 I66 H7 H7 H 0 1 N N N 0.257 28.669 9.378 2.681 4.278 0.837 H7 I66 34 I66 H8 H8 H 0 1 N N N 0.662 26.245 9.425 0.297 4.599 0.359 H8 I66 35 I66 H9 H9 H 0 1 N N N 6.695 24.375 7.377 -4.021 2.596 -0.541 H9 I66 36 I66 H10 H10 H 0 1 N N N 7.731 22.161 7.079 -6.295 1.790 -1.017 H10 I66 37 I66 H11 H11 H 0 1 N N N 6.294 20.160 6.878 -6.752 -0.625 -1.123 H11 I66 38 I66 H12 H12 H 0 1 N N N 3.846 20.373 6.989 -4.938 -2.248 -0.763 H12 I66 39 I66 H13 H13 H 0 1 N N N 2.783 22.579 7.263 -2.655 -1.464 -0.291 H13 I66 40 I66 H14 H14 H 0 1 N N N 4.483 29.133 6.001 3.181 -0.347 1.433 H14 I66 41 I66 H15 H15 H 0 1 N N N 3.542 30.491 6.705 1.575 -1.039 1.105 H15 I66 42 I66 H17 H17 H 0 1 N N N 7.119 30.142 6.746 3.802 0.897 -1.396 H17 I66 43 I66 H18 H18 H 0 1 N N N 5.822 31.266 6.215 4.720 0.011 -0.136 H18 I66 44 I66 H19 H19 H 0 1 N N N 7.878 31.824 8.160 4.159 -0.837 -3.032 H19 I66 45 I66 H20 H20 H 0 1 N N N 6.429 32.832 7.823 5.722 -0.849 -2.151 H20 I66 46 I66 H21 H21 H 0 1 N N N 6.845 30.742 10.038 4.051 -3.080 -2.359 H21 I66 47 I66 H22 H22 H 0 1 N N N 5.904 32.272 10.095 5.198 -2.825 -1.010 H22 I66 48 I66 H23 H23 H 0 1 N N N 4.074 31.341 8.847 3.445 -2.535 0.437 H23 I66 49 I66 H24 H24 H 0 1 N N N 4.596 29.915 9.806 2.301 -2.828 -0.904 H24 I66 50 # 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 I66 C5 C4 SING N N 1 I66 C4 O3 SING N N 2 I66 O3 C2 SING N N 3 I66 C2 O1 DOUB N N 4 I66 C2 C6 SING N N 5 I66 C22 C8 SING N N 6 I66 C22 N23 SING N N 7 I66 C19 C20 DOUB Y N 8 I66 C19 C18 SING Y N 9 I66 C20 C21 SING Y N 10 I66 C24 N23 SING N N 11 I66 C24 C25 SING N N 12 I66 C6 C15 DOUB Y N 13 I66 C6 C7 SING Y N 14 I66 C18 C17 DOUB Y N 15 I66 C21 C16 DOUB Y N 16 I66 C17 C16 SING Y N 17 I66 C16 C15 SING N N 18 I66 C15 O14 SING Y N 19 I66 C8 C7 DOUB Y N 20 I66 C8 C9 SING Y N 21 I66 C7 C13 SING Y N 22 I66 N23 C27 SING N N 23 I66 C25 C26 SING N N 24 I66 O14 C13 SING Y N 25 I66 O10 C9 SING N N 26 I66 C9 C11 DOUB Y N 27 I66 C13 C12 DOUB Y N 28 I66 C11 C12 SING Y N 29 I66 C27 C26 SING N N 30 I66 C4 H1 SING N N 31 I66 C4 H2 SING N N 32 I66 C5 H3 SING N N 33 I66 C5 H4 SING N N 34 I66 C5 H5 SING N N 35 I66 O10 H6 SING N N 36 I66 C11 H7 SING N N 37 I66 C12 H8 SING N N 38 I66 C17 H9 SING N N 39 I66 C18 H10 SING N N 40 I66 C19 H11 SING N N 41 I66 C20 H12 SING N N 42 I66 C21 H13 SING N N 43 I66 C22 H14 SING N N 44 I66 C22 H15 SING N N 45 I66 C24 H17 SING N N 46 I66 C24 H18 SING N N 47 I66 C25 H19 SING N N 48 I66 C25 H20 SING N N 49 I66 C26 H21 SING N N 50 I66 C26 H22 SING N N 51 I66 C27 H23 SING N N 52 I66 C27 H24 SING N N 53 # 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 I66 SMILES ACDLabs 12.01 "O=C(OCC)c1c3c(c(O)ccc3oc1c2ccccc2)CN4CCCC4" I66 InChI InChI 1.03 "InChI=1S/C22H23NO4/c1-2-26-22(25)20-19-16(14-23-12-6-7-13-23)17(24)10-11-18(19)27-21(20)15-8-4-3-5-9-15/h3-5,8-11,24H,2,6-7,12-14H2,1H3" I66 InChIKey InChI 1.03 VIMMVCAKDVTEMS-UHFFFAOYSA-N I66 SMILES_CANONICAL CACTVS 3.385 "CCOC(=O)c1c(oc2ccc(O)c(CN3CCCC3)c12)c4ccccc4" I66 SMILES CACTVS 3.385 "CCOC(=O)c1c(oc2ccc(O)c(CN3CCCC3)c12)c4ccccc4" I66 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CCOC(=O)c1c2c(ccc(c2CN3CCCC3)O)oc1c4ccccc4" I66 SMILES "OpenEye OEToolkits" 1.7.6 "CCOC(=O)c1c2c(ccc(c2CN3CCCC3)O)oc1c4ccccc4" # 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 I66 "SYSTEMATIC NAME" ACDLabs 12.01 "ethyl 5-hydroxy-2-phenyl-4-(pyrrolidin-1-ylmethyl)-1-benzofuran-3-carboxylate" I66 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "ethyl 5-oxidanyl-2-phenyl-4-(pyrrolidin-1-ylmethyl)-1-benzofuran-3-carboxylate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site I66 "Create component" 2014-01-17 RCSB I66 "Initial release" 2017-07-05 RCSB #