data_5EL # _chem_comp.id 5EL _chem_comp.name "4-(4-{[(3S)-3-HYDROXY-1-AZABICYCLO[2.2.2]OCT-3-YL]ETHYNYL}PHENOXY)-N-(PYRIDIN-4-YLMETHYL)BENZAMIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C28 H27 N3 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2011-05-13 _chem_comp.pdbx_modified_date 2011-06-24 _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 453.532 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 5EL _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 2YIG _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 5EL C1 C1 C 0 1 Y N N 55.382 -14.534 22.886 1.892 -0.713 -0.366 C1 5EL 1 5EL C2 C2 C 0 1 Y N N 54.564 -13.664 23.550 0.706 -1.315 -0.004 C2 5EL 2 5EL C3 C3 C 0 1 Y N N 54.831 -13.236 24.838 0.705 -2.354 0.917 C3 5EL 3 5EL C4 C4 C 0 1 Y N N 55.925 -13.691 25.549 1.899 -2.790 1.477 C4 5EL 4 5EL C5 C5 C 0 1 Y N N 56.768 -14.587 24.895 3.089 -2.193 1.121 C5 5EL 5 5EL C6 C6 C 0 1 Y N N 56.484 -14.986 23.590 3.094 -1.149 0.194 C6 5EL 6 5EL C7 C7 C 0 1 N N N 57.389 -15.847 22.965 4.328 -0.527 -0.179 C7 5EL 7 5EL C8 C8 C 0 1 N N N 58.185 -16.552 22.432 5.340 -0.017 -0.486 C8 5EL 8 5EL C9 C9 C 0 1 N N S 59.107 -17.443 21.730 6.609 0.623 -0.870 C9 5EL 9 5EL C10 C10 C 0 1 N N N 60.005 -18.095 22.787 7.766 -0.038 -0.116 C10 5EL 10 5EL N1 N1 N 0 1 N N N 61.398 -17.869 22.213 8.450 0.968 0.706 N1 5EL 11 5EL C11 C11 C 0 1 N N N 61.579 -18.452 20.873 9.029 2.029 -0.130 C11 5EL 12 5EL C12 C12 C 0 1 N N N 60.696 -17.650 19.858 7.908 2.748 -0.885 C12 5EL 13 5EL C13 C13 C 0 1 N N N 59.860 -16.671 20.634 6.566 2.112 -0.504 C13 5EL 14 5EL C14 C14 C 0 1 N N N 60.761 -15.704 21.304 6.378 2.237 1.014 C14 5EL 15 5EL C15 C15 C 0 1 N N N 61.727 -16.441 22.211 7.542 1.531 1.715 C15 5EL 16 5EL O1 O1 O 0 1 N N N 58.339 -18.464 21.073 6.810 0.479 -2.278 O1 5EL 17 5EL O2 O2 O 0 1 N N N 53.996 -12.343 25.482 -0.466 -2.944 1.272 O2 5EL 18 5EL C16 C16 C 0 1 Y N N 52.655 -12.470 25.676 -1.607 -2.495 0.692 C16 5EL 19 5EL C17 C17 C 0 1 Y N N 51.994 -13.694 25.559 -2.054 -3.068 -0.493 C17 5EL 20 5EL C18 C18 C 0 1 Y N N 50.637 -13.747 25.803 -3.211 -2.615 -1.086 C18 5EL 21 5EL C19 C19 C 0 1 Y N N 49.987 -12.594 26.164 -3.937 -1.577 -0.494 C19 5EL 22 5EL C20 C20 C 0 1 Y N N 50.614 -11.383 26.299 -3.484 -1.004 0.698 C20 5EL 23 5EL C21 C21 C 0 1 Y N N 51.981 -11.323 26.037 -2.329 -1.466 1.286 C21 5EL 24 5EL C22 C22 C 0 1 N N N 48.550 -12.655 26.475 -5.178 -1.088 -1.126 C22 5EL 25 5EL O3 O3 O 0 1 N N N 48.047 -11.834 27.244 -5.570 -1.588 -2.162 O3 5EL 26 5EL N2 N2 N 0 1 N N N 47.891 -13.713 25.917 -5.876 -0.087 -0.553 N2 5EL 27 5EL C23 C23 C 0 1 N N N 46.549 -14.072 26.325 -7.108 0.398 -1.181 C23 5EL 28 5EL C24 C24 C 0 1 Y N N 45.530 -13.206 25.748 -7.691 1.511 -0.348 C24 5EL 29 5EL C25 C25 C 0 1 Y N N 45.863 -12.116 24.963 -7.335 2.831 -0.578 C25 5EL 30 5EL C26 C26 C 0 1 Y N N 44.866 -11.272 24.493 -7.890 3.825 0.206 C26 5EL 31 5EL N3 N3 N 0 1 Y N N 43.560 -11.498 24.725 -8.748 3.529 1.162 N3 5EL 32 5EL C27 C27 C 0 1 Y N N 43.264 -12.606 25.453 -9.110 2.285 1.409 C27 5EL 33 5EL C28 C28 C 0 1 Y N N 44.196 -13.471 26.009 -8.601 1.239 0.663 C28 5EL 34 5EL H1 H1 H 0 1 N N N 55.181 -14.850 21.873 1.892 0.092 -1.086 H1 5EL 35 5EL H2 H2 H 0 1 N N N 53.678 -13.298 23.052 -0.224 -0.977 -0.437 H2 5EL 36 5EL H4 H4 H 0 1 N N N 56.117 -13.368 26.562 1.895 -3.599 2.194 H4 5EL 37 5EL H5 H5 H 0 1 N N N 57.642 -14.972 25.399 4.016 -2.533 1.557 H5 5EL 38 5EL H101 H101 H 0 0 N N N 59.886 -17.625 23.774 7.377 -0.829 0.526 H101 5EL 39 5EL H102 H102 H 0 0 N N N 59.781 -19.165 22.913 8.470 -0.464 -0.831 H102 5EL 40 5EL H13 H13 H 0 1 N N N 59.161 -16.152 19.962 5.752 2.605 -1.035 H13 5EL 41 5EL HA HA H 0 1 N N N 58.924 -19.053 20.611 6.853 -0.439 -2.577 HA 5EL 42 5EL H111 H111 H 0 0 N N N 62.637 -18.387 20.579 9.559 2.742 0.502 H111 5EL 43 5EL H112 H112 H 0 0 N N N 61.271 -19.508 20.882 9.725 1.589 -0.845 H112 5EL 44 5EL H151 H151 H 0 0 N N N 61.646 -16.044 23.234 7.156 0.729 2.344 H151 5EL 45 5EL H152 H152 H 0 0 N N N 62.755 -16.301 21.844 8.084 2.249 2.332 H152 5EL 46 5EL H121 H121 H 0 0 N N N 61.339 -17.111 19.146 7.903 3.804 -0.612 H121 5EL 47 5EL H122 H122 H 0 0 N N N 60.045 -18.340 19.302 8.068 2.648 -1.959 H122 5EL 48 5EL H141 H141 H 0 0 N N N 61.328 -15.148 20.543 6.367 3.290 1.295 H141 5EL 49 5EL H142 H142 H 0 0 N N N 60.162 -15.003 21.903 5.438 1.768 1.305 H142 5EL 50 5EL H17 H17 H 0 1 N N N 52.536 -14.586 25.282 -1.493 -3.870 -0.950 H17 5EL 51 5EL H21 H21 H 0 1 N N N 52.509 -10.384 26.116 -1.981 -1.026 2.209 H21 5EL 52 5EL H18 H18 H 0 1 N N N 50.097 -14.678 25.712 -3.558 -3.060 -2.007 H18 5EL 53 5EL H20 H20 H 0 1 N N N 50.065 -10.502 26.599 -4.043 -0.202 1.158 H20 5EL 54 5EL HB HB H 0 1 N N N 48.347 -14.253 25.209 -5.564 0.311 0.274 HB 5EL 55 5EL H231 H231 H 0 0 N N N 46.352 -15.104 25.998 -6.884 0.771 -2.180 H231 5EL 56 5EL H232 H232 H 0 0 N N N 46.488 -13.996 27.421 -7.827 -0.418 -1.250 H232 5EL 57 5EL H25 H25 H 0 1 N N N 46.897 -11.922 24.717 -6.632 3.079 -1.359 H25 5EL 58 5EL H28 H28 H 0 1 N N N 43.895 -14.311 26.617 -8.904 0.223 0.867 H28 5EL 59 5EL H26 H26 H 0 1 N N N 45.149 -10.402 23.920 -7.618 4.855 0.033 H26 5EL 60 5EL H27 H27 H 0 1 N N N 42.220 -12.832 25.612 -9.815 2.082 2.201 H27 5EL 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 5EL C1 C2 SING Y N 1 5EL C1 C6 DOUB Y N 2 5EL C2 C3 DOUB Y N 3 5EL C3 C4 SING Y N 4 5EL C3 O2 SING N N 5 5EL C4 C5 DOUB Y N 6 5EL C5 C6 SING Y N 7 5EL C6 C7 SING N N 8 5EL C7 C8 TRIP N N 9 5EL C8 C9 SING N N 10 5EL C9 C10 SING N N 11 5EL C9 C13 SING N N 12 5EL C9 O1 SING N N 13 5EL C10 N1 SING N N 14 5EL N1 C11 SING N N 15 5EL N1 C15 SING N N 16 5EL C11 C12 SING N N 17 5EL C12 C13 SING N N 18 5EL C13 C14 SING N N 19 5EL C14 C15 SING N N 20 5EL O2 C16 SING N N 21 5EL C16 C17 SING Y N 22 5EL C16 C21 DOUB Y N 23 5EL C17 C18 DOUB Y N 24 5EL C18 C19 SING Y N 25 5EL C19 C20 DOUB Y N 26 5EL C19 C22 SING N N 27 5EL C20 C21 SING Y N 28 5EL C22 O3 DOUB N N 29 5EL C22 N2 SING N N 30 5EL N2 C23 SING N N 31 5EL C23 C24 SING N N 32 5EL C24 C25 DOUB Y N 33 5EL C24 C28 SING Y N 34 5EL C25 C26 SING Y N 35 5EL C26 N3 DOUB Y N 36 5EL N3 C27 SING Y N 37 5EL C27 C28 DOUB Y N 38 5EL C1 H1 SING N N 39 5EL C2 H2 SING N N 40 5EL C4 H4 SING N N 41 5EL C5 H5 SING N N 42 5EL C10 H101 SING N N 43 5EL C10 H102 SING N N 44 5EL C13 H13 SING N N 45 5EL O1 HA SING N N 46 5EL C11 H111 SING N N 47 5EL C11 H112 SING N N 48 5EL C15 H151 SING N N 49 5EL C15 H152 SING N N 50 5EL C12 H121 SING N N 51 5EL C12 H122 SING N N 52 5EL C14 H141 SING N N 53 5EL C14 H142 SING N N 54 5EL C17 H17 SING N N 55 5EL C21 H21 SING N N 56 5EL C18 H18 SING N N 57 5EL C20 H20 SING N N 58 5EL N2 HB SING N N 59 5EL C23 H231 SING N N 60 5EL C23 H232 SING N N 61 5EL C25 H25 SING N N 62 5EL C28 H28 SING N N 63 5EL C26 H26 SING N N 64 5EL C27 H27 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 5EL SMILES ACDLabs 12.01 "O=C(NCc1ccncc1)c5ccc(Oc4ccc(C#CC3(O)C2CCN(CC2)C3)cc4)cc5" 5EL SMILES_CANONICAL CACTVS 3.370 "O[C@]1(CN2CCC1CC2)C#Cc3ccc(Oc4ccc(cc4)C(=O)NCc5ccncc5)cc3" 5EL SMILES CACTVS 3.370 "O[C]1(CN2CCC1CC2)C#Cc3ccc(Oc4ccc(cc4)C(=O)NCc5ccncc5)cc3" 5EL SMILES_CANONICAL "OpenEye OEToolkits" 1.7.2 "c1cc(ccc1C#C[C@@]2(CN3CCC2CC3)O)Oc4ccc(cc4)C(=O)NCc5ccncc5" 5EL SMILES "OpenEye OEToolkits" 1.7.2 "c1cc(ccc1C#CC2(CN3CCC2CC3)O)Oc4ccc(cc4)C(=O)NCc5ccncc5" 5EL InChI InChI 1.03 "InChI=1S/C28H27N3O3/c32-27(30-19-22-10-15-29-16-11-22)23-3-7-26(8-4-23)34-25-5-1-21(2-6-25)9-14-28(33)20-31-17-12-24(28)13-18-31/h1-8,10-11,15-16,24,33H,12-13,17-20H2,(H,30,32)/t28-/m0/s1" 5EL InChIKey InChI 1.03 FEOIBPWKGPFSTB-NDEPHWFRSA-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 5EL "SYSTEMATIC NAME" ACDLabs 12.01 "4-(4-{[(3S)-3-hydroxy-1-azabicyclo[2.2.2]oct-3-yl]ethynyl}phenoxy)-N-(pyridin-4-ylmethyl)benzamide" 5EL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.2 "4-[4-[2-[(3S)-3-oxidanyl-1-azabicyclo[2.2.2]octan-3-yl]ethynyl]phenoxy]-N-(pyridin-4-ylmethyl)benzamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 5EL "Create component" 2011-05-13 EBI 5EL "Modify aromatic_flag" 2011-06-04 RCSB 5EL "Modify descriptor" 2011-06-04 RCSB #