data_E9A # _chem_comp.id E9A _chem_comp.name "1-methyl-3-(2-{[(1R,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-2-oxoethyl)-2-(phenoxymethyl)-1H-1,3-benzimidazol-3-ium" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C27 H35 N2 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 1 _chem_comp.pdbx_initial_date 2017-12-13 _chem_comp.pdbx_modified_date 2024-04-25 _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 435.578 _chem_comp.one_letter_code ? _chem_comp.three_letter_code E9A _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 6BUV _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.pdbx_n_terminal_atom_flag _chem_comp_atom.pdbx_backbone_atom_flag _chem_comp_atom.pdbx_c_terminal_atom_flag _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 E9A C8 C1 C 0 1 N N R N N N -0.109 60.834 59.063 -3.190 0.382 -0.730 C8 E9A 1 E9A N1 N1 N 0 1 Y N N N N N -4.839 59.063 56.276 2.894 -2.078 -0.751 N1 E9A 2 E9A C7 C2 C 0 1 N N N N N N -2.151 64.041 59.462 -6.229 -0.644 1.400 C7 E9A 3 E9A O O1 O 0 1 N N N N N N -1.011 60.597 57.926 -2.171 0.197 0.288 O E9A 4 E9A C6 C3 C 0 1 N N N N N N -0.245 64.074 57.853 -4.858 -1.971 -0.214 C6 E9A 5 E9A C5 C4 C 0 1 N N N N N N -1.151 63.173 58.704 -4.858 -0.768 0.732 C5 E9A 6 E9A C1 C5 C 0 1 N N S N N N 0.375 59.968 61.418 -2.892 2.858 -0.578 C1 E9A 7 E9A C2 C6 C 0 1 N N N N N N 0.201 61.390 61.915 -4.263 2.982 0.089 C2 E9A 8 E9A C3 C7 C 0 1 N N N N N N -0.784 62.163 61.054 -4.561 1.708 0.884 C3 E9A 9 E9A C4 C8 C 0 1 N N R N N N -0.307 62.250 59.605 -4.561 0.506 -0.062 C4 E9A 10 E9A N N2 N 1 1 Y N N N N N -2.812 59.798 55.938 1.075 -1.547 0.331 N E9A 11 E9A C C9 C 0 1 N N N N N N 1.837 59.561 61.301 -2.595 4.131 -1.372 C E9A 12 E9A C10 C10 C 0 1 N N N N N N -0.500 59.879 56.901 -1.087 -0.516 -0.057 C10 E9A 13 E9A C11 C11 C 0 1 N N N N N N -1.380 59.777 55.673 0.013 -0.749 0.947 C11 E9A 14 E9A C12 C12 C 0 1 Y N N N N N -3.546 58.706 56.206 2.102 -1.065 -0.306 C12 E9A 15 E9A C13 C13 C 0 1 N N N N N N -5.977 58.188 56.517 4.140 -1.937 -1.510 C13 E9A 16 E9A C14 C14 C 0 1 Y N N N N N -4.940 60.438 56.032 2.309 -3.263 -0.351 C14 E9A 17 E9A C15 C15 C 0 1 Y N N N N N -3.657 60.898 55.802 1.140 -2.904 0.341 C15 E9A 18 E9A C16 C16 C 0 1 Y N N N N N -3.424 62.218 55.447 0.321 -3.904 0.872 C16 E9A 19 E9A C17 C17 C 0 1 Y N N N N N -4.516 63.063 55.337 0.662 -5.217 0.715 C17 E9A 20 E9A C18 C18 C 0 1 Y N N N N N -5.806 62.605 55.587 1.816 -5.572 0.031 C18 E9A 21 E9A C19 C19 C 0 1 Y N N N N N -6.037 61.285 55.945 2.641 -4.602 -0.498 C19 E9A 22 E9A C20 C20 C 0 1 N N N N N N -2.942 57.297 56.315 2.375 0.402 -0.520 C20 E9A 23 E9A C21 C21 C 0 1 Y N N N N N -1.728 56.423 58.233 3.494 2.220 0.526 C21 E9A 24 E9A C22 C22 C 0 1 Y N N N N N -1.689 56.275 59.612 4.253 2.773 1.547 C22 E9A 25 E9A C23 C23 C 0 1 Y N N N N N -0.589 55.675 60.201 4.598 4.110 1.503 C23 E9A 26 E9A C24 C24 C 0 1 Y N N N N N 0.459 55.224 59.429 4.187 4.897 0.442 C24 E9A 27 E9A C25 C25 C 0 1 Y N N N N N 0.412 55.362 58.059 3.430 4.347 -0.576 C25 E9A 28 E9A C26 C26 C 0 1 Y N N N N N -0.679 55.957 57.450 3.083 3.011 -0.536 C26 E9A 29 E9A C9 C27 C 0 1 N N N N N N -0.375 59.756 60.100 -2.892 1.655 -1.524 C9 E9A 30 E9A O1 O2 O 0 1 N N N N N N 0.587 59.381 56.928 -0.992 -0.970 -1.173 O1 E9A 31 E9A O2 O3 O 0 1 N N N N N N -2.826 57.085 57.725 3.158 0.903 0.565 O2 E9A 32 E9A H16 H1 H 0 1 N N N N N N 0.932 60.738 58.721 -3.190 -0.475 -1.403 H16 E9A 33 E9A H14 H2 H 0 1 N N N N N N -2.803 63.401 60.074 -6.441 -1.551 1.966 H14 E9A 34 E9A H15 H3 H 0 1 N N N N N N -1.608 64.741 60.114 -6.229 0.213 2.073 H15 E9A 35 E9A H13 H4 H 0 1 N N N N N N -2.762 64.608 58.744 -6.994 -0.506 0.636 H13 E9A 36 E9A H12 H5 H 0 1 N N N N N N 0.478 63.453 57.304 -5.623 -1.832 -0.978 H12 E9A 37 E9A H11 H6 H 0 1 N N N N N N -0.859 64.641 57.138 -3.881 -2.059 -0.689 H11 E9A 38 E9A H10 H7 H 0 1 N N N N N N 0.295 64.774 58.508 -5.070 -2.878 0.352 H10 E9A 39 E9A H9 H8 H 0 1 N N N N N N -1.721 62.531 58.016 -4.093 -0.906 1.496 H9 E9A 40 E9A H3 H9 H 0 1 N N N N N N -0.088 59.304 62.163 -2.127 2.719 0.186 H3 E9A 41 E9A H4 H10 H 0 1 N N N N N N 1.175 61.900 61.889 -4.263 3.838 0.763 H4 E9A 42 E9A H5 H11 H 0 1 N N N N N N -0.172 61.364 62.950 -5.028 3.120 -0.675 H5 E9A 43 E9A H7 H12 H 0 1 N N N N N N -0.891 63.181 61.458 -3.796 1.569 1.648 H7 E9A 44 E9A H6 H13 H 0 1 N N N N N N -1.759 61.654 61.080 -5.537 1.796 1.359 H6 E9A 45 E9A H8 H14 H 0 1 N N N N N N 0.695 62.702 59.643 -5.326 0.644 -0.826 H8 E9A 46 E9A H2 H15 H 0 1 N N N N N N 2.342 59.727 62.264 -2.595 4.988 -0.699 H2 E9A 47 E9A H1 H16 H 0 1 N N N N N N 1.901 58.496 61.032 -1.618 4.043 -1.848 H1 E9A 48 E9A H H17 H 0 1 N N N N N N 2.325 60.166 60.522 -3.360 4.270 -2.137 H E9A 49 E9A H20 H18 H 0 1 N N N N N N -1.142 58.834 55.160 -0.389 -1.282 1.809 H20 E9A 50 E9A H19 H19 H 0 1 N N N N N N -1.143 60.624 55.012 0.419 0.210 1.270 H19 E9A 51 E9A H23 H20 H 0 1 N N N N N N -5.622 57.160 56.680 4.980 -1.872 -0.819 H23 E9A 52 E9A H22 H21 H 0 1 N N N N N N -6.522 58.533 57.408 4.269 -2.802 -2.160 H22 E9A 53 E9A H21 H22 H 0 1 N N N N N N -6.648 58.211 55.645 4.096 -1.031 -2.115 H21 E9A 54 E9A H24 H23 H 0 1 N N N N N N -2.422 62.576 55.262 -0.579 -3.639 1.406 H24 E9A 55 E9A H25 H24 H 0 1 N N N N N N -4.364 64.094 55.053 0.027 -5.987 1.127 H25 E9A 56 E9A H26 H25 H 0 1 N N N N N N -6.639 63.287 55.501 2.072 -6.615 -0.085 H26 E9A 57 E9A H27 H26 H 0 1 N N N N N N -7.036 60.928 56.149 3.538 -4.884 -1.029 H27 E9A 58 E9A H29 H27 H 0 1 N N N N N N -3.607 56.549 55.859 2.919 0.538 -1.454 H29 E9A 59 E9A H28 H28 H 0 1 N N N N N N -1.956 57.255 55.830 1.430 0.944 -0.567 H28 E9A 60 E9A H30 H29 H 0 1 N N N N N N -2.510 56.625 60.221 4.574 2.159 2.376 H30 E9A 61 E9A H31 H30 H 0 1 N N N N N N -0.552 55.560 61.274 5.188 4.542 2.297 H31 E9A 62 E9A H32 H31 H 0 1 N N N N N N 1.316 54.763 59.897 4.457 5.942 0.410 H32 E9A 63 E9A H33 H32 H 0 1 N N N N N N 1.233 55.003 57.456 3.109 4.964 -1.403 H33 E9A 64 E9A H34 H33 H 0 1 N N N N N N -0.715 56.058 56.375 2.491 2.582 -1.332 H34 E9A 65 E9A H18 H34 H 0 1 N N N N N N -1.454 59.739 60.314 -1.915 1.567 -2.000 H18 E9A 66 E9A H17 H35 H 0 1 N N N N N N -0.069 58.787 59.679 -3.657 1.794 -2.288 H17 E9A 67 # 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 E9A C17 C16 DOUB Y N 1 E9A C17 C18 SING Y N 2 E9A C16 C15 SING Y N 3 E9A C18 C19 DOUB Y N 4 E9A C11 N SING N N 5 E9A C11 C10 SING N N 6 E9A C15 N SING Y N 7 E9A C15 C14 DOUB Y N 8 E9A N C12 DOUB Y N 9 E9A C19 C14 SING Y N 10 E9A C14 N1 SING Y N 11 E9A C12 N1 SING Y N 12 E9A C12 C20 SING N N 13 E9A N1 C13 SING N N 14 E9A C20 O2 SING N N 15 E9A C10 O1 DOUB N N 16 E9A C10 O SING N N 17 E9A C26 C25 DOUB Y N 18 E9A C26 C21 SING Y N 19 E9A O2 C21 SING N N 20 E9A C6 C5 SING N N 21 E9A O C8 SING N N 22 E9A C25 C24 SING Y N 23 E9A C21 C22 DOUB Y N 24 E9A C5 C7 SING N N 25 E9A C5 C4 SING N N 26 E9A C8 C4 SING N N 27 E9A C8 C9 SING N N 28 E9A C24 C23 DOUB Y N 29 E9A C4 C3 SING N N 30 E9A C22 C23 SING Y N 31 E9A C9 C1 SING N N 32 E9A C3 C2 SING N N 33 E9A C C1 SING N N 34 E9A C1 C2 SING N N 35 E9A C8 H16 SING N N 36 E9A C7 H14 SING N N 37 E9A C7 H15 SING N N 38 E9A C7 H13 SING N N 39 E9A C6 H12 SING N N 40 E9A C6 H11 SING N N 41 E9A C6 H10 SING N N 42 E9A C5 H9 SING N N 43 E9A C1 H3 SING N N 44 E9A C2 H4 SING N N 45 E9A C2 H5 SING N N 46 E9A C3 H7 SING N N 47 E9A C3 H6 SING N N 48 E9A C4 H8 SING N N 49 E9A C H2 SING N N 50 E9A C H1 SING N N 51 E9A C H SING N N 52 E9A C11 H20 SING N N 53 E9A C11 H19 SING N N 54 E9A C13 H23 SING N N 55 E9A C13 H22 SING N N 56 E9A C13 H21 SING N N 57 E9A C16 H24 SING N N 58 E9A C17 H25 SING N N 59 E9A C18 H26 SING N N 60 E9A C19 H27 SING N N 61 E9A C20 H29 SING N N 62 E9A C20 H28 SING N N 63 E9A C22 H30 SING N N 64 E9A C23 H31 SING N N 65 E9A C24 H32 SING N N 66 E9A C25 H33 SING N N 67 E9A C26 H34 SING N N 68 E9A C9 H18 SING N N 69 E9A C9 H17 SING N N 70 # 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 E9A SMILES ACDLabs 12.01 "CC(C)C1CCC(C)CC1OC(=O)C[n+]1c2ccccc2n(C)c1COc1ccccc1" E9A InChI InChI 1.06 "InChI=1S/C27H35N2O3/c1-19(2)22-15-14-20(3)16-25(22)32-27(30)17-29-24-13-9-8-12-23(24)28(4)26(29)18-31-21-10-6-5-7-11-21/h5-13,19-20,22,25H,14-18H2,1-4H3/q+1/t20-,22+,25+/m0/s1" E9A InChIKey InChI 1.06 HACNGQQLOZYIEB-NIRIFSCTSA-N E9A SMILES_CANONICAL CACTVS 3.385 "C[C@H]1CC[C@H](C(C)C)[C@@H](C1)OC(=O)C[n+]2c(COc3ccccc3)n(C)c4ccccc24" E9A SMILES CACTVS 3.385 "C[CH]1CC[CH](C(C)C)[CH](C1)OC(=O)C[n+]2c(COc3ccccc3)n(C)c4ccccc24" E9A SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "C[C@H]1CC[C@@H]([C@@H](C1)OC(=O)C[n+]2c3ccccc3n(c2COc4ccccc4)C)C(C)C" E9A SMILES "OpenEye OEToolkits" 2.0.7 "CC1CCC(C(C1)OC(=O)C[n+]2c3ccccc3n(c2COc4ccccc4)C)C(C)C" # 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 E9A "SYSTEMATIC NAME" ACDLabs 12.01 "1-methyl-3-(2-{[(1R,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-2-oxoethyl)-2-(phenoxymethyl)-1H-1,3-benzimidazol-3-ium" E9A "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "[(1~{R},2~{R},5~{S})-5-methyl-2-propan-2-yl-cyclohexyl] 2-[3-methyl-2-(phenoxymethyl)benzimidazol-1-ium-1-yl]ethanoate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site E9A "Create component" 2017-12-13 RCSB E9A "Initial release" 2018-12-12 RCSB E9A "Modify charge" 2024-04-25 RCSB #