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 
# 
