data_A1IHE
# 
_chem_comp.id                                    A1IHE 
_chem_comp.name                                  "2-[[(2~{R},3~{R},4~{S},5~{S},6~{R})-2-(3,4-dichlorophenyl)sulfanyl-6-(hydroxymethyl)-5-oxidanyl-3-prop-2-ynoxy-oxan-4-yl]oxymethyl]-3-methyl-benzimidazole-5-carboxylic acid" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H24 Cl2 N2 O7 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2024-07-08 
_chem_comp.pdbx_modified_date                    2025-03-07 
_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                        567.438 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1IHE 
_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        9FYJ 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBE 
_chem_comp.pdbx_pcm                              ? 
# 
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 
A1IHE C2   C1  C  0 1 N N N N N N 14.793 5.787 -9.268  2.175   3.836  0.279  C2   A1IHE 1  
A1IHE C3   C2  C  0 1 N N R N N N 13.418 6.096 -9.802  1.747   2.376  0.117  C3   A1IHE 2  
A1IHE O1   O1  O  0 1 N N N N N N 15.815 6.514 -9.915  3.593   3.935  0.137  O1   A1IHE 3  
A1IHE C5   C3  C  0 1 N N R N N N 12.154 5.984 -11.825 1.969   0.208  1.118  C5   A1IHE 4  
A1IHE C7   C4  C  0 1 Y N N N N N 13.510 8.010 -12.994 4.336   -0.460 -0.219 C7   A1IHE 5  
A1IHE O4   O2  O  0 1 N N N N N N 13.369 5.635 -11.164 2.289   1.599  1.187  O4   A1IHE 6  
A1IHE C11  C5  C  0 1 Y N N N N N 15.942 8.362 -14.261 7.081   -0.439 0.138  C11  A1IHE 7  
A1IHE C13  C6  C  0 1 Y N N N N N 14.886 7.798 -14.948 6.250   0.021  1.144  C13  A1IHE 8  
A1IHE C14  C7  C  0 1 Y N N N N N 13.670 7.621 -14.318 4.880   0.013  0.969  C14  A1IHE 9  
A1IHE C15  C8  C  0 1 N N R N N N 10.932 5.441 -11.085 0.451   0.030  1.188  C15  A1IHE 10 
A1IHE C17  C9  C  0 1 N N N N N N 9.412  5.449 -12.904 0.068   -2.055 2.306  C17  A1IHE 11 
A1IHE C18  C10 C  0 1 N N N N N N 9.056  4.035 -12.869 -0.273  -3.466 2.060  C18  A1IHE 12 
A1IHE C19  C11 C  0 1 N N N N N N 8.818  2.884 -12.861 -0.544  -4.591 1.864  C19  A1IHE 13 
A1IHE C20  C12 C  0 1 N N S N N N 10.960 5.829 -9.615  -0.200  0.815  0.045  C20  A1IHE 14 
A1IHE C22  C13 C  0 1 N N N N N N 8.793  5.941 -8.584  -2.299  0.783  -1.112 C22  A1IHE 15 
A1IHE C23  C14 C  0 1 Y N N N N N 7.824  5.174 -7.759  -3.785  0.668  -0.888 C23  A1IHE 16 
A1IHE C25  C15 C  0 1 Y N N N N N 6.540  4.551 -6.156  -5.856  1.220  -0.521 C25  A1IHE 17 
A1IHE C26  C16 C  0 1 Y N N N N N 5.843  4.396 -4.960  -7.080  1.854  -0.279 C26  A1IHE 18 
A1IHE C27  C17 C  0 1 Y N N N N N 4.872  3.416 -4.873  -8.219  1.116  -0.160 C27  A1IHE 19 
A1IHE C28  C18 C  0 1 Y N N N N N 4.583  2.583 -5.957  -8.178  -0.280 -0.278 C28  A1IHE 20 
A1IHE C29  C19 C  0 1 N N N N N N 3.533  1.510 -5.824  -9.418  -1.067 -0.146 C29  A1IHE 21 
A1IHE C32  C20 C  0 1 Y N N N N N 5.277  2.734 -7.159  -6.966  -0.927 -0.520 C32  A1IHE 22 
A1IHE C33  C21 C  0 1 Y N N N N N 6.245  3.720 -7.233  -5.807  -0.182 -0.642 C33  A1IHE 23 
A1IHE C35  C22 C  0 1 N N N N N N 7.136  3.565 -9.606  -3.931  -1.841 -1.071 C35  A1IHE 24 
A1IHE C36  C23 C  0 1 N N S N N N 12.296 5.449 -9.000  0.219   2.285  0.146  C36  A1IHE 25 
A1IHE C8   C24 C  0 1 Y N N N N N 14.575 8.575 -12.311 5.171   -0.922 -1.228 C8   A1IHE 26 
A1IHE C9   C25 C  0 1 Y N N N N N 15.784 8.752 -12.947 6.542   -0.911 -1.048 C9   A1IHE 27 
A1IHE N24  N1  N  0 1 Y N N N N N 7.534  5.456 -6.504  -4.588  1.673  -0.684 N24  A1IHE 28 
A1IHE N34  N2  N  0 1 Y N N N N N 7.085  4.138 -8.257  -4.482  -0.498 -0.876 N34  A1IHE 29 
A1IHE O16  O3  O  0 1 N N N N N N 9.710  5.958 -11.603 0.125   -1.355 1.061  O16  A1IHE 30 
A1IHE O21  O4  O  0 1 N N N N N N 9.934  5.136 -8.906  -1.622  0.716  0.145  O21  A1IHE 31 
A1IHE O30  O5  O  0 1 N N N N N N 2.800  1.546 -4.799  -10.590 -0.443 0.088  O30  A1IHE 32 
A1IHE O31  O6  O  0 1 N N N N N N 3.462  0.635 -6.719  -9.384  -2.277 -0.248 O31  A1IHE 33 
A1IHE O37  O7  O  0 1 N N N N N N 12.398 4.025 -8.985  -0.269  2.837  1.371  O37  A1IHE 34 
A1IHE S6   S1  S  0 1 N N N N N N 11.973 7.771 -12.152 2.588   -0.479 -0.443 S6   A1IHE 35 
A1IHE CL10 CL1 CL 0 0 N N N N N N 17.076 9.511 -12.082 7.587   -1.488 -2.307 CL10 A1IHE 36 
A1IHE CL12 CL2 CL 0 0 N N N N N N 17.468 8.526 -15.050 8.802   -0.427 0.361  CL12 A1IHE 37 
A1IHE H2A  H1  H  0 1 N N N N N N 14.988 4.713 -9.404  1.690   4.443  -0.485 H2A  A1IHE 38 
A1IHE H2B  H2  H  0 1 N N N N N N 14.815 6.031 -8.196  1.883   4.193  1.266  H2B  A1IHE 39 
A1IHE H3   H3  H  0 1 N N N N N N 13.273 7.186 -9.780  2.116   1.992  -0.834 H3   A1IHE 40 
A1IHE H1   H4  H  0 1 N N N N N N 16.656 6.281 -9.540  3.936   4.834  0.228  H1   A1IHE 41 
A1IHE H5   H5  H  0 1 N N N N N N 12.158 5.524 -12.824 2.435   -0.314 1.954  H5   A1IHE 42 
A1IHE H13  H6  H  0 1 N N N N N N 15.011 7.495 -15.977 6.674   0.387  2.068  H13  A1IHE 43 
A1IHE H14  H7  H  0 1 N N N N N N 12.843 7.180 -14.855 4.233   0.373  1.755  H14  A1IHE 44 
A1IHE H15  H8  H  0 1 N N N N N N 10.937 4.344 -11.159 0.083   0.405  2.143  H15  A1IHE 45 
A1IHE H17A H9  H  0 0 N N N N N N 8.569  6.017 -13.323 -0.693  -1.603 2.942  H17A A1IHE 46 
A1IHE H17B H10 H  0 0 N N N N N N 10.296 5.577 -13.546 1.038   -1.997 2.800  H17B A1IHE 47 
A1IHE H19  H11 H  0 1 N N N N N N 8.603  1.846 -12.854 -0.787  -5.598 1.689  H19  A1IHE 48 
A1IHE H20  H12 H  0 1 N N N N N N 10.819 6.916 -9.527  0.128   0.407  -0.911 H20  A1IHE 49 
A1IHE H22A H13 H  0 0 N N N N N N 9.123  6.827 -8.022  -1.964  -0.034 -1.750 H22A A1IHE 50 
A1IHE H22B H14 H  0 0 N N N N N N 8.302  6.259 -9.515  -2.077  1.735  -1.594 H22B A1IHE 51 
A1IHE H26  H15 H  0 1 N N N N N N 6.058  5.032 -4.114  -7.122  2.929  -0.185 H26  A1IHE 52 
A1IHE H27  H16 H  0 1 N N N N N N 4.326  3.292 -3.949  -9.160  1.611  0.028  H27  A1IHE 53 
A1IHE H32  H17 H  0 1 N N N N N N 5.064  2.099 -8.007  -6.933  -2.003 -0.612 H32  A1IHE 54 
A1IHE H35B H18 H  0 0 N N N N N N 7.894  4.095 -10.202 -3.953  -2.092 -2.131 H35B A1IHE 55 
A1IHE H35A H19 H  0 0 N N N N N N 7.400  2.499 -9.542  -2.902  -1.867 -0.713 H35A A1IHE 56 
A1IHE H35C H20 H  0 0 N N N N N N 6.152  3.671 -10.087 -4.528  -2.563 -0.513 H35C A1IHE 57 
A1IHE H36  H21 H  0 1 N N N N N N 12.332 5.837 -7.971  -0.195  2.841  -0.695 H36  A1IHE 58 
A1IHE H8   H22 H  0 1 N N N N N N 14.457 8.876 -11.281 4.751   -1.290 -2.152 H8   A1IHE 59 
A1IHE H2   H23 H  0 1 N N N N N N 2.195  0.814 -4.816  -11.376 -1.000 0.166  H2   A1IHE 60 
A1IHE H37  H24 H  0 1 N N N N N N 13.230 3.771 -8.603  -0.040  3.767  1.502  H37  A1IHE 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 
A1IHE O1  C2   SING N N 1  
A1IHE C2  C3   SING N N 2  
A1IHE C3  O4   SING N N 3  
A1IHE O4  C5   SING N N 4  
A1IHE C5  S6   SING N N 5  
A1IHE S6  C7   SING N N 6  
A1IHE C7  C8   DOUB Y N 7  
A1IHE C8  C9   SING Y N 8  
A1IHE C9  CL10 SING N N 9  
A1IHE C9  C11  DOUB Y N 10 
A1IHE C11 CL12 SING N N 11 
A1IHE C11 C13  SING Y N 12 
A1IHE C13 C14  DOUB Y N 13 
A1IHE C5  C15  SING N N 14 
A1IHE C15 O16  SING N N 15 
A1IHE O16 C17  SING N N 16 
A1IHE C17 C18  SING N N 17 
A1IHE C18 C19  TRIP N N 18 
A1IHE C15 C20  SING N N 19 
A1IHE C20 O21  SING N N 20 
A1IHE O21 C22  SING N N 21 
A1IHE C22 C23  SING N N 22 
A1IHE C23 N24  DOUB Y N 23 
A1IHE N24 C25  SING Y N 24 
A1IHE C25 C26  DOUB Y N 25 
A1IHE C26 C27  SING Y N 26 
A1IHE C27 C28  DOUB Y N 27 
A1IHE C28 C29  SING N N 28 
A1IHE C29 O30  SING N N 29 
A1IHE C29 O31  DOUB N N 30 
A1IHE C28 C32  SING Y N 31 
A1IHE C25 C33  SING Y N 32 
A1IHE C33 N34  SING Y N 33 
A1IHE N34 C35  SING N N 34 
A1IHE C20 C36  SING N N 35 
A1IHE C36 O37  SING N N 36 
A1IHE C36 C3   SING N N 37 
A1IHE C14 C7   SING Y N 38 
A1IHE N34 C23  SING Y N 39 
A1IHE C33 C32  DOUB Y N 40 
A1IHE C2  H2A  SING N N 41 
A1IHE C2  H2B  SING N N 42 
A1IHE C3  H3   SING N N 43 
A1IHE O1  H1   SING N N 44 
A1IHE C5  H5   SING N N 45 
A1IHE C13 H13  SING N N 46 
A1IHE C14 H14  SING N N 47 
A1IHE C15 H15  SING N N 48 
A1IHE C17 H17A SING N N 49 
A1IHE C17 H17B SING N N 50 
A1IHE C19 H19  SING N N 51 
A1IHE C20 H20  SING N N 52 
A1IHE C22 H22A SING N N 53 
A1IHE C22 H22B SING N N 54 
A1IHE C26 H26  SING N N 55 
A1IHE C27 H27  SING N N 56 
A1IHE C32 H32  SING N N 57 
A1IHE C35 H35B SING N N 58 
A1IHE C35 H35A SING N N 59 
A1IHE C35 H35C SING N N 60 
A1IHE C36 H36  SING N N 61 
A1IHE C8  H8   SING N N 62 
A1IHE O30 H2   SING N N 63 
A1IHE O37 H37  SING N N 64 
# 
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 
A1IHE InChI            InChI                1.06  "InChI=1S/C25H24Cl2N2O7S/c1-3-8-34-23-22(35-12-20-28-17-7-4-13(24(32)33)9-18(17)29(20)2)21(31)19(11-30)36-25(23)37-14-5-6-15(26)16(27)10-14/h1,4-7,9-10,19,21-23,25,30-31H,8,11-12H2,2H3,(H,32,33)/t19-,21+,22+,23-,25-/m1/s1" 
A1IHE InChIKey         InChI                1.06  QFRHUULPFZESGE-BQYMIBSYSA-N                                                                                                                                                                                                    
A1IHE SMILES_CANONICAL CACTVS               3.385 "Cn1c(CO[C@H]2[C@@H](O)[C@@H](CO)O[C@H](Sc3ccc(Cl)c(Cl)c3)[C@@H]2OCC#C)nc4ccc(cc14)C(O)=O"                                                                                                                                     
A1IHE SMILES           CACTVS               3.385 "Cn1c(CO[CH]2[CH](O)[CH](CO)O[CH](Sc3ccc(Cl)c(Cl)c3)[CH]2OCC#C)nc4ccc(cc14)C(O)=O"                                                                                                                                             
A1IHE SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "Cn1c2cc(ccc2nc1CO[C@H]3[C@H]([C@H](O[C@@H]([C@@H]3OCC#C)Sc4ccc(c(c4)Cl)Cl)CO)O)C(=O)O"                                                                                                                                        
A1IHE SMILES           "OpenEye OEToolkits" 2.0.7 "Cn1c2cc(ccc2nc1COC3C(C(OC(C3OCC#C)Sc4ccc(c(c4)Cl)Cl)CO)O)C(=O)O"                                                                                                                                                              
# 
_pdbx_chem_comp_identifier.comp_id           A1IHE 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   2.0.7 
_pdbx_chem_comp_identifier.identifier        "2-[[(2~{R},3~{R},4~{S},5~{S},6~{R})-2-(3,4-dichlorophenyl)sulfanyl-6-(hydroxymethyl)-5-oxidanyl-3-prop-2-ynoxy-oxan-4-yl]oxymethyl]-3-methyl-benzimidazole-5-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 
A1IHE "Create component" 2024-07-08 PDBE 
A1IHE "Initial release"  2025-03-12 RCSB 
# 
