data_A1D5I
# 
_chem_comp.id                                    A1D5I 
_chem_comp.name                                  Macitentan 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H20 Br2 N6 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2024-01-19 
_chem_comp.pdbx_modified_date                    2024-11-11 
_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                        588.273 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1D5I 
_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        8XVJ 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBC 
_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 
A1D5I C1  C1  C  0 1 N N N N N N 155.441 146.281 130.431 6.565  1.133  4.623  C1  A1D5I 1  
A1D5I C2  C2  C  0 1 N N N N N N 154.802 147.528 131.000 6.819  1.694  3.223  C2  A1D5I 2  
A1D5I C3  C3  C  0 1 N N N N N N 155.220 147.766 132.436 6.150  0.793  2.183  C3  A1D5I 3  
A1D5I C4  C4  C  0 1 Y N N N N N 152.504 149.053 134.084 3.597  1.115  -0.747 C4  A1D5I 4  
A1D5I C5  C5  C  0 1 Y N N N N N 152.398 150.234 134.855 2.216  0.867  -0.795 C5  A1D5I 5  
A1D5I C6  C6  C  0 1 Y N N N N N 152.080 151.426 134.174 1.359  1.955  -1.002 C6  A1D5I 6  
A1D5I C8  C7  C  0 1 N N N N N N 151.789 153.790 134.115 -0.786 2.935  -1.273 C8  A1D5I 7  
A1D5I C9  C8  C  0 1 N N N N N N 151.944 154.955 135.044 -2.263 2.535  -1.305 C9  A1D5I 8  
A1D5I C10 C9  C  0 1 Y N N N N N 153.600 155.875 136.463 -3.937 1.639  0.120  C10 A1D5I 9  
A1D5I C11 C10 C  0 1 Y N N N N N 153.160 157.921 137.319 -5.593 0.779  1.465  C11 A1D5I 10 
A1D5I C12 C11 C  0 1 Y N N N N N 154.293 157.834 138.099 -6.482 0.859  0.403  C12 A1D5I 11 
A1D5I C13 C12 C  0 1 Y N N N N N 155.050 156.685 137.999 -6.022 1.354  -0.808 C13 A1D5I 12 
A1D5I C14 C13 C  0 1 Y N N N N N 152.634 150.210 136.324 1.681  -0.506 -0.631 C14 A1D5I 13 
A1D5I C15 C14 C  0 1 Y N N N N N 152.043 149.249 137.138 1.973  -1.488 -1.577 C15 A1D5I 14 
A1D5I C16 C15 C  0 1 Y N N N N N 152.276 149.210 138.499 1.473  -2.764 -1.419 C16 A1D5I 15 
A1D5I C17 C16 C  0 1 Y N N N N N 153.132 150.132 139.056 0.683  -3.070 -0.325 C17 A1D5I 16 
A1D5I C7  C17 C  0 1 Y N N N N N 151.994 150.287 132.229 3.186  3.355  -1.092 C7  A1D5I 17 
A1D5I C18 C18 C  0 1 Y N N N N N 153.750 151.089 138.285 0.390  -2.099 0.617  C18 A1D5I 18 
A1D5I C19 C19 C  0 1 Y N N N N N 153.504 151.115 136.926 0.890  -0.821 0.472  C19 A1D5I 19 
A1D5I N1  N1  N  0 1 N N N N N N 154.814 146.666 133.315 6.394  1.330  0.842  N1  A1D5I 20 
A1D5I N2  N2  N  0 1 N N N N N N 152.804 147.865 134.612 4.492  0.078  -0.545 N2  A1D5I 21 
A1D5I N3  N3  N  0 1 Y N N N N N 151.877 151.455 132.876 1.882  3.168  -1.144 N3  A1D5I 22 
A1D5I N4  N4  N  0 1 Y N N N N N 152.292 149.104 132.760 4.031  2.362  -0.904 N4  A1D5I 23 
A1D5I N5  N5  N  0 1 Y N N N N N 152.802 156.936 136.494 -4.342 1.173  1.290  N5  A1D5I 24 
A1D5I N6  N6  N  0 1 Y N N N N N 154.707 155.692 137.176 -4.758 1.730  -0.913 N6  A1D5I 25 
A1D5I O1  O1  O  0 1 N N N N N N 152.471 146.390 132.661 6.411  1.195  -1.622 O1  A1D5I 26 
A1D5I O2  O2  O  0 1 N N N N N N 153.296 145.491 134.788 6.755  -0.859 -0.240 O2  A1D5I 27 
A1D5I O3  O3  O  0 1 N N N N N N 151.980 152.574 134.874 0.017  1.773  -1.058 O3  A1D5I 28 
A1D5I O4  O4  O  0 1 N N N N N N 153.244 154.882 135.642 -2.650 2.039  -0.022 O4  A1D5I 29 
A1D5I S1  S1  S  0 1 N N N N N N 153.282 146.522 133.815 6.118  0.387  -0.491 S1  A1D5I 30 
A1D5I BR1 BR1 BR 0 0 N N N N N N 154.787 159.232 139.263 -8.279 0.308  0.604  BR1 A1D5I 31 
A1D5I BR2 BR2 BR 0 0 N N N N N N 153.464 150.088 140.924 0.001  -4.822 -0.116 BR2 A1D5I 32 
A1D5I H1  H1  H  0 1 N N N N N N 155.114 146.143 129.390 7.042  1.775  5.364  H1  A1D5I 33 
A1D5I H2  H2  H  0 1 N N N N N N 156.536 146.384 130.461 5.492  1.097  4.811  H2  A1D5I 34 
A1D5I H3  H3  H  0 1 N N N N N N 155.139 145.409 131.029 6.981  0.128  4.693  H3  A1D5I 35 
A1D5I H4  H4  H  0 1 N N N N N N 155.105 148.393 130.392 6.404  2.700  3.153  H4  A1D5I 36 
A1D5I H5  H5  H  0 1 N N N N N N 153.708 147.418 130.961 7.893  1.731  3.035  H5  A1D5I 37 
A1D5I H6  H6  H  0 1 N N N N N N 156.315 147.867 132.475 6.566  -0.213 2.252  H6  A1D5I 38 
A1D5I H7  H7  H  0 1 N N N N N N 154.753 148.696 132.792 5.077  0.756  2.370  H7  A1D5I 39 
A1D5I H8  H8  H  0 1 N N N N N N 152.541 153.850 133.314 -0.514 3.395  -2.222 H8  A1D5I 40 
A1D5I H9  H9  H  0 1 N N N N N N 150.782 153.798 133.673 -0.620 3.646  -0.463 H9  A1D5I 41 
A1D5I H10 H10 H  0 1 N N N N N N 151.845 155.895 134.482 -2.869 3.405  -1.557 H10 A1D5I 42 
A1D5I H11 H11 H  0 1 N N N N N N 151.172 154.913 135.826 -2.412 1.758  -2.055 H11 A1D5I 43 
A1D5I H12 H12 H  0 1 N N N N N N 152.547 158.808 137.377 -5.918 0.399  2.422  H12 A1D5I 44 
A1D5I H13 H13 H  0 1 N N N N N N 155.941 156.587 138.601 -6.688 1.429  -1.655 H13 A1D5I 45 
A1D5I H14 H14 H  0 1 N N N N N N 151.386 148.515 136.695 2.589  -1.250 -2.431 H14 A1D5I 46 
A1D5I H15 H15 H  0 1 N N N N N N 151.793 148.467 139.117 1.699  -3.526 -2.151 H15 A1D5I 47 
A1D5I H16 H16 H  0 1 N N N N N N 151.829 150.308 131.162 3.575  4.355  -1.217 H16 A1D5I 48 
A1D5I H17 H17 H  0 1 N N N N N N 154.417 151.809 138.735 -0.227 -2.344 1.469  H17 A1D5I 49 
A1D5I H18 H18 H  0 1 N N N N N N 153.999 151.856 136.315 0.664  -0.065 1.210  H18 A1D5I 50 
A1D5I H19 H19 H  0 1 N N N N N N 155.036 145.819 132.832 6.717  2.239  0.735  H19 A1D5I 51 
A1D5I H20 H20 H  0 1 N N N N N N 151.981 147.590 135.108 4.167  -0.829 -0.435 H20 A1D5I 52 
# 
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 
A1D5I C1  C2  SING N N 1  
A1D5I C2  C3  SING N N 2  
A1D5I C7  N4  DOUB Y N 3  
A1D5I C7  N3  SING Y N 4  
A1D5I C3  N1  SING N N 5  
A1D5I O1  S1  DOUB N N 6  
A1D5I N4  C4  SING Y N 7  
A1D5I N3  C6  DOUB Y N 8  
A1D5I N1  S1  SING N N 9  
A1D5I S1  N2  SING N N 10 
A1D5I S1  O2  DOUB N N 11 
A1D5I C4  N2  SING N N 12 
A1D5I C4  C5  DOUB Y N 13 
A1D5I C8  O3  SING N N 14 
A1D5I C8  C9  SING N N 15 
A1D5I C6  C5  SING Y N 16 
A1D5I C6  O3  SING N N 17 
A1D5I C5  C14 SING N N 18 
A1D5I C9  O4  SING N N 19 
A1D5I O4  C10 SING N N 20 
A1D5I C14 C19 DOUB Y N 21 
A1D5I C14 C15 SING Y N 22 
A1D5I C10 N5  DOUB Y N 23 
A1D5I C10 N6  SING Y N 24 
A1D5I N5  C11 SING Y N 25 
A1D5I C19 C18 SING Y N 26 
A1D5I C15 C16 DOUB Y N 27 
A1D5I N6  C13 DOUB Y N 28 
A1D5I C11 C12 DOUB Y N 29 
A1D5I C13 C12 SING Y N 30 
A1D5I C12 BR1 SING N N 31 
A1D5I C18 C17 DOUB Y N 32 
A1D5I C16 C17 SING Y N 33 
A1D5I C17 BR2 SING N N 34 
A1D5I C1  H1  SING N N 35 
A1D5I C1  H2  SING N N 36 
A1D5I C1  H3  SING N N 37 
A1D5I C2  H4  SING N N 38 
A1D5I C2  H5  SING N N 39 
A1D5I C3  H6  SING N N 40 
A1D5I C3  H7  SING N N 41 
A1D5I C8  H8  SING N N 42 
A1D5I C8  H9  SING N N 43 
A1D5I C9  H10 SING N N 44 
A1D5I C9  H11 SING N N 45 
A1D5I C11 H12 SING N N 46 
A1D5I C13 H13 SING N N 47 
A1D5I C15 H14 SING N N 48 
A1D5I C16 H15 SING N N 49 
A1D5I C7  H16 SING N N 50 
A1D5I C18 H17 SING N N 51 
A1D5I C19 H18 SING N N 52 
A1D5I N1  H19 SING N N 53 
A1D5I N2  H20 SING N N 54 
# 
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 
A1D5I InChI            InChI                1.06  "InChI=1S/C19H20Br2N6O4S/c1-2-7-26-32(28,29)27-17-16(13-3-5-14(20)6-4-13)18(25-12-24-17)30-8-9-31-19-22-10-15(21)11-23-19/h3-6,10-12,26H,2,7-9H2,1H3,(H,24,25,27)" 
A1D5I InChIKey         InChI                1.06  JGCMEBMXRHSZKX-UHFFFAOYSA-N                                                                                                                                        
A1D5I SMILES_CANONICAL CACTVS               3.385 "CCCN[S](=O)(=O)Nc1ncnc(OCCOc2ncc(Br)cn2)c1c3ccc(Br)cc3"                                                                                                           
A1D5I SMILES           CACTVS               3.385 "CCCN[S](=O)(=O)Nc1ncnc(OCCOc2ncc(Br)cn2)c1c3ccc(Br)cc3"                                                                                                           
A1D5I SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "CCCNS(=O)(=O)Nc1c(c(ncn1)OCCOc2ncc(cn2)Br)c3ccc(cc3)Br"                                                                                                           
A1D5I SMILES           "OpenEye OEToolkits" 2.0.7 "CCCNS(=O)(=O)Nc1c(c(ncn1)OCCOc2ncc(cn2)Br)c3ccc(cc3)Br"                                                                                                           
# 
_pdbx_chem_comp_identifier.comp_id           A1D5I 
_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        "6-[2-(5-bromanylpyrimidin-2-yl)oxyethoxy]-5-(4-bromophenyl)-~{N}-(propylsulfamoyl)pyrimidin-4-amine" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
A1D5I "Create component" 2024-01-19 PDBC 
A1D5I "Initial release"  2024-08-28 RCSB 
A1D5I "Modify name"      2024-11-11 PDBC 
# 
