data_A1ECF
# 
_chem_comp.id                                    A1ECF 
_chem_comp.name                                  Tolvaptan 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C26 H25 Cl N2 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "N-[4-[[(5S)-7-chloranyl-5-oxidanyl-2,3,4,5-tetrahydro-1-benzazepin-1-yl]carbonyl]-3-methyl-phenyl]-2-methyl-benzamide" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2024-09-26 
_chem_comp.pdbx_modified_date                    2025-12-05 
_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                        448.941 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1ECF 
_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        9JMQ 
_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 
A1ECF C10  C1  C  0 1 N N N N N N 106.376 106.721 67.553 4.896  -1.098 -0.557 C10  A1ECF 1  
A1ECF C11  C2  C  0 1 Y N N N N N 109.114 107.287 69.004 3.164  1.236  0.522  C11  A1ECF 2  
A1ECF C12  C3  C  0 1 Y N N N N N 108.148 106.140 69.240 2.882  0.313  -0.468 C12  A1ECF 3  
A1ECF C13  C4  C  0 1 N N N N N N 107.324 104.428 67.498 2.665  -2.054 -0.196 C13  A1ECF 4  
A1ECF C14  C5  C  0 1 Y N N N N N 110.036 107.738 70.155 2.678  2.525  0.432  C14  A1ECF 5  
A1ECF C15  C6  C  0 1 Y N N N N N 108.059 105.448 70.623 2.077  0.670  -1.543 C15  A1ECF 6  
A1ECF C16  C7  C  0 1 Y N N N N N 108.139 103.181 67.837 1.196  -1.914 -0.155 C16  A1ECF 7  
A1ECF C07  C8  C  0 1 N N N N N N 107.960 108.612 67.030 5.424  0.564  1.288  C07  A1ECF 8  
A1ECF C08  C9  C  0 1 N N N N N N 106.980 107.590 66.460 5.595  -0.855 0.760  C08  A1ECF 9  
A1ECF C09  C10 C  0 1 N N S N N N 109.252 108.039 67.644 3.985  0.818  1.727  C09  A1ECF 10 
A1ECF C17  C11 C  0 1 Y N N N N N 109.971 107.056 71.515 1.885  2.885  -0.645 C17  A1ECF 11 
A1ECF C18  C12 C  0 1 Y N N N N N 108.982 105.911 71.750 1.582  1.958  -1.626 C18  A1ECF 12 
A1ECF C19  C13 C  0 1 Y N N N N N 109.634 103.026 67.606 0.387  -2.815 -0.853 C19  A1ECF 13 
A1ECF C20  C14 C  0 1 Y N N N N N 107.329 101.995 68.354 0.612  -0.885 0.588  C20  A1ECF 14 
A1ECF C21  C15 C  0 1 Y N N N N N 110.324 101.713 67.933 -0.982 -2.682 -0.812 C21  A1ECF 15 
A1ECF C22  C16 C  0 1 Y N N N N N 109.526 100.540 68.495 -1.561 -1.652 -0.077 C22  A1ECF 16 
A1ECF C23  C17 C  0 1 Y N N N N N 108.016 100.673 68.685 -0.758 -0.757 0.624  C23  A1ECF 17 
A1ECF C24  C18 C  0 1 N N N N N N 110.463 104.182 67.070 1.014  -3.930 -1.650 C24  A1ECF 18 
A1ECF C25  C19 C  0 1 N N N N N N 111.464 99.116  69.398 -3.506 -0.298 0.068  C25  A1ECF 19 
A1ECF C26  C20 C  0 1 Y N N N N N 111.965 97.700  69.603 -4.970 -0.165 0.220  C26  A1ECF 20 
A1ECF C27  C21 C  0 1 Y N N N N N 112.085 96.768  68.413 -5.565 1.098  0.202  C27  A1ECF 21 
A1ECF C28  C22 C  0 1 Y N N N N N 112.324 97.248  71.000 -5.765 -1.301 0.376  C28  A1ECF 22 
A1ECF C29  C23 C  0 1 Y N N N N N 112.576 95.356  68.647 -6.932 1.216  0.344  C29  A1ECF 23 
A1ECF C30  C24 C  0 1 N N N N N N 111.723 97.203  66.993 -4.715 2.331  0.029  C30  A1ECF 24 
A1ECF C31  C25 C  0 1 Y N N N N N 112.816 95.840  71.240 -7.131 -1.170 0.517  C31  A1ECF 25 
A1ECF C32  C26 C  0 1 Y N N N N N 112.932 94.909  70.049 -7.713 0.085  0.504  C32  A1ECF 26 
A1ECF N05  N1  N  0 1 N N N N N N 107.292 105.760 68.125 3.439  -0.970 -0.400 N05  A1ECF 27 
A1ECF N06  N2  N  0 1 N N N N N N 110.150 99.270  68.794 -2.948 -1.520 -0.038 N06  A1ECF 28 
A1ECF O02  O1  O  0 1 N N N N N N 109.865 107.192 66.700 3.438  -0.378 2.286  O02  A1ECF 29 
A1ECF O03  O2  O  0 1 N N N N N N 106.609 104.216 66.588 3.176  -3.147 -0.047 O03  A1ECF 30 
A1ECF O04  O3  O  0 1 N N N N N N 112.135 100.023 69.723 -2.805 0.695  0.038  O04  A1ECF 31 
A1ECF CL01 CL1 CL 0 0 N N N N N N 111.046 107.606 72.828 1.271  4.505  -0.764 CL01 A1ECF 32 
A1ECF H101 H1  H  0 0 N N N N N N 106.020 107.380 68.359 5.245  -0.369 -1.288 H101 A1ECF 33 
A1ECF H102 H2  H  0 0 N N N N N N 105.524 106.172 67.125 5.133  -2.102 -0.909 H102 A1ECF 34 
A1ECF H141 H3  H  0 0 N N N N N N 110.735 108.546 69.995 2.915  3.248  1.198  H141 A1ECF 35 
A1ECF H151 H4  H  0 0 N N N N N N 107.353 104.648 70.789 1.840  -0.053 -2.308 H151 A1ECF 36 
A1ECF H072 H5  H  0 0 N N N N N N 108.248 109.293 66.216 6.089  0.711  2.139  H072 A1ECF 37 
A1ECF H071 H6  H  0 0 N N N N N N 107.437 109.179 67.814 5.689  1.271  0.502  H071 A1ECF 38 
A1ECF H082 H7  H  0 0 N N N N N N 106.170 108.123 65.940 5.199  -1.552 1.499  H082 A1ECF 39 
A1ECF H081 H8  H  0 0 N N N N N N 107.512 106.945 65.745 6.659  -1.054 0.633  H081 A1ECF 40 
A1ECF H091 H9  H  0 0 N N N N N N 109.920 108.893 67.827 3.967  1.612  2.473  H091 A1ECF 41 
A1ECF H181 H10 H  0 0 N N N N N N 108.936 105.429 72.715 0.956  2.241  -2.459 H181 A1ECF 42 
A1ECF H201 H11 H  0 0 N N N N N N 106.262 102.092 68.487 1.234  -0.190 1.132  H201 A1ECF 43 
A1ECF H211 H12 H  0 0 N N N N N N 111.386 101.609 67.767 -1.608 -3.377 -1.352 H211 A1ECF 44 
A1ECF H231 H13 H  0 0 N N N N N N 107.438 99.837  69.051 -1.211 0.038  1.198  H231 A1ECF 45 
A1ECF H242 H14 H  0 0 N N N N N N 110.838 104.785 67.910 1.081  -4.825 -1.032 H242 A1ECF 46 
A1ECF H243 H15 H  0 0 N N N N N N 111.313 103.787 66.494 0.400  -4.140 -2.526 H243 A1ECF 47 
A1ECF H241 H16 H  0 0 N N N N N N 109.838 104.810 66.418 2.012  -3.632 -1.969 H241 A1ECF 48 
A1ECF H281 H17 H  0 0 N N N N N N 112.228 97.934  71.829 -5.312 -2.282 0.386  H281 A1ECF 49 
A1ECF H291 H18 H  0 0 N N N N N N 112.672 94.670  67.818 -7.393 2.192  0.330  H291 A1ECF 50 
A1ECF H302 H19 H  0 0 N N N N N N 110.660 96.991  66.804 -4.304 2.627  0.993  H302 A1ECF 51 
A1ECF H301 H20 H  0 0 N N N N N N 111.907 98.282  66.882 -3.900 2.116  -0.663 H301 A1ECF 52 
A1ECF H303 H21 H  0 0 N N N N N N 112.341 96.649  66.271 -5.326 3.140  -0.370 H303 A1ECF 53 
A1ECF H311 H22 H  0 0 N N N N N N 113.078 95.506  72.233 -7.747 -2.048 0.638  H311 A1ECF 54 
A1ECF H321 H23 H  0 0 N N N N N N 113.278 93.898  70.205 -8.783 0.183  0.615  H321 A1ECF 55 
A1ECF H061 H24 H  0 0 N N N N N N 109.642 98.439  68.569 -3.512 -2.308 -0.087 H061 A1ECF 56 
A1ECF H021 H25 H  0 0 N N N N N N 110.664 106.832 67.068 2.523  -0.289 2.586  H021 A1ECF 57 
# 
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 
A1ECF C08 C07  SING N N 1  
A1ECF C08 C10  SING N N 2  
A1ECF O03 C13  DOUB N N 3  
A1ECF O02 C09  SING N N 4  
A1ECF C30 C27  SING N N 5  
A1ECF C07 C09  SING N N 6  
A1ECF C24 C19  SING N N 7  
A1ECF C13 C16  SING N N 8  
A1ECF C13 N05  SING N N 9  
A1ECF C10 N05  SING N N 10 
A1ECF C19 C16  DOUB Y N 11 
A1ECF C19 C21  SING Y N 12 
A1ECF C09 C11  SING N N 13 
A1ECF C16 C20  SING Y N 14 
A1ECF C21 C22  DOUB Y N 15 
A1ECF N05 C12  SING N N 16 
A1ECF C20 C23  DOUB Y N 17 
A1ECF C27 C29  DOUB Y N 18 
A1ECF C27 C26  SING Y N 19 
A1ECF C22 C23  SING Y N 20 
A1ECF C22 N06  SING N N 21 
A1ECF C29 C32  SING Y N 22 
A1ECF N06 C25  SING N N 23 
A1ECF C11 C12  DOUB Y N 24 
A1ECF C11 C14  SING Y N 25 
A1ECF C12 C15  SING Y N 26 
A1ECF C25 C26  SING N N 27 
A1ECF C25 O04  DOUB N N 28 
A1ECF C26 C28  DOUB Y N 29 
A1ECF C32 C31  DOUB Y N 30 
A1ECF C14 C17  DOUB Y N 31 
A1ECF C15 C18  DOUB Y N 32 
A1ECF C28 C31  SING Y N 33 
A1ECF C17 C18  SING Y N 34 
A1ECF C17 CL01 SING N N 35 
A1ECF C10 H101 SING N N 36 
A1ECF C10 H102 SING N N 37 
A1ECF C14 H141 SING N N 38 
A1ECF C15 H151 SING N N 39 
A1ECF C07 H072 SING N N 40 
A1ECF C07 H071 SING N N 41 
A1ECF C08 H082 SING N N 42 
A1ECF C08 H081 SING N N 43 
A1ECF C09 H091 SING N N 44 
A1ECF C18 H181 SING N N 45 
A1ECF C20 H201 SING N N 46 
A1ECF C21 H211 SING N N 47 
A1ECF C23 H231 SING N N 48 
A1ECF C24 H242 SING N N 49 
A1ECF C24 H243 SING N N 50 
A1ECF C24 H241 SING N N 51 
A1ECF C28 H281 SING N N 52 
A1ECF C29 H291 SING N N 53 
A1ECF C30 H302 SING N N 54 
A1ECF C30 H301 SING N N 55 
A1ECF C30 H303 SING N N 56 
A1ECF C31 H311 SING N N 57 
A1ECF C32 H321 SING N N 58 
A1ECF N06 H061 SING N N 59 
A1ECF O02 H021 SING N N 60 
# 
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 
A1ECF InChI            InChI                1.06  "InChI=1S/C26H25ClN2O3/c1-16-6-3-4-7-20(16)25(31)28-19-10-11-21(17(2)14-19)26(32)29-13-5-8-24(30)22-15-18(27)9-12-23(22)29/h3-4,6-7,9-12,14-15,24,30H,5,8,13H2,1-2H3,(H,28,31)/t24-/m0/s1" 
A1ECF InChIKey         InChI                1.06  GYHCTFXIZSNGJT-DEOSSOPVSA-N                                                                                                                                                                
A1ECF SMILES_CANONICAL CACTVS               3.385 "Cc1ccccc1C(=O)Nc2ccc(c(C)c2)C(=O)N3CCC[C@H](O)c4cc(Cl)ccc34"                                                                                                                              
A1ECF SMILES           CACTVS               3.385 "Cc1ccccc1C(=O)Nc2ccc(c(C)c2)C(=O)N3CCC[CH](O)c4cc(Cl)ccc34"                                                                                                                               
A1ECF SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "Cc1ccccc1C(=O)Nc2ccc(c(c2)C)C(=O)N3CCC[C@@H](c4c3ccc(c4)Cl)O"                                                                                                                             
A1ECF SMILES           "OpenEye OEToolkits" 2.0.7 "Cc1ccccc1C(=O)Nc2ccc(c(c2)C)C(=O)N3CCCC(c4c3ccc(c4)Cl)O"                                                                                                                                  
# 
_pdbx_chem_comp_identifier.comp_id           A1ECF 
_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        "~{N}-[4-[[(5~{S})-7-chloranyl-5-oxidanyl-2,3,4,5-tetrahydro-1-benzazepin-1-yl]carbonyl]-3-methyl-phenyl]-2-methyl-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 
A1ECF "Create component" 2024-09-26 PDBC 
A1ECF "Initial release"  2025-12-10 RCSB 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      A1ECF 
_pdbx_chem_comp_synonyms.name         "N-[4-[[(5S)-7-chloranyl-5-oxidanyl-2,3,4,5-tetrahydro-1-benzazepin-1-yl]carbonyl]-3-methyl-phenyl]-2-methyl-benzamide" 
_pdbx_chem_comp_synonyms.provenance   PDB 
_pdbx_chem_comp_synonyms.type         ? 
# 
