data_A1H5D
# 
_chem_comp.id                                    A1H5D 
_chem_comp.name                                  Hydroxychloroquine 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H26 Cl N3 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "2-[[(4~{R})-4-[(7-chloranylquinolin-4-yl)amino]pentyl]-ethyl-amino]ethanol" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2024-02-27 
_chem_comp.pdbx_modified_date                    2024-09-27 
_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                        335.872 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1H5D 
_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        8S5Z 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBE 
# 
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 
A1H5D C14  C1  C  0 1 N N N N N N 162.178 159.470 155.533 6.653  -0.461 0.135  C14  A1H5D 1  
A1H5D C13  C2  C  0 1 Y N N N N N 156.843 161.483 160.061 -1.350 1.457  0.054  C13  A1H5D 2  
A1H5D C12  C3  C  0 1 N N N N N N 160.751 162.055 156.525 3.336  -2.185 -0.128 C12  A1H5D 3  
A1H5D C11  C4  C  0 1 N N N N N N 157.314 157.745 159.622 0.448  3.652  -1.459 C11  A1H5D 4  
A1H5D C06  C5  C  0 1 N N N N N N 159.053 159.442 160.051 2.125  1.819  -1.200 C06  A1H5D 5  
A1H5D C07  C6  C  0 1 N N N N N N 160.113 159.360 158.963 2.560  0.642  -0.323 C07  A1H5D 6  
A1H5D C08  C7  C  0 1 N N R N N N 157.694 159.207 159.409 0.817  2.401  -0.660 C08  A1H5D 7  
A1H5D C09  C8  C  0 1 N N N N N N 160.408 160.760 158.443 3.868  0.060  -0.863 C09  A1H5D 8  
A1H5D C10  C9  C  0 1 N N N N N N 162.094 160.178 156.878 5.648  -1.503 -0.360 C10  A1H5D 9  
A1H5D C15  C10 C  0 1 N N N N N N 159.355 162.392 156.030 3.504  -3.114 1.076  C15  A1H5D 10 
A1H5D C16  C11 C  0 1 Y N N N N N 156.741 162.140 161.237 -2.394 0.507  -0.051 C16  A1H5D 11 
A1H5D C17  C12 C  0 1 Y N N N N N 157.090 162.170 158.923 -1.460 2.437  1.029  C17  A1H5D 12 
A1H5D C18  C13 C  0 1 Y N N N N N 156.889 163.514 161.274 -3.494 0.598  0.836  C18  A1H5D 13 
A1H5D C19  C14 C  0 1 Y N N N N N 156.492 161.442 162.404 -2.358 -0.514 -1.010 C19  A1H5D 14 
A1H5D C20  C15 C  0 1 Y N N N N N 157.239 163.545 158.968 -2.571 2.458  1.860  C20  A1H5D 15 
A1H5D C21  C16 C  0 1 Y N N N N N 156.787 164.188 162.475 -4.532 -0.343 0.735  C21  A1H5D 16 
A1H5D C22  C17 C  0 1 Y N N N N N 156.387 162.116 163.604 -3.381 -1.410 -1.080 C22  A1H5D 17 
A1H5D C23  C18 C  0 1 Y N N N N N 156.535 163.489 163.638 -4.466 -1.324 -0.209 C23  A1H5D 18 
A1H5D N03  N1  N  0 1 N N N N N N 160.756 160.704 157.039 4.286  -1.069 -0.021 N03  A1H5D 19 
A1H5D N04  N2  N  0 1 N N N N N N 156.686 160.043 160.021 -0.250 1.406  -0.788 N04  A1H5D 20 
A1H5D N05  N3  N  0 1 Y N N N N N 157.134 164.199 160.141 -3.533 1.571  1.754  N05  A1H5D 21 
A1H5D O02  O1  O  0 1 N N N N N N 163.220 158.539 155.582 6.603  -0.392 1.562  O02  A1H5D 22 
A1H5D CL01 CL1 CL 0 0 N N N N N N 156.400 164.356 165.186 -5.753 -2.483 -0.328 CL01 A1H5D 23 
A1H5D H142 H1  H  0 0 N N N N N N 162.375 160.205 154.739 7.656  -0.746 -0.179 H142 A1H5D 24 
A1H5D H141 H2  H  0 0 N N N N N N 161.229 158.953 155.327 6.403  0.513  -0.285 H141 A1H5D 25 
A1H5D H122 H3  H  0 0 N N N N N N 161.466 162.136 155.693 3.529  -2.740 -1.045 H122 A1H5D 26 
A1H5D H121 H4  H  0 0 N N N N N N 161.038 162.754 157.324 2.318  -1.795 -0.147 H121 A1H5D 27 
A1H5D H111 H5  H  0 0 N N N N N N 158.074 157.097 159.161 -0.484 4.067  -1.075 H111 A1H5D 28 
A1H5D H112 H6  H  0 0 N N N N N N 157.258 157.534 160.700 1.242  4.392  -1.364 H112 A1H5D 29 
A1H5D H113 H7  H  0 0 N N N N N N 156.335 157.549 159.159 0.322  3.388  -2.509 H113 A1H5D 30 
A1H5D H061 H8  H  0 0 N N N N N N 159.242 158.673 160.814 2.898  2.587  -1.186 H061 A1H5D 31 
A1H5D H062 H9  H  0 0 N N N N N N 159.076 160.437 160.520 1.974  1.473  -2.222 H062 A1H5D 32 
A1H5D H072 H10 H  0 0 N N N N N N 159.746 158.731 158.138 2.711  0.988  0.700  H072 A1H5D 33 
A1H5D H071 H11 H  0 0 N N N N N N 161.032 158.921 159.378 1.787  -0.126 -0.336 H071 A1H5D 34 
A1H5D H081 H12 H  0 0 N N N N N N 157.760 159.412 158.330 0.943  2.665  0.390  H081 A1H5D 35 
A1H5D H092 H13 H  0 0 N N N N N N 161.247 161.189 159.009 3.717  -0.286 -1.886 H092 A1H5D 36 
A1H5D H091 H14 H  0 0 N N N N N N 159.517 161.392 158.572 4.641  0.829  -0.850 H091 A1H5D 37 
A1H5D H102 H15 H  0 0 N N N N N N 162.312 159.465 157.687 5.737  -1.608 -1.441 H102 A1H5D 38 
A1H5D H101 H16 H  0 0 N N N N N N 162.822 161.002 156.910 5.853  -2.461 0.117  H101 A1H5D 39 
A1H5D H153 H17 H  0 0 N N N N N N 159.343 163.419 155.637 2.739  -3.890 1.046  H153 A1H5D 40 
A1H5D H152 H18 H  0 0 N N N N N N 159.070 161.691 155.232 4.491  -3.575 1.044  H152 A1H5D 41 
A1H5D H151 H19 H  0 0 N N N N N N 158.641 162.310 156.863 3.401  -2.539 1.996  H151 A1H5D 42 
A1H5D H171 H20 H  0 0 N N N N N N 157.171 161.647 157.981 -0.684 3.179  1.141  H171 A1H5D 43 
A1H5D H191 H21 H  0 0 N N N N N N 156.380 160.368 162.377 -1.522 -0.590 -1.691 H191 A1H5D 44 
A1H5D H201 H22 H  0 0 N N N N N N 157.440 164.095 158.061 -2.646 3.225  2.616  H201 A1H5D 45 
A1H5D H211 H23 H  0 0 N N N N N N 156.904 165.261 162.504 -5.379 -0.290 1.403  H211 A1H5D 46 
A1H5D H221 H24 H  0 0 N N N N N N 156.189 161.571 164.515 -3.352 -2.197 -1.819 H221 A1H5D 47 
A1H5D H041 H26 H  0 0 N N N N N N 155.831 159.862 159.534 -0.187 0.711  -1.462 H041 A1H5D 48 
A1H5D H021 H27 H  0 0 N N N N N N 163.283 158.090 154.747 7.267  0.193  1.951  H021 A1H5D 49 
# 
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 
A1H5D C14 O02  SING N N 1  
A1H5D C14 C10  SING N N 2  
A1H5D C15 C12  SING N N 3  
A1H5D C12 N03  SING N N 4  
A1H5D C10 N03  SING N N 5  
A1H5D N03 C09  SING N N 6  
A1H5D C09 C07  SING N N 7  
A1H5D C17 C20  DOUB Y N 8  
A1H5D C17 C13  SING Y N 9  
A1H5D C07 C06  SING N N 10 
A1H5D C20 N05  SING Y N 11 
A1H5D C08 C11  SING N N 12 
A1H5D C08 N04  SING N N 13 
A1H5D C08 C06  SING N N 14 
A1H5D N04 C13  SING N N 15 
A1H5D C13 C16  DOUB Y N 16 
A1H5D N05 C18  DOUB Y N 17 
A1H5D C16 C18  SING Y N 18 
A1H5D C16 C19  SING Y N 19 
A1H5D C18 C21  SING Y N 20 
A1H5D C19 C22  DOUB Y N 21 
A1H5D C21 C23  DOUB Y N 22 
A1H5D C22 C23  SING Y N 23 
A1H5D C23 CL01 SING N N 24 
A1H5D C14 H142 SING N N 25 
A1H5D C14 H141 SING N N 26 
A1H5D C12 H122 SING N N 27 
A1H5D C12 H121 SING N N 28 
A1H5D C11 H111 SING N N 29 
A1H5D C11 H112 SING N N 30 
A1H5D C11 H113 SING N N 31 
A1H5D C06 H061 SING N N 32 
A1H5D C06 H062 SING N N 33 
A1H5D C07 H072 SING N N 34 
A1H5D C07 H071 SING N N 35 
A1H5D C08 H081 SING N N 36 
A1H5D C09 H092 SING N N 37 
A1H5D C09 H091 SING N N 38 
A1H5D C10 H102 SING N N 39 
A1H5D C10 H101 SING N N 40 
A1H5D C15 H153 SING N N 41 
A1H5D C15 H152 SING N N 42 
A1H5D C15 H151 SING N N 43 
A1H5D C17 H171 SING N N 44 
A1H5D C19 H191 SING N N 45 
A1H5D C20 H201 SING N N 46 
A1H5D C21 H211 SING N N 47 
A1H5D C22 H221 SING N N 48 
A1H5D N04 H041 SING N N 49 
A1H5D O02 H021 SING N N 50 
# 
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 
A1H5D InChI            InChI                1.06  "InChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21)/t14-/m1/s1" 
A1H5D InChIKey         InChI                1.06  XXSMGPRMXLTPCZ-CQSZACIVSA-N                                                                                                                     
A1H5D SMILES_CANONICAL CACTVS               3.385 "CCN(CCO)CCC[C@@H](C)Nc1ccnc2cc(Cl)ccc12"                                                                                                       
A1H5D SMILES           CACTVS               3.385 "CCN(CCO)CCC[CH](C)Nc1ccnc2cc(Cl)ccc12"                                                                                                         
A1H5D SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "CCN(CCC[C@@H](C)Nc1ccnc2c1ccc(c2)Cl)CCO"                                                                                                       
A1H5D SMILES           "OpenEye OEToolkits" 2.0.7 "CCN(CCCC(C)Nc1ccnc2c1ccc(c2)Cl)CCO"                                                                                                            
# 
_pdbx_chem_comp_identifier.comp_id           A1H5D 
_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-[[(4~{R})-4-[(7-chloranylquinolin-4-yl)amino]pentyl]-ethyl-amino]ethanol" 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      A1H5D 
_pdbx_chem_comp_synonyms.name         "2-[[(4~{R})-4-[(7-chloranylquinolin-4-yl)amino]pentyl]-ethyl-amino]ethanol" 
_pdbx_chem_comp_synonyms.provenance   PDB 
_pdbx_chem_comp_synonyms.type         ? 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
A1H5D "Create component" 2024-02-27 PDBE 
A1H5D "Initial release"  2024-10-02 RCSB 
# 
