data_A1A4J
# 
_chem_comp.id                                    A1A4J 
_chem_comp.name                                  N-Methyltetrahydropalmatine 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H28 N O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "(7~{S},13~{a}~{S})-2,3,9,10-tetramethoxy-7-methyl-6,8,13,13~{a}-tetrahydro-5~{H}-isoquinolino[3,2-a]isoquinoline" 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     2024-09-03 
_chem_comp.pdbx_modified_date                    2025-09-12 
_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                        370.462 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1A4J 
_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        9DGF 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
_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 
A1A4J C1   C1  C 0 1 Y N N N N N 70.118 46.487 7.321  3.661  -1.090 0.777  C1   A1A4J 1  
A1A4J C20  C2  C 0 1 N N N N N N 65.821 42.727 13.598 -6.655 1.657  0.956  C20  A1A4J 2  
A1A4J C21  C3  C 0 1 N N N N N N 65.527 47.330 6.469  4.349  3.079  -1.456 C21  A1A4J 3  
A1A4J C22  C4  C 0 1 N N N N N N 69.337 40.896 7.145  0.573  -1.961 -1.585 C22  A1A4J 4  
A1A4J C2   C5  C 0 1 Y N N N N N 69.966 45.048 6.917  2.315  -1.013 0.449  C2   A1A4J 5  
A1A4J C3   C6  C 0 1 N N N N N N 71.122 44.193 7.425  1.409  -2.139 0.882  C3   A1A4J 6  
A1A4J C4   C7  C 0 1 N N N N N N 70.836 42.703 7.236  -0.058 -1.742 0.695  C4   A1A4J 7  
A1A4J C5   C8  C 0 1 N N N N N N 69.152 42.519 8.899  -1.585 -1.126 -1.085 C5   A1A4J 8  
A1A4J C6   C9  C 0 1 Y N N N N N 67.670 42.661 9.299  -2.396 -0.102 -0.339 C6   A1A4J 9  
A1A4J C7   C10 C 0 1 Y N N N N N 67.318 42.676 10.772 -3.783 -0.187 -0.386 C7   A1A4J 10 
A1A4J C8   C11 C 0 1 Y N N N N N 65.987 42.753 11.203 -4.563 0.747  0.286  C8   A1A4J 11 
A1A4J C9   C12 C 0 1 Y N N N N N 64.981 42.686 10.200 -3.952 1.764  1.002  C9   A1A4J 12 
A1A4J C10  C13 C 0 1 Y N N N N N 65.289 42.769 8.824  -2.574 1.842  1.046  C10  A1A4J 13 
A1A4J C11  C14 C 0 1 Y N N N N N 66.749 42.887 8.409  -1.794 0.908  0.380  C11  A1A4J 14 
A1A4J C12  C15 C 0 1 N N N N N N 67.050 42.711 6.919  -0.297 1.021  0.475  C12  A1A4J 15 
A1A4J C13  C16 C 0 1 N N S N N N 68.518 43.063 6.612  0.382  0.197  -0.624 C13  A1A4J 16 
A1A4J C14  C17 C 0 1 Y N N N N N 68.766 44.576 6.786  1.847  0.072  -0.262 C14  A1A4J 17 
A1A4J C15  C18 C 0 1 Y N N N N N 67.617 45.525 6.508  2.714  1.077  -0.655 C15  A1A4J 18 
A1A4J N1   N1  N 1 1 N N S N N N 69.445 42.310 7.475  -0.203 -1.150 -0.637 N1   A1A4J 19 
A1A4J C16  C19 C 0 1 Y N N N N N 67.860 46.914 6.590  4.058  1.003  -0.331 C16  A1A4J 20 
A1A4J O1   O1  O 0 1 N N N N N N 66.826 47.853 6.604  4.909  1.991  -0.717 O1   A1A4J 21 
A1A4J C17  C20 C 0 1 Y N N N N N 69.172 47.381 6.806  4.533  -0.086 0.392  C17  A1A4J 22 
A1A4J C18  C21 C 0 1 N N N N N N 70.571 49.241 6.458  6.266  -1.313 1.463  C18  A1A4J 23 
A1A4J O2   O2  O 0 1 N N N N N N 69.366 48.752 6.973  5.850  -0.166 0.719  O2   A1A4J 24 
A1A4J O3   O3  O 0 1 N N N N N N 68.354 42.587 11.724 -4.378 -1.186 -1.091 O3   A1A4J 25 
A1A4J O4   O4  O 0 1 N N N N N N 65.688 43.438 12.397 -5.919 0.663  0.241  O4   A1A4J 26 
A1A4J C19  C22 C 0 1 N N N N N N 68.709 41.276 12.098 -4.651 -2.401 -0.389 C19  A1A4J 27 
A1A4J H11  H1  H 0 1 N N N N N N 70.914 46.814 7.973  4.030  -1.935 1.339  H11  A1A4J 28 
A1A4J H202 H2  H 0 0 N N N N N N 65.557 43.380 14.443 -7.723 1.474  0.837  H202 A1A4J 29 
A1A4J H203 H3  H 0 0 N N N N N N 65.149 41.856 13.585 -6.394 1.613  2.013  H203 A1A4J 30 
A1A4J H201 H4  H 0 0 N N N N N N 66.861 42.386 13.709 -6.410 2.644  0.562  H201 A1A4J 31 
A1A4J H213 H5  H 0 0 N N N N N N 64.796 48.152 6.493  3.583  3.570  -0.856 H213 A1A4J 32 
A1A4J H211 H6  H 0 0 N N N N N N 65.445 46.794 5.512  5.134  3.795  -1.700 H211 A1A4J 33 
A1A4J H212 H7  H 0 0 N N N N N N 65.324 46.635 7.297  3.903  2.701  -2.376 H212 A1A4J 34 
A1A4J H03  H8  H 0 1 N N N N N N 68.303 40.558 7.311  0.193  -2.982 -1.586 H03  A1A4J 35 
A1A4J H02  H9  H 0 1 N N N N N N 69.607 40.744 6.090  0.480  -1.538 -2.586 H02  A1A4J 36 
A1A4J H01  H10 H 0 1 N N N N N N 70.019 40.317 7.785  1.622  -1.963 -1.288 H01  A1A4J 37 
A1A4J H31  H11 H 0 1 N N N N N N 72.034 44.456 6.869  1.623  -3.024 0.283  H31  A1A4J 38 
A1A4J H32  H12 H 0 1 N N N N N N 71.274 44.396 8.495  1.592  -2.365 1.932  H32  A1A4J 39 
A1A4J H41  H13 H 0 1 N N N N N N 71.475 42.141 7.933  -0.691 -2.626 0.776  H41  A1A4J 40 
A1A4J H42  H14 H 0 1 N N N N N N 71.095 42.433 6.202  -0.342 -1.015 1.456  H42  A1A4J 41 
A1A4J H52  H15 H 0 1 N N N N N N 69.563 41.661 9.451  -2.026 -2.111 -0.929 H52  A1A4J 42 
A1A4J H51  H16 H 0 1 N N N N N N 69.669 43.438 9.212  -1.610 -0.892 -2.149 H51  A1A4J 43 
A1A4J H91  H17 H 0 1 N N N N N N 63.950 42.568 10.500 -4.553 2.494  1.524  H91  A1A4J 44 
A1A4J H101 H18 H 0 0 N N N N N N 64.505 42.749 8.082  -2.100 2.636  1.604  H101 A1A4J 45 
A1A4J H122 H19 H 0 0 N N N N N N 66.863 41.665 6.634  -0.009 2.067  0.368  H122 A1A4J 46 
A1A4J H121 H20 H 0 0 N N N N N N 66.391 43.373 6.337  0.029  0.658  1.449  H121 A1A4J 47 
A1A4J H131 H21 H 0 0 N N N N N N 68.718 42.804 5.562  0.267  0.682  -1.593 H131 A1A4J 48 
A1A4J H151 H22 H 0 0 N N N N N N 66.637 45.149 6.254  2.341  1.920  -1.217 H151 A1A4J 49 
A1A4J H183 H23 H 0 0 N N N N N N 70.633 50.325 6.636  7.337  -1.251 1.657  H183 A1A4J 50 
A1A4J H181 H24 H 0 0 N N N N N N 71.413 48.739 6.956  5.727  -1.348 2.409  H181 A1A4J 51 
A1A4J H182 H25 H 0 0 N N N N N N 70.614 49.044 5.377  6.053  -2.215 0.889  H182 A1A4J 52 
A1A4J H193 H26 H 0 0 N N N N N N 69.520 41.313 12.840 -5.125 -3.112 -1.066 H193 A1A4J 53 
A1A4J H192 H27 H 0 0 N N N N N N 67.835 40.770 12.535 -3.718 -2.822 -0.014 H192 A1A4J 54 
A1A4J H191 H28 H 0 0 N N N N N N 69.048 40.721 11.211 -5.319 -2.195 0.447  H191 A1A4J 55 
# 
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 
A1A4J O1  C16  SING N N 1  
A1A4J O1  C21  SING N N 2  
A1A4J O2  C17  SING N N 3  
A1A4J O2  C18  SING N N 4  
A1A4J O3  C7   SING N N 5  
A1A4J O3  C19  SING N N 6  
A1A4J O4  C8   SING N N 7  
A1A4J O4  C20  SING N N 8  
A1A4J N1  C4   SING N N 9  
A1A4J N1  C5   SING N N 10 
A1A4J N1  C13  SING N N 11 
A1A4J N1  C22  SING N N 12 
A1A4J C1  C2   DOUB Y N 13 
A1A4J C1  C17  SING Y N 14 
A1A4J C2  C3   SING N N 15 
A1A4J C2  C14  SING Y N 16 
A1A4J C3  C4   SING N N 17 
A1A4J C5  C6   SING N N 18 
A1A4J C6  C7   DOUB Y N 19 
A1A4J C6  C11  SING Y N 20 
A1A4J C7  C8   SING Y N 21 
A1A4J C8  C9   DOUB Y N 22 
A1A4J C9  C10  SING Y N 23 
A1A4J C10 C11  DOUB Y N 24 
A1A4J C11 C12  SING N N 25 
A1A4J C12 C13  SING N N 26 
A1A4J C13 C14  SING N N 27 
A1A4J C14 C15  DOUB Y N 28 
A1A4J C15 C16  SING Y N 29 
A1A4J C16 C17  DOUB Y N 30 
A1A4J C1  H11  SING N N 31 
A1A4J C20 H202 SING N N 32 
A1A4J C20 H203 SING N N 33 
A1A4J C20 H201 SING N N 34 
A1A4J C21 H213 SING N N 35 
A1A4J C21 H211 SING N N 36 
A1A4J C21 H212 SING N N 37 
A1A4J C22 H03  SING N N 38 
A1A4J C22 H02  SING N N 39 
A1A4J C22 H01  SING N N 40 
A1A4J C3  H31  SING N N 41 
A1A4J C3  H32  SING N N 42 
A1A4J C4  H41  SING N N 43 
A1A4J C4  H42  SING N N 44 
A1A4J C5  H52  SING N N 45 
A1A4J C5  H51  SING N N 46 
A1A4J C9  H91  SING N N 47 
A1A4J C10 H101 SING N N 48 
A1A4J C12 H122 SING N N 49 
A1A4J C12 H121 SING N N 50 
A1A4J C13 H131 SING N N 51 
A1A4J C15 H151 SING N N 52 
A1A4J C18 H183 SING N N 53 
A1A4J C18 H181 SING N N 54 
A1A4J C18 H182 SING N N 55 
A1A4J C19 H193 SING N N 56 
A1A4J C19 H192 SING N N 57 
A1A4J C19 H191 SING N N 58 
# 
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 
A1A4J SMILES           ACDLabs              14.52 "COc1c2C[N+]3(C)CCc4cc(OC)c(OC)cc4C3Cc2ccc1OC"                                                                                                              
A1A4J InChI            InChI                1.06  "InChI=1S/C22H28NO4/c1-23-9-8-15-11-20(25-3)21(26-4)12-16(15)18(23)10-14-6-7-19(24-2)22(27-5)17(14)13-23/h6-7,11-12,18H,8-10,13H2,1-5H3/q+1/t18-,23-/m0/s1" 
A1A4J InChIKey         InChI                1.06  BMQBFTBKHPYZFM-MBSDFSHPSA-N                                                                                                                                 
A1A4J SMILES_CANONICAL CACTVS               3.385 "COc1ccc2C[C@H]3c4cc(OC)c(OC)cc4CC[N@@+]3(C)Cc2c1OC"                                                                                                        
A1A4J SMILES           CACTVS               3.385 "COc1ccc2C[CH]3c4cc(OC)c(OC)cc4CC[N+]3(C)Cc2c1OC"                                                                                                           
A1A4J SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "C[N@@+]12CCc3cc(c(cc3[C@@H]1Cc4ccc(c(c4C2)OC)OC)OC)OC"                                                                                                     
A1A4J SMILES           "OpenEye OEToolkits" 2.0.7 "C[N+]12CCc3cc(c(cc3C1Cc4ccc(c(c4C2)OC)OC)OC)OC"                                                                                                            
# 
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 
A1A4J "SYSTEMATIC NAME" ACDLabs              14.52 "(7S,13aS)-2,3,9,10-tetramethoxy-7-methyl-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-7-ium"                
A1A4J "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "(7~{S},13~{a}~{S})-2,3,9,10-tetramethoxy-7-methyl-6,8,13,13~{a}-tetrahydro-5~{H}-isoquinolino[3,2-a]isoquinolin-7-ium" 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      A1A4J 
_pdbx_chem_comp_synonyms.name         "(7~{S},13~{a}~{S})-2,3,9,10-tetramethoxy-7-methyl-6,8,13,13~{a}-tetrahydro-5~{H}-isoquinolino[3,2-a]isoquinoline" 
_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 
A1A4J "Create component" 2024-09-03 RCSB 
A1A4J "Initial release"  2025-09-17 RCSB 
# 
