data_A1A4I
# 
_chem_comp.id                                    A1A4I 
_chem_comp.name                                  "(S)-cis-N-methylcanadine" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H24 N O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "(7S,13aS)-9,10-dimethoxy-7-methyl-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium" 
_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                        354.420 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1A4I 
_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        9DG6 
_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 
A1A4I C1   C1  C 0 1 Y N N N N N 35.942 -45.159 6.294  -2.907 -0.878 -0.909 C1   A1A4I 1  
A1A4I C2   C2  C 0 1 Y N N N N N 35.481 -46.575 6.227  -4.245 -0.854 -0.547 C2   A1A4I 2  
A1A4I C3   C3  C 0 1 Y N N N N N 34.211 -46.912 6.087  -4.714 0.052  0.417  C3   A1A4I 3  
A1A4I C4   C4  C 0 1 Y N N N N N 33.134 -45.834 5.959  -3.855 0.949  1.031  C4   A1A4I 4  
A1A4I O1   O1  O 0 1 N N N N N N 36.298 -47.899 6.335  -5.282 -1.606 -0.981 O1   A1A4I 5  
A1A4I O2   O2  O 0 1 N N N N N N 34.149 -48.139 6.054  -6.042 -0.138 0.582  O2   A1A4I 6  
A1A4I C4A  C5  C 0 1 Y N N N N N 33.630 -44.367 6.021  -2.509 0.919  0.661  C4A  A1A4I 7  
A1A4I O4   O3  O 0 1 N N N N N N 35.674 -42.862 11.455 4.197  1.342  -0.808 O4   A1A4I 8  
A1A4I C5   C6  C 0 1 N N N N N N 32.808 -43.316 5.976  -1.590 1.910  1.334  C5   A1A4I 9  
A1A4I O5   O4  O 0 1 N N N N N N 38.281 -42.920 12.047 5.705  -0.804 0.022  O5   A1A4I 10 
A1A4I C6   C7  C 0 1 N N N N N N 32.880 -42.349 7.003  -0.127 1.545  1.070  C6   A1A4I 11 
A1A4I N7   N1  N 1 1 N N S N N N 34.305 -42.071 7.388  0.020  1.272  -0.361 N7   A1A4I 12 
A1A4I C8   C8  C 0 1 N N N N N N 34.730 -42.643 8.560  1.404  1.334  -0.799 C8   A1A4I 13 
A1A4I C8A  C9  C 0 1 Y N N N N N 36.067 -42.693 8.940  2.197  0.145  -0.328 C8A  A1A4I 14 
A1A4I C9   C10 C 0 1 Y N N N N N 36.635 -42.793 10.425 3.584  0.212  -0.363 C9   A1A4I 15 
A1A4I C10  C11 C 0 1 Y N N N N N 37.895 -42.824 10.694 4.347  -0.871 0.056  C10  A1A4I 16 
A1A4I C11  C12 C 0 1 Y N N N N N 38.782 -42.771 9.876  3.719  -2.020 0.508  C11  A1A4I 17 
A1A4I C12  C13 C 0 1 Y N N N N N 38.560 -42.680 8.612  2.340  -2.080 0.544  C12  A1A4I 18 
A1A4I C12A C14 C 0 0 Y N N N N N 37.080 -42.640 8.008  1.577  -0.999 0.131  C12A A1A4I 19 
A1A4I C13  C15 C 0 1 N N N N N N 36.754 -42.519 6.509  0.078  -1.103 0.207  C13  A1A4I 20 
A1A4I C13A C16 C 0 0 N N S N N N 35.242 -42.669 6.235  -0.585 -0.030 -0.663 C13A A1A4I 21 
A1A4I C14  C17 C 0 1 Y N N N N N 34.856 -44.098 6.162  -2.051 0.023  -0.280 C14  A1A4I 22 
A1A4I C18  C18 C 0 1 N N N N N N 35.167 -48.842 6.180  -6.323 -1.430 0.003  C18  A1A4I 23 
A1A4I C19  C19 C 0 1 N N N N N N 35.464 -41.651 12.144 4.496  2.344  0.165  C19  A1A4I 24 
A1A4I C20  C20 C 0 1 N N N N N N 38.103 -44.168 12.681 6.423  -1.956 0.468  C20  A1A4I 25 
A1A4I C07  C21 C 0 1 N N N N N N 34.485 -40.620 7.499  -0.738 2.291  -1.100 C07  A1A4I 26 
A1A4I H01  H1  H 0 1 N N N N N N 36.982 -44.901 6.428  -2.541 -1.574 -1.649 H01  A1A4I 27 
A1A4I H02  H2  H 0 1 N N N N N N 32.090 -46.080 5.833  -4.214 1.648  1.771  H02  A1A4I 28 
A1A4I H03  H3  H 0 1 N N N N N N 33.002 -42.794 5.027  -1.788 2.908  0.943  H03  A1A4I 29 
A1A4I H04  H4  H 0 1 N N N N N N 31.781 -43.709 5.974  -1.776 1.903  2.408  H04  A1A4I 30 
A1A4I H05  H5  H 0 1 N N N N N N 32.336 -42.720 7.884  0.517  2.377  1.355  H05  A1A4I 31 
A1A4I H06  H6  H 0 1 N N N N N N 32.415 -41.416 6.651  0.140  0.659  1.645  H06  A1A4I 32 
A1A4I H08  H7  H 0 1 N N N N N N 34.206 -42.107 9.365  1.431  1.368  -1.888 H08  A1A4I 33 
A1A4I H21  H8  H 0 1 N N N N N N 34.385 -43.687 8.530  1.860  2.242  -0.406 H21  A1A4I 34 
A1A4I H09  H9  H 0 1 N N N N N N 39.805 -42.801 10.220 4.306  -2.867 0.831  H09  A1A4I 35 
A1A4I H10  H10 H 0 1 N N N N N N 39.401 -42.629 7.937  1.852  -2.977 0.897  H10  A1A4I 36 
A1A4I H12  H11 H 0 1 N N N N N N 37.084 -41.532 6.152  -0.231 -2.088 -0.140 H12  A1A4I 37 
A1A4I H11  H12 H 0 1 N N N N N N 37.294 -43.306 5.963  -0.238 -0.972 1.242  H11  A1A4I 38 
A1A4I H13  H13 H 0 1 N N N N N N 34.995 -42.164 5.289  -0.461 -0.269 -1.719 H13  A1A4I 39 
A1A4I H1   H14 H 0 1 N N N N N N 35.312 -49.469 5.288  -7.303 -1.430 -0.474 H1   A1A4I 40 
A1A4I H14  H15 H 0 1 N N N N N N 35.080 -49.484 7.069  -6.266 -2.210 0.762  H14  A1A4I 41 
A1A4I H16  H16 H 0 1 N N N N N N 34.703 -41.800 12.924 4.983  3.190  -0.322 H16  A1A4I 42 
A1A4I H15  H17 H 0 1 N N N N N N 36.406 -41.325 12.609 3.573  2.679  0.637  H15  A1A4I 43 
A1A4I H17  H18 H 0 1 N N N N N N 35.119 -40.882 11.437 5.162  1.929  0.921  H17  A1A4I 44 
A1A4I H19  H19 H 0 1 N N N N N N 38.443 -44.101 13.725 6.166  -2.165 1.506  H19  A1A4I 45 
A1A4I H20  H20 H 0 1 N N N N N N 37.038 -44.442 12.659 6.157  -2.813 -0.152 H20  A1A4I 46 
A1A4I H18  H21 H 0 1 N N N N N N 38.689 -44.934 12.153 7.494  -1.770 0.389  H18  A1A4I 47 
A1A4I H07A H22 H 0 0 N N N N N N 35.525 -40.400 7.781  -0.344 3.279  -0.863 H07A A1A4I 48 
A1A4I H07  H23 H 0 1 N N N N N N 34.259 -40.148 6.532  -0.644 2.109  -2.170 H07  A1A4I 49 
A1A4I H07B H24 H 0 0 N N N N N N 33.805 -40.224 8.268  -1.788 2.240  -0.814 H07B A1A4I 50 
# 
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 
A1A4I O1   C2   SING N N 1  
A1A4I O1   C18  SING N N 2  
A1A4I O2   C3   SING N N 3  
A1A4I O2   C18  SING N N 4  
A1A4I O4   C9   SING N N 5  
A1A4I O4   C19  SING N N 6  
A1A4I O5   C10  SING N N 7  
A1A4I O5   C20  SING N N 8  
A1A4I N7   C6   SING N N 9  
A1A4I N7   C8   SING N N 10 
A1A4I N7   C13A SING N N 11 
A1A4I N7   C07  SING N N 12 
A1A4I C1   C2   DOUB Y N 13 
A1A4I C1   C14  SING Y N 14 
A1A4I C2   C3   SING Y N 15 
A1A4I C3   C4   DOUB Y N 16 
A1A4I C4   C4A  SING Y N 17 
A1A4I C4A  C5   SING N N 18 
A1A4I C4A  C14  DOUB Y N 19 
A1A4I C5   C6   SING N N 20 
A1A4I C8   C8A  SING N N 21 
A1A4I C8A  C9   DOUB Y N 22 
A1A4I C8A  C12A SING Y N 23 
A1A4I C9   C10  SING Y N 24 
A1A4I C10  C11  DOUB Y N 25 
A1A4I C11  C12  SING Y N 26 
A1A4I C12  C12A DOUB Y N 27 
A1A4I C12A C13  SING N N 28 
A1A4I C13  C13A SING N N 29 
A1A4I C13A C14  SING N N 30 
A1A4I C1   H01  SING N N 31 
A1A4I C4   H02  SING N N 32 
A1A4I C5   H03  SING N N 33 
A1A4I C5   H04  SING N N 34 
A1A4I C6   H05  SING N N 35 
A1A4I C6   H06  SING N N 36 
A1A4I C8   H08  SING N N 37 
A1A4I C8   H21  SING N N 38 
A1A4I C11  H09  SING N N 39 
A1A4I C12  H10  SING N N 40 
A1A4I C13  H12  SING N N 41 
A1A4I C13  H11  SING N N 42 
A1A4I C13A H13  SING N N 43 
A1A4I C18  H1   SING N N 44 
A1A4I C18  H14  SING N N 45 
A1A4I C19  H16  SING N N 46 
A1A4I C19  H15  SING N N 47 
A1A4I C19  H17  SING N N 48 
A1A4I C20  H19  SING N N 49 
A1A4I C20  H20  SING N N 50 
A1A4I C20  H18  SING N N 51 
A1A4I C07  H07A SING N N 52 
A1A4I C07  H07  SING N N 53 
A1A4I C07  H07B 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 
A1A4I SMILES           ACDLabs              14.52 "COc1c(OC)ccc2CC3c4cc5OCOc5cc4CC[N+]3(C)Cc12"                                                                                                                
A1A4I InChI            InChI                1.06  "InChI=1S/C21H24NO4/c1-22-7-6-14-9-19-20(26-12-25-19)10-15(14)17(22)8-13-4-5-18(23-2)21(24-3)16(13)11-22/h4-5,9-10,17H,6-8,11-12H2,1-3H3/q+1/t17-,22-/m0/s1" 
A1A4I InChIKey         InChI                1.06  IPABSWBNWMXCHM-JTSKRJEESA-N                                                                                                                                  
A1A4I SMILES_CANONICAL CACTVS               3.385 "COc1ccc2C[C@H]3c4cc5OCOc5cc4CC[N@@+]3(C)Cc2c1OC"                                                                                                            
A1A4I SMILES           CACTVS               3.385 "COc1ccc2C[CH]3c4cc5OCOc5cc4CC[N+]3(C)Cc2c1OC"                                                                                                               
A1A4I SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "C[N@@+]12CCc3cc4c(cc3[C@@H]1Cc5ccc(c(c5C2)OC)OC)OCO4"                                                                                                       
A1A4I SMILES           "OpenEye OEToolkits" 2.0.7 "C[N+]12CCc3cc4c(cc3C1Cc5ccc(c(c5C2)OC)OC)OCO4"                                                                                                              
# 
_pdbx_chem_comp_identifier.comp_id           A1A4I 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           ACDLabs 
_pdbx_chem_comp_identifier.program_version   14.52 
_pdbx_chem_comp_identifier.identifier        "(7S,13aS)-9,10-dimethoxy-7-methyl-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
A1A4I "Create component" 2024-09-03 RCSB 
A1A4I "Initial release"  2025-09-17 RCSB 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      A1A4I 
_pdbx_chem_comp_synonyms.name         "(7S,13aS)-9,10-dimethoxy-7-methyl-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium" 
_pdbx_chem_comp_synonyms.provenance   PDB 
_pdbx_chem_comp_synonyms.type         ? 
# 
