data_A1A4H
# 
_chem_comp.id                                    A1A4H 
_chem_comp.name                                  "(R)-reticuline" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H23 N O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "(1R)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol" 
_chem_comp.pdbx_formal_charge                    0 
_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                        329.390 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1A4H 
_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        9DGA 
_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 
A1A4H C1   C1  C 0 1 Y N N N N N 67.457 42.292 10.195 1.724  -0.004 0.226  C1   A1A4H 1  
A1A4H C2   C2  C 0 1 Y N N N N N 67.941 42.435 8.904  2.162  1.270  -0.102 C2   A1A4H 2  
A1A4H C3   C3  C 0 1 Y N N N N N 67.167 42.998 7.909  3.513  1.529  -0.252 C3   A1A4H 3  
A1A4H O4   O1  O 0 1 N N N N N N 67.646 43.124 6.641  3.937  2.781  -0.572 O4   A1A4H 4  
A1A4H C5   C4  C 0 1 Y N N N N N 65.890 43.435 8.216  4.436  0.503  -0.072 C5   A1A4H 5  
A1A4H C11  C5  C 0 1 N N N N N N 66.792 42.412 12.904 0.767  -2.411 1.268  C11  A1A4H 6  
A1A4H C10  C6  C 0 1 N N N N N N 65.651 42.605 11.899 2.207  -2.421 0.755  C10  A1A4H 7  
A1A4H C9   C7  C 0 1 Y N N N N N 66.194 42.735 10.500 2.639  -1.020 0.405  C9   A1A4H 8  
A1A4H C8   C8  C 0 1 Y N N N N N 65.406 43.304 9.508  3.994  -0.767 0.252  C8   A1A4H 9  
A1A4H C14  C9  C 0 1 N N R N N N 68.366 41.678 11.228 0.243  -0.233 0.381  C14  A1A4H 10 
A1A4H N12  N1  N 0 1 N N N N N N 67.650 41.302 12.449 -0.066 -1.664 0.312  N12  A1A4H 11 
A1A4H C16  C10 C 0 1 N N N N N N 69.424 42.740 11.538 -0.501 0.499  -0.739 C16  A1A4H 12 
A1A4H C17  C11 C 0 1 Y N N N N N 69.797 43.282 10.186 -1.986 0.410  -0.497 C17  A1A4H 13 
A1A4H C18  C12 C 0 1 Y N N N N N 69.345 44.508 9.734  -2.600 1.309  0.355  C18  A1A4H 14 
A1A4H C19  C13 C 0 1 Y N N N N N 69.701 44.959 8.467  -3.965 1.230  0.579  C19  A1A4H 15 
A1A4H C21  C14 C 0 1 Y N N N N N 70.509 44.164 7.663  -4.715 0.244  -0.056 C21  A1A4H 16 
A1A4H C24  C15 C 0 1 Y N N N N N 70.936 42.939 8.113  -4.093 -0.654 -0.909 C24  A1A4H 17 
A1A4H C25  C16 C 0 1 Y N N N N N 70.579 42.504 9.369  -2.731 -0.565 -1.132 C25  A1A4H 18 
A1A4H C13  C17 C 0 1 N N N N N N 68.603 40.889 13.491 0.113  -2.174 -1.054 C13  A1A4H 19 
A1A4H O6   O2  O 0 1 N N N N N N 65.149 43.997 7.230  5.766  0.748  -0.216 O6   A1A4H 20 
A1A4H C7   C18 C 0 1 N N N N N N 65.776 45.093 6.559  6.654  -0.355 -0.017 C7   A1A4H 21 
A1A4H O20  O3  O 0 1 N N N N N N 69.274 46.171 8.019  -4.571 2.113  1.417  O20  A1A4H 22 
A1A4H O22  O4  O 0 1 N N N N N N 70.885 44.529 6.419  -6.055 0.162  0.160  O22  A1A4H 23 
A1A4H C23  C19 C 0 1 N N N N N N 70.729 43.472 5.473  -6.760 -0.875 -0.525 C23  A1A4H 24 
A1A4H H2   H1  H 0 1 N N N N N N 68.941 42.100 8.672  1.445  2.066  -0.241 H2   A1A4H 25 
A1A4H HO4  H2  H 0 1 N N N N N N 68.530 42.778 6.600  4.117  3.344  0.193  HO4  A1A4H 26 
A1A4H H11  H3  H 0 1 N N N N N N 67.387 43.335 12.969 0.401  -3.434 1.351  H11  A1A4H 27 
A1A4H H11A H4  H 0 0 N N N N N N 66.375 42.174 13.894 0.729  -1.924 2.242  H11A A1A4H 28 
A1A4H H10A H5  H 0 0 N N N N N N 64.977 41.737 11.946 2.863  -2.821 1.527  H10A A1A4H 29 
A1A4H H10  H6  H 0 1 N N N N N N 65.093 43.517 12.156 2.270  -3.051 -0.133 H10  A1A4H 30 
A1A4H H8   H7  H 0 1 N N N N N N 64.410 43.647 9.745  4.708  -1.566 0.388  H8   A1A4H 31 
A1A4H H14  H8  H 0 1 N N N N N N 68.861 40.795 10.798 -0.083 0.160  1.344  H14  A1A4H 32 
A1A4H H16A H10 H 0 0 N N N N N N 69.008 43.533 12.177 -0.197 1.545  -0.754 H16A A1A4H 33 
A1A4H H16  H11 H 0 1 N N N N N N 70.297 42.290 12.034 -0.261 0.037  -1.696 H16  A1A4H 34 
A1A4H H18  H12 H 0 1 N N N N N N 68.715 45.116 10.365 -2.016 2.073  0.847  H18  A1A4H 35 
A1A4H H24  H13 H 0 1 N N N N N N 71.552 42.317 7.481  -4.672 -1.420 -1.403 H24  A1A4H 36 
A1A4H H25  H14 H 0 1 N N N N N N 70.918 41.539 9.716  -2.248 -1.263 -1.800 H25  A1A4H 37 
A1A4H H13B H15 H 0 0 N N N N N N 69.223 40.062 13.115 -0.078 -3.247 -1.069 H13B A1A4H 38 
A1A4H H13A H16 H 0 0 N N N N N N 69.248 41.740 13.756 -0.585 -1.672 -1.724 H13A A1A4H 39 
A1A4H H13  H17 H 0 1 N N N N N N 68.050 40.557 14.382 1.134  -1.982 -1.382 H13  A1A4H 40 
A1A4H H7B  H18 H 0 1 N N N N N N 65.102 45.481 5.781  6.422  -1.142 -0.734 H7B  A1A4H 41 
A1A4H H7   H19 H 0 1 N N N N N N 65.995 45.890 7.285  7.682  -0.024 -0.161 H7   A1A4H 42 
A1A4H H7A  H20 H 0 1 N N N N N N 66.713 44.751 6.096  6.534  -0.738 0.996  H7A  A1A4H 43 
A1A4H HO20 H21 H 0 0 N N N N N N 69.606 46.320 7.142  -4.890 2.915  0.980  HO20 A1A4H 44 
A1A4H H23B H22 H 0 0 N N N N N N 71.048 43.819 4.479  -6.645 -0.743 -1.601 H23B A1A4H 45 
A1A4H H23  H23 H 0 1 N N N N N N 71.346 42.614 5.777  -6.356 -1.844 -0.233 H23  A1A4H 46 
A1A4H H23A H24 H 0 0 N N N N N N 69.673 43.168 5.434  -7.818 -0.828 -0.265 H23A A1A4H 47 
# 
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 
A1A4H C11 C10  SING N N 1  
A1A4H C11 N12  SING N N 2  
A1A4H C10 C9   SING N N 3  
A1A4H C9  C8   DOUB Y N 4  
A1A4H C9  C1   SING Y N 5  
A1A4H C8  C5   SING Y N 6  
A1A4H C5  C3   DOUB Y N 7  
A1A4H C5  O6   SING N N 8  
A1A4H C3  C2   SING Y N 9  
A1A4H C3  O4   SING N N 10 
A1A4H C2  C1   DOUB Y N 11 
A1A4H C1  C14  SING N N 12 
A1A4H C14 N12  SING N N 13 
A1A4H C14 C16  SING N N 14 
A1A4H N12 C13  SING N N 15 
A1A4H C16 C17  SING N N 16 
A1A4H C17 C18  DOUB Y N 17 
A1A4H C17 C25  SING Y N 18 
A1A4H C18 C19  SING Y N 19 
A1A4H C19 C21  DOUB Y N 20 
A1A4H C19 O20  SING N N 21 
A1A4H C21 C24  SING Y N 22 
A1A4H C21 O22  SING N N 23 
A1A4H C24 C25  DOUB Y N 24 
A1A4H O6  C7   SING N N 25 
A1A4H O22 C23  SING N N 26 
A1A4H C2  H2   SING N N 27 
A1A4H O4  HO4  SING N N 28 
A1A4H C11 H11  SING N N 29 
A1A4H C11 H11A SING N N 30 
A1A4H C10 H10A SING N N 31 
A1A4H C10 H10  SING N N 32 
A1A4H C8  H8   SING N N 33 
A1A4H C14 H14  SING N N 34 
A1A4H C16 H16A SING N N 35 
A1A4H C16 H16  SING N N 36 
A1A4H C18 H18  SING N N 37 
A1A4H C24 H24  SING N N 38 
A1A4H C25 H25  SING N N 39 
A1A4H C13 H13B SING N N 40 
A1A4H C13 H13A SING N N 41 
A1A4H C13 H13  SING N N 42 
A1A4H C7  H7B  SING N N 43 
A1A4H C7  H7   SING N N 44 
A1A4H C7  H7A  SING N N 45 
A1A4H O20 HO20 SING N N 46 
A1A4H C23 H23B SING N N 47 
A1A4H C23 H23  SING N N 48 
A1A4H C23 H23A SING N N 49 
# 
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 
A1A4H SMILES           ACDLabs              14.52 "COc1ccc(cc1O)CC1c2cc(O)c(cc2CCN1C)OC"                                                                                        
A1A4H InChI            InChI                1.06  "InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3" 
A1A4H InChIKey         InChI                1.06  BHLYRWXGMIUIHG-UHFFFAOYSA-N                                                                                                   
A1A4H SMILES_CANONICAL CACTVS               3.385 "COc1ccc(C[C@H]2N(C)CCc3cc(OC)c(O)cc23)cc1O"                                                                                  
A1A4H SMILES           CACTVS               3.385 "COc1ccc(C[CH]2N(C)CCc3cc(OC)c(O)cc23)cc1O"                                                                                   
A1A4H SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "CN1CCc2cc(c(cc2[C@H]1Cc3ccc(c(c3)O)OC)O)OC"                                                                                  
A1A4H SMILES           "OpenEye OEToolkits" 2.0.7 "CN1CCc2cc(c(cc2C1Cc3ccc(c(c3)O)OC)O)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 
A1A4H "SYSTEMATIC NAME" ACDLabs              14.52 "(1R)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol"      
A1A4H "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "(1~{R})-6-methoxy-1-[(4-methoxy-3-oxidanyl-phenyl)methyl]-2-methyl-3,4-dihydro-1~{H}-isoquinolin-7-ol" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
A1A4H "Create component" 2024-09-03 RCSB 
A1A4H "Initial release"  2025-09-17 RCSB 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      A1A4H 
_pdbx_chem_comp_synonyms.name         "(1R)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol" 
_pdbx_chem_comp_synonyms.provenance   PDB 
_pdbx_chem_comp_synonyms.type         ? 
# 
