data_4NQ
# 
_chem_comp.id                                    4NQ 
_chem_comp.name                                  Dextromethorphan 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H25 N O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         3-methoxy-17-methyl-9alpha,13alpha,14alpha-morphinan 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2015-04-21 
_chem_comp.pdbx_modified_date                    2025-11-11 
_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                        271.397 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     4NQ 
_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        9DGE 
_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 
4NQ C1  C1  C 0 1 Y N N N N N 34.835 -47.185 7.291  1.324  -1.473 1.347  C1  4NQ 1  
4NQ C2  C2  C 0 1 Y N N N N N 35.843 -47.895 6.663  2.577  -1.181 0.854  C2  4NQ 2  
4NQ C3  C3  C 0 1 Y N N N N N 37.027 -47.217 6.323  2.720  -0.237 -0.154 C3  4NQ 3  
4NQ C4  C4  C 0 1 Y N N N N N 37.192 -45.859 6.598  1.597  0.396  -0.661 C4  4NQ 4  
4NQ C5  C5  C 0 1 N N N N N N 37.816 -43.223 7.916  -0.479 2.216  -1.178 C5  4NQ 5  
4NQ C6  C6  C 0 1 N N N N N N 38.193 -43.288 9.409  -0.067 3.015  0.061  C6  4NQ 6  
4NQ C7  C7  C 0 1 N N N N N N 37.124 -42.704 10.345 -1.229 3.047  1.056  C7  4NQ 7  
4NQ C8  C8  C 0 1 N N N N N N 35.744 -43.317 10.059 -1.580 1.617  1.470  C8  4NQ 8  
4NQ C9  C9  C 0 1 N N S N N N 33.930 -43.572 8.181  -2.297 -0.629 0.642  C9  4NQ 9  
4NQ C10 C10 C 0 1 N N N N N N 33.832 -45.111 8.271  -1.137 -1.192 1.441  C10 4NQ 10 
4NQ C11 C11 C 0 1 Y N N N N N 34.979 -45.814 7.585  0.197  -0.834 0.843  C11 4NQ 11 
4NQ C12 C12 C 0 1 Y N N N N N 36.173 -45.134 7.242  0.338  0.093  -0.166 C12 4NQ 12 
4NQ C13 C13 C 0 1 N N S N N N 36.369 -43.630 7.531  -0.851 0.795  -0.770 C13 4NQ 13 
4NQ C14 C14 C 0 1 N N S N N N 35.343 -43.101 8.583  -2.003 0.817  0.237  C14 4NQ 14 
4NQ C15 C15 C 0 1 N N N N N N 36.008 -42.879 6.217  -1.302 -0.008 -1.999 C15 4NQ 15 
4NQ C16 C16 C 0 1 N N N N N N 34.546 -43.028 5.766  -1.569 -1.447 -1.541 C16 4NQ 16 
4NQ C17 C17 C 0 1 N N N N N N 32.270 -43.429 6.388  -2.957 -2.822 -0.115 C17 4NQ 17 
4NQ C18 C18 C 0 1 N N N N N N 39.096 -48.386 6.483  5.063  -0.630 -0.066 C18 4NQ 18 
4NQ O1  O1  O 0 1 N N N N N N 37.980 -47.971 5.705  3.953  0.064  -0.639 O1  4NQ 19 
4NQ N1  N1  N 0 1 N N N N N N 33.564 -42.976 6.868  -2.619 -1.450 -0.518 N1  4NQ 20 
4NQ H1  H1  H 0 1 N N N N N N 33.920 -47.691 7.561  1.216  -2.209 2.130  H1  4NQ 21 
4NQ H2  H2  H 0 1 N N N N N N 35.723 -48.945 6.439  3.446  -1.684 1.252  H2  4NQ 22 
4NQ H3  H3  H 0 1 N N N N N N 38.108 -45.361 6.315  1.703  1.129  -1.447 H3  4NQ 23 
4NQ H4  H4  H 0 1 N N N N N N 38.503 -43.888 7.372  -1.338 2.694  -1.649 H4  4NQ 24 
4NQ H5  H5  H 0 1 N N N N N N 37.968 -42.186 7.581  0.351  2.185  -1.883 H5  4NQ 25 
4NQ H6  H6  H 0 1 N N N N N N 38.353 -44.342 9.681  0.798  2.543  0.527  H6  4NQ 26 
4NQ H7  H7  H 0 1 N N N N N N 39.127 -42.725 9.556  0.189  4.033  -0.233 H7  4NQ 27 
4NQ H8  H8  H 0 1 N N N N N N 37.403 -42.918 11.387 -0.938 3.620  1.936  H8  4NQ 28 
4NQ H9  H9  H 0 1 N N N N N N 37.072 -41.615 10.196 -2.095 3.516  0.587  H9  4NQ 29 
4NQ H10 H10 H 0 1 N N N N N N 34.996 -42.840 10.709 -0.711 1.149  1.932  H10 4NQ 30 
4NQ H11 H11 H 0 1 N N N N N N 35.778 -44.396 10.269 -2.403 1.638  2.184  H11 4NQ 31 
4NQ H12 H12 H 0 1 N N N N N N 33.235 -43.166 8.931  -3.176 -0.629 1.286  H12 4NQ 32 
4NQ H13 H13 H 0 1 N N N N N N 32.891 -45.431 7.799  -1.180 -0.794 2.455  H13 4NQ 33 
4NQ H14 H14 H 0 1 N N N N N N 33.827 -45.401 9.332  -1.230 -2.277 1.484  H14 4NQ 34 
4NQ H15 H15 H 0 1 N N N N N N 35.332 -42.010 8.445  -2.889 1.258  -0.220 H15 4NQ 35 
4NQ H16 H16 H 0 1 N N N N N N 36.654 -43.265 5.415  -2.215 0.425  -2.409 H16 4NQ 36 
4NQ H17 H17 H 0 1 N N N N N N 36.211 -41.809 6.369  -0.517 0.001  -2.755 H17 4NQ 37 
4NQ H18 H18 H 0 1 N N N N N N 34.318 -42.214 5.062  -1.891 -2.045 -2.394 H18 4NQ 38 
4NQ H19 H19 H 0 1 N N N N N N 34.440 -43.996 5.255  -0.655 -1.871 -1.125 H19 4NQ 39 
4NQ H20 H20 H 0 1 N N N N N N 31.539 -43.390 7.209  -2.090 -3.286 0.356  H20 4NQ 40 
4NQ H21 H21 H 0 1 N N N N N N 31.935 -42.777 5.568  -3.786 -2.799 0.592  H21 4NQ 41 
4NQ H22 H22 H 0 1 N N N N N N 32.356 -44.463 6.023  -3.245 -3.398 -0.994 H22 4NQ 42 
4NQ H23 H23 H 0 1 N N N N N N 39.778 -48.982 5.859  5.110  -0.421 1.002  H23 4NQ 43 
4NQ H24 H24 H 0 1 N N N N N N 39.627 -47.501 6.863  4.940  -1.702 -0.221 H24 4NQ 44 
4NQ H25 H25 H 0 1 N N N N N N 38.746 -48.996 7.329  5.985  -0.297 -0.543 H25 4NQ 45 
# 
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 
4NQ O1  C3  SING N N 1  
4NQ O1  C18 SING N N 2  
4NQ C16 C15 SING N N 3  
4NQ C16 N1  SING N N 4  
4NQ C15 C13 SING N N 5  
4NQ C3  C4  DOUB Y N 6  
4NQ C3  C2  SING Y N 7  
4NQ C17 N1  SING N N 8  
4NQ C4  C12 SING Y N 9  
4NQ C2  C1  DOUB Y N 10 
4NQ N1  C9  SING N N 11 
4NQ C12 C13 SING N N 12 
4NQ C12 C11 DOUB Y N 13 
4NQ C1  C11 SING Y N 14 
4NQ C13 C5  SING N N 15 
4NQ C13 C14 SING N N 16 
4NQ C11 C10 SING N N 17 
4NQ C5  C6  SING N N 18 
4NQ C9  C10 SING N N 19 
4NQ C9  C14 SING N N 20 
4NQ C14 C8  SING N N 21 
4NQ C6  C7  SING N N 22 
4NQ C8  C7  SING N N 23 
4NQ C1  H1  SING N N 24 
4NQ C2  H2  SING N N 25 
4NQ C4  H3  SING N N 26 
4NQ C5  H4  SING N N 27 
4NQ C5  H5  SING N N 28 
4NQ C6  H6  SING N N 29 
4NQ C6  H7  SING N N 30 
4NQ C7  H8  SING N N 31 
4NQ C7  H9  SING N N 32 
4NQ C8  H10 SING N N 33 
4NQ C8  H11 SING N N 34 
4NQ C9  H12 SING N N 35 
4NQ C10 H13 SING N N 36 
4NQ C10 H14 SING N N 37 
4NQ C14 H15 SING N N 38 
4NQ C15 H16 SING N N 39 
4NQ C15 H17 SING N N 40 
4NQ C16 H18 SING N N 41 
4NQ C16 H19 SING N N 42 
4NQ C17 H20 SING N N 43 
4NQ C17 H21 SING N N 44 
4NQ C17 H22 SING N N 45 
4NQ C18 H23 SING N N 46 
4NQ C18 H24 SING N N 47 
4NQ C18 H25 SING N N 48 
# 
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 
4NQ SMILES           ACDLabs              14.52   "COc1ccc2CC3C4CCCCC4(CCN3C)c2c1"                                                                                                       
4NQ InChI            InChI                1.06    "InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m1/s1" 
4NQ InChIKey         InChI                1.06    MKXZASYAUGDDCJ-NJAFHUGGSA-N                                                                                                            
4NQ SMILES_CANONICAL CACTVS               3.385   "COc1ccc2C[C@H]3[C@H]4CCCC[C@@]4(CCN3C)c2c1"                                                                                           
4NQ SMILES           CACTVS               3.385   "COc1ccc2C[CH]3[CH]4CCCC[C]4(CCN3C)c2c1"                                                                                               
4NQ SMILES_CANONICAL "OpenEye OEToolkits" 3.1.0.0 "CN1CC[C@@]23CCCC[C@@H]2[C@@H]1Cc4c3cc(cc4)OC"                                                                                         
4NQ SMILES           "OpenEye OEToolkits" 3.1.0.0 "CN1CCC23CCCCC2C1Cc4c3cc(cc4)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 
4NQ "SYSTEMATIC NAME" ACDLabs              14.52   3-methoxy-17-methyl-9alpha,13alpha,14alpha-morphinan                                                         
4NQ "SYSTEMATIC NAME" "OpenEye OEToolkits" 3.1.0.0 "(1~{S},9~{S},10~{S})-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
4NQ "Create component"              2015-04-21 RCSB 
4NQ "Modify coordinates"            2025-09-09 RCSB 
4NQ "Modify model coordinates code" 2025-09-11 RCSB 
4NQ "Initial release"               2025-09-17 RCSB 
4NQ "Modify synonyms"               2025-11-11 RCSB 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      4NQ 
_pdbx_chem_comp_synonyms.name         3-methoxy-17-methyl-9alpha,13alpha,14alpha-morphinan 
_pdbx_chem_comp_synonyms.provenance   ? 
_pdbx_chem_comp_synonyms.type         ? 
# 
