data_A1AFU
# 
_chem_comp.id                                    A1AFU 
_chem_comp.name                                  2-bromo-N,N-diethyl-6-methyl-9,10-didehydroergoline-8beta-carboxamide 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H24 Br N3 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2024-02-26 
_chem_comp.pdbx_modified_date                    2025-03-28 
_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                        402.328 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1AFU 
_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        9ARZ 
_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 
A1AFU C10  C1  C  0 1 N N N N N N 130.189 134.889 97.250  2.165  1.771  -1.033 C10  A1AFU 1  
A1AFU C11  C2  C  0 1 Y N N N N N 134.106 135.182 100.234 -2.264 -0.014 0.049  C11  A1AFU 2  
A1AFU C12  C3  C  0 1 Y N N N N N 133.976 136.680 98.199  -0.257 -1.576 -0.221 C12  A1AFU 3  
A1AFU C13  C4  C  0 1 Y N N N N N 134.600 136.127 99.320  -1.650 -1.330 -0.082 C13  A1AFU 4  
A1AFU C06  C5  C  0 1 N N R N N N 132.238 134.799 98.590  -0.098 0.923  -0.717 C06  A1AFU 5  
A1AFU C07  C6  C  0 1 N N N N N N 132.605 136.179 97.975  0.570  -0.356 -0.285 C07  A1AFU 6  
A1AFU C08  C7  C  0 1 N N N N N N 132.738 134.635 100.070 -1.399 1.219  0.041  C08  A1AFU 7  
A1AFU C09  C8  C  0 1 N N R N N N 130.324 136.394 97.035  2.748  0.779  -0.021 C09  A1AFU 8  
A1AFU C14  C9  C  0 1 N N N N N N 131.714 136.887 97.266  1.851  -0.428 0.030  C14  A1AFU 9  
A1AFU C15  C10 C  0 1 Y N N N N N 135.886 136.472 99.695  -2.646 -2.308 -0.016 C15  A1AFU 10 
A1AFU C16  C11 C  0 1 N N N N N N 130.526 133.052 98.755  0.254  3.201  -1.424 C16  A1AFU 11 
A1AFU C17  C12 C  0 1 N N N N N N 130.003 136.714 95.605  4.131  0.366  -0.453 C17  A1AFU 12 
A1AFU C18  C13 C  0 1 Y N N N N N 135.091 134.956 101.158 -3.568 -0.249 0.167  C18  A1AFU 13 
A1AFU C19  C14 C  0 1 Y N N N N N 134.712 137.611 97.460  0.106  -2.900 -0.315 C19  A1AFU 14 
A1AFU C20  C15 C  0 1 Y N N N N N 136.633 137.397 98.969  -2.239 -3.640 -0.082 C20  A1AFU 15 
A1AFU C21  C16 C  0 1 Y N N N N N 136.015 137.959 97.842  -0.874 -3.890 -0.278 C21  A1AFU 16 
A1AFU C22  C17 C  0 1 N N N N N N 128.460 137.325 93.793  4.746  0.169  1.897  C22  A1AFU 17 
A1AFU C23  C18 C  0 1 N N N N N N 127.529 137.095 96.065  6.451  -0.182 0.051  C23  A1AFU 18 
A1AFU C24  C19 C  0 1 N N N N N N 128.444 136.059 92.961  4.868  1.607  2.405  C24  A1AFU 19 
A1AFU C25  C20 C  0 1 N N N N N N 127.455 138.453 96.726  6.603  -1.694 -0.128 C25  A1AFU 20 
A1AFU N03  N1  N  0 1 N N N N N N 130.784 134.480 98.530  0.786  2.078  -0.641 N03  A1AFU 21 
A1AFU N04  N2  N  0 1 Y N N N N N 136.168 135.742 100.825 -3.817 -1.622 0.103  N04  A1AFU 22 
A1AFU N05  N3  N  0 1 N N N N N N 128.704 137.024 95.196  5.082  0.124  0.472  N05  A1AFU 23 
A1AFU O02  O1  O  0 1 N N N N N N 130.937 136.682 94.805  4.389  0.251  -1.632 O02  A1AFU 24 
A1AFU BR01 BR1 BR 0 0 N N N N N N 135.011 133.784 102.632 -4.894 1.085  0.363  BR01 A1AFU 25 
A1AFU H1   H1  H  0 1 N N N N N N 129.122 134.620 97.248  2.759  2.686  -1.033 H1   A1AFU 26 
A1AFU H2   H2  H  0 1 N N N N N N 130.701 134.362 96.431  2.173  1.330  -2.030 H2   A1AFU 27 
A1AFU H3   H3  H  0 1 N N N N N N 132.766 134.039 97.996  -0.362 0.806  -1.768 H3   A1AFU 28 
A1AFU H4   H4  H  0 1 N N N N N N 132.053 135.172 100.742 -1.930 2.033  -0.452 H4   A1AFU 29 
A1AFU H5   H5  H  0 1 N N N N N N 132.745 133.566 100.331 -1.165 1.505  1.067  H5   A1AFU 30 
A1AFU H6   H6  H  0 1 N N N N N N 129.625 136.922 97.700  2.794  1.244  0.964  H6   A1AFU 31 
A1AFU H7   H7  H  0 1 N N N N N N 132.010 137.839 96.851  2.265  -1.379 0.333  H7   A1AFU 32 
A1AFU H8   H8  H  0 1 N N N N N N 130.971 132.745 99.713  0.201  2.918  -2.476 H8   A1AFU 33 
A1AFU H9   H9  H  0 1 N N N N N N 129.441 132.875 98.782  -0.744 3.454  -1.066 H9   A1AFU 34 
A1AFU H10  H10 H  0 1 N N N N N N 130.973 132.466 97.939  0.909  4.065  -1.313 H10  A1AFU 35 
A1AFU H11  H11 H  0 1 N N N N N N 134.272 138.067 96.585  1.141  -3.167 -0.471 H11  A1AFU 36 
A1AFU H12  H12 H  0 1 N N N N N N 137.637 137.668 99.259  -2.955 -4.447 -0.036 H12  A1AFU 37 
A1AFU H13  H13 H  0 1 N N N N N N 136.559 138.681 97.251  -0.555 -4.919 -0.354 H13  A1AFU 38 
A1AFU H14  H14 H  0 1 N N N N N N 129.256 137.988 93.424  5.431  -0.472 2.452  H14  A1AFU 39 
A1AFU H15  H15 H  0 1 N N N N N N 127.488 137.831 93.697  3.724  -0.182 2.040  H15  A1AFU 40 
A1AFU H16  H16 H  0 1 N N N N N N 126.622 136.932 95.465  7.151  0.165  0.811  H16  A1AFU 41 
A1AFU H17  H17 H  0 1 N N N N N N 127.601 136.317 96.839  6.662  0.319  -0.894 H17  A1AFU 42 
A1AFU H18  H18 H  0 1 N N N N N N 128.258 136.314 91.907  4.618  1.639  3.466  H18  A1AFU 43 
A1AFU H19  H19 H  0 1 N N N N N N 129.415 135.550 93.049  5.890  1.957  2.262  H19  A1AFU 44 
A1AFU H20  H20 H  0 1 N N N N N N 127.647 135.393 93.323  4.183  2.248  1.850  H20  A1AFU 45 
A1AFU H21  H21 H  0 1 N N N N N N 126.569 138.497 97.377  6.392  -2.195 0.816  H21  A1AFU 46 
A1AFU H22  H22 H  0 1 N N N N N N 128.361 138.617 97.328  5.903  -2.042 -0.888 H22  A1AFU 47 
A1AFU H23  H23 H  0 1 N N N N N N 127.382 139.233 95.954  7.622  -1.923 -0.441 H23  A1AFU 48 
A1AFU H25  H25 H  0 1 N N N N N N 137.030 135.778 101.330 -4.694 -2.030 0.166  H25  A1AFU 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 
A1AFU C24 C22  SING N N 1  
A1AFU C22 N05  SING N N 2  
A1AFU O02 C17  DOUB N N 3  
A1AFU N05 C17  SING N N 4  
A1AFU N05 C23  SING N N 5  
A1AFU C17 C09  SING N N 6  
A1AFU C23 C25  SING N N 7  
A1AFU C09 C10  SING N N 8  
A1AFU C09 C14  SING N N 9  
A1AFU C10 N03  SING N N 10 
A1AFU C14 C07  DOUB N N 11 
A1AFU C19 C21  DOUB Y N 12 
A1AFU C19 C12  SING Y N 13 
A1AFU C21 C20  SING Y N 14 
A1AFU C07 C12  SING N N 15 
A1AFU C07 C06  SING N N 16 
A1AFU C12 C13  DOUB Y N 17 
A1AFU N03 C06  SING N N 18 
A1AFU N03 C16  SING N N 19 
A1AFU C06 C08  SING N N 20 
A1AFU C20 C15  DOUB Y N 21 
A1AFU C13 C15  SING Y N 22 
A1AFU C13 C11  SING Y N 23 
A1AFU C15 N04  SING Y N 24 
A1AFU C08 C11  SING N N 25 
A1AFU C11 C18  DOUB Y N 26 
A1AFU N04 C18  SING Y N 27 
A1AFU C18 BR01 SING N N 28 
A1AFU C10 H1   SING N N 29 
A1AFU C10 H2   SING N N 30 
A1AFU C06 H3   SING N N 31 
A1AFU C08 H4   SING N N 32 
A1AFU C08 H5   SING N N 33 
A1AFU C09 H6   SING N N 34 
A1AFU C14 H7   SING N N 35 
A1AFU C16 H8   SING N N 36 
A1AFU C16 H9   SING N N 37 
A1AFU C16 H10  SING N N 38 
A1AFU C19 H11  SING N N 39 
A1AFU C20 H12  SING N N 40 
A1AFU C21 H13  SING N N 41 
A1AFU C22 H14  SING N N 42 
A1AFU C22 H15  SING N N 43 
A1AFU C23 H16  SING N N 44 
A1AFU C23 H17  SING N N 45 
A1AFU C24 H18  SING N N 46 
A1AFU C24 H19  SING N N 47 
A1AFU C24 H20  SING N N 48 
A1AFU C25 H21  SING N N 49 
A1AFU C25 H22  SING N N 50 
A1AFU C25 H23  SING N N 51 
A1AFU N04 H25  SING N N 52 
# 
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 
A1AFU SMILES           ACDLabs              12.01 "CCN(CC)C(=O)C1C=C2C(Cc3c(Br)[NH]c4cccc2c34)N(C)C1"                                                                                                   
A1AFU InChI            InChI                1.06  "InChI=1S/C20H24BrN3O/c1-4-24(5-2)20(25)12-9-14-13-7-6-8-16-18(13)15(19(21)22-16)10-17(14)23(3)11-12/h6-9,12,17,22H,4-5,10-11H2,1-3H3/t12-,17-/m1/s1" 
A1AFU InChIKey         InChI                1.06  VKRAXSZEDRWLAG-SJKOYZFVSA-N                                                                                                                           
A1AFU SMILES_CANONICAL CACTVS               3.385 "CCN(CC)C(=O)[C@H]1CN(C)[C@@H]2Cc3c(Br)[nH]c4cccc(C2=C1)c34"                                                                                          
A1AFU SMILES           CACTVS               3.385 "CCN(CC)C(=O)[CH]1CN(C)[CH]2Cc3c(Br)[nH]c4cccc(C2=C1)c34"                                                                                             
A1AFU SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "CCN(CC)C(=O)[C@H]1CN([C@@H]2Cc3c4c(cccc4[nH]c3Br)C2=C1)C"                                                                                            
A1AFU SMILES           "OpenEye OEToolkits" 2.0.7 "CCN(CC)C(=O)C1CN(C2Cc3c4c(cccc4[nH]c3Br)C2=C1)C"                                                                                                     
# 
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 
A1AFU "SYSTEMATIC NAME" ACDLabs              12.01 2-bromo-N,N-diethyl-6-methyl-9,10-didehydroergoline-8beta-carboxamide                                                        
A1AFU "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "(6~{a}~{R},9~{R})-5-bromanyl-~{N},~{N}-diethyl-7-methyl-6,6~{a},8,9-tetrahydro-4~{H}-indolo[4,3-fg]quinoline-9-carboxamide" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
A1AFU "Create component" 2024-02-26 RCSB 
A1AFU "Initial release"  2025-04-02 RCSB 
# 
