data_H8J # _chem_comp.id H8J _chem_comp.name "(8alpha)-N-[(2S)-1-hydroxybutan-2-yl]-1,6-dimethyl-9,10-didehydroergoline-8-carboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H27 N3 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms methysergide _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2018-06-15 _chem_comp.pdbx_modified_date 2021-03-01 _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 353.458 _chem_comp.one_letter_code ? _chem_comp.three_letter_code H8J _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 6DRZ _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site RCSB # # 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.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 H8J CAA C1 C 0 1 N N N 22.959 22.397 12.467 5.806 1.214 0.057 CAA H8J 1 H8J CAB C2 C 0 1 N N N 22.530 18.930 6.267 -0.622 4.017 -0.302 CAB H8J 2 H8J CAC C3 C 0 1 N N N 26.389 12.385 5.162 -6.641 -0.964 0.293 CAC H8J 3 H8J CAF C4 C 0 1 N N N 22.943 16.706 9.672 0.507 -0.028 0.145 CAF H8J 4 H8J CAG C5 C 0 1 Y N N 25.819 13.499 9.499 -2.654 -2.955 -0.807 CAG H8J 5 H8J CAH C6 C 0 1 Y N N 24.998 14.618 9.664 -1.556 -2.105 -0.689 CAH H8J 6 H8J CAI C7 C 0 1 Y N N 26.121 12.991 8.239 -3.964 -2.585 -0.526 CAI H8J 7 H8J CAJ C8 C 0 1 Y N N 24.934 14.354 5.270 -4.827 0.765 0.619 CAJ H8J 8 H8J CAK C9 C 0 1 N N N 21.605 21.780 12.644 5.877 -0.284 0.361 CAK H8J 9 H8J CAL C10 C 0 1 N N N 20.806 19.842 13.955 4.865 -2.512 -0.141 CAL H8J 10 H8J CAM C11 C 0 1 N N N 23.565 16.289 6.121 -2.494 1.954 0.725 CAM H8J 11 H8J CAN C12 C 0 1 N N N 22.423 18.736 8.616 1.093 2.308 -0.373 CAN H8J 12 H8J CAP C13 C 0 1 N N N 22.404 18.639 11.109 2.865 0.570 -0.239 CAP H8J 13 H8J CAQ C14 C 0 1 N N N 23.652 16.355 8.517 -0.759 0.278 -0.077 CAQ H8J 14 H8J CAR C15 C 0 1 Y N N 24.386 15.165 6.157 -3.508 0.865 0.494 CAR H8J 15 H8J CAS C16 C 0 1 Y N N 24.484 15.219 8.514 -1.739 -0.808 -0.269 CAS H8J 16 H8J CAT C17 C 0 1 Y N N 25.612 13.592 7.166 -4.186 -1.278 -0.094 CAT H8J 17 H8J CAU C18 C 0 1 Y N N 24.816 14.678 7.334 -3.070 -0.444 0.025 CAU H8J 18 H8J CAV C19 C 0 1 N N R 22.133 17.849 9.811 1.555 1.034 0.344 CAV H8J 19 H8J CAW C20 C 0 1 N N S 21.742 20.278 12.846 4.723 -1.002 -0.341 CAW H8J 20 H8J CAX C21 C 0 1 N N R 23.662 17.160 7.375 -1.260 1.696 -0.151 CAX H8J 21 H8J NAO N1 N 0 1 N N N 21.444 19.573 11.633 3.450 -0.551 0.226 NAO H8J 22 H8J NAY N2 N 0 1 N N N 22.465 17.997 7.363 -0.228 2.679 0.157 NAY H8J 23 H8J NAZ N3 N 0 1 Y N N 25.661 13.421 5.849 -5.249 -0.509 0.271 NAZ H8J 24 H8J OAD O1 O 0 1 N N N 23.458 18.472 11.694 3.392 1.206 -1.127 OAD H8J 25 H8J OAE O2 O 0 1 N N N 21.303 18.634 14.545 4.950 -2.801 1.256 OAE H8J 26 H8J H1 H1 H 0 1 N N N 22.852 23.482 12.322 6.628 1.726 0.558 H1 H8J 27 H8J H2 H2 H 0 1 N N N 23.569 22.206 13.362 5.883 1.370 -1.019 H2 H8J 28 H8J H3 H3 H 0 1 N N N 23.451 21.956 11.587 4.858 1.613 0.416 H3 H8J 29 H8J H4 H4 H 0 1 N N N 21.626 19.557 6.264 -1.547 4.314 0.193 H4 H8J 30 H8J H5 H5 H 0 1 N N N 23.418 19.569 6.381 0.165 4.731 -0.060 H5 H8J 31 H8J H6 H6 H 0 1 N N N 22.596 18.377 5.318 -0.777 4.000 -1.381 H6 H8J 32 H8J H7 H7 H 0 1 N N N 26.905 11.749 5.897 -7.101 -0.773 -0.676 H7 H8J 33 H8J H8 H8 H 0 1 N N N 25.689 11.773 4.575 -6.671 -2.033 0.506 H8 H8J 34 H8J H9 H9 H 0 1 N N N 27.130 12.842 4.489 -7.188 -0.424 1.067 H9 H8J 35 H8J H10 H10 H 0 1 N N N 23.024 16.048 10.524 0.797 -1.068 0.191 H10 H8J 36 H8J H11 H11 H 0 1 N N N 26.230 13.016 10.373 -2.476 -3.967 -1.138 H11 H8J 37 H8J H12 H12 H 0 1 N N N 24.769 15.004 10.646 -0.565 -2.464 -0.927 H12 H8J 38 H8J H13 H13 H 0 1 N N N 26.757 12.125 8.134 -4.780 -3.284 -0.639 H13 H8J 39 H8J H14 H14 H 0 1 N N N 24.802 14.445 4.202 -5.478 1.563 0.945 H14 H8J 40 H8J H15 H15 H 0 1 N N N 21.115 22.223 13.523 6.826 -0.683 0.003 H15 H8J 41 H8J H16 H16 H 0 1 N N N 20.996 21.973 11.748 5.801 -0.440 1.437 H16 H8J 42 H8J H17 H17 H 0 1 N N N 20.751 20.630 14.721 3.997 -3.018 -0.564 H17 H8J 43 H8J H18 H18 H 0 1 N N N 19.803 19.663 13.540 5.769 -2.862 -0.640 H18 H8J 44 H8J H19 H19 H 0 1 N N N 23.849 16.899 5.251 -2.930 2.918 0.464 H19 H8J 45 H8J H20 H20 H 0 1 N N N 22.523 15.955 6.010 -2.200 1.960 1.775 H20 H8J 46 H8J H21 H21 H 0 1 N N N 23.397 19.225 8.769 1.801 3.114 -0.181 H21 H8J 47 H8J H22 H22 H 0 1 N N N 21.636 19.501 8.547 1.029 2.123 -1.445 H22 H8J 48 H8J H23 H23 H 0 1 N N N 21.070 17.567 9.792 1.677 1.235 1.408 H23 H8J 49 H8J H24 H24 H 0 1 N N N 22.775 20.061 13.155 4.748 -0.773 -1.407 H24 H8J 50 H8J H25 H25 H 0 1 N N N 24.569 17.780 7.325 -1.559 1.877 -1.183 H25 H8J 51 H8J H26 H26 H 0 1 N N N 20.579 19.729 11.157 3.028 -1.060 0.936 H26 H8J 52 H8J H28 H28 H 0 1 N N N 20.719 18.357 15.241 5.041 -3.742 1.458 H28 H8J 53 # # 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 H8J CAC NAZ SING N N 1 H8J CAJ NAZ SING Y N 2 H8J CAJ CAR DOUB Y N 3 H8J NAZ CAT SING Y N 4 H8J CAM CAR SING N N 5 H8J CAM CAX SING N N 6 H8J CAR CAU SING Y N 7 H8J CAB NAY SING N N 8 H8J CAT CAU DOUB Y N 9 H8J CAT CAI SING Y N 10 H8J CAU CAS SING Y N 11 H8J NAY CAX SING N N 12 H8J NAY CAN SING N N 13 H8J CAX CAQ SING N N 14 H8J CAI CAG DOUB Y N 15 H8J CAS CAQ SING N N 16 H8J CAS CAH DOUB Y N 17 H8J CAQ CAF DOUB N N 18 H8J CAN CAV SING N N 19 H8J CAG CAH SING Y N 20 H8J CAF CAV SING N N 21 H8J CAV CAP SING N N 22 H8J CAP NAO SING N N 23 H8J CAP OAD DOUB N N 24 H8J NAO CAW SING N N 25 H8J CAA CAK SING N N 26 H8J CAK CAW SING N N 27 H8J CAW CAL SING N N 28 H8J CAL OAE SING N N 29 H8J CAA H1 SING N N 30 H8J CAA H2 SING N N 31 H8J CAA H3 SING N N 32 H8J CAB H4 SING N N 33 H8J CAB H5 SING N N 34 H8J CAB H6 SING N N 35 H8J CAC H7 SING N N 36 H8J CAC H8 SING N N 37 H8J CAC H9 SING N N 38 H8J CAF H10 SING N N 39 H8J CAG H11 SING N N 40 H8J CAH H12 SING N N 41 H8J CAI H13 SING N N 42 H8J CAJ H14 SING N N 43 H8J CAK H15 SING N N 44 H8J CAK H16 SING N N 45 H8J CAL H17 SING N N 46 H8J CAL H18 SING N N 47 H8J CAM H19 SING N N 48 H8J CAM H20 SING N N 49 H8J CAN H21 SING N N 50 H8J CAN H22 SING N N 51 H8J CAV H23 SING N N 52 H8J CAW H24 SING N N 53 H8J CAX H25 SING N N 54 H8J NAO H26 SING N N 55 H8J OAE H28 SING N N 56 # # 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 H8J SMILES ACDLabs 12.01 "CCC(CO)NC(=O)C3C=C2c4cccc1c4c(cn1C)CC2N(C)C3" H8J InChI InChI 1.03 "InChI=1S/C21H27N3O2/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7-18-20(16)13(10-23(18)2)9-19(17)24(3)11-14/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26)/t14-,15+,19-/m1/s1" H8J InChIKey InChI 1.03 KPJZHOPZRAFDTN-ZRGWGRIASA-N H8J SMILES_CANONICAL CACTVS 3.385 "CC[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2Cc3cn(C)c4cccc(C2=C1)c34" H8J SMILES CACTVS 3.385 "CC[CH](CO)NC(=O)[CH]1CN(C)[CH]2Cc3cn(C)c4cccc(C2=C1)c34" H8J SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "CC[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2Cc3cn(c4c3c(ccc4)C2=C1)C)C" H8J SMILES "OpenEye OEToolkits" 2.0.6 "CCC(CO)NC(=O)C1CN(C2Cc3cn(c4c3c(ccc4)C2=C1)C)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 H8J "SYSTEMATIC NAME" ACDLabs 12.01 "(8alpha)-N-[(2S)-1-hydroxybutan-2-yl]-1,6-dimethyl-9,10-didehydroergoline-8-carboxamide" H8J "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "(6~{a}~{R},9~{R})-4,7-dimethyl-~{N}-[(2~{S})-1-oxidanylbutan-2-yl]-6,6~{a},8,9-tetrahydroindolo[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 H8J "Create component" 2018-06-15 RCSB H8J "Initial release" 2018-08-29 RCSB H8J "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id H8J _pdbx_chem_comp_synonyms.name methysergide _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##