data_H8D # _chem_comp.id H8D _chem_comp.name "(8beta)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-9,10-didehydroergoline-8-carboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H25 N3 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms methylergonovine _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2018-06-15 _chem_comp.pdbx_modified_date 2020-06-17 _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 339.431 _chem_comp.one_letter_code ? _chem_comp.three_letter_code H8D _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 6DRY _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 H8D C4 C1 C 0 1 Y N N -26.390 -13.029 8.218 3.863 2.945 -0.147 C4 H8D 1 H8D C14 C2 C 0 1 N N R -22.698 -18.023 9.927 -1.232 -1.314 0.324 C14 H8D 2 H8D C5 C3 C 0 1 Y N N -26.156 -13.593 9.475 2.516 3.204 -0.372 C5 H8D 3 H8D C6 C4 C 0 1 Y N N -24.632 -15.145 8.439 1.840 0.924 -0.087 C6 H8D 4 H8D C11 C5 C 0 1 N N R -23.744 -16.937 7.397 1.627 -1.614 -0.259 C11 H8D 5 H8D C7 C6 C 0 1 Y N N -24.330 -14.986 6.217 3.792 -0.634 0.436 C7 H8D 6 H8D C8 C7 C 0 1 Y N N -24.824 -14.189 5.269 5.095 -0.409 0.574 C8 H8D 7 H8D C9 C8 C 0 1 N N N -23.753 -16.221 8.598 0.982 -0.275 -0.018 C9 H8D 8 H8D C10 C9 C 0 1 N N N -23.457 -16.856 9.811 -0.305 -0.131 0.245 C10 H8D 9 H8D C12 C10 C 0 1 N N N -22.791 -18.789 6.311 1.233 -3.956 -0.675 C12 H8D 10 H8D C13 C11 C 0 1 N N N -22.957 -18.790 8.642 -0.649 -2.444 -0.533 C13 H8D 11 H8D N1 N1 N 0 1 Y N N -25.681 -13.312 5.828 5.373 0.936 0.384 N1 H8D 12 H8D N2 N2 N 0 1 N N N -22.703 -17.975 7.455 0.710 -2.729 -0.061 N2 H8D 13 H8D C3 C12 C 0 1 Y N N -24.920 -14.542 7.295 3.210 0.669 0.139 C3 H8D 14 H8D N3 N3 N 0 1 N N N -21.822 -19.644 11.568 -3.289 0.057 0.396 N3 H8D 15 H8D C1 C13 C 0 1 Y N N -25.758 -13.526 7.152 4.228 1.625 0.117 C1 H8D 16 H8D C15 C14 C 0 1 N N N -23.439 -16.042 6.200 2.898 -1.839 0.571 C15 H8D 17 H8D C16 C15 C 0 1 N N N -22.906 -18.908 11.147 -2.591 -0.929 -0.200 C16 H8D 18 H8D C19 C16 C 0 1 N N S -21.896 -20.388 12.796 -4.611 0.432 -0.114 C19 H8D 19 H8D C2 C17 C 0 1 Y N N -25.261 -14.670 9.590 1.515 2.235 -0.348 C2 H8D 20 H8D C20 C18 C 0 1 N N N -21.625 -21.859 12.564 -5.431 1.066 1.011 C20 H8D 21 H8D C21 C19 C 0 1 N N N -22.857 -22.526 11.957 -5.697 0.023 2.099 C21 H8D 22 H8D C22 C20 C 0 1 N N N -20.888 -19.860 13.784 -4.451 1.436 -1.257 C22 H8D 23 H8D O1 O1 O 0 1 N N N -24.112 -18.969 11.761 -3.057 -1.507 -1.160 O1 H8D 24 H8D O2 O2 O 0 1 N N N -21.372 -18.654 14.340 -3.884 2.646 -0.752 O2 H8D 25 H8D H1 H1 H 0 1 N N N -27.074 -12.200 8.110 4.599 3.734 -0.180 H1 H8D 26 H8D H2 H2 H 0 1 N N N -21.634 -17.743 9.919 -1.318 -1.645 1.359 H2 H8D 27 H8D H3 H3 H 0 1 N N N -26.658 -13.205 10.349 2.226 4.224 -0.579 H3 H8D 28 H8D H4 H4 H 0 1 N N N -24.721 -17.415 7.233 1.933 -1.637 -1.305 H4 H8D 29 H8D H5 H5 H 0 1 N N N -24.576 -14.238 4.219 5.832 -1.166 0.798 H5 H8D 30 H8D H7 H7 H 0 1 N N N -23.842 -16.413 10.718 -0.701 0.860 0.408 H7 H8D 31 H8D H9 H9 H 0 1 N N N -22.013 -19.566 6.352 2.192 -4.208 -0.222 H9 H8D 32 H8D H10 H10 H 0 1 N N N -23.782 -19.264 6.275 0.529 -4.773 -0.512 H10 H8D 33 H8D H11 H11 H 0 1 N N N -22.646 -18.173 5.411 1.366 -3.799 -1.745 H11 H8D 34 H8D H12 H12 H 0 1 N N N -24.007 -19.117 8.630 -1.267 -3.336 -0.433 H12 H8D 35 H8D H13 H13 H 0 1 N N N -22.298 -19.671 8.615 -0.618 -2.134 -1.577 H13 H8D 36 H8D H14 H14 H 0 1 N N N -26.185 -12.606 5.331 6.258 1.330 0.433 H14 H8D 37 H8D H16 H16 H 0 1 N N N -20.985 -19.661 11.021 -2.917 0.520 1.163 H16 H8D 38 H8D H17 H17 H 0 1 N N N -23.556 -16.614 5.267 2.650 -1.992 1.622 H17 H8D 39 H8D H18 H18 H 0 1 N N N -22.409 -15.662 6.271 3.413 -2.720 0.187 H18 H8D 40 H8D H19 H19 H 0 1 N N N -22.901 -20.282 13.230 -5.124 -0.457 -0.481 H19 H8D 41 H8D H20 H20 H 0 1 N N N -25.064 -15.121 10.551 0.488 2.512 -0.534 H20 H8D 42 H8D H21 H21 H 0 1 N N N -21.385 -22.341 13.523 -4.877 1.902 1.438 H21 H8D 43 H8D H22 H22 H 0 1 N N N -20.774 -21.969 11.875 -6.379 1.425 0.612 H22 H8D 44 H8D H23 H23 H 0 1 N N N -22.652 -23.594 11.792 -6.251 -0.813 1.672 H23 H8D 45 H8D H24 H24 H 0 1 N N N -23.709 -22.418 12.645 -4.748 -0.335 2.498 H24 H8D 46 H8D H25 H25 H 0 1 N N N -23.098 -22.046 10.997 -6.281 0.475 2.900 H25 H8D 47 H8D H26 H26 H 0 1 N N N -20.735 -20.599 14.584 -3.793 1.017 -2.019 H26 H8D 48 H8D H27 H27 H 0 1 N N N -19.933 -19.672 13.271 -5.426 1.647 -1.695 H27 H8D 49 H8D H28 H28 H 0 1 N N N -20.740 -18.316 14.964 -3.753 3.330 -1.423 H28 H8D 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 H8D C8 N1 SING Y N 1 H8D C8 C7 DOUB Y N 2 H8D N1 C1 SING Y N 3 H8D C15 C7 SING N N 4 H8D C15 C11 SING N N 5 H8D C7 C3 SING Y N 6 H8D C12 N2 SING N N 7 H8D C1 C3 DOUB Y N 8 H8D C1 C4 SING Y N 9 H8D C3 C6 SING Y N 10 H8D C11 N2 SING N N 11 H8D C11 C9 SING N N 12 H8D N2 C13 SING N N 13 H8D C4 C5 DOUB Y N 14 H8D C6 C9 SING N N 15 H8D C6 C2 DOUB Y N 16 H8D C9 C10 DOUB N N 17 H8D C13 C14 SING N N 18 H8D C5 C2 SING Y N 19 H8D C10 C14 SING N N 20 H8D C14 C16 SING N N 21 H8D C16 N3 SING N N 22 H8D C16 O1 DOUB N N 23 H8D N3 C19 SING N N 24 H8D C21 C20 SING N N 25 H8D C20 C19 SING N N 26 H8D C19 C22 SING N N 27 H8D C22 O2 SING N N 28 H8D C4 H1 SING N N 29 H8D C14 H2 SING N N 30 H8D C5 H3 SING N N 31 H8D C11 H4 SING N N 32 H8D C8 H5 SING N N 33 H8D C10 H7 SING N N 34 H8D C12 H9 SING N N 35 H8D C12 H10 SING N N 36 H8D C12 H11 SING N N 37 H8D C13 H12 SING N N 38 H8D C13 H13 SING N N 39 H8D N1 H14 SING N N 40 H8D N3 H16 SING N N 41 H8D C15 H17 SING N N 42 H8D C15 H18 SING N N 43 H8D C19 H19 SING N N 44 H8D C2 H20 SING N N 45 H8D C20 H21 SING N N 46 H8D C20 H22 SING N N 47 H8D C21 H23 SING N N 48 H8D C21 H24 SING N N 49 H8D C21 H25 SING N N 50 H8D C22 H26 SING N N 51 H8D C22 H27 SING N N 52 H8D O2 H28 SING N N 53 # # 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 H8D SMILES ACDLabs 12.01 "c3ccc2C=1C(N(C)CC(C(NC(CO)CC)=O)C=1)Cc4c2c3nc4" H8D InChI InChI 1.03 "InChI=1S/C20H25N3O2/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/t13-,14+,18-/m1/s1" H8D InChIKey InChI 1.03 UNBRKDKAWYKMIV-QWQRMKEZSA-N H8D SMILES_CANONICAL CACTVS 3.385 "CC[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2Cc3c[nH]c4cccc(C2=C1)c34" H8D SMILES CACTVS 3.385 "CC[CH](CO)NC(=O)[CH]1CN(C)[CH]2Cc3c[nH]c4cccc(C2=C1)c34" H8D SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "CC[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)C" H8D SMILES "OpenEye OEToolkits" 2.0.6 "CCC(CO)NC(=O)C1CN(C2Cc3c[nH]c4c3c(ccc4)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 H8D "SYSTEMATIC NAME" ACDLabs 12.01 "(8beta)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-9,10-didehydroergoline-8-carboxamide" H8D "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "(6~{a}~{R},9~{R})-7-methyl-~{N}-[(2~{S})-1-oxidanylbutan-2-yl]-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 H8D "Create component" 2018-06-15 RCSB H8D "Other modification" 2018-06-25 RCSB H8D "Initial release" 2018-08-29 RCSB H8D "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id H8D _pdbx_chem_comp_synonyms.name methylergonovine _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##