data_LOB # _chem_comp.id LOB _chem_comp.name LOBELINE _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H27 N O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "2-{(2S,6R)-6-[(2R)-2-HYDROXY-2-PHENYLETHYL]-1-METHYLPIPERIDIN-2-YL}-1-PHENYLETHANONE" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2005-08-04 _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 337.455 _chem_comp.one_letter_code ? _chem_comp.three_letter_code LOB _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details ? _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 2BYS _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # # 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 LOB O1 O1 O 0 1 N N N -5.815 22.584 6.149 -3.541 -1.410 -0.892 O1 LOB 1 LOB C3 C3 C 0 1 N N N -5.871 23.800 6.088 -3.641 -0.350 -0.311 C3 LOB 2 LOB C1 C1 C 0 1 Y N N -5.293 24.612 7.229 -4.968 0.247 -0.091 C1 LOB 3 LOB C2 C2 C 0 1 Y N N -4.770 23.956 8.351 -6.117 -0.406 -0.550 C2 LOB 4 LOB C5 C5 C 0 1 Y N N -4.231 24.683 9.414 -7.357 0.160 -0.340 C5 LOB 5 LOB C6 C6 C 0 1 Y N N -4.209 26.076 9.373 -7.466 1.370 0.322 C6 LOB 6 LOB C7 C7 C 0 1 Y N N -4.721 26.740 8.264 -6.334 2.022 0.779 C7 LOB 7 LOB C4 C4 C 0 1 Y N N -5.254 26.009 7.201 -5.087 1.466 0.583 C4 LOB 8 LOB C8 C8 C 0 1 N N N -6.479 24.410 4.837 -2.406 0.356 0.185 C8 LOB 9 LOB C9 C9 C 0 1 N N S -7.993 24.207 4.642 -1.182 -0.531 -0.051 C9 LOB 10 LOB C12 C12 C 0 1 N N N -8.451 22.786 4.915 -1.285 -1.782 0.823 C12 LOB 11 LOB C15 C15 C 0 1 N N N -9.907 22.675 4.529 -0.075 -2.683 0.557 C15 LOB 12 LOB C13 C13 C 0 1 N N N -10.029 22.710 3.017 1.207 -1.878 0.794 C13 LOB 13 LOB C11 C11 C 0 1 N N R -9.269 23.854 2.338 1.180 -0.622 -0.078 C11 LOB 14 LOB N1 N1 N 0 1 N N N -8.316 24.573 3.234 0.034 0.216 0.293 N1 LOB 15 LOB C22 C22 C 0 1 N N N -8.314 26.014 3.004 0.069 1.392 -0.586 C22 LOB 16 LOB C14 C14 C 0 1 N N N -8.490 23.320 1.119 2.474 0.168 0.128 C14 LOB 17 LOB C16 C16 C 0 1 N N R -8.077 24.436 0.155 3.663 -0.668 -0.352 C16 LOB 18 LOB O2 O2 O 0 1 N N N -6.700 24.744 0.374 3.546 -0.899 -1.757 O2 LOB 19 LOB C17 C17 C 0 1 Y N N -8.264 24.115 -1.291 4.944 0.073 -0.070 C17 LOB 20 LOB C18 C18 C 0 1 Y N N -7.861 22.897 -1.838 5.706 -0.258 1.035 C18 LOB 21 LOB C20 C20 C 0 1 Y N N -8.045 22.631 -3.197 6.881 0.421 1.294 C20 LOB 22 LOB C21 C21 C 0 1 Y N N -8.626 23.585 -4.031 7.295 1.433 0.447 C21 LOB 23 LOB C10 C10 C 0 1 Y N N -9.015 24.812 -3.492 6.534 1.764 -0.658 C10 LOB 24 LOB C19 C19 C 0 1 Y N N -8.830 25.075 -2.134 5.361 1.081 -0.919 C19 LOB 25 LOB H2 H2 H 0 1 N N N -4.784 22.854 8.395 -6.033 -1.350 -1.068 H2 LOB 26 LOB H5 H5 H 0 1 N N N -3.821 24.153 10.290 -8.245 -0.343 -0.694 H5 LOB 27 LOB H6 H6 H 0 1 N N N -3.787 26.649 10.216 -8.440 1.808 0.483 H6 LOB 28 LOB H7 H7 H 0 1 N N N -4.706 27.842 8.224 -6.428 2.966 1.296 H7 LOB 29 LOB H4 H4 H 0 1 N N N -5.652 26.544 6.322 -4.205 1.976 0.940 H4 LOB 30 LOB H8C1 1H8C H 0 0 N N N -5.932 24.045 3.937 -2.507 0.560 1.251 H8C1 LOB 31 LOB H8C2 2H8C H 0 0 N N N -6.237 25.498 4.794 -2.283 1.296 -0.355 H8C2 LOB 32 LOB H9 H9 H 0 1 N N N -8.539 24.898 5.326 -1.143 -0.824 -1.100 H9 LOB 33 LOB H121 1H12 H 0 0 N N N -8.260 22.468 5.966 -2.200 -2.321 0.581 H121 LOB 34 LOB H122 2H12 H 0 0 N N N -7.813 22.024 4.408 -1.299 -1.492 1.874 H122 LOB 35 LOB H151 1H15 H 0 0 N N N -10.535 23.453 5.022 -0.100 -3.034 -0.475 H151 LOB 36 LOB H152 2H15 H 0 0 N N N -10.394 21.775 4.971 -0.100 -3.537 1.235 H152 LOB 37 LOB H131 1H13 H 0 0 N N N -11.102 22.727 2.716 2.072 -2.486 0.531 H131 LOB 38 LOB H132 2H13 H 0 0 N N N -9.722 21.730 2.582 1.267 -1.591 1.844 H132 LOB 39 LOB H11 H11 H 0 1 N N N -10.018 24.593 1.970 1.094 -0.910 -1.126 H11 LOB 40 LOB H221 1H22 H 0 0 N N N -8.556 26.288 1.951 0.070 1.069 -1.627 H221 LOB 41 LOB H222 2H22 H 0 0 N N N -7.345 26.466 3.320 -0.809 2.011 -0.399 H222 LOB 42 LOB H223 3H22 H 0 0 N N N -8.998 26.531 3.717 0.970 1.970 -0.384 H223 LOB 43 LOB H141 1H14 H 0 0 N N N -9.066 22.525 0.590 2.429 1.096 -0.442 H141 LOB 44 LOB H142 2H14 H 0 0 N N N -7.608 22.718 1.438 2.595 0.397 1.187 H142 LOB 45 LOB H16 H16 H 0 1 N N N -8.680 25.343 0.392 3.672 -1.622 0.174 H16 LOB 46 LOB HA HA H 0 1 N N N -6.444 25.436 -0.224 3.600 -0.035 -2.188 HA LOB 47 LOB H18 H18 H 0 1 N N N -7.392 22.136 -1.191 5.382 -1.049 1.696 H18 LOB 48 LOB H20 H20 H 0 1 N N N -7.728 21.660 -3.613 7.476 0.163 2.157 H20 LOB 49 LOB H21 H21 H 0 1 N N N -8.776 23.373 -5.103 8.213 1.965 0.650 H21 LOB 50 LOB H10 H10 H 0 1 N N N -9.471 25.577 -4.142 6.857 2.555 -1.319 H10 LOB 51 LOB H19 H19 H 0 1 N N N -9.134 26.052 -1.721 4.766 1.340 -1.783 H19 LOB 52 # # 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 LOB O1 C3 DOUB N N 1 LOB C3 C1 SING N N 2 LOB C3 C8 SING N N 3 LOB C1 C2 DOUB Y N 4 LOB C1 C4 SING Y N 5 LOB C2 C5 SING Y N 6 LOB C2 H2 SING N N 7 LOB C5 C6 DOUB Y N 8 LOB C5 H5 SING N N 9 LOB C6 C7 SING Y N 10 LOB C6 H6 SING N N 11 LOB C7 C4 DOUB Y N 12 LOB C7 H7 SING N N 13 LOB C4 H4 SING N N 14 LOB C8 C9 SING N N 15 LOB C8 H8C1 SING N N 16 LOB C8 H8C2 SING N N 17 LOB C9 C12 SING N N 18 LOB C9 N1 SING N N 19 LOB C9 H9 SING N N 20 LOB C12 C15 SING N N 21 LOB C12 H121 SING N N 22 LOB C12 H122 SING N N 23 LOB C15 C13 SING N N 24 LOB C15 H151 SING N N 25 LOB C15 H152 SING N N 26 LOB C13 C11 SING N N 27 LOB C13 H131 SING N N 28 LOB C13 H132 SING N N 29 LOB C11 N1 SING N N 30 LOB C11 C14 SING N N 31 LOB C11 H11 SING N N 32 LOB N1 C22 SING N N 33 LOB C22 H221 SING N N 34 LOB C22 H222 SING N N 35 LOB C22 H223 SING N N 36 LOB C14 C16 SING N N 37 LOB C14 H141 SING N N 38 LOB C14 H142 SING N N 39 LOB C16 O2 SING N N 40 LOB C16 C17 SING N N 41 LOB C16 H16 SING N N 42 LOB O2 HA SING N N 43 LOB C17 C18 DOUB Y N 44 LOB C17 C19 SING Y N 45 LOB C18 C20 SING Y N 46 LOB C18 H18 SING N N 47 LOB C20 C21 DOUB Y N 48 LOB C20 H20 SING N N 49 LOB C21 C10 SING Y N 50 LOB C21 H21 SING N N 51 LOB C10 C19 DOUB Y N 52 LOB C10 H10 SING N N 53 LOB C19 H19 SING N N 54 # # 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 LOB SMILES ACDLabs 10.04 "O=C(c1ccccc1)CC3N(C)C(CC(O)c2ccccc2)CCC3" LOB SMILES_CANONICAL CACTVS 3.341 "CN1[C@H](CCC[C@H]1CC(=O)c2ccccc2)C[C@@H](O)c3ccccc3" LOB SMILES CACTVS 3.341 "CN1[CH](CCC[CH]1CC(=O)c2ccccc2)C[CH](O)c3ccccc3" LOB SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[N@@]1[C@H](CCC[C@H]1CC(=O)c2ccccc2)C[C@H](c3ccccc3)O" LOB SMILES "OpenEye OEToolkits" 1.5.0 "CN1C(CCCC1CC(=O)c2ccccc2)CC(c3ccccc3)O" LOB InChI InChI 1.03 "InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m1/s1" LOB InChIKey InChI 1.03 MXYUKLILVYORSK-QHAWAJNXSA-N # # 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 LOB "SYSTEMATIC NAME" ACDLabs 10.04 "2-{(2S,6R)-6-[(2R)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl}-1-phenylethanone" LOB "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[(1R,2S,6R)-6-[(2R)-2-hydroxy-2-phenyl-ethyl]-1-methyl-piperidin-2-yl]-1-phenyl-ethanone" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site LOB "Create component" 2005-08-04 EBI LOB "Modify descriptor" 2011-06-04 RCSB LOB "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id LOB _pdbx_chem_comp_synonyms.name "2-{(2S,6R)-6-[(2R)-2-HYDROXY-2-PHENYLETHYL]-1-METHYLPIPERIDIN-2-YL}-1-PHENYLETHANONE" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##