data_BCG # _chem_comp.id BCG _chem_comp.name "3-(BENZOYLOXY)-8-METHYL-8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC ACID" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C16 H19 N O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms BENZOYLECGONINE _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2003-09-15 _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 289.326 _chem_comp.one_letter_code ? _chem_comp.three_letter_code BCG _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 1QYG _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 BCG C1 C1 C 0 1 N N R 22.446 -1.263 26.259 -0.181 -0.879 3.049 C1 BCG 1 BCG C2 C2 C 0 1 N N R 23.823 -1.870 25.848 -0.614 -0.922 1.575 C2 BCG 2 BCG C3 C3 C 0 1 N N S 23.717 -2.306 24.354 0.443 -0.209 0.727 C3 BCG 3 BCG C4 C4 C 0 1 N N N 22.510 -3.075 23.988 0.682 1.232 1.303 C4 BCG 4 BCG C5 C5 C 0 1 N N S 21.202 -2.329 24.566 1.028 1.101 2.795 C5 BCG 5 BCG C6 C6 C 0 1 N N N 21.157 -0.837 24.176 2.101 -0.000 2.951 C6 BCG 6 BCG C7 C7 C 0 1 N N N 22.012 -0.081 25.348 1.302 -1.309 3.119 C7 BCG 7 BCG C8 C8 C 0 1 N N N 26.129 -2.532 24.009 0.869 -0.113 -1.657 C8 BCG 8 BCG C9 C9 C 0 1 Y N N 27.150 -3.532 23.593 0.398 -0.021 -3.054 C9 BCG 9 BCG C10 C10 C 0 1 Y N N 26.774 -4.854 23.191 -0.968 0.055 -3.330 C10 BCG 10 BCG C11 C11 C 0 1 Y N N 27.829 -5.763 22.752 -1.400 0.147 -4.637 C11 BCG 11 BCG C12 C12 C 0 1 Y N N 29.174 -5.322 22.736 -0.484 0.152 -5.673 C12 BCG 12 BCG C13 C13 C 0 1 Y N N 29.523 -3.999 23.172 0.870 0.070 -5.408 C13 BCG 13 BCG C14 C14 C 0 1 Y N N 28.487 -3.135 23.589 1.317 -0.015 -4.105 C14 BCG 14 BCG C15 C15 C 0 1 N N N 24.295 -3.002 26.772 -1.942 -0.227 1.419 C15 BCG 15 BCG C16 C16 C 0 1 N N N 20.109 -2.054 26.875 0.124 0.548 4.917 C16 BCG 16 BCG N1 N1 N 0 1 N N N 21.364 -2.356 26.057 -0.169 0.544 3.478 N1 BCG 17 BCG O1 O1 O 0 1 N N N 24.923 -3.025 23.964 -0.019 -0.118 -0.645 O1 BCG 18 BCG O2 O2 O 0 1 N N N 26.419 -1.384 24.289 2.058 -0.185 -1.421 O2 BCG 19 BCG O3 O3 O 0 1 N N N 25.348 -3.099 27.321 -2.517 -0.142 0.209 O3 BCG 20 BCG O4 O4 O 0 1 N N N 23.370 -3.904 26.858 -2.489 0.253 2.382 O4 BCG 21 BCG H1 H1 H 0 1 N N N 22.546 -0.905 27.310 -0.819 -1.496 3.682 H1 BCG 22 BCG H2 H2 H 0 1 N N N 24.616 -1.095 25.962 -0.704 -1.959 1.251 H2 BCG 23 BCG H3 H3 H 0 1 N N N 23.615 -1.354 23.781 1.374 -0.775 0.759 H3 BCG 24 BCG H41 1H4 H 0 1 N N N 22.441 -3.255 22.889 -0.221 1.829 1.180 H41 BCG 25 BCG H42 2H4 H 0 1 N N N 22.570 -4.137 24.320 1.509 1.704 0.774 H42 BCG 26 BCG H5 H5 H 0 1 N N N 20.286 -2.829 24.172 1.346 2.049 3.228 H5 BCG 27 BCG H61 1H6 H 0 1 N N N 21.517 -0.625 23.142 2.727 -0.049 2.060 H61 BCG 28 BCG H62 2H6 H 0 1 N N N 20.126 -0.435 24.033 2.712 0.186 3.834 H62 BCG 29 BCG H71 1H7 H 0 1 N N N 21.467 0.739 25.871 1.534 -2.002 2.310 H71 BCG 30 BCG H72 2H7 H 0 1 N N N 22.847 0.560 24.980 1.519 -1.766 4.084 H72 BCG 31 BCG H10 H10 H 0 1 N N N 25.714 -5.159 23.218 -1.684 0.052 -2.522 H10 BCG 32 BCG H11 H11 H 0 1 N N N 27.607 -6.794 22.428 -2.457 0.212 -4.851 H11 BCG 33 BCG H12 H12 H 0 1 N N N 29.955 -6.014 22.381 -0.829 0.219 -6.695 H12 BCG 34 BCG H13 H13 H 0 1 N N N 30.569 -3.652 23.186 1.580 0.075 -6.222 H13 BCG 35 BCG H14 H14 H 0 1 N N N 28.731 -2.112 23.923 2.375 -0.078 -3.899 H14 BCG 36 BCG H161 1H16 H 0 0 N N N 19.331 -2.839 26.729 1.050 0.002 5.101 H161 BCG 37 BCG H162 2H16 H 0 0 N N N 20.349 -1.910 27.954 0.235 1.576 5.262 H162 BCG 38 BCG H163 3H16 H 0 0 N N N 19.709 -1.037 26.651 -0.692 0.070 5.457 H163 BCG 39 BCG HO3 HO3 H 0 1 N N N 25.640 -3.799 27.892 -3.369 0.303 0.108 HO3 BCG 40 # # 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 BCG C1 C2 SING N N 1 BCG C1 C7 SING N N 2 BCG C1 N1 SING N N 3 BCG C1 H1 SING N N 4 BCG C2 C3 SING N N 5 BCG C2 C15 SING N N 6 BCG C2 H2 SING N N 7 BCG C3 C4 SING N N 8 BCG C3 O1 SING N N 9 BCG C3 H3 SING N N 10 BCG C4 C5 SING N N 11 BCG C4 H41 SING N N 12 BCG C4 H42 SING N N 13 BCG C5 C6 SING N N 14 BCG C5 N1 SING N N 15 BCG C5 H5 SING N N 16 BCG C6 C7 SING N N 17 BCG C6 H61 SING N N 18 BCG C6 H62 SING N N 19 BCG C7 H71 SING N N 20 BCG C7 H72 SING N N 21 BCG C8 C9 SING N N 22 BCG C8 O1 SING N N 23 BCG C8 O2 DOUB N N 24 BCG C9 C10 SING Y N 25 BCG C9 C14 DOUB Y N 26 BCG C10 C11 DOUB Y N 27 BCG C10 H10 SING N N 28 BCG C11 C12 SING Y N 29 BCG C11 H11 SING N N 30 BCG C12 C13 DOUB Y N 31 BCG C12 H12 SING N N 32 BCG C13 C14 SING Y N 33 BCG C13 H13 SING N N 34 BCG C14 H14 SING N N 35 BCG C15 O3 SING N N 36 BCG C15 O4 DOUB N N 37 BCG C16 N1 SING N N 38 BCG C16 H161 SING N N 39 BCG C16 H162 SING N N 40 BCG C16 H163 SING N N 41 BCG O3 HO3 SING N N 42 # # 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 BCG SMILES ACDLabs 10.04 "O=C(O)C3C1N(C)C(CC1)CC3OC(=O)c2ccccc2" BCG SMILES_CANONICAL CACTVS 3.341 "CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3ccccc3)C(O)=O" BCG SMILES CACTVS 3.341 "CN1[CH]2CC[CH]1[CH]([CH](C2)OC(=O)c3ccccc3)C(O)=O" BCG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[N@]1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3ccccc3)C(=O)O" BCG SMILES "OpenEye OEToolkits" 1.5.0 "CN1C2CCC1C(C(C2)OC(=O)c3ccccc3)C(=O)O" BCG InChI InChI 1.03 "InChI=1S/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11-,12+,13-,14+/m0/s1" BCG InChIKey InChI 1.03 GVGYEFKIHJTNQZ-RFQIPJPRSA-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 BCG "SYSTEMATIC NAME" ACDLabs 10.04 "(1R,2R,3S,5S)-8-methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic acid" BCG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(1R,2R,3S,5S,8S)-8-methyl-3-(phenylcarbonyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylic acid" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site BCG "Create component" 2003-09-15 RCSB BCG "Modify descriptor" 2011-06-04 RCSB BCG "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id BCG _pdbx_chem_comp_synonyms.name BENZOYLECGONINE _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##