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                    2008-10-14 
_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 InChI            InChI                1.02b InChI=1/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/f/h18H 
BCG InChIKey         InChI                1.02b GVGYEFKIHJTNQZ-GDMJBRMWDH                                                                                                                       
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                                                                                                           
# 
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" 
# 
