data_OBE
# 
_chem_comp.id                                    OBE 
_chem_comp.name                                  "3-(3-HYDROXY-BENZOYLOXY)-8-METHYL-8-AZA-BICYCLO[3.2.1]OCTANE-2-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H19 N O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         META-OXYBENZOYLECGONINE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-11-20 
_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                        305.326 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     OBE 
_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        1RIV 
_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 
OBE C1   C1   C 0  1 N N R 22.868 -1.275 26.887 3.387  -0.055 -0.875 C1   OBE 1  
OBE C2   C2   C 0  1 N N R 24.275 -1.939 26.472 1.946  -0.588 -0.922 C2   OBE 2  
OBE C3   C3   C 0  1 N N S 24.138 -2.362 24.940 1.024  0.415  -0.222 C3   OBE 3  
OBE C4   C4   C 0  1 N N N 22.871 -3.166 24.663 1.574  0.711  1.220  C4   OBE 4  
OBE C5   C5   C 0  1 N N S 21.664 -2.301 25.232 3.040  1.156  1.093  C5   OBE 5  
OBE C6   C6   C 0  1 N N N 21.662 -0.798 24.780 3.129  2.227  -0.017 C6   OBE 6  
OBE C7   C7   C 0  1 N N N 22.479 -0.084 25.940 3.358  1.430  -1.318 C7   OBE 7  
OBE C8   C8   C 0  1 N N N 26.611 -2.572 24.563 -1.385 0.679  -0.141 C8   OBE 8  
OBE C9   C9   C 0  1 Y N N 27.638 -3.593 24.110 -2.747 0.115  -0.051 C9   OBE 9  
OBE C10  C10  C 0  1 Y N N 29.020 -3.290 24.139 -3.857 0.960  -0.052 C10  OBE 10 
OBE C11  C11  C 0  1 Y N N 29.975 -4.271 23.717 -5.132 0.423  0.025  C11  OBE 11 
OBE C12  C12  C 0  1 Y N N 29.538 -5.557 23.265 -5.302 -0.951 0.117  C12  OBE 12 
OBE C13  C13  C 0  1 Y N N 28.177 -5.873 23.227 -4.203 -1.790 0.124  C13  OBE 13 
OBE C14  C14  C 0  1 Y N N 27.196 -4.899 23.653 -2.929 -1.267 0.041  C14  OBE 14 
OBE C15  C15  C 0  1 N N N 24.725 -3.136 27.406 1.876  -1.918 -0.217 C15  OBE 15 
OBE C16  C16  C 0  1 N N N 20.533 -2.037 27.441 5.250  0.244  0.656  C16  OBE 16 
OBE N1   N1   N 1  1 N N N 21.820 -2.333 26.716 3.805  0.002  0.550  N1   OBE 17 
OBE O1   O1   O 0  1 N N N 25.350 -3.062 24.488 -0.315 -0.139 -0.134 O1   OBE 18 
OBE O2   O2   O 0  1 N N N 26.881 -1.489 24.963 -1.230 1.881  -0.221 O2   OBE 19 
OBE O3   O3   O -1 1 N N N 25.782 -3.225 27.941 0.847  -2.259 0.342  O3   OBE 20 
OBE O4   O4   O 0  1 N N N 23.810 -4.086 27.519 2.849  -2.653 -0.205 O4   OBE 21 
OBE O5   O5   O 0  1 N N N 31.267 -3.891 23.783 -6.216 1.243  0.018  O5   OBE 22 
OBE H1   H1   H 0  1 N N N 22.946 -0.890 27.930 4.065  -0.653 -1.484 H1   OBE 23 
OBE H2   H2   H 0  1 N N N 25.097 -1.198 26.609 1.634  -0.708 -1.959 H2   OBE 24 
OBE H3   H3   H 0  1 N N N 24.037 -1.426 24.342 0.995  1.342  -0.795 H3   OBE 25 
OBE H41  1H4  H 0  1 N N N 22.905 -4.203 25.072 1.511  -0.192 1.827  H41  OBE 26 
OBE H42  2H4  H 0  1 N N N 22.749 -3.446 23.591 0.985  1.504  1.680  H42  OBE 27 
OBE H5   H5   H 0  1 N N N 20.712 -2.734 24.847 3.445  1.510  2.041  H5   OBE 28 
OBE H61  1H6  H 0  1 N N N 20.651 -0.369 24.588 2.198  2.791  -0.076 H61  OBE 29 
OBE H62  2H6  H 0  1 N N N 22.055 -0.618 23.752 3.968  2.898  0.169  H62  OBE 30 
OBE H71  1H7  H 0  1 N N N 23.340 0.532  25.590 2.539  1.601  -2.017 H71  OBE 31 
OBE H72  2H7  H 0  1 N N N 21.938 0.752  26.443 4.309  1.709  -1.772 H72  OBE 32 
OBE H10  H10  H 0  1 N N N 29.350 -2.297 24.488 -3.723 2.030  -0.124 H10  OBE 33 
OBE H12  H12  H 0  1 N N N 30.265 -6.320 22.939 -6.297 -1.367 0.182  H12  OBE 34 
OBE H13  H13  H 0  1 N N N 27.882 -6.873 22.867 -4.342 -2.859 0.196  H13  OBE 35 
OBE H14  H14  H 0  1 N N N 26.122 -5.150 23.630 -2.073 -1.925 0.046  H14  OBE 36 
OBE H161 1H16 H 0  0 N N N 20.135 -1.039 27.144 5.530  0.322  1.707  H161 OBE 37 
OBE H162 2H16 H 0  0 N N N 19.754 -2.824 27.314 5.792  -0.582 0.196  H162 OBE 38 
OBE H163 3H16 H 0  0 N N N 20.726 -1.847 28.523 5.502  1.173  0.144  H163 OBE 39 
OBE HN1  HN1  H 0  1 N N N 22.075 -3.240 27.108 3.553  -0.849 1.029  HN1  OBE 40 
OBE HO5  HO5  H 0  1 N N N 31.900 -4.541 23.503 -6.402 1.469  0.939  HO5  OBE 41 
# 
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 
OBE C1  C2   SING N N 1  
OBE C1  C7   SING N N 2  
OBE C1  N1   SING N N 3  
OBE C1  H1   SING N N 4  
OBE C2  C3   SING N N 5  
OBE C2  C15  SING N N 6  
OBE C2  H2   SING N N 7  
OBE C3  C4   SING N N 8  
OBE C3  O1   SING N N 9  
OBE C3  H3   SING N N 10 
OBE C4  C5   SING N N 11 
OBE C4  H41  SING N N 12 
OBE C4  H42  SING N N 13 
OBE C5  C6   SING N N 14 
OBE C5  N1   SING N N 15 
OBE C5  H5   SING N N 16 
OBE C6  C7   SING N N 17 
OBE C6  H61  SING N N 18 
OBE C6  H62  SING N N 19 
OBE C7  H71  SING N N 20 
OBE C7  H72  SING N N 21 
OBE C8  C9   SING N N 22 
OBE C8  O1   SING N N 23 
OBE C8  O2   DOUB N N 24 
OBE C9  C10  DOUB Y N 25 
OBE C9  C14  SING Y N 26 
OBE C10 C11  SING Y N 27 
OBE C10 H10  SING N N 28 
OBE C11 C12  DOUB Y N 29 
OBE C11 O5   SING N N 30 
OBE C12 C13  SING Y N 31 
OBE C12 H12  SING N N 32 
OBE C13 C14  DOUB Y N 33 
OBE C13 H13  SING N N 34 
OBE C14 H14  SING N N 35 
OBE C15 O3   SING N N 36 
OBE C15 O4   DOUB N N 37 
OBE C16 N1   SING N N 38 
OBE C16 H161 SING N N 39 
OBE C16 H162 SING N N 40 
OBE C16 H163 SING N N 41 
OBE N1  HN1  SING N N 42 
OBE O5  HO5  SING N N 43 
# 
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 
OBE SMILES           ACDLabs              10.04 [O-]C(=O)C3C1[NH+](C)C(CC1)CC3OC(=O)c2cccc(O)c2                                                                                                             
OBE InChI            InChI                1.02b InChI=1/C16H19NO5/c1-17-10-5-6-12(17)14(15(19)20)13(8-10)22-16(21)9-3-2-4-11(18)7-9/h2-4,7,10,12-14,18H,5-6,8H2,1H3,(H,19,20)/t10-,12+,13-,14+/m0/s1/f/h17H 
OBE InChIKey         InChI                1.02b XCJJCRPRQYXLRE-ROWRQELLDV                                                                                                                                   
OBE SMILES_CANONICAL CACTVS               3.341 C[NH+]1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3cccc(O)c3)C([O-])=O                                                                                            
OBE SMILES           CACTVS               3.341 C[NH+]1[CH]2CC[CH]1[CH]([CH](C2)OC(=O)c3cccc(O)c3)C([O-])=O                                                                                                 
OBE SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[N@H+]1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3cccc(c3)O)C(=O)[O-]                                                                                           
OBE SMILES           "OpenEye OEToolkits" 1.5.0 C[NH+]1C2CCC1C(C(C2)OC(=O)c3cccc(c3)O)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 
OBE "SYSTEMATIC NAME" ACDLabs              10.04 (1R,2R,3S,5S,8S)-3-{[(3-hydroxyphenyl)carbonyl]oxy}-8-methyl-8-azoniabicyclo[3.2.1]octane-2-carboxylate 
OBE "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (1R,2R,3S,5S,8S)-3-(3-hydroxyphenyl)carbonyloxy-8-methyl-8-azoniabicyclo[3.2.1]octane-2-carboxylate     
# 
