data_CCA
# 
_chem_comp.id                                    CCA 
_chem_comp.name                                  "2-BENZOYLOXY-8-METHYL-8-AZA-BICYCLO[3.2.1]OCTANE-3-CARBOXYLIC ACID METHYL ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C17 H22 N O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         COCAINE 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     2001-04-12 
_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                        304.361 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CCA 
_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        1EHQ 
_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 
CCA C1  C1  C 0 1 N N N 43.190 43.339 25.569 -2.019 3.971  -0.025 C1  CCA 1  
CCA O5  O5  O 0 1 N N N 43.925 44.506 25.226 -2.083 2.700  0.674  O5  CCA 2  
CCA C6  C6  C 0 1 N N N 44.880 44.907 26.187 -1.431 1.632  0.187  C6  CCA 3  
CCA O7  O7  O 0 1 N N N 45.033 44.486 27.334 -0.790 1.729  -0.833 O7  CCA 4  
CCA C8  C8  C 0 1 N N S 45.768 46.015 25.644 -1.498 0.313  0.912  C8  CCA 5  
CCA C10 C10 C 0 1 N N S 45.965 47.169 26.671 -2.939 -0.221 0.876  C10 CCA 6  
CCA N12 N12 N 1 1 N N N 46.667 46.679 27.876 -3.343 -0.296 -0.556 N12 CCA 7  
CCA C14 C14 C 0 1 N N N 46.594 47.664 28.981 -4.785 -0.554 -0.673 C14 CCA 8  
CCA C18 C18 C 0 1 N N N 46.873 48.258 26.070 -2.899 -1.724 1.333  C18 CCA 9  
CCA C21 C21 C 0 1 N N N 48.284 47.852 26.541 -2.657 -2.522 0.035  C21 CCA 10 
CCA C24 C24 C 0 1 N N R 48.031 46.558 27.323 -2.566 -1.452 -1.077 C24 CCA 11 
CCA C26 C26 C 0 1 N N N 48.104 45.330 26.386 -1.099 -1.005 -1.180 C26 CCA 12 
CCA C29 C29 C 0 1 N N R 47.122 45.423 25.199 -0.575 -0.697 0.225  C29 CCA 13 
CCA O1  O1  O 0 1 N N N 47.035 44.128 24.639 0.763  -0.141 0.129  O1  CCA 14 
CCA C2  C2  C 0 1 N N N 46.363 44.044 23.394 1.835  -0.957 0.147  C2  CCA 15 
CCA O3  O3  O 0 1 N N N 46.257 45.013 22.638 1.682  -2.158 0.243  O3  CCA 16 
CCA C4  C4  C 0 1 Y N N 45.791 42.778 23.092 3.196  -0.391 0.049  C4  CCA 17 
CCA C5  C5  C 0 1 Y N N 45.058 42.590 21.902 4.309  -1.234 0.067  C5  CCA 18 
CCA C7  C7  C 0 1 Y N N 44.473 41.347 21.607 5.577  -0.699 -0.025 C7  CCA 19 
CCA C9  C9  C 0 1 Y N N 44.619 40.270 22.494 5.747  0.670  -0.134 C9  CCA 20 
CCA C11 C11 C 0 1 Y N N 45.338 40.447 23.686 4.649  1.511  -0.152 C11 CCA 21 
CCA C13 C13 C 0 1 Y N N 45.916 41.689 23.986 3.375  0.989  -0.067 C13 CCA 22 
CCA H2  H2  H 0 1 N N N 42.436 43.022 24.810 -0.981 4.301  -0.085 H2  CCA 23 
CCA H3  H3  H 0 1 N N N 43.885 42.497 25.797 -2.421 3.853  -1.031 H3  CCA 24 
CCA H4  H4  H 0 1 N N N 42.706 43.465 26.565 -2.605 4.713  0.516  H4  CCA 25 
CCA H9  H9  H 0 1 N N N 45.258 46.465 24.760 -1.185 0.449  1.947  H9  CCA 26 
CCA H11 H11 H 0 1 N N N 44.953 47.563 26.924 -3.625 0.374  1.478  H11 CCA 27 
CCA H13 H13 H 0 1 N N N 46.293 45.825 28.290 -3.094 0.554  -1.040 H13 CCA 28 
CCA H15 H15 H 0 1 N N N 47.123 47.294 29.890 -5.339 0.251  -0.192 H15 CCA 29 
CCA H16 H16 H 0 1 N N N 46.974 48.663 28.664 -5.060 -0.605 -1.727 H16 CCA 30 
CCA H17 H17 H 0 1 N N N 45.539 47.946 29.208 -5.025 -1.501 -0.189 H17 CCA 31 
CCA H19 H19 H 0 1 N N N 46.773 48.385 24.966 -3.851 -2.006 1.781  H19 CCA 32 
CCA H20 H20 H 0 1 N N N 46.580 49.300 26.334 -2.084 -1.890 2.038  H20 CCA 33 
CCA H22 H22 H 0 1 N N N 49.038 47.761 25.724 -3.492 -3.197 -0.156 H22 CCA 34 
CCA H23 H23 H 0 1 N N N 48.828 48.640 27.111 -1.724 -3.081 0.101  H23 CCA 35 
CCA H25 H25 H 0 1 N N N 48.796 46.416 28.121 -2.953 -1.813 -2.030 H25 CCA 36 
CCA H27 H27 H 0 1 N N N 49.146 45.161 26.029 -1.033 -0.110 -1.799 H27 CCA 37 
CCA H28 H28 H 0 1 N N N 47.952 44.383 26.955 -0.505 -1.803 -1.625 H28 CCA 38 
CCA H30 H30 H 0 1 N N N 47.481 46.127 24.413 -0.544 -1.616 0.810  H30 CCA 39 
CCA H6  H6  H 0 1 N N N 44.940 43.426 21.192 4.177  -2.303 0.153  H6  CCA 40 
CCA H8  H8  H 0 1 N N N 43.896 41.216 20.675 6.439  -1.350 -0.011 H8  CCA 41 
CCA H10 H10 H 0 1 N N N 44.171 39.290 22.255 6.743  1.084  -0.206 H10 CCA 42 
CCA H12 H12 H 0 1 N N N 45.449 39.605 24.390 4.789  2.579  -0.237 H12 CCA 43 
CCA H14 H14 H 0 1 N N N 46.472 41.810 24.930 2.518  1.646  -0.081 H14 CCA 44 
# 
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 
CCA C1  O5  SING N N 1  
CCA C1  H2  SING N N 2  
CCA C1  H3  SING N N 3  
CCA C1  H4  SING N N 4  
CCA O5  C6  SING N N 5  
CCA C6  O7  DOUB N N 6  
CCA C6  C8  SING N N 7  
CCA C8  C10 SING N N 8  
CCA C8  C29 SING N N 9  
CCA C8  H9  SING N N 10 
CCA C10 N12 SING N N 11 
CCA C10 C18 SING N N 12 
CCA C10 H11 SING N N 13 
CCA N12 C14 SING N N 14 
CCA N12 C24 SING N N 15 
CCA N12 H13 SING N N 16 
CCA C14 H15 SING N N 17 
CCA C14 H16 SING N N 18 
CCA C14 H17 SING N N 19 
CCA C18 C21 SING N N 20 
CCA C18 H19 SING N N 21 
CCA C18 H20 SING N N 22 
CCA C21 C24 SING N N 23 
CCA C21 H22 SING N N 24 
CCA C21 H23 SING N N 25 
CCA C24 C26 SING N N 26 
CCA C24 H25 SING N N 27 
CCA C26 C29 SING N N 28 
CCA C26 H27 SING N N 29 
CCA C26 H28 SING N N 30 
CCA C29 O1  SING N N 31 
CCA C29 H30 SING N N 32 
CCA O1  C2  SING N N 33 
CCA C2  O3  DOUB N N 34 
CCA C2  C4  SING N N 35 
CCA C4  C5  DOUB Y N 36 
CCA C4  C13 SING Y N 37 
CCA C5  C7  SING Y N 38 
CCA C5  H6  SING N N 39 
CCA C7  C9  DOUB Y N 40 
CCA C7  H8  SING N N 41 
CCA C9  C11 SING Y N 42 
CCA C9  H10 SING N N 43 
CCA C11 C13 DOUB Y N 44 
CCA C11 H12 SING N N 45 
CCA C13 H14 SING N N 46 
# 
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 
CCA SMILES           ACDLabs              10.04 O=C(OC)C3C1[NH+](C)C(CC1)CC3OC(=O)c2ccccc2                                                                                                                   
CCA InChI            InChI                1.02b InChI=1/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/p+1/t12-,13+,14-,15+/m1/s1/fC17H22NO4/h18H/q+1 
CCA InChIKey         InChI                1.02b ZPUCINDJVBIVPJ-APABHBPDDS                                                                                                                                    
CCA SMILES_CANONICAL CACTVS               3.341 COC(=O)[C@@H]1[C@@H](C[C@H]2CC[C@@H]1[NH+]2C)OC(=O)c3ccccc3                                                                                                  
CCA SMILES           CACTVS               3.341 COC(=O)[CH]1[CH](C[CH]2CC[CH]1[NH+]2C)OC(=O)c3ccccc3                                                                                                         
CCA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[N@@H+]1[C@@H]2CC[C@H]1[C@@H]([C@@H](C2)OC(=O)c3ccccc3)C(=O)OC                                                                                              
CCA SMILES           "OpenEye OEToolkits" 1.5.0 C[NH+]1C2CCC1C(C(C2)OC(=O)c3ccccc3)C(=O)OC                                                                                                                   
# 
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 
CCA "SYSTEMATIC NAME" ACDLabs              10.04 (1S,2S,3R,5R,8R)-2-(methoxycarbonyl)-8-methyl-3-[(phenylcarbonyl)oxy]-8-azoniabicyclo[3.2.1]octane  
CCA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "methyl (1S,2S,3R,5R,8R)-8-methyl-3-(phenylcarbonyloxy)-8-azoniabicyclo[3.2.1]octane-2-carboxylate" 
# 
