data_XOP
# 
_chem_comp.id                                    XOP 
_chem_comp.name                                  "8-METHYL-8-AZABICYCLO[3.2.1]OCTAN-3-YL PHENYLPHOSPHONATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H20 N O3 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2010-11-25 
_chem_comp.pdbx_modified_date                    2024-09-27 
_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                        281.287 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     XOP 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2XZP 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
_chem_comp.pdbx_pcm                              Y 
# 
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.pdbx_backbone_atom_flag 
_chem_comp_atom.pdbx_n_terminal_atom_flag 
_chem_comp_atom.pdbx_c_terminal_atom_flag 
_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 
XOP C1   C1   C 0 1 Y N N N N N -12.906 1.527  1.292  -2.358 -0.055 0.016  C1   XOP 1  
XOP C2   C2   C 0 1 Y N N N N N -13.811 2.162  0.444  -1.975 -1.381 0.079  C2   XOP 2  
XOP C3   C3   C 0 1 Y N N N N N -13.625 3.495  0.022  -2.931 -2.379 0.055  C3   XOP 3  
XOP C4   C4   C 0 1 Y N N N N N -12.574 4.243  0.453  -4.271 -2.050 -0.031 C4   XOP 4  
XOP C5   C5   C 0 1 Y N N N N N -11.667 3.628  1.263  -4.654 -0.724 -0.093 C5   XOP 5  
XOP C6   C6   C 0 1 Y N N N N N -11.857 2.317  1.660  -3.698 0.274  -0.070 C6   XOP 6  
XOP C7   C7   C 0 1 N N N N N N -14.472 -2.107 1.166  1.565  1.357  0.148  C7   XOP 7  
XOP C8   C8   C 0 1 N N N N N N -16.011 -2.016 1.093  2.345  0.885  1.379  C8   XOP 8  
XOP C9   C9   C 0 1 N N R N N N -16.567 -2.113 -0.318 2.820  -0.558 1.143  C9   XOP 9  
XOP N    N    N 0 1 N N N N N N -16.061 -3.415 -0.879 3.771  -0.527 -0.000 N    XOP 10 
XOP O1   O1   O 0 1 N N N N N N -11.755 -0.704 2.202  -1.260 2.052  1.292  O1   XOP 11 
XOP O2   O2   O 0 1 N N N N N N -13.785 -0.853 0.760  0.364  0.593  0.024  O2   XOP 12 
XOP O3   O3   O 0 1 N Y N N N N ?       ?      ?      -1.287 2.212  -1.227 O3   XOP 13 
XOP P    P    P 0 1 N N N N N N -13.030 -0.096 1.869  -1.103 1.255  0.054  P    XOP 14 
XOP C10  C10  C 0 1 N N N N N N -15.950 -1.125 -1.327 1.613  -1.376 0.630  C10  XOP 15 
XOP C11  C11  C 0 1 N N N N N N -14.623 -1.781 -1.866 1.643  -1.206 -0.903 C11  XOP 16 
XOP C12  C12  C 0 1 N N S N N N -14.631 -3.187 -1.237 2.890  -0.292 -1.176 C12  XOP 17 
XOP C13  C13  C 0 1 N N N N N N -13.864 -3.099 0.112  2.420  1.169  -1.109 C13  XOP 18 
XOP C14  C14  C 0 1 N N N N N N -16.763 -3.947 -2.126 4.486  -1.804 -0.125 C14  XOP 19 
XOP H2   H2   H 0 1 N N N N N N -14.679 1.619  0.100  -0.928 -1.638 0.146  H2   XOP 20 
XOP H3   H3   H 0 1 N N N N N N -14.336 3.934  -0.662 -2.631 -3.415 0.103  H3   XOP 21 
XOP H4   H4   H 0 1 N N N N N N -12.463 5.278  0.166  -5.018 -2.830 -0.050 H4   XOP 22 
XOP H5   H5   H 0 1 N N N N N N -10.794 4.168  1.597  -5.701 -0.467 -0.160 H5   XOP 23 
XOP H6   H6   H 0 1 N N N N N N -11.115 1.884  2.314  -3.998 1.311  -0.114 H6   XOP 24 
XOP H7   H7   H 0 1 N N N N N N -14.316 -2.394 2.216  1.314  2.412  0.261  H7   XOP 25 
XOP H8   H8   H 0 1 N N N N N N -16.429 -2.846 1.681  3.207  1.533  1.536  H8   XOP 26 
XOP H8A  H8A  H 0 1 N N N N N N -16.294 -1.027 1.483  1.698  0.919  2.256  H8A  XOP 27 
XOP H9   H9   H 0 1 N N N N N N -17.651 -1.956 -0.221 3.264  -0.995 2.037  H9   XOP 28 
XOP HO3  HO3  H 0 1 N N N N N N ?       ?      ?      -1.198 1.756  -2.075 HO3  XOP 29 
XOP H10  H10  H 0 1 N N N N N N -16.649 -0.942 -2.157 1.725  -2.426 0.898  H10  XOP 30 
XOP H10A H10A H 0 0 N N N N N N -15.740 -0.158 -0.847 0.684  -0.978 1.039  H10A XOP 31 
XOP H11  H11  H 0 1 N N N N N N -14.617 -1.832 -2.965 1.770  -2.173 -1.389 H11  XOP 32 
XOP H11A H11A H 0 0 N N N N N N -13.726 -1.203 -1.601 0.729  -0.724 -1.249 H11A XOP 33 
XOP H12  H12  H 0 1 N N N N N N -14.198 -3.955 -1.895 3.379  -0.533 -2.120 H12  XOP 34 
XOP H13  H13  H 0 1 N N N N N N -12.840 -2.762 -0.109 1.820  1.401  -1.989 H13  XOP 35 
XOP H13A H13A H 0 0 N N N N N N -13.920 -4.100 0.564  3.286  1.830  -1.071 H13A XOP 36 
XOP H14  H14  H 0 1 N N N N N N -17.835 -4.075 -1.917 3.769  -2.608 -0.288 H14  XOP 37 
XOP H14A H14A H 0 0 N N N N N N -16.633 -3.233 -2.952 5.175  -1.754 -0.968 H14A XOP 38 
XOP H14B H14B H 0 0 N N N N N N -16.326 -4.917 -2.407 5.046  -1.997 0.790  H14B XOP 39 
# 
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 
XOP C2  C1   DOUB Y N 1  
XOP C1  C6   SING Y N 2  
XOP C1  P    SING N N 3  
XOP C3  C2   SING Y N 4  
XOP C2  H2   SING N N 5  
XOP C3  C4   DOUB Y N 6  
XOP C3  H3   SING N N 7  
XOP C4  C5   SING Y N 8  
XOP C4  H4   SING N N 9  
XOP C5  C6   DOUB Y N 10 
XOP C5  H5   SING N N 11 
XOP C6  H6   SING N N 12 
XOP C13 C7   SING N N 13 
XOP O2  C7   SING N N 14 
XOP C8  C7   SING N N 15 
XOP C7  H7   SING N N 16 
XOP C9  C8   SING N N 17 
XOP C8  H8   SING N N 18 
XOP C8  H8A  SING N N 19 
XOP C10 C9   SING N N 20 
XOP N   C9   SING N N 21 
XOP C9  H9   SING N N 22 
XOP C14 N    SING N N 23 
XOP C12 N    SING N N 24 
XOP P   O1   DOUB N N 25 
XOP O3  HO3  SING N N 26 
XOP O2  P    SING N N 27 
XOP O3  P    SING N N 28 
XOP C11 C10  SING N N 29 
XOP C10 H10  SING N N 30 
XOP C10 H10A SING N N 31 
XOP C11 C12  SING N N 32 
XOP C11 H11  SING N N 33 
XOP C11 H11A SING N N 34 
XOP C12 C13  SING N N 35 
XOP C12 H12  SING N N 36 
XOP C13 H13  SING N N 37 
XOP C13 H13A SING N N 38 
XOP C14 H14  SING N N 39 
XOP C14 H14A SING N N 40 
XOP C14 H14B SING N N 41 
# 
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 
XOP SMILES           ACDLabs              12.01 "OP(OC2CC1N(C)C(CC1)C2)c3ccccc3"                                                                                              
XOP SMILES_CANONICAL CACTVS               3.352 "CN1[C@@H]2CC[C@H]1CC(C2)O[P](O)(=O)c3ccccc3"                                                                                 
XOP SMILES           CACTVS               3.352 "CN1[CH]2CC[CH]1CC(C2)O[P](O)(=O)c3ccccc3"                                                                                    
XOP SMILES_CANONICAL "OpenEye OEToolkits" 1.6.1 "CN1[C@@H]2CC[C@H]1CC(C2)O[P@@](=O)(c3ccccc3)O"                                                                               
XOP SMILES           "OpenEye OEToolkits" 1.6.1 "CN1C2CCC1CC(C2)OP(=O)(c3ccccc3)O"                                                                                            
XOP InChI            InChI                1.03  "InChI=1S/C14H20NO3P/c1-15-11-7-8-12(15)10-13(9-11)18-19(16,17)14-5-3-2-4-6-14/h2-6,11-13H,7-10H2,1H3,(H,16,17)/t11-,12+,13+" 
XOP InChIKey         InChI                1.03  DUXLOXDDMDLSLH-ITGUQSILSA-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 
XOP "SYSTEMATIC NAME" ACDLabs              12.01 "(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl hydrogen (R)-phenylphosphonite" 
XOP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]oxy-phenyl-phosphinic 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 
XOP "Create component"     2010-11-25 EBI  
XOP "Modify aromatic_flag" 2011-06-04 RCSB 
XOP "Modify descriptor"    2011-06-04 RCSB 
XOP "Modify PCM"           2024-09-27 PDBE 
# 
_pdbx_chem_comp_pcm.pcm_id                             1 
_pdbx_chem_comp_pcm.comp_id                            XOP 
_pdbx_chem_comp_pcm.modified_residue_id                TYR 
_pdbx_chem_comp_pcm.type                               None 
_pdbx_chem_comp_pcm.category                           "Covalent chemical modification" 
_pdbx_chem_comp_pcm.position                           "Amino-acid side chain" 
_pdbx_chem_comp_pcm.polypeptide_position               "Any position" 
_pdbx_chem_comp_pcm.comp_id_linking_atom               P 
_pdbx_chem_comp_pcm.modified_residue_id_linking_atom   OH 
_pdbx_chem_comp_pcm.uniprot_specific_ptm_accession     ? 
_pdbx_chem_comp_pcm.uniprot_generic_ptm_accession      ? 
# 
