data_XDA
# 
_chem_comp.id                                    XDA 
_chem_comp.name                                  "4-{[2-(phosphonooxy)ethyl]carbamoyl}benzyl [(1R,6S)-6-(dimethylcarbamoyl)cyclohex-2-en-1-yl]carbamate" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H28 N3 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2014-01-07 
_chem_comp.pdbx_modified_date                    2014-05-30 
_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                        469.425 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     XDA 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        4O5T 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
XDA O8   O8   O 0 1 N N N -14.805 0.516  -23.068 4.596  -1.942 0.391  O8   XDA 1  
XDA C7   C7   C 0 1 N N N -14.162 1.094  -22.204 5.728  -1.983 -0.041 C7   XDA 2  
XDA N9   N9   N 0 1 N N N -13.334 2.100  -22.509 6.200  -3.122 -0.587 N9   XDA 3  
XDA C11  C11  C 0 1 N N N -13.085 2.509  -23.885 7.608  -3.216 -0.981 C11  XDA 4  
XDA C10  C10  C 0 1 N N N -12.589 2.929  -21.570 5.306  -4.265 -0.785 C10  XDA 5  
XDA C4   C4   C 0 1 N N S -14.275 0.641  -20.771 6.606  -0.760 0.027  C4   XDA 6  
XDA C5   C5   C 0 1 N N N -15.733 0.313  -20.428 6.881  -0.243 -1.391 C5   XDA 7  
XDA C6   C6   C 0 1 N N N -15.962 -1.136 -20.006 7.913  0.884  -1.303 C6   XDA 8  
XDA C1   C1   C 0 1 N N N -15.160 -2.082 -20.861 7.504  1.878  -0.257 C1   XDA 9  
XDA C2   C2   C 0 1 N N N -13.896 -1.787 -21.121 6.629  1.641  0.667  C2   XDA 10 
XDA C3   C3   C 0 1 N N R -13.300 -0.516 -20.571 5.893  0.342  0.814  C3   XDA 11 
XDA N12  N12  N 0 1 N N N -12.033 -0.240 -21.226 4.528  0.496  0.304  N12  XDA 12 
XDA C13  C13  C 0 1 N N N -11.125 0.617  -20.764 3.565  1.000  1.100  C13  XDA 13 
XDA O14  O14  O 0 1 N N N -11.262 1.237  -19.722 3.828  1.326  2.241  O14  XDA 14 
XDA O15  O15  O 0 1 N N N -9.937  0.841  -21.586 2.310  1.143  0.632  O15  XDA 15 
XDA C16  C16  C 0 1 N N N -9.001  1.893  -21.324 1.324  1.692  1.545  C16  XDA 16 
XDA C17  C17  C 0 1 Y N N -7.891  1.326  -20.480 -0.011 1.777  0.851  C17  XDA 17 
XDA C22  C22  C 0 1 Y N N -6.891  0.590  -21.093 -0.352 2.920  0.151  C22  XDA 18 
XDA C21  C21  C 0 1 Y N N -5.862  0.053  -20.328 -1.572 3.004  -0.487 C21  XDA 19 
XDA C18  C18  C 0 1 Y N N -7.873  1.521  -19.099 -0.888 0.708  0.912  C18  XDA 20 
XDA C19  C19  C 0 1 Y N N -6.843  0.975  -18.330 -2.111 0.779  0.278  C19  XDA 21 
XDA C20  C20  C 0 1 Y N N -5.828  0.248  -18.950 -2.464 1.932  -0.425 C20  XDA 22 
XDA C23  C23  C 0 1 N N N -4.706  -0.378 -18.174 -3.773 2.015  -1.106 C23  XDA 23 
XDA O24  O24  O 0 1 N N N -4.535  -1.567 -18.360 -4.076 3.019  -1.721 O24  XDA 24 
XDA N25  N25  N 0 1 N N N -3.906  0.268  -17.325 -4.632 0.978  -1.044 N25  XDA 25 
XDA C26  C26  C 0 1 N N N -3.947  1.686  -17.039 -5.930 1.060  -1.719 C26  XDA 26 
XDA C27  C27  C 0 1 N N N -2.523  2.209  -16.949 -6.705 -0.240 -1.494 C27  XDA 27 
XDA O28  O28  O 0 1 N N N -1.856  1.851  -18.157 -7.009 -0.379 -0.105 O28  XDA 28 
XDA P29  P29  P 0 1 N N N -0.539  2.629  -18.653 -7.820 -1.634 0.494  P29  XDA 29 
XDA O31  O31  O 0 1 N N N -0.821  4.087  -18.372 -6.952 -2.976 0.297  O31  XDA 30 
XDA O30  O30  O 0 1 N N N 0.555   2.017  -17.809 -8.094 -1.397 2.063  O30  XDA 31 
XDA O32  O32  O 0 1 N N N -0.431  2.298  -20.122 -9.111 -1.772 -0.217 O32  XDA 32 
XDA H11B H11B H 0 0 N N N -12.376 3.350  -23.896 8.210  -3.493 -0.116 H11B XDA 33 
XDA H11A H11A H 0 0 N N N -12.660 1.664  -24.447 7.718  -3.973 -1.758 H11A XDA 34 
XDA H11C H11C H 0 0 N N N -14.031 2.821  -24.351 7.944  -2.252 -1.364 H11C XDA 35 
XDA H10C H10C H 0 0 N N N -12.797 2.597  -20.542 4.845  -4.198 -1.771 H10C XDA 36 
XDA H10B H10B H 0 0 N N N -11.512 2.837  -21.774 5.877  -5.190 -0.713 H10B XDA 37 
XDA H10A H10A H 0 0 N N N -12.896 3.979  -21.685 4.530  -4.256 -0.020 H10A XDA 38 
XDA H4   H4   H 0 1 N N N -13.954 1.470  -20.123 7.547  -1.011 0.518  H4   XDA 39 
XDA H5A  H5A  H 0 1 N N N -16.050 0.968  -19.603 7.274  -1.053 -2.006 H5A  XDA 40 
XDA H5B  H5B  H 0 1 N N N -16.351 0.516  -21.315 5.958  0.138  -1.827 H5B  XDA 41 
XDA H6B  H6B  H 0 1 N N N -17.031 -1.376 -20.110 8.885  0.464  -1.043 H6B  XDA 42 
XDA H6A  H6A  H 0 1 N N N -15.659 -1.257 -18.955 7.983  1.385  -2.268 H6A  XDA 43 
XDA H1   H1   H 0 1 N N N -15.607 -2.983 -21.254 7.970  2.852  -0.275 H1   XDA 44 
XDA H2   H2   H 0 1 N N N -13.295 -2.453 -21.723 6.415  2.427  1.376  H2   XDA 45 
XDA H3   H3   H 0 1 N N N -13.132 -0.645 -19.492 5.854  0.066  1.868  H3   XDA 46 
XDA H12  H12  H 0 1 N N N -11.830 -0.724 -22.077 4.318  0.236  -0.606 H12  XDA 47 
XDA H16A H16A H 0 0 N N N -8.592  2.274  -22.272 1.239  1.046  2.419  H16A XDA 48 
XDA H16B H16B H 0 0 N N N -9.500  2.711  -20.784 1.634  2.689  1.859  H16B XDA 49 
XDA H22  H22  H 0 1 N N N -6.910  0.434  -22.161 0.339  3.749  0.104  H22  XDA 50 
XDA H21  H21  H 0 1 N N N -5.082  -0.520 -20.807 -1.838 3.898  -1.032 H21  XDA 51 
XDA H18  H18  H 0 1 N N N -8.656  2.094  -18.624 -0.614 -0.184 1.456  H18  XDA 52 
XDA H19  H19  H 0 1 N N N -6.833  1.115  -17.259 -2.795 -0.056 0.326  H19  XDA 53 
XDA H25  H25  H 0 1 N N N -3.218  -0.275 -16.844 -4.391 0.177  -0.553 H25  XDA 54 
XDA H26A H26A H 0 0 N N N -4.483  2.210  -17.844 -6.498 1.897  -1.313 H26A XDA 55 
XDA H26B H26B H 0 0 N N N -4.464  1.856  -16.083 -5.775 1.211  -2.787 H26B XDA 56 
XDA H27A H27A H 0 0 N N N -2.010  1.755  -16.088 -7.631 -0.214 -2.068 H27A XDA 57 
XDA H27B H27B H 0 0 N N N -2.532  3.303  -16.835 -6.099 -1.085 -1.819 H27B XDA 58 
XDA H5   H5   H 0 1 N N N -0.884  4.562  -19.193 -6.091 -2.956 0.737  H5   XDA 59 
XDA H6   H6   H 0 1 N N N 1.140   1.514  -18.364 -8.579 -2.116 2.490  H6   XDA 60 
# 
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 
XDA C11 N9   SING N N 1  
XDA O8  C7   DOUB N N 2  
XDA N9  C7   SING N N 3  
XDA N9  C10  SING N N 4  
XDA C7  C4   SING N N 5  
XDA O15 C16  SING N N 6  
XDA O15 C13  SING N N 7  
XDA C16 C17  SING N N 8  
XDA N12 C13  SING N N 9  
XDA N12 C3   SING N N 10 
XDA C2  C1   DOUB N N 11 
XDA C2  C3   SING N N 12 
XDA C22 C17  DOUB Y N 13 
XDA C22 C21  SING Y N 14 
XDA C1  C6   SING N N 15 
XDA C4  C3   SING N N 16 
XDA C4  C5   SING N N 17 
XDA C13 O14  DOUB N N 18 
XDA C17 C18  SING Y N 19 
XDA C5  C6   SING N N 20 
XDA C21 C20  DOUB Y N 21 
XDA O32 P29  DOUB N N 22 
XDA C18 C19  DOUB Y N 23 
XDA C20 C19  SING Y N 24 
XDA C20 C23  SING N N 25 
XDA P29 O31  SING N N 26 
XDA P29 O28  SING N N 27 
XDA P29 O30  SING N N 28 
XDA O24 C23  DOUB N N 29 
XDA C23 N25  SING N N 30 
XDA O28 C27  SING N N 31 
XDA N25 C26  SING N N 32 
XDA C26 C27  SING N N 33 
XDA C11 H11B SING N N 34 
XDA C11 H11A SING N N 35 
XDA C11 H11C SING N N 36 
XDA C10 H10C SING N N 37 
XDA C10 H10B SING N N 38 
XDA C10 H10A SING N N 39 
XDA C4  H4   SING N N 40 
XDA C5  H5A  SING N N 41 
XDA C5  H5B  SING N N 42 
XDA C6  H6B  SING N N 43 
XDA C6  H6A  SING N N 44 
XDA C1  H1   SING N N 45 
XDA C2  H2   SING N N 46 
XDA C3  H3   SING N N 47 
XDA N12 H12  SING N N 48 
XDA C16 H16A SING N N 49 
XDA C16 H16B SING N N 50 
XDA C22 H22  SING N N 51 
XDA C21 H21  SING N N 52 
XDA C18 H18  SING N N 53 
XDA C19 H19  SING N N 54 
XDA N25 H25  SING N N 55 
XDA C26 H26A SING N N 56 
XDA C26 H26B SING N N 57 
XDA C27 H27A SING N N 58 
XDA C27 H27B SING N N 59 
XDA O31 H5   SING N N 60 
XDA O30 H6   SING N N 61 
# 
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 
XDA SMILES           ACDLabs              12.01 "O=P(O)(O)OCCNC(=O)c1ccc(cc1)COC(=O)NC2C=CCCC2C(=O)N(C)C"                                                                                                                                            
XDA InChI            InChI                1.03  "InChI=1S/C20H28N3O8P/c1-23(2)19(25)16-5-3-4-6-17(16)22-20(26)30-13-14-7-9-15(10-8-14)18(24)21-11-12-31-32(27,28)29/h4,6-10,16-17H,3,5,11-13H2,1-2H3,(H,21,24)(H,22,26)(H2,27,28,29)/t16-,17+/m0/s1" 
XDA InChIKey         InChI                1.03  MBWSSOJOAZHENI-DLBZAZTESA-N                                                                                                                                                                          
XDA SMILES_CANONICAL CACTVS               3.385 "CN(C)C(=O)[C@H]1CCC=C[C@H]1NC(=O)OCc2ccc(cc2)C(=O)NCCO[P](O)(O)=O"                                                                                                                                  
XDA SMILES           CACTVS               3.385 "CN(C)C(=O)[CH]1CCC=C[CH]1NC(=O)OCc2ccc(cc2)C(=O)NCCO[P](O)(O)=O"                                                                                                                                    
XDA SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CN(C)C(=O)[C@H]1CCC=C[C@H]1NC(=O)OCc2ccc(cc2)C(=O)NCCOP(=O)(O)O"                                                                                                                                    
XDA SMILES           "OpenEye OEToolkits" 1.7.6 "CN(C)C(=O)C1CCC=CC1NC(=O)OCc2ccc(cc2)C(=O)NCCOP(=O)(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 
XDA "SYSTEMATIC NAME" ACDLabs              12.01 "4-{[2-(phosphonooxy)ethyl]carbamoyl}benzyl [(1R,6S)-6-(dimethylcarbamoyl)cyclohex-2-en-1-yl]carbamate"       
XDA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "[4-(2-phosphonooxyethylcarbamoyl)phenyl]methyl N-[(1R,6S)-6-(dimethylcarbamoyl)cyclohex-2-en-1-yl]carbamate" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
XDA "Create component" 2014-01-07 PDBJ 
XDA "Initial release"  2014-06-04 RCSB 
# 
