data_WPG
#

_chem_comp.id                                   WPG
_chem_comp.name                                 
;(3-{(3R,4R)-3-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-4-[(2R)-2-hydroxy-2-phosphonoethoxy]pyrrolidin-1-yl}-3-oxopropy
l)phosphonic acid
;

_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C14 H22 N6 O10 P2"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "[3R,4R]-4-guanin-9-yl-3-((R)-2-hydroxy-2-phosphonoethyl)oxy-1-N-(phosphonopropionyl)pyrrolidine"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2016-01-14
_chem_comp.pdbx_modified_date                   2020-06-17
_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                       496.306
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    WPG
_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       5HIG
_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
WPG  C4   C1   C  0  1  Y  N  N  -40.784  -10.095  25.155   3.329   1.655  -0.177  C4   WPG   1  
WPG  C5   C2   C  0  1  Y  N  N  -41.371  -10.156  26.421   4.047   2.396   0.767  C5   WPG   2  
WPG  C6   C3   C  0  1  N  N  N  -40.690   -9.519  27.503   5.437   2.572   0.575  C6   WPG   3  
WPG  C8   C4   C  0  1  Y  N  N  -42.683  -11.306  25.032   1.978   2.368   1.412  C8   WPG   4  
WPG  N1   N1   N  0  1  N  N  N  -39.530   -8.850  27.250   6.010   2.015  -0.515  N1   WPG   5  
WPG  N2   N2   N  0  1  N  N  N  -37.741   -8.093  25.822   5.865   0.748  -2.498  N2   WPG   6  
WPG  N3   N3   N  0  1  N  N  N  -39.592   -9.399  24.970   3.964   1.132  -1.233  N3   WPG   7  
WPG  OAI  O1   O  0  1  N  N  N  -45.738  -16.091  20.510  -0.684  -4.601   0.339  OAI  WPG   8  
WPG  PBF  P1   P  0  1  N  N  N  -45.245  -15.553  21.909   0.718  -4.342  -0.059  PBF  WPG   9  
WPG  OAJ  O2   O  0  1  N  N  N  -45.048  -16.682  22.955   1.463  -5.741  -0.343  OAJ  WPG  10  
WPG  OAE  O3   O  0  1  N  N  N  -46.194  -14.498  22.430   0.740  -3.441  -1.393  OAE  WPG  11  
WPG  CAZ  C5   C  0  1  N  N  R  -43.637  -14.704  21.557   1.577  -3.458   1.285  CAZ  WPG  12  
WPG  OAF  O4   O  0  1  N  N  N  -43.931  -13.692  20.665   2.931  -3.208   0.901  OAF  WPG  13  
WPG  CAN  C6   C  0  1  N  N  N  -43.002  -14.129  22.812   0.870  -2.129   1.555  CAN  WPG  14  
WPG  OAT  O5   O  0  1  N  N  N  -41.887  -13.283  22.624   0.889  -1.330   0.371  OAT  WPG  15  
WPG  CBA  C7   C  0  1  N  N  R  -42.090  -11.983  22.170   0.250  -0.060   0.516  CBA  WPG  16  
WPG  CAO  C8   C  0  1  N  N  N  -41.489  -11.899  20.833  -1.201  -0.102  -0.025  CAO  WPG  17  
WPG  NBC  N4   N  0  1  N  N  N  -40.762  -10.619  20.827  -1.510   1.293  -0.386  NBC  WPG  18  
WPG  CAU  C9   C  0  1  N  N  N  -39.725  -10.193  19.918  -2.744   1.830  -0.461  CAU  WPG  19  
WPG  OAB  O6   O  0  1  N  N  N  -39.224   -9.080  20.063  -2.881   2.995  -0.768  OAB  WPG  20  
WPG  CAL  C10  C  0  1  N  N  N  -39.286  -11.081  18.786  -3.954   0.982  -0.162  CAL  WPG  21  
WPG  CAM  C11  C  0  1  N  N  N  -38.121  -10.513  18.009  -5.220   1.827  -0.319  CAM  WPG  22  
WPG  PBE  P2   P  0  1  N  N  N  -36.496  -10.703  18.871  -6.683   0.802   0.043  PBE  WPG  23  
WPG  OAG  O7   O  0  1  N  N  N  -36.331   -9.624  19.986  -6.809  -0.363  -1.062  OAG  WPG  24  
WPG  OAH  O8   O  0  1  N  N  N  -35.420  -10.499  17.733  -6.541   0.195   1.385  OAH  WPG  25  
WPG  OAD  O9   O  0  1  N  N  N  -36.303  -12.100  19.467  -8.005   1.721   0.007  OAD  WPG  26  
WPG  CAP  C12  C  0  1  N  N  N  -41.225   -9.810  21.967  -0.250   2.003  -0.650  CAP  WPG  27  
WPG  CBB  C13  C  0  1  N  N  R  -41.320  -10.963  22.903   0.899   0.999  -0.415  CBB  WPG  28  
WPG  N9   N5   N  0  1  Y  N  N  -41.642  -10.809  24.330   2.029   1.651   0.251  N9   WPG  29  
WPG  C2   C14  C  0  1  N  N  N  -38.980   -8.799  26.017   5.257   1.303  -1.401  C2   WPG  30  
WPG  O6   O10  O  0  1  N  N  N  -41.215   -9.555  28.775   6.102   3.211   1.372  O6   WPG  31  
WPG  N7   N6   N  0  1  Y  N  N  -42.558  -10.900  26.339   3.167   2.800   1.715  N7   WPG  32  
WPG  H1   H1   H  0  1  N  N  N  -43.479  -11.918  24.634   1.086   2.544   1.994  H1   WPG  33  
WPG  H2   H2   H  0  1  N  N  N  -37.331   -8.045  24.911   5.342   0.238  -3.136  H2   WPG  34  
WPG  H3   H3   H  0  1  N  N  N  -37.290   -7.650  26.597   6.818   0.866  -2.636  H3   WPG  35  
WPG  H5   H5   H  0  1  N  N  N  -45.263  -17.520  22.562   1.058  -6.265  -1.048  H5   WPG  36  
WPG  H6   H6   H  0  1  N  N  N  -46.900  -14.371  21.807   1.628  -3.232  -1.712  H6   WPG  37  
WPG  H7   H7   H  0  1  N  N  N  -42.976  -15.465  21.116   1.563  -4.068   2.188  H7   WPG  38  
WPG  H8   H8   H  0  1  N  N  N  -43.136  -13.220  20.448   3.020  -2.670   0.102  H8   WPG  39  
WPG  H9   H9   H  0  1  N  N  N  -43.774  -13.552  23.342  -0.163  -2.320   1.848  H9   WPG  40  
WPG  H10  H10  H  0  1  N  N  N  -42.679  -14.973  23.440   1.383  -1.601   2.358  H10  WPG  41  
WPG  H11  H11  H  0  1  N  N  N  -43.157  -11.718  22.137   0.271   0.269   1.555  H11  WPG  42  
WPG  H12  H12  H  0  1  N  N  N  -42.268  -11.906  20.057  -1.259  -0.743  -0.905  H12  WPG  43  
WPG  H13  H13  H  0  1  N  N  N  -40.798  -12.738  20.666  -1.883  -0.457   0.747  H13  WPG  44  
WPG  H14  H14  H  0  1  N  N  N  -40.133  -11.217  18.098  -3.990   0.142  -0.856  H14  WPG  45  
WPG  H15  H15  H  0  1  N  N  N  -38.990  -12.056  19.200  -3.891   0.607   0.859  H15  WPG  46  
WPG  H16  H16  H  0  1  N  N  N  -38.064  -11.030  17.040  -5.184   2.667   0.375  H16  WPG  47  
WPG  H17  H17  H  0  1  N  N  N  -38.303   -9.441  17.842  -5.282   2.202  -1.340  H17  WPG  48  
WPG  H18  H18  H  0  1  N  N  N  -35.609   -9.047  19.765  -6.905  -0.037  -1.967  H18  WPG  49  
WPG  H19  H19  H  0  1  N  N  N  -35.584  -12.536  19.026  -8.823   1.240   0.191  H19  WPG  50  
WPG  H20  H20  H  0  1  N  N  N  -40.491   -9.056  22.286  -0.231   2.353  -1.682  H20  WPG  51  
WPG  H21  H21  H  0  1  N  N  N  -42.194   -9.323  21.784  -0.150   2.847   0.032  H21  WPG  52  
WPG  H22  H22  H  0  1  N  N  N  -40.298  -11.369  22.912   1.213   0.545  -1.355  H22  WPG  53  
WPG  H23  H23  H  0  1  N  N  N  -39.070   -8.380  28.003   6.962   2.122  -0.668  H23  WPG  54  
#   #
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
WPG  OAH  PBE  DOUB  N  N   1  
WPG  CAM  CAL  SING  N  N   2  
WPG  CAM  PBE  SING  N  N   3  
WPG  CAL  CAU  SING  N  N   4  
WPG  PBE  OAD  SING  N  N   5  
WPG  PBE  OAG  SING  N  N   6  
WPG  CAU  OAB  DOUB  N  N   7  
WPG  CAU  NBC  SING  N  N   8  
WPG  OAI  PBF  DOUB  N  N   9  
WPG  OAF  CAZ  SING  N  N  10  
WPG  NBC  CAO  SING  N  N  11  
WPG  NBC  CAP  SING  N  N  12  
WPG  CAO  CBA  SING  N  N  13  
WPG  CAZ  PBF  SING  N  N  14  
WPG  CAZ  CAN  SING  N  N  15  
WPG  PBF  OAE  SING  N  N  16  
WPG  PBF  OAJ  SING  N  N  17  
WPG  CAP  CBB  SING  N  N  18  
WPG  CBA  OAT  SING  N  N  19  
WPG  CBA  CBB  SING  N  N  20  
WPG  OAT  CAN  SING  N  N  21  
WPG  CBB  N9   SING  N  N  22  
WPG  N9   C8   SING  Y  N  23  
WPG  N9   C4   SING  Y  N  24  
WPG  N3   C4   SING  N  N  25  
WPG  N3   C2   DOUB  N  N  26  
WPG  C8   N7   DOUB  Y  N  27  
WPG  C4   C5   DOUB  Y  N  28  
WPG  N2   C2   SING  N  N  29  
WPG  C2   N1   SING  N  N  30  
WPG  N7   C5   SING  Y  N  31  
WPG  C5   C6   SING  N  N  32  
WPG  N1   C6   SING  N  N  33  
WPG  C6   O6   DOUB  N  N  34  
WPG  C8   H1   SING  N  N  35  
WPG  N2   H2   SING  N  N  36  
WPG  N2   H3   SING  N  N  37  
WPG  OAJ  H5   SING  N  N  38  
WPG  OAE  H6   SING  N  N  39  
WPG  CAZ  H7   SING  N  N  40  
WPG  OAF  H8   SING  N  N  41  
WPG  CAN  H9   SING  N  N  42  
WPG  CAN  H10  SING  N  N  43  
WPG  CBA  H11  SING  N  N  44  
WPG  CAO  H12  SING  N  N  45  
WPG  CAO  H13  SING  N  N  46  
WPG  CAL  H14  SING  N  N  47  
WPG  CAL  H15  SING  N  N  48  
WPG  CAM  H16  SING  N  N  49  
WPG  CAM  H17  SING  N  N  50  
WPG  OAG  H18  SING  N  N  51  
WPG  OAD  H19  SING  N  N  52  
WPG  CAP  H20  SING  N  N  53  
WPG  CAP  H21  SING  N  N  54  
WPG  CBB  H22  SING  N  N  55  
WPG  N1   H23  SING  N  N  56  
#   #
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
WPG  SMILES            ACDLabs               12.01  "c12c(C(=O)NC(N)=N1)ncn2C3C(OCC(P(=O)(O)O)O)CN(C3)C(=O)CCP(O)(O)=O"  
WPG  InChI             InChI                 1.03   "InChI=1S/C14H22N6O10P2/c15-14-17-12-11(13(23)18-14)16-6-20(12)7-3-19(9(21)1-2-31(24,25)26)4-8(7)30-5-10(22)32(27,28)29/h6-8,10,22H,1-5H2,(H2,24,25,26)(H2,27,28,29)(H3,15,17,18,23)/t7-,8-,10-/m1/s1"  
WPG  InChIKey          InChI                 1.03   RBYFDIJTTUISNF-NQMVMOMDSA-N  
WPG  SMILES_CANONICAL  CACTVS                3.385  "NC1=Nc2n(cnc2C(=O)N1)[C@@H]3CN(C[C@H]3OC[C@H](O)[P](O)(O)=O)C(=O)CC[P](O)(O)=O"  
WPG  SMILES            CACTVS                3.385  "NC1=Nc2n(cnc2C(=O)N1)[CH]3CN(C[CH]3OC[CH](O)[P](O)(O)=O)C(=O)CC[P](O)(O)=O"  
WPG  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.4  "c1nc2c(n1[C@@H]3CN(C[C@H]3OC[C@H](O)P(=O)(O)O)C(=O)CCP(=O)(O)O)N=C(NC2=O)N"  
WPG  SMILES            "OpenEye OEToolkits"  2.0.4  "c1nc2c(n1C3CN(CC3OCC(O)P(=O)(O)O)C(=O)CCP(=O)(O)O)N=C(NC2=O)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
WPG  "SYSTEMATIC NAME"  ACDLabs               12.01  "(3-{(3R,4R)-3-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-4-[(2R)-2-hydroxy-2-phosphonoethoxy]pyrrolidin-1-yl}-3-oxopropyl)phosphonic acid"  
WPG  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  2.0.4  "[3-[(3~{R},4~{R})-3-(2-azanyl-6-oxidanylidene-1~{H}-purin-9-yl)-4-[(2~{R})-2-oxidanyl-2-phosphono-ethoxy]pyrrolidin-1-yl]-3-oxidanylidene-propyl]phosphonic 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
WPG  "Create component"  2016-01-14  RCSB  
WPG  "Initial release"   2017-12-06  RCSB  
WPG  "Modify synonyms"   2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     WPG
_pdbx_chem_comp_synonyms.name        "[3R,4R]-4-guanin-9-yl-3-((R)-2-hydroxy-2-phosphonoethyl)oxy-1-N-(phosphonopropionyl)pyrrolidine"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
