data_AU1
#

_chem_comp.id                                   AU1
_chem_comp.name                                 "5'-O-[(R)-hydroxy(phosphonoamino)phosphoryl]adenosine"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C10 H16 N6 O9 P2"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "Adenosine 5-(alpha,beta-imido)diphosphate"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2013-05-03
_chem_comp.pdbx_modified_date                   2021-03-13
_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                       426.216
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    AU1
_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       4KH5
_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
AU1  O1A    O1A  O  0  1  N  N  N  -5.590  14.726  -26.560  -4.253  -0.282  -2.135  O1A    AU1   1  
AU1  PA     PA   P  0  1  N  N  N  -4.733  13.483  -26.466  -3.638  -0.496  -0.662  PA     AU1   2  
AU1  O2A    O2A  O  0  1  N  N  N  -4.092  12.963  -27.730  -4.401  -1.550   0.043  O2A    AU1   3  
AU1  N3A    N3A  N  0  1  N  N  N  -5.722  12.227  -25.748  -3.741   0.945   0.203  N3A    AU1   4  
AU1  PB     PB   P  0  1  N  N  N  -6.199  10.737  -26.537  -5.341   1.445   0.353  PB     AU1   5  
AU1  O2B    O2B  O  0  1  N  N  N  -5.050  10.316  -27.422  -5.920   1.657  -0.993  O2B    AU1   6  
AU1  O1B    O1B  O  0  1  N  N  N  -7.456  11.093  -27.294  -6.186   0.316   1.129  O1B    AU1   7  
AU1  O3B    O3B  O  0  1  N  N  N  -6.423   9.799  -25.375  -5.396   2.823   1.184  O3B    AU1   8  
AU1  "O5'"  O5*  O  0  1  N  N  N  -3.525  13.771  -25.436  -2.096  -0.940  -0.784  "O5'"  AU1   9  
AU1  "C5'"  C5*  C  0  1  N  N  N  -3.006  15.080  -25.205  -1.360  -1.503   0.305  "C5'"  AU1  10  
AU1  "C4'"  C4*  C  0  1  N  N  R  -1.945  15.023  -24.113   0.069  -1.809  -0.150  "C4'"  AU1  11  
AU1  "C3'"  C3*  C  0  1  N  N  S  -2.482  15.484  -22.759   0.846  -2.533   0.971  "C3'"  AU1  12  
AU1  "O3'"  O3*  O  0  1  N  N  N  -2.395  14.396  -21.826   0.857  -3.943   0.744  "O3'"  AU1  13  
AU1  "C2'"  C2*  C  0  1  N  N  R  -1.585  16.640  -22.330   2.276  -1.957   0.868  "C2'"  AU1  14  
AU1  "O2'"  O2*  O  0  1  N  N  N  -1.072  16.457  -21.001   3.214  -2.994   0.574  "O2'"  AU1  15  
AU1  "C1'"  C1*  C  0  1  N  N  R  -0.438  16.646  -23.337   2.193  -0.953  -0.303  "C1'"  AU1  16  
AU1  "O4'"  O4*  O  0  1  N  N  N  -0.857  15.880  -24.466   0.799  -0.584  -0.375  "O4'"  AU1  17  
AU1  N9     N9   N  0  1  Y  N  N   0.007  18.002  -23.771   3.022   0.223  -0.027  N9     AU1  18  
AU1  C4     C4   C  0  1  Y  N  N   1.201  18.264  -24.314   4.365   0.347  -0.276  C4     AU1  19  
AU1  C5     C5   C  0  1  Y  N  N   1.227  19.715  -24.591   4.720   1.640   0.144  C5     AU1  20  
AU1  N7     N7   N  0  1  Y  N  N   0.035  20.201  -24.196   3.595   2.228   0.619  N7     AU1  21  
AU1  C8     C8   C  0  1  Y  N  N  -0.689  19.158  -23.715   2.598   1.398   0.520  C8     AU1  22  
AU1  N3     N3   N  0  1  Y  N  N   2.304  17.522  -24.618   5.301  -0.445  -0.789  N3     AU1  23  
AU1  C2     C2   C  0  1  Y  N  N   3.405  18.088  -25.163   6.544  -0.028  -0.904  C2     AU1  24  
AU1  N1     N1   N  0  1  Y  N  N   3.494  19.408  -25.447   6.925   1.178  -0.523  N1     AU1  25  
AU1  C6     C6   C  0  1  Y  N  N   2.473  20.266  -25.195   6.059   2.040   0.002  C6     AU1  26  
AU1  N6     N6   N  0  1  N  N  N   2.588  21.584  -25.490   6.468   3.301   0.397  N6     AU1  27  
AU1  H1     H1   H  0  1  N  N  N  -5.610  15.030  -27.460  -3.801   0.396  -2.655  H1     AU1  28  
AU1  H2     H2   H  0  1  N  N  N  -6.578  12.677  -25.492  -3.176   1.663  -0.224  H2     AU1  29  
AU1  H3     H3   H  0  1  N  N  N  -7.305  10.988  -28.226  -5.862   0.125   2.020  H3     AU1  30  
AU1  H4     H4   H  0  1  N  N  N  -5.786   9.095  -25.409  -6.290   3.171   1.309  H4     AU1  31  
AU1  H5     H5   H  0  1  N  N  N  -2.557  15.465  -26.132  -1.333  -0.792   1.131  H5     AU1  32  
AU1  H6     H6   H  0  1  N  N  N  -3.822  15.747  -24.889  -1.842  -2.423   0.632  H6     AU1  33  
AU1  H7     H7   H  0  1  N  N  N  -1.592  13.986  -24.017   0.056  -2.416  -1.055  H7     AU1  34  
AU1  H8     H8   H  0  1  N  N  N  -3.519  15.834  -22.867   0.412  -2.305   1.945  H8     AU1  35  
AU1  H9     H9   H  0  1  N  N  N  -2.727  14.675  -20.981   1.333  -4.447   1.418  H9     AU1  36  
AU1  H10    H10  H  0  1  N  N  N  -2.143  17.585  -22.405   2.550  -1.446   1.792  H10    AU1  37  
AU1  H11    H11  H  0  1  N  N  N  -1.792  16.454  -20.381   3.262  -3.684   1.250  H11    AU1  38  
AU1  H12    H12  H  0  1  N  N  N   0.419  16.143  -22.866   2.508  -1.428  -1.232  H12    AU1  39  
AU1  H13    H13  H  0  1  N  N  N  -1.696  19.242  -23.335   1.583   1.610   0.822  H13    AU1  40  
AU1  H14    H14  H  0  1  N  N  N   4.253  17.456  -25.382   7.280  -0.696  -1.324  H14    AU1  41  
AU1  H15    H15  H  0  1  N  N  N   3.488  21.760  -25.888   7.395   3.566   0.293  H15    AU1  42  
AU1  H16    H16  H  0  1  N  N  N   1.878  21.842  -26.145   5.826   3.921   0.779  H16    AU1  43  
#   #
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
AU1  O2A    PA     DOUB  N  N   1  
AU1  O2B    PB     DOUB  N  N   2  
AU1  O1B    PB     SING  N  N   3  
AU1  O1A    PA     SING  N  N   4  
AU1  PB     N3A    SING  N  N   5  
AU1  PB     O3B    SING  N  N   6  
AU1  PA     N3A    SING  N  N   7  
AU1  PA     "O5'"  SING  N  N   8  
AU1  N6     C6     SING  N  N   9  
AU1  N1     C6     DOUB  Y  N  10  
AU1  N1     C2     SING  Y  N  11  
AU1  "O5'"  "C5'"  SING  N  N  12  
AU1  "C5'"  "C4'"  SING  N  N  13  
AU1  C6     C5     SING  Y  N  14  
AU1  C2     N3     DOUB  Y  N  15  
AU1  N3     C4     SING  Y  N  16  
AU1  C5     C4     DOUB  Y  N  17  
AU1  C5     N7     SING  Y  N  18  
AU1  "O4'"  "C4'"  SING  N  N  19  
AU1  "O4'"  "C1'"  SING  N  N  20  
AU1  C4     N9     SING  Y  N  21  
AU1  N7     C8     DOUB  Y  N  22  
AU1  "C4'"  "C3'"  SING  N  N  23  
AU1  N9     C8     SING  Y  N  24  
AU1  N9     "C1'"  SING  N  N  25  
AU1  "C1'"  "C2'"  SING  N  N  26  
AU1  "C3'"  "C2'"  SING  N  N  27  
AU1  "C3'"  "O3'"  SING  N  N  28  
AU1  "C2'"  "O2'"  SING  N  N  29  
AU1  O1A    H1     SING  N  N  30  
AU1  N3A    H2     SING  N  N  31  
AU1  O1B    H3     SING  N  N  32  
AU1  O3B    H4     SING  N  N  33  
AU1  "C5'"  H5     SING  N  N  34  
AU1  "C5'"  H6     SING  N  N  35  
AU1  "C4'"  H7     SING  N  N  36  
AU1  "C3'"  H8     SING  N  N  37  
AU1  "O3'"  H9     SING  N  N  38  
AU1  "C2'"  H10    SING  N  N  39  
AU1  "O2'"  H11    SING  N  N  40  
AU1  "C1'"  H12    SING  N  N  41  
AU1  C8     H13    SING  N  N  42  
AU1  C2     H14    SING  N  N  43  
AU1  N6     H15    SING  N  N  44  
AU1  N6     H16    SING  N  N  45  
#   #
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
AU1  SMILES            ACDLabs               12.01  "O=P(O)(O)NP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O"  
AU1  InChI             InChI                 1.03   "InChI=1S/C10H16N6O9P2/c11-8-5-9(13-2-12-8)16(3-14-5)10-7(18)6(17)4(25-10)1-24-27(22,23)15-26(19,20)21/h2-4,6-7,10,17-18H,1H2,(H2,11,12,13)(H4,15,19,20,21,22,23)/t4-,6-,7-,10-/m1/s1"  
AU1  InChIKey          InChI                 1.03   FJNYKURUYWTJIG-KQYNXXCUSA-N  
AU1  SMILES_CANONICAL  CACTVS                3.370  "Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P](O)(=O)N[P](O)(O)=O)[C@@H](O)[C@H]3O"  
AU1  SMILES            CACTVS                3.370  "Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)N[P](O)(O)=O)[CH](O)[CH]3O"  
AU1  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.6  "c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(NP(=O)(O)O)O)O)O)N"  
AU1  SMILES            "OpenEye OEToolkits"  1.7.6  "c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(NP(=O)(O)O)O)O)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
AU1  "SYSTEMATIC NAME"  ACDLabs               12.01  "5'-O-[(R)-hydroxy(phosphonoamino)phosphoryl]adenosine"  
AU1  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.7.6  "[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-oxidanyl-phosphoryl]amino]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
AU1  "Create component"  2013-05-03  RCSB  
AU1  "Modify atom id"    2013-06-04  RCSB  
AU1  "Initial release"   2013-07-17  RCSB  
AU1  "Modify synonyms"   2021-03-13  RCSB  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     AU1
_pdbx_chem_comp_synonyms.name        "Adenosine 5-(alpha,beta-imido)diphosphate"
_pdbx_chem_comp_synonyms.provenance  PDB
_pdbx_chem_comp_synonyms.type        ?
##
