data_AQH
#

_chem_comp.id                                   AQH
_chem_comp.name                                 "[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3R,4R,5R,6S)-6-[(1R)-1,2-dihydroxyethyl]-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl dihydrogen diphosphate"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C17 H27 N5 O16 P2"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        ?
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2014-09-30
_chem_comp.pdbx_modified_date                   2020-01-26
_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                       619.368
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    AQH
_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       4RB4
_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
AQH  PA     PA     P  0  1  N  N  N  -11.760  -72.661  -53.276  -0.045   1.847  -1.385  PA     AQH   1  
AQH  PB     PB     P  0  1  N  N  N   -9.369  -71.316  -52.660  -2.875   1.078  -0.955  PB     AQH   2  
AQH  "C7'"  "C7'"  C  0  1  N  N  N   -5.258  -70.716  -47.630  -6.832  -2.361  -1.957  "C7'"  AQH   3  
AQH  "O7'"  "O7'"  O  0  1  N  N  N   -3.890  -70.378  -47.861  -7.322  -3.566  -2.548  "O7'"  AQH   4  
AQH  "C6'"  "C6'"  C  0  1  N  N  R   -6.209  -70.652  -48.859  -7.395  -2.221  -0.542  "C6'"  AQH   5  
AQH  "O6'"  "O6'"  O  0  1  N  N  N   -5.449  -70.288  -50.017  -6.889  -3.276   0.278  "O6'"  AQH   6  
AQH  "C5'"  "C5'"  C  0  1  N  N  S   -7.007  -71.962  -49.180  -6.972  -0.872   0.044  "C5'"  AQH   7  
AQH  "O5'"  "O5'"  O  0  1  N  N  N   -7.658  -71.781  -50.510  -5.549  -0.751  -0.016  "O5'"  AQH   8  
AQH  "C4'"  "C4'"  C  0  1  N  N  R   -8.064  -72.366  -48.113  -7.429  -0.784   1.503  "C4'"  AQH   9  
AQH  "O4'"  "O4'"  O  0  1  N  N  N   -7.362  -72.572  -46.900  -8.855  -0.846   1.561  "O4'"  AQH  10  
AQH  "C3'"  "C3'"  C  0  1  N  N  R   -8.832  -73.636  -48.545  -6.950   0.543   2.100  "C3'"  AQH  11  
AQH  "O3'"  "O3'"  O  0  1  N  N  N   -9.791  -73.997  -47.555  -7.308   0.602   3.482  "O3'"  AQH  12  
AQH  "C2'"  "C2'"  C  0  1  N  N  R   -9.552  -73.282  -49.872  -5.427   0.632   1.961  "C2'"  AQH  13  
AQH  "O2'"  "O2'"  O  0  1  N  N  N  -13.020  -74.482  -58.099   7.085   2.167   0.707  "O2'"  AQH  14  
AQH  "C1'"  "C1'"  C  0  1  N  N  R   -8.463  -72.945  -50.902  -5.047   0.489   0.485  "C1'"  AQH  15  
AQH  C1D    C1D    C  0  1  N  N  R  -12.503  -76.640  -56.941   5.240   0.548   0.692  C1D    AQH  16  
AQH  N1     N1     N  0  1  Y  N  N  -14.649  -81.319  -57.942   9.081  -2.928   1.074  N1     AQH  17  
AQH  O1A    O1A    O  0  1  N  N  N  -12.183  -72.653  -51.929   0.272   1.192  -2.821  O1A    AQH  18  
AQH  O3A    O3A    O  0  1  N  N  N   -9.586  -70.245  -51.634  -3.221   0.139  -2.217  O3A    AQH  19  
AQH  C2     C2     C  0  1  Y  N  N  -13.306  -80.996  -57.915   8.885  -1.832   1.785  C2     AQH  20  
AQH  C2D    C2D    C  0  1  N  N  R  -12.711  -75.126  -56.863   5.897   1.778   0.015  C2D    AQH  21  
AQH  O2A    O2A    O  0  1  N  N  N  -12.938  -72.435  -54.115  -0.388   3.276  -1.559  O2A    AQH  22  
AQH  O1B    O1B    O  0  1  N  N  N   -8.441  -70.875  -53.660  -3.330   2.459  -1.229  O1B    AQH  23  
AQH  C3D    C3D    C  0  1  N  N  S  -11.450  -74.659  -56.188   4.794   2.855   0.160  C3D    AQH  24  
AQH  N3     N3     N  0  1  Y  N  N  -12.962  -79.683  -57.625   7.860  -1.032   1.582  N3     AQH  25  
AQH  O2B    O2B    O  0  1  N  N  N  -10.630  -71.638  -53.385  -1.285   1.076  -0.705  O2B    AQH  26  
AQH  O3B    O3B    O  0  1  N  N  N   -8.894  -72.766  -52.103  -3.625   0.515   0.354  O3B    AQH  27  
AQH  O3D    O3D    O  0  1  N  N  N  -10.341  -74.482  -57.087   5.058   3.691   1.289  O3D    AQH  28  
AQH  C4     C4     C  0  1  Y  N  N  -13.896  -78.672  -57.360   6.967  -1.302   0.636  C4     AQH  29  
AQH  C4D    C4D    C  0  1  N  N  R  -11.163  -75.773  -55.267   3.502   2.045   0.379  C4D    AQH  30  
AQH  O4D    O4D    O  0  1  N  N  N  -11.802  -76.969  -55.753   3.852   0.653   0.308  O4D    AQH  31  
AQH  C5     C5     C  0  1  Y  N  N  -15.308  -78.985  -57.382   7.131  -2.456  -0.148  C5     AQH  32  
AQH  C5D    C5D    C  0  1  N  N  N  -11.609  -75.311  -53.889   2.486   2.382  -0.714  C5D    AQH  33  
AQH  O5D    O5D    O  0  1  N  N  N  -11.010  -73.993  -53.604   1.251   1.717  -0.439  O5D    AQH  34  
AQH  C6     C6     C  0  1  Y  N  N  -15.653  -80.347  -57.683   8.241  -3.279   0.106  C6     AQH  35  
AQH  N6     N6     N  0  1  N  N  N  -16.944  -80.679  -57.714   8.455  -4.429  -0.634  N6     AQH  36  
AQH  N7     N7     N  0  1  Y  N  N  -15.958  -77.874  -57.103   6.098  -2.493  -1.025  N7     AQH  37  
AQH  C8     C8     C  0  1  Y  N  N  -15.079  -76.907  -56.912   5.330  -1.461  -0.833  C8     AQH  38  
AQH  N9     N9     N  0  1  Y  N  N  -13.812  -77.388  -57.067   5.824  -0.695   0.181  N9     AQH  39  
AQH  O      O      O  0  1  N  N  N  -10.048  -71.832  -50.006  -4.816  -0.416   2.716  O      AQH  40  
AQH  H1     H1     H  0  1  N  N  N   -5.649  -70.024  -46.869  -5.743  -2.394  -1.914  H1     AQH  41  
AQH  H2     H2     H  0  1  N  N  N   -5.286  -71.744  -47.240  -7.145  -1.508  -2.559  H2     AQH  42  
AQH  H3     H3     H  0  1  N  N  N   -3.404  -70.450  -47.048  -7.004  -3.720  -3.448  H3     AQH  43  
AQH  H4     H4     H  0  1  N  N  N   -6.949  -69.863  -48.658  -8.483  -2.277  -0.576  H4     AQH  44  
AQH  H5     H5     H  0  1  N  N  N   -4.959  -69.494  -49.838  -5.925  -3.288   0.355  H5     AQH  45  
AQH  H6     H6     H  0  1  N  N  N   -6.279  -72.783  -49.257  -7.430  -0.067  -0.530  H6     AQH  46  
AQH  H7     H7     H  0  1  N  N  N   -8.783  -71.541  -48.004  -7.004  -1.613   2.068  H7     AQH  47  
AQH  H8     H8     H  0  1  N  N  N   -7.974  -72.822  -46.218  -9.215  -0.796   2.458  H8     AQH  48  
AQH  H9     H9     H  0  1  N  N  N   -8.118  -74.453  -48.724  -7.415   1.372   1.567  H9     AQH  49  
AQH  H10    H10    H  0  1  N  N  N   -9.344  -74.213  -46.745  -7.035   1.417   3.925  H10    AQH  50  
AQH  H11    H11    H  0  1  N  N  N  -10.274  -74.041  -50.208  -5.083   1.597   2.334  H11    AQH  51  
AQH  H12    H12    H  0  1  N  N  N  -13.131  -73.550  -57.952   7.532   2.932   0.322  H12    AQH  52  
AQH  H13    H13    H  0  1  N  N  N   -7.779  -73.807  -50.900  -5.480   1.313  -0.083  H13    AQH  53  
AQH  H14    H14    H  0  1  N  N  N  -11.881  -76.863  -57.821   5.344   0.605   1.776  H14    AQH  54  
AQH  H15    H15    H  0  1  N  N  N  -13.121  -72.504  -51.892   0.505   0.255  -2.783  H15    AQH  55  
AQH  H16    H16    H  0  1  N  N  N   -9.061  -69.484  -51.854  -2.950  -0.783  -2.107  H16    AQH  56  
AQH  H17    H17    H  0  1  N  N  N  -12.549  -81.740  -58.113   9.592  -1.584   2.563  H17    AQH  57  
AQH  H18    H18    H  0  1  N  N  N  -13.542  -74.950  -56.164   6.109   1.577  -1.035  H18    AQH  58  
AQH  H19    H19    H  0  1  N  N  N  -11.647  -73.736  -55.623   4.722   3.451  -0.749  H19    AQH  59  
AQH  H20    H20    H  0  1  N  N  N   -9.581  -74.188  -56.599   5.890   4.180   1.230  H20    AQH  60  
AQH  H21    H21    H  0  1  N  N  N  -10.075  -75.933  -55.237   3.082   2.275   1.358  H21    AQH  61  
AQH  H22    H22    H  0  1  N  N  N  -12.706  -75.230  -53.865   2.321   3.460  -0.737  H22    AQH  62  
AQH  H23    H23    H  0  1  N  N  N  -11.278  -76.037  -53.132   2.868   2.053  -1.680  H23    AQH  63  
AQH  H24    H24    H  0  1  N  N  N  -17.034  -81.650  -57.934   9.225  -4.988  -0.449  H24    AQH  64  
AQH  H25    H25    H  0  1  N  N  N  -17.355  -80.501  -56.820   7.835  -4.675  -1.338  H25    AQH  65  
AQH  H26    H26    H  0  1  N  N  N  -15.327  -75.884  -56.669   4.434  -1.242  -1.395  H26    AQH  66  
AQH  H27    H27    H  0  1  N  N  N  -10.796  -71.699  -49.436  -3.850  -0.420   2.674  H27    AQH  67  
#   #
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
AQH  "O2'"  C2D    SING  N  N   1  
AQH  N1     C2     DOUB  Y  N   2  
AQH  N1     C6     SING  Y  N   3  
AQH  C2     N3     SING  Y  N   4  
AQH  N6     C6     SING  N  N   5  
AQH  C6     C5     DOUB  Y  N   6  
AQH  N3     C4     DOUB  Y  N   7  
AQH  C5     C4     SING  Y  N   8  
AQH  C5     N7     SING  Y  N   9  
AQH  C4     N9     SING  Y  N  10  
AQH  N7     C8     DOUB  Y  N  11  
AQH  O3D    C3D    SING  N  N  12  
AQH  N9     C1D    SING  N  N  13  
AQH  N9     C8     SING  Y  N  14  
AQH  C1D    C2D    SING  N  N  15  
AQH  C1D    O4D    SING  N  N  16  
AQH  C2D    C3D    SING  N  N  17  
AQH  C3D    C4D    SING  N  N  18  
AQH  O4D    C4D    SING  N  N  19  
AQH  C4D    C5D    SING  N  N  20  
AQH  O2A    PA     DOUB  N  N  21  
AQH  C5D    O5D    SING  N  N  22  
AQH  O1B    PB     DOUB  N  N  23  
AQH  O5D    PA     SING  N  N  24  
AQH  O2B    PA     SING  N  N  25  
AQH  O2B    PB     SING  N  N  26  
AQH  PA     O1A    SING  N  N  27  
AQH  PB     O3B    SING  N  N  28  
AQH  PB     O3A    SING  N  N  29  
AQH  O3B    "C1'"  SING  N  N  30  
AQH  "C1'"  "O5'"  SING  N  N  31  
AQH  "C1'"  "C2'"  SING  N  N  32  
AQH  "O5'"  "C5'"  SING  N  N  33  
AQH  "O6'"  "C6'"  SING  N  N  34  
AQH  O      "C2'"  SING  N  N  35  
AQH  "C2'"  "C3'"  SING  N  N  36  
AQH  "C5'"  "C6'"  SING  N  N  37  
AQH  "C5'"  "C4'"  SING  N  N  38  
AQH  "C6'"  "C7'"  SING  N  N  39  
AQH  "C3'"  "C4'"  SING  N  N  40  
AQH  "C3'"  "O3'"  SING  N  N  41  
AQH  "C4'"  "O4'"  SING  N  N  42  
AQH  "O7'"  "C7'"  SING  N  N  43  
AQH  "C7'"  H1     SING  N  N  44  
AQH  "C7'"  H2     SING  N  N  45  
AQH  "O7'"  H3     SING  N  N  46  
AQH  "C6'"  H4     SING  N  N  47  
AQH  "O6'"  H5     SING  N  N  48  
AQH  "C5'"  H6     SING  N  N  49  
AQH  "C4'"  H7     SING  N  N  50  
AQH  "O4'"  H8     SING  N  N  51  
AQH  "C3'"  H9     SING  N  N  52  
AQH  "O3'"  H10    SING  N  N  53  
AQH  "C2'"  H11    SING  N  N  54  
AQH  "O2'"  H12    SING  N  N  55  
AQH  "C1'"  H13    SING  N  N  56  
AQH  C1D    H14    SING  N  N  57  
AQH  O1A    H15    SING  N  N  58  
AQH  O3A    H16    SING  N  N  59  
AQH  C2     H17    SING  N  N  60  
AQH  C2D    H18    SING  N  N  61  
AQH  C3D    H19    SING  N  N  62  
AQH  O3D    H20    SING  N  N  63  
AQH  C4D    H21    SING  N  N  64  
AQH  C5D    H22    SING  N  N  65  
AQH  C5D    H23    SING  N  N  66  
AQH  N6     H24    SING  N  N  67  
AQH  N6     H25    SING  N  N  68  
AQH  C8     H26    SING  N  N  69  
AQH  O      H27    SING  N  N  70  
#   #
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
AQH  SMILES            ACDLabs               12.01  "O=P(OP(=O)(OC1OC(C(O)C(O)C1O)C(O)CO)O)(OCC4OC(n2c3ncnc(N)c3nc2)C(O)C4O)O"  
AQH  InChI             InChI                 1.03   "InChI=1S/C17H27N5O16P2/c18-14-7-15(20-3-19-14)22(4-21-7)16-11(28)8(25)6(35-16)2-34-39(30,31)38-40(32,33)37-17-12(29)9(26)10(27)13(36-17)5(24)1-23/h3-6,8-13,16-17,23-29H,1-2H2,(H,30,31)(H,32,33)(H2,18,19,20)/t5-,6-,8-,9-,10-,11-,12-,13+,16-,17-/m1/s1"  
AQH  InChIKey          InChI                 1.03   KMSFWBYFWSKGGR-GZNZTODLSA-N  
AQH  SMILES_CANONICAL  CACTVS                3.385  "Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P](O)(=O)O[P](O)(=O)O[C@H]4O[C@@H]([C@H](O)CO)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H]3O"  
AQH  SMILES            CACTVS                3.385  "Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)O[P](O)(=O)O[CH]4O[CH]([CH](O)CO)[CH](O)[CH](O)[CH]4O)[CH](O)[CH]3O"  
AQH  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.6  "c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)O[C@@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)[C@@H](CO)O)O)O)O)O)O)N"  
AQH  SMILES            "OpenEye OEToolkits"  1.7.6  "c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OC4C(C(C(C(O4)C(CO)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
AQH  "SYSTEMATIC NAME"  ACDLabs               12.01  "[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3R,4R,5R,6S)-6-[(1R)-1,2-dihydroxyethyl]-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)"  
AQH  "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] [(2R,3R,4R,5R,6S)-6-[(1R)-1,2-bis(oxidanyl)ethyl]-3,4,5-tris(oxidanyl)oxan-2-yl] hydrogen phosphate"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
AQH  "Create component"    2014-09-30  PDBJ  
AQH  "Initial release"     2014-11-05  RCSB  
AQH  "Other modification"  2020-01-26  RCSB  
##
