data_DBG
#

_chem_comp.id                                   DBG
_chem_comp.name                                 "3-AMINOBENZOPHENONE-4-YL-AMINOHYDROXYPHOSPHINYLAMINOPHOSPHONIC ACID-GUANYLATE ESTER"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C23 H27 N8 O13 P3"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        DABP-GPPNHP
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    1999-07-08
_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                       716.428
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    DBG
_chem_comp.pdbx_model_coordinates_details       ?
_chem_comp.pdbx_model_coordinates_missing_flag  Y
_chem_comp.pdbx_ideal_coordinates_details       ?
_chem_comp.pdbx_ideal_coordinates_missing_flag  N
_chem_comp.pdbx_model_coordinates_db_code       1RVD
_chem_comp.pdbx_subcomponent_list               ?
_chem_comp.pdbx_processing_site                 EBI
#   #
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
DBG  C22     C22   C  0  1  Y  N  N       ?       ?       ?   4.799  5.912  -1.602  C22     DBG   1  
DBG  C21     C21   C  0  1  Y  N  N       ?       ?       ?   4.973  5.959  -2.985  C21     DBG   2  
DBG  C20     C20   C  0  1  Y  N  N       ?       ?       ?   6.253  5.865  -3.531  C20     DBG   3  
DBG  C19     C19   C  0  1  Y  N  N       ?       ?       ?   7.359  5.724  -2.694  C19     DBG   4  
DBG  C18     C18   C  0  1  Y  N  N       ?       ?       ?   7.186  5.677  -1.310  C18     DBG   5  
DBG  C17     C17   C  0  1  Y  N  N       ?       ?       ?   5.910  5.772  -0.804  C17     DBG   6  
DBG  C16     C16   C  0  1  N  N  N       ?       ?       ?   5.724  5.722   0.677  C16     DBG   7  
DBG  O16     O16   O  0  1  N  N  N       ?       ?       ?   6.742  5.596   1.375  O16     DBG   8  
DBG  C15     C15   C  0  1  Y  N  N       ?       ?       ?   2.418  4.746   2.146  C15     DBG   9  
DBG  N15     N15   N  0  1  N  N  N       ?       ?       ?   1.685  3.562   2.385  N15     DBG  10  
DBG  C14     C14   C  0  1  Y  N  N       ?       ?       ?   3.675  4.657   1.547  C14     DBG  11  
DBG  C13     C13   C  0  1  Y  N  N       ?       ?       ?   4.414  5.814   1.302  C13     DBG  12  
DBG  C12     C12   C  0  1  Y  N  N       ?       ?       ?   3.897  7.060   1.656  C12     DBG  13  
DBG  C11     C11   C  0  1  Y  N  N       ?       ?       ?   2.641  7.150   2.255  C11     DBG  14  
DBG  C10     C10   C  0  1  Y  N  N       ?       ?       ?   1.900  5.993   2.500  C10     DBG  15  
DBG  N3G     N3G   N  0  1  N  N  N   5.417  33.254  23.386   0.630  6.106   3.107  N3G     DBG  16  
DBG  PG      PG    P  0  1  N  N  R   5.581  32.524  22.061  -0.146  7.514   3.495  PG      DBG  17  
DBG  O1G     O1G   O  0  1  N  N  N   5.388  31.087  22.295   0.687  8.113   4.765  O1G     DBG  18  
DBG  O2G     O2G   O  0  1  N  N  N   4.560  33.041  21.155  -0.272  8.592   2.442  O2G     DBG  19  
DBG  N3B     N3B   N  0  1  N  N  N   7.032  32.780  21.490  -1.577  6.999   4.171  N3B     DBG  20  
DBG  PB      PB    P  0  1  N  N  S   7.435  32.245  20.056  -2.692  6.506   3.057  PB      DBG  21  
DBG  O1B     O1B   O  0  1  N  N  N   7.471  30.776  20.009  -4.091  6.344   3.865  O1B     DBG  22  
DBG  O2B     O2B   O  0  1  N  N  N   6.618  32.841  19.015  -2.856  7.345   1.817  O2B     DBG  23  
DBG  O3A     O3A   O  0  1  N  N  N   8.927  32.803  19.873  -2.345  4.958   2.720  O3A     DBG  24  
DBG  PA      PA    P  0  1  N  N  S   9.464  34.328  19.614  -3.038  3.894   1.723  PA      DBG  25  
DBG  O1A     O1A   O  0  1  N  N  N   9.539  34.634  18.154  -2.055  2.612   1.808  O1A     DBG  26  
DBG  O2A     O2A   O  0  1  N  N  N   8.656  35.299  20.404  -4.480  3.600   2.019  O2A     DBG  27  
DBG  "O5'"   O5*   O  0  1  N  N  N  10.956  34.236  20.189  -2.733  4.494   0.252  "O5'"   DBG  28  
DBG  "C5'"   C5*   C  0  1  N  N  N  11.280  34.210  21.561  -3.088  3.719  -0.880  "C5'"   DBG  29  
DBG  "C4'"   C4*   C  0  1  N  N  R  12.690  34.673  21.750  -2.709  4.481  -2.142  "C4'"   DBG  30  
DBG  "O4'"   O4*   O  0  1  N  N  N  13.609  33.887  20.949  -1.275  4.674  -2.144  "O4'"   DBG  31  
DBG  "C2'"   C2*   C  0  1  N  N  R  13.509  35.986  19.888  -1.771  2.932  -3.670  "C2'"   DBG  32  
DBG  "O2'"   O2*   O  0  1  N  N  N  14.303  37.092  19.517  -1.616  2.544  -5.019  "O2'"   DBG  33  
DBG  "C3'"   C3*   C  0  1  N  N  S  12.929  36.151  21.305  -3.043  3.719  -3.420  "C3'"   DBG  34  
DBG  "O3'"   O3*   O  0  1  N  N  N  13.851  36.797  22.155  -3.237  4.658  -4.478  "O3'"   DBG  35  
DBG  "C1'"   C1*   C  0  1  N  N  R  14.365  34.730  20.059  -0.708  3.932  -3.240  "C1'"   DBG  36  
DBG  N9      N9    N  0  1  Y  N  N  14.565  33.977  18.822   0.551  3.319  -2.822  N9      DBG  37  
DBG  C4      C4    C  0  1  Y  N  N  15.723  33.522  18.341   1.655  3.092  -3.591  C4      DBG  38  
DBG  N3      N3    N  0  1  Y  N  N  16.918  33.728  18.870   1.789  3.396  -4.901  N3      DBG  39  
DBG  C2      C2    C  0  1  Y  N  N  17.944  33.304  18.120   2.964  3.064  -5.389  C2      DBG  40  
DBG  N2      N2    N  0  1  N  N  N  19.214  33.561  18.486   3.297  3.290  -6.700  N2      DBG  41  
DBG  N1      N1    N  0  1  Y  N  N  17.733  32.577  16.955   3.971  2.453  -4.605  N1      DBG  42  
DBG  C6      C6    C  0  1  Y  N  N  16.524  32.516  16.305   3.854  2.129  -3.247  C6      DBG  43  
DBG  O6      O6    O  0  1  N  N  N  16.463  31.995  15.201   4.723  1.600  -2.566  O6      DBG  44  
DBG  C5      C5    C  0  1  Y  N  N  15.445  32.954  17.151   2.561  2.502  -2.743  C5      DBG  45  
DBG  N7      N7    N  0  1  Y  N  N  14.068  32.924  16.938   2.063  2.355  -1.482  N7      DBG  46  
DBG  C8      C8    C  0  1  Y  N  N  13.622  33.468  17.989   0.846  2.858  -1.561  C8      DBG  47  
DBG  H22     H22   H  0  1  N  N  N       ?       ?       ?   3.797  5.985  -1.188  H22     DBG  48  
DBG  H21     H21   H  0  1  N  N  N       ?       ?       ?   4.111  6.068  -3.637  H21     DBG  49  
DBG  H20     H20   H  0  1  N  N  N       ?       ?       ?   6.388  5.902  -4.608  H20     DBG  50  
DBG  H19     H19   H  0  1  N  N  N       ?       ?       ?   8.356  5.652  -3.118  H19     DBG  51  
DBG  H18     H18   H  0  1  N  N  N       ?       ?       ?   8.055  5.567  -0.667  H18     DBG  52  
DBG  H151    1H15  H  0  0  N  N  N       ?       ?       ?   2.020  2.913   3.066  H151    DBG  53  
DBG  H152    2H15  H  0  0  N  N  N       ?       ?       ?   0.901  3.351   1.803  H152    DBG  54  
DBG  H14     H14   H  0  1  N  N  N       ?       ?       ?   4.078  3.685   1.270  H14     DBG  55  
DBG  H12     H12   H  0  1  N  N  N       ?       ?       ?   4.465  7.968   1.470  H12     DBG  56  
DBG  H11     H11   H  0  1  N  N  N       ?       ?       ?   2.248  8.126   2.527  H11     DBG  57  
DBG  HNG3    3HNG  H  0  0  N  N  N   5.074  34.009  23.944   0.178  5.204   3.239  HNG3    DBG  58  
DBG  HOG1    1HOG  H  0  0  N  N  N   5.346  30.633  21.462   0.318  8.887   5.242  HOG1    DBG  59  
DBG  HNB3    3HNB  H  0  0  N  N  N   7.142  33.773  21.454  -1.482  6.418   5.003  HNB3    DBG  60  
DBG  HOB1    1HOB  H  0  0  N  N  N   7.479  30.488  19.104  -4.900  6.110   3.363  HOB1    DBG  61  
DBG  HOA1    1HOA  H  0  0  N  N  N   9.555  35.575  18.028  -2.316  1.783   1.354  HOA1    DBG  62  
DBG  "H5'1"  1H5*  H  0  0  N  N  N  10.599  34.876  22.111  -2.557  2.764  -0.834  "H5'1"  DBG  63  
DBG  "H5'2"  2H5*  H  0  0  N  N  N  11.177  33.183  21.942  -4.166  3.531  -0.854  "H5'2"  DBG  64  
DBG  "H4'"   H4*   H  0  1  N  N  N  12.865  34.567  22.831  -3.175  5.471  -2.121  "H4'"   DBG  65  
DBG  "H2'"   H2*   H  0  1  N  N  N  12.745  35.915  19.100  -1.748  2.036  -3.038  "H2'"   DBG  66  
DBG  "HO2'"  HO2*  H  0  0  N  N  N  14.481  37.625  20.283  -2.107  1.713  -5.139  "HO2'"  DBG  67  
DBG  "H3'"   H3*   H  0  1  N  N  N  12.019  36.769  21.339  -3.941  3.099  -3.357  "H3'"   DBG  68  
DBG  "HO3'"  HO3*  H  0  0  N  N  N  14.665  36.942  21.688  -3.700  5.415  -4.090  "HO3'"  DBG  69  
DBG  "H1'"   H1*   H  0  1  N  N  N  15.363  35.024  20.417  -0.438  4.629  -4.041  "H1'"   DBG  70  
DBG  HN21    1HN2  H  0  0  N  N  N  19.853  33.177  17.820   4.183  3.695  -6.897  HN21    DBG  71  
DBG  HN22    2HN2  H  0  0  N  N  N  19.480  34.065  19.308   2.641  3.039  -7.402  HN22    DBG  72  
DBG  HN1     HN1   H  0  1  N  N  N  18.503  32.070  16.568   4.850  2.230  -5.064  HN1     DBG  73  
DBG  H8      H8    H  0  1  N  N  N  12.566  33.524  18.208   0.136  2.918  -0.748  H8      DBG  74  
#   #
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
DBG  C22    C21     SING  Y  N   1  
DBG  C22    C17     DOUB  Y  N   2  
DBG  C22    H22     SING  N  N   3  
DBG  C21    C20     DOUB  Y  N   4  
DBG  C21    H21     SING  N  N   5  
DBG  C20    C19     SING  Y  N   6  
DBG  C20    H20     SING  N  N   7  
DBG  C19    C18     DOUB  Y  N   8  
DBG  C19    H19     SING  N  N   9  
DBG  C18    C17     SING  Y  N  10  
DBG  C18    H18     SING  N  N  11  
DBG  C17    C16     SING  N  N  12  
DBG  C16    O16     DOUB  N  N  13  
DBG  C16    C13     SING  N  N  14  
DBG  C15    N15     SING  N  N  15  
DBG  C15    C14     DOUB  Y  N  16  
DBG  C15    C10     SING  Y  N  17  
DBG  N15    H151    SING  N  N  18  
DBG  N15    H152    SING  N  N  19  
DBG  C14    C13     SING  Y  N  20  
DBG  C14    H14     SING  N  N  21  
DBG  C13    C12     DOUB  Y  N  22  
DBG  C12    C11     SING  Y  N  23  
DBG  C12    H12     SING  N  N  24  
DBG  C11    C10     DOUB  Y  N  25  
DBG  C11    H11     SING  N  N  26  
DBG  C10    N3G     SING  N  N  27  
DBG  N3G    PG      SING  N  N  28  
DBG  N3G    HNG3    SING  N  N  29  
DBG  PG     O1G     SING  N  N  30  
DBG  PG     O2G     DOUB  N  N  31  
DBG  PG     N3B     SING  N  N  32  
DBG  O1G    HOG1    SING  N  N  33  
DBG  N3B    PB      SING  N  N  34  
DBG  N3B    HNB3    SING  N  N  35  
DBG  PB     O1B     SING  N  N  36  
DBG  PB     O2B     DOUB  N  N  37  
DBG  PB     O3A     SING  N  N  38  
DBG  O1B    HOB1    SING  N  N  39  
DBG  O3A    PA      SING  N  N  40  
DBG  PA     O1A     SING  N  N  41  
DBG  PA     O2A     DOUB  N  N  42  
DBG  PA     "O5'"   SING  N  N  43  
DBG  O1A    HOA1    SING  N  N  44  
DBG  "O5'"  "C5'"   SING  N  N  45  
DBG  "C5'"  "C4'"   SING  N  N  46  
DBG  "C5'"  "H5'1"  SING  N  N  47  
DBG  "C5'"  "H5'2"  SING  N  N  48  
DBG  "C4'"  "O4'"   SING  N  N  49  
DBG  "C4'"  "C3'"   SING  N  N  50  
DBG  "C4'"  "H4'"   SING  N  N  51  
DBG  "O4'"  "C1'"   SING  N  N  52  
DBG  "C2'"  "O2'"   SING  N  N  53  
DBG  "C2'"  "C3'"   SING  N  N  54  
DBG  "C2'"  "C1'"   SING  N  N  55  
DBG  "C2'"  "H2'"   SING  N  N  56  
DBG  "O2'"  "HO2'"  SING  N  N  57  
DBG  "C3'"  "O3'"   SING  N  N  58  
DBG  "C3'"  "H3'"   SING  N  N  59  
DBG  "O3'"  "HO3'"  SING  N  N  60  
DBG  "C1'"  N9      SING  N  N  61  
DBG  "C1'"  "H1'"   SING  N  N  62  
DBG  N9     C4      SING  Y  N  63  
DBG  N9     C8      SING  Y  N  64  
DBG  C4     N3      SING  Y  N  65  
DBG  C4     C5      DOUB  Y  N  66  
DBG  N3     C2      DOUB  Y  N  67  
DBG  C2     N2      SING  N  N  68  
DBG  C2     N1      SING  Y  N  69  
DBG  N2     HN21    SING  N  N  70  
DBG  N2     HN22    SING  N  N  71  
DBG  N1     C6      SING  Y  N  72  
DBG  N1     HN1     SING  N  N  73  
DBG  C6     O6      DOUB  N  N  74  
DBG  C6     C5      SING  Y  N  75  
DBG  C5     N7      SING  Y  N  76  
DBG  N7     C8      DOUB  Y  N  77  
DBG  C8     H8      SING  N  N  78  
#   #
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
DBG  SMILES            ACDLabs               10.04  "O=C(c1ccccc1)c2ccc(c(N)c2)NP(=O)(O)NP(=O)(O)OP(=O)(O)OCC5OC(n4cnc3c4N=C(N)NC3=O)C(O)C5O"  
DBG  SMILES_CANONICAL  CACTVS                3.341  "NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@H](CO[P@](O)(=O)O[P@](O)(=O)N[P@](O)(=O)Nc4ccc(cc4N)C(=O)c5ccccc5)[C@@H](O)[C@H]3O"  
DBG  SMILES            CACTVS                3.341  "NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH](CO[P](O)(=O)O[P](O)(=O)N[P](O)(=O)Nc4ccc(cc4N)C(=O)c5ccccc5)[CH](O)[CH]3O"  
DBG  SMILES_CANONICAL  "OpenEye OEToolkits"  1.5.0  "c1ccc(cc1)C(=O)c2ccc(c(c2)N)N[P@@](=O)(N[P@](=O)(O)O[P@](=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)n4cnc5c4N=C(NC5=O)N)O)O)O"  
DBG  SMILES            "OpenEye OEToolkits"  1.5.0  "c1ccc(cc1)C(=O)c2ccc(c(c2)N)NP(=O)(NP(=O)(O)OP(=O)(O)OCC3C(C(C(O3)n4cnc5c4N=C(NC5=O)N)O)O)O"  
DBG  InChI             InChI                 1.03   "InChI=1S/C23H27N8O13P3/c24-13-8-12(17(32)11-4-2-1-3-5-11)6-7-14(13)29-45(36,37)30-46(38,39)44-47(40,41)42-9-15-18(33)19(34)22(43-15)31-10-26-16-20(31)27-23(25)28-21(16)35/h1-8,10,15,18-19,22,33-34H,9,24H2,(H,40,41)(H3,25,27,28,35)(H4,29,30,36,37,38,39)/t15-,18-,19-,22-/m1/s1"  
DBG  InChIKey          InChI                 1.03   MXYGEAAJPIMEHV-CIVUBGFFSA-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
DBG  "SYSTEMATIC NAME"  ACDLabs               10.04  "5'-O-[(R)-{[(S)-{[(S)-{[2-amino-4-(phenylcarbonyl)phenyl]amino}(hydroxy)phosphoryl]amino}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]guanosine"  
DBG  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.5.0  "[[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-N-[[[2-amino-4-(phenylcarbonyl)phenyl]amino]-hydroxy-phosphoryl]phosphonamidic 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
DBG  "Create component"   1999-07-08  EBI   
DBG  "Modify descriptor"  2011-06-04  RCSB  
DBG  "Modify synonyms"    2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     DBG
_pdbx_chem_comp_synonyms.name        DABP-GPPNHP
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
