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                    2008-10-14 
_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 InChI            InChI                1.02b 
;InChI=1/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/f/h28-30,36,38,40H,25H2
;
DBG InChIKey         InChI                1.02b MXYGEAAJPIMEHV-RMEMQNSRDY 
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 
# 
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" 
# 
