data_GP5
# 
_chem_comp.id                                    GP5 
_chem_comp.name                                  DIGUANOSINE-PENTAPHOSPHATE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H29 N10 O24 P5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-11-09 
_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                        948.366 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GP5 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2BBW 
_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 
GP5 O6     O6   O 0 1 N N N 10.109 5.950  0.597   12.193  -5.785 -0.243 O6     GP5 1  
GP5 C6     C6   C 0 1 N N N 11.231 5.973  1.102   12.436  -4.592 -0.315 C6     GP5 2  
GP5 N1     N1   N 0 1 N N N 11.571 6.959  2.021   13.695  -4.154 -0.535 N1     GP5 3  
GP5 C2     C2   C 0 1 N N N 12.857 6.969  2.566   13.956  -2.818 -0.608 C2     GP5 4  
GP5 N2     N2   N 0 1 N N N 13.121 7.924  3.443   15.245  -2.402 -0.826 N2     GP5 5  
GP5 N3     N3   N 0 1 N N N 13.774 6.022  2.224   13.008  -1.917 -0.479 N3     GP5 6  
GP5 C4     C4   C 0 1 Y N N 13.463 5.051  1.332   11.737  -2.276 -0.265 C4     GP5 7  
GP5 C5     C5   C 0 1 Y N N 12.183 5.022  0.763   11.405  -3.633 -0.175 C5     GP5 8  
GP5 N7     N7   N 0 1 Y N N 12.124 3.993  -0.071  10.070  -3.708 0.042  N7     GP5 9  
GP5 C8     C8   C 0 1 Y N N 13.296 3.377  -0.044  9.573   -2.506 0.089  C8     GP5 10 
GP5 N9     N9   N 0 1 Y N N 14.120 4.000  0.805   10.566  -1.588 -0.095 N9     GP5 11 
GP5 "C1'"  C1*  C 0 1 N N S 15.517 3.495  0.995   10.408  -0.132 -0.109 "C1'"  GP5 12 
GP5 "O4'"  O4*  O 0 1 N N N 16.019 3.815  -0.307  9.040   0.228  -0.399 "O4'"  GP5 13 
GP5 "C2'"  C2*  C 0 1 N N S 16.544 4.162  1.884   10.649  0.457  1.305  "C2'"  GP5 14 
GP5 "O2'"  O2*  O 0 1 N N N 16.561 3.518  3.166   12.037  0.712  1.527  "O2'"  GP5 15 
GP5 "C3'"  C3*  C 0 1 N N R 17.840 3.853  1.128   9.845   1.781  1.244  "C3'"  GP5 16 
GP5 "O3'"  O3*  O 0 1 N N N 18.462 2.709  1.710   10.713  2.879  0.954  "O3'"  GP5 17 
GP5 "C4'"  C4*  C 0 1 N N S 17.388 3.494  -0.292  8.845   1.565  0.092  "C4'"  GP5 18 
GP5 "C5'"  C5*  C 0 1 N N N 17.885 4.427  -1.399  7.413   1.727  0.606  "C5'"  GP5 19 
GP5 "O5'"  O5*  O 0 1 N N N 18.379 3.693  -2.539  6.499   1.625  -0.489 "O5'"  GP5 20 
GP5 PCC    PCC  P 0 1 N N R 17.487 3.109  -3.807  5.020   1.804  0.121  PCC    GP5 21 
GP5 OAN    OAN  O 0 1 N N N 16.102 2.537  -3.192  4.810   0.815  1.202  OAN    GP5 22 
GP5 OAE    OAE  O 0 1 N N N 17.239 4.134  -4.838  4.861   3.291  0.716  OAE    GP5 23 
GP5 OBG    OBG  O 0 1 N N N 18.361 1.847  -4.329  3.929   1.570  -1.040 OBG    GP5 24 
GP5 PCE    PCE  P 0 1 N N S 19.207 1.201  -3.112  2.509   1.365  -0.309 PCE    GP5 25 
GP5 OAP    OAP  O 0 1 N N N 18.823 -0.345 -2.817  2.347   2.386  0.750  OAP    GP5 26 
GP5 OAG    OAG  O 0 1 N N N 20.516 1.899  -2.815  2.451   -0.104 0.348  OAG    GP5 27 
GP5 OBI    OBI  O 0 1 N N N 20.227 0.384  -4.192  1.324   1.517  -1.388 OBI    GP5 28 
GP5 PCG    PCG  P 0 1 N N R 19.890 -0.512 -5.537  -0.020  1.834  -0.560 PCG    GP5 29 
GP5 OAR    OAR  O 0 1 N N N 18.556 -1.315 -5.214  -0.049  1.011  0.669  OAR    GP5 30 
GP5 OAI    OAI  O 0 1 N N N 19.731 0.312  -6.763  -0.050  3.394  -0.162 OAI    GP5 31 
GP5 OBJ    OBJ  O 0 1 N N N 20.952 -1.663 -5.848  -1.304  1.488  -1.469 OBJ    GP5 32 
GP5 PCF    PCF  P 0 1 N N R 22.215 -2.171 -5.013  -2.574  1.440  -0.480 PCF    GP5 33 
GP5 OAQ    OAQ  O 0 1 N N N 21.682 -3.141 -3.853  -2.530  2.601  0.437  OAQ    GP5 34 
GP5 OAH    OAH  O 0 1 N N N 23.067 -1.078 -4.443  -2.535  0.077  0.377  OAH    GP5 35 
GP5 OBH    OBH  O 0 1 N N N 23.060 -3.019 -6.013  -3.930  1.491  -1.346 OBH    GP5 36 
GP5 PCD    PCD  P 0 1 N N S 22.659 -4.343 -6.800  -5.101  1.969  -0.350 PCD    GP5 37 
GP5 OAO    OAO  O 0 1 N N N 23.520 -5.424 -6.086  -4.922  1.322  0.969  OAO    GP5 38 
GP5 OAF    OAF  O 0 1 N N N 21.221 -4.728 -6.801  -5.036  3.568  -0.176 OAF    GP5 39 
GP5 OBD    OBD  O 0 1 N N N 23.290 -4.001 -8.213  -6.530  1.553  -0.962 OBD    GP5 40 
GP5 CAV    CAV  C 0 1 N N N 22.637 -3.014 -9.055  -7.514  1.896  0.016  CAV    GP5 41 
GP5 CBZ    CBZ  C 0 1 N N R 22.729 -3.467 -10.518 -8.903  1.525  -0.507 CBZ    GP5 42 
GP5 OBF    OBF  O 0 1 N N N 24.120 -3.571 -10.904 -9.018  0.096  -0.619 OBF    GP5 43 
GP5 CBV    CBV  C 0 1 N N S 22.162 -4.894 -10.562 -9.981  1.997  0.489  CBV    GP5 44 
GP5 OAL    OAL  O 0 1 N N N 21.391 -5.021 -11.745 -10.874 2.923  -0.133 OAL    GP5 45 
GP5 CBW    CBW  C 0 1 N N R 23.390 -5.799 -10.618 -10.732 0.696  0.876  CBW    GP5 46 
GP5 OAM    OAM  O 0 1 N N N 23.090 -6.979 -11.382 -12.140 0.924  0.951  OAM    GP5 47 
GP5 CXB    CXB  C 0 1 N N R 24.403 -4.905 -11.334 -10.386 -0.243 -0.308 CXB    GP5 48 
GP5 NBY    NBY  N 0 1 Y N N 25.813 -5.157 -10.966 -10.491 -1.648 0.095  NBY    GP5 49 
GP5 CAT    CAT  C 0 1 Y N N 26.298 -5.433 -9.741  -9.488  -2.416 0.610  CAT    GP5 50 
GP5 NAX    NAX  N 0 1 Y N N 27.616 -5.586 -9.821  -9.932  -3.614 0.856  NAX    GP5 51 
GP5 CBP    CBP  C 0 1 Y N N 27.975 -5.403 -11.093 -11.242 -3.685 0.516  CBP    GP5 52 
GP5 CBR    CBR  C 0 1 Y N N 26.823 -5.113 -11.819 -11.614 -2.427 0.031  CBR    GP5 53 
GP5 NAZ    NAZ  N 0 1 N N N 26.861 -4.871 -13.150 -12.869 -2.221 -0.385 NAZ    GP5 54 
GP5 CBL    CBL  C 0 1 N N N 28.031 -4.899 -13.805 -13.767 -3.180 -0.337 CBL    GP5 55 
GP5 NAB    NAB  N 0 1 N N N 28.076 -4.666 -15.111 -15.043 -2.921 -0.770 NAB    GP5 56 
GP5 NBB    NBB  N 0 1 N N N 29.219 -5.177 -13.117 -13.466 -4.425 0.130  NBB    GP5 57 
GP5 CBN    CBN  C 0 1 N N N 29.198 -5.426 -11.752 -12.218 -4.709 0.562  CBN    GP5 58 
GP5 OAD    OAD  O 0 1 N N N 30.253 -5.665 -11.172 -11.939 -5.819 0.982  OAD    GP5 59 
GP5 HN1    HN1  H 0 1 N N N 10.887 7.665  2.292   14.418  -4.793 -0.634 HN1    GP5 60 
GP5 HN21   1HN2 H 0 0 N N N 12.431 7.900  4.194   15.446  -1.454 -0.884 HN21   GP5 61 
GP5 HN22   2HN2 H 0 0 N N N 14.060 7.931  3.841   15.956  -3.055 -0.919 HN22   GP5 62 
GP5 H8     H8   H 0 1 N N N 13.547 2.482  -0.638  8.532   -2.271 0.251  H8     GP5 63 
GP5 "H1'"  H1*  H 0 1 N N N 15.419 2.481  1.449   11.085  0.320  -0.833 "H1'"  GP5 64 
GP5 "H2'"  H2*  H 0 1 N N N 16.366 5.247  2.070   10.249  -0.206 2.072  "H2'"  GP5 65 
GP5 H2     H2   H 0 1 N N N 17.206 3.937  3.724   12.105  1.160  2.382  H2     GP5 66 
GP5 "H3'"  H3*  H 0 1 N N N 18.559 4.705  1.153   9.317   1.951  2.182  "H3'"  GP5 67 
GP5 H1     H1   H 0 1 N N N 19.266 2.517  1.241   11.314  2.966  1.706  H1     GP5 68 
GP5 "H4'"  H4*  H 0 1 N N N 17.733 2.450  -0.479  9.036   2.284  -0.704 "H4'"  GP5 69 
GP5 "H5'1" 1H5* H 0 0 N N N 18.650 5.141  -1.014  7.197   0.944  1.333  "H5'1" GP5 70 
GP5 "H5'2" 2H5* H 0 0 N N N 17.097 5.158  -1.697  7.305   2.702  1.080  "H5'2" GP5 71 
GP5 HAE    HAE  H 0 1 N N N 16.728 3.799  -5.565  5.005   3.903  -0.019 HAE    GP5 72 
GP5 HAG    HAG  H 0 1 N N N 21.013 1.519  -2.100  2.560   -0.738 -0.374 HAG    GP5 73 
GP5 HAI    HAI  H 0 1 N N N 19.537 -0.204 -7.537  -0.030  3.894  -0.990 HAI    GP5 74 
GP5 HAH    HAH  H 0 1 N N N 23.818 -1.380 -3.946  -2.565  -0.653 -0.257 HAH    GP5 75 
GP5 HAF    HAF  H 0 1 N N N 20.982 -5.518 -7.271  -5.157  3.951  -1.056 HAF    GP5 76 
GP5 HAV1   1HAV H 0 0 N N N 23.045 -1.988 -8.902  -7.315  1.351  0.938  HAV1   GP5 77 
GP5 HAV2   2HAV H 0 0 N N N 21.587 -2.813 -8.738  -7.474  2.968  0.211  HAV2   GP5 78 
GP5 HBZ    HBZ  H 0 1 N N N 22.191 -2.753 -11.184 -9.069  1.987  -1.480 HBZ    GP5 79 
GP5 HBV    HBV  H 0 1 N N N 21.512 -5.148 -9.692  -9.518  2.446  1.367  HBV    GP5 80 
GP5 HAL    HAL  H 0 1 N N N 21.040 -5.903 -11.772 -11.557 3.134  0.519  HAL    GP5 81 
GP5 HBW    HBW  H 0 1 N N N 23.750 -6.165 -9.628  -10.354 0.292  1.815  HBW    GP5 82 
GP5 HAM    HAM  H 0 1 N N N 23.854 -7.542 -11.417 -12.288 1.512  1.704  HAM    GP5 83 
GP5 HXB    HXB  H 0 1 N N N 24.303 -5.096 -12.428 -11.035 -0.040 -1.161 HXB    GP5 84 
GP5 HAT    HAT  H 0 1 N N N 25.706 -5.520 -8.814  -8.476  -2.081 0.786  HAT    GP5 85 
GP5 HAB1   1HAB H 0 0 N N N 27.630 -3.767 -15.291 -15.716 -3.619 -0.742 HAB1   GP5 86 
GP5 HAB2   2HAB H 0 0 N N N 28.966 -4.687 -15.609 -15.272 -2.040 -1.105 HAB2   GP5 87 
GP5 HBB    HBB  H 0 1 N N N 30.109 -5.198 -13.615 -14.152 -5.111 0.151  HBB    GP5 88 
# 
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 
GP5 O6    C6     DOUB N N 1  
GP5 C6    N1     SING N N 2  
GP5 C6    C5     SING N N 3  
GP5 N1    C2     SING N N 4  
GP5 N1    HN1    SING N N 5  
GP5 C2    N2     SING N N 6  
GP5 C2    N3     DOUB N N 7  
GP5 N2    HN21   SING N N 8  
GP5 N2    HN22   SING N N 9  
GP5 N3    C4     SING N N 10 
GP5 C4    C5     DOUB Y N 11 
GP5 C4    N9     SING Y N 12 
GP5 C5    N7     SING Y N 13 
GP5 N7    C8     DOUB Y N 14 
GP5 C8    N9     SING Y N 15 
GP5 C8    H8     SING N N 16 
GP5 N9    "C1'"  SING N N 17 
GP5 "C1'" "O4'"  SING N N 18 
GP5 "C1'" "C2'"  SING N N 19 
GP5 "C1'" "H1'"  SING N N 20 
GP5 "O4'" "C4'"  SING N N 21 
GP5 "C2'" "O2'"  SING N N 22 
GP5 "C2'" "C3'"  SING N N 23 
GP5 "C2'" "H2'"  SING N N 24 
GP5 "O2'" H2     SING N N 25 
GP5 "C3'" "O3'"  SING N N 26 
GP5 "C3'" "C4'"  SING N N 27 
GP5 "C3'" "H3'"  SING N N 28 
GP5 "O3'" H1     SING N N 29 
GP5 "C4'" "C5'"  SING N N 30 
GP5 "C4'" "H4'"  SING N N 31 
GP5 "C5'" "O5'"  SING N N 32 
GP5 "C5'" "H5'1" SING N N 33 
GP5 "C5'" "H5'2" SING N N 34 
GP5 "O5'" PCC    SING N N 35 
GP5 PCC   OAN    DOUB N N 36 
GP5 PCC   OAE    SING N N 37 
GP5 PCC   OBG    SING N N 38 
GP5 OAE   HAE    SING N N 39 
GP5 OBG   PCE    SING N N 40 
GP5 PCE   OAP    DOUB N N 41 
GP5 PCE   OAG    SING N N 42 
GP5 PCE   OBI    SING N N 43 
GP5 OAG   HAG    SING N N 44 
GP5 OBI   PCG    SING N N 45 
GP5 PCG   OAR    DOUB N N 46 
GP5 PCG   OAI    SING N N 47 
GP5 PCG   OBJ    SING N N 48 
GP5 OAI   HAI    SING N N 49 
GP5 OBJ   PCF    SING N N 50 
GP5 PCF   OAQ    DOUB N N 51 
GP5 PCF   OAH    SING N N 52 
GP5 PCF   OBH    SING N N 53 
GP5 OAH   HAH    SING N N 54 
GP5 OBH   PCD    SING N N 55 
GP5 PCD   OAO    DOUB N N 56 
GP5 PCD   OAF    SING N N 57 
GP5 PCD   OBD    SING N N 58 
GP5 OAF   HAF    SING N N 59 
GP5 OBD   CAV    SING N N 60 
GP5 CAV   CBZ    SING N N 61 
GP5 CAV   HAV1   SING N N 62 
GP5 CAV   HAV2   SING N N 63 
GP5 CBZ   OBF    SING N N 64 
GP5 CBZ   CBV    SING N N 65 
GP5 CBZ   HBZ    SING N N 66 
GP5 OBF   CXB    SING N N 67 
GP5 CBV   OAL    SING N N 68 
GP5 CBV   CBW    SING N N 69 
GP5 CBV   HBV    SING N N 70 
GP5 OAL   HAL    SING N N 71 
GP5 CBW   OAM    SING N N 72 
GP5 CBW   CXB    SING N N 73 
GP5 CBW   HBW    SING N N 74 
GP5 OAM   HAM    SING N N 75 
GP5 CXB   NBY    SING N N 76 
GP5 CXB   HXB    SING N N 77 
GP5 NBY   CAT    SING Y N 78 
GP5 NBY   CBR    SING Y N 79 
GP5 CAT   NAX    DOUB Y N 80 
GP5 CAT   HAT    SING N N 81 
GP5 NAX   CBP    SING Y N 82 
GP5 CBP   CBR    DOUB Y N 83 
GP5 CBP   CBN    SING N N 84 
GP5 CBR   NAZ    SING N N 85 
GP5 NAZ   CBL    DOUB N N 86 
GP5 CBL   NAB    SING N N 87 
GP5 CBL   NBB    SING N N 88 
GP5 NAB   HAB1   SING N N 89 
GP5 NAB   HAB2   SING N N 90 
GP5 NBB   CBN    SING N N 91 
GP5 NBB   HBB    SING N N 92 
GP5 CBN   OAD    DOUB N N 93 
# 
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 
GP5 InChI            InChI                1.02b 
;InChI=1/C20H29N10O24P5/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(49-17)1-47-55(37,38)51-57(41,42)53-59(45,46)54-58(43,44)52-56(39,40)48-2-6-10(32)12(34)18(50-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6+,9-,10+,11-,12+,17-,18+/f/h27-28,37,39,41,43,45H,21-22H2
;
GP5 InChIKey         InChI                1.02b RELSGTOCAPVUGP-KMOQSRAFDY 
GP5 SMILES_CANONICAL CACTVS               3.341 NC1=Nc2n(cnc2C(=O)N1)[C@H]3O[C@@H](CO[P@](O)(=O)O[P@@](O)(=O)O[P@](O)(=O)O[P@@](O)(=O)O[P@](O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)n5cnc6C(=O)NC(=Nc56)N)[C@H](O)[C@@H]3O 
GP5 SMILES           CACTVS               3.341 NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH](CO[P](O)(=O)O[P](O)(=O)O[P](O)(=O)O[P](O)(=O)O[P](O)(=O)OC[CH]4O[CH]([CH](O)[CH]4O)n5cnc6C(=O)NC(=Nc56)N)[CH](O)[CH]3O 
GP5 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc2c(n1[C@@H]3[C@H]([C@H]([C@@H](O3)CO[P@@](=O)(O)O[P@@](=O)(O)OP(=O)(O)O[P@](=O)(O)O[P@@](=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)n5cnc6c5N=C(NC6=O)N)O)O)O)O)N=C(NC2=O)N 
GP5 SMILES           "OpenEye OEToolkits" 1.5.0 c1nc2c(n1C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OCC4C(C(C(O4)n5cnc6c5N=C(NC6=O)N)O)O)O)O)N=C(NC2=O)N 
# 
_pdbx_chem_comp_identifier.comp_id           GP5 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   1.5.0 
_pdbx_chem_comp_identifier.identifier        
;[[[[[(2S,3R,4S,5S)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl] [(2S,3R,4S,5S)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl hydrogen phosphate
;
# 
