data_GP3
# 
_chem_comp.id                                    GP3 
_chem_comp.name                                  "DIGUANOSINE-5'-TRIPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H27 N10 O18 P3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_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                        788.406 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GP3 
_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        1CKO 
_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 
GP3 N9A  AN9  N 0 1 Y N N 44.687 61.859 -3.237 0.224  -0.696 -8.635  N9A  GP3 1  
GP3 C8A  AC8  C 0 1 Y N N 45.326 62.778 -2.439 -0.954 -1.289 -8.287  C8A  GP3 2  
GP3 N7A  AN7  N 0 1 Y N N 44.936 64.034 -2.568 -1.243 -2.230 -9.138  N7A  GP3 3  
GP3 C5A  AC5  C 0 1 Y N N 43.978 63.957 -3.550 -0.270 -2.296 -10.080 C5A  GP3 4  
GP3 C6A  AC6  C 0 1 N N N 43.204 64.964 -4.065 -0.057 -3.105 -11.221 C6A  GP3 5  
GP3 O6A  AO6  O 0 1 N N N 43.279 66.116 -3.709 -0.857 -3.971 -11.531 O6A  GP3 6  
GP3 N1A  AN1  N 0 1 N N N 42.308 64.540 -5.036 1.051  -2.889 -11.962 N1A  GP3 7  
GP3 C2A  AC2  C 0 1 N N N 42.203 63.258 -5.449 1.941  -1.921 -11.603 C2A  GP3 8  
GP3 N2A  AN2  N 0 1 N N N 41.308 62.965 -6.421 3.062  -1.728 -12.372 N2A  GP3 9  
GP3 N3A  AN3  N 0 1 N N N 42.931 62.269 -4.950 1.755  -1.164 -10.546 N3A  GP3 10 
GP3 C4A  AC4  C 0 1 Y N N 43.804 62.672 -3.997 0.677  -1.315 -9.767  C4A  GP3 11 
GP3 O5D  AO5* O 0 1 N N N 46.514 58.176 -6.505 0.413  1.078  -3.750  O5D  GP3 12 
GP3 C5D  AC5* C 0 1 N N N 45.170 58.181 -6.027 0.003  1.996  -4.765  C5D  GP3 13 
GP3 C4D  AC4* C 0 1 N N R 45.083 58.568 -4.632 0.790  1.722  -6.048  C4D  GP3 14 
GP3 O4D  AO4* O 0 1 N N N 45.508 59.904 -4.429 0.522  0.386  -6.526  O4D  GP3 15 
GP3 C3D  AC3* C 0 1 N N S 43.658 58.569 -4.287 0.311  2.651  -7.185  C3D  GP3 16 
GP3 O3D  AO3* O 0 1 N N N 43.158 57.264 -4.015 1.185  3.774  -7.316  O3D  GP3 17 
GP3 C2D  AC2* C 0 1 N N R 43.614 59.375 -3.097 0.375  1.763  -8.450  C2D  GP3 18 
GP3 O2D  AO2* O 0 1 N N N 43.749 58.483 -1.996 1.289  2.312  -9.401  O2D  GP3 19 
GP3 C1D  AC1* C 0 1 N N R 44.883 60.342 -3.236 0.883  0.402  -7.925  C1D  GP3 20 
GP3 PA   PA   P 0 1 N N R 47.164 56.795 -6.906 -0.450 1.422  -2.435  PA   GP3 21 
GP3 O1A  O1A  O 0 1 N N N 48.126 57.031 -8.005 -0.182 2.817  -2.020  O1A  GP3 22 
GP3 O2A  O2A  O 0 1 N N N 47.597 56.082 -5.687 -2.017 1.252  -2.762  O2A  GP3 23 
GP3 O3A  O3A  O 0 1 N N N 45.912 56.095 -7.447 -0.038 0.420  -1.245  O3A  GP3 24 
GP3 PB   PB   P 0 1 N N N 45.746 54.908 -8.355 -0.935 0.819  0.030   PB   GP3 25 
GP3 O1B  O1B  O 0 1 N N N 46.552 55.143 -9.559 -2.368 0.672  -0.307  O1B  GP3 26 
GP3 O2B  O2B  O 0 1 N N N 44.272 54.677 -8.491 -0.635 2.347  0.440   O2B  GP3 27 
GP3 O3B  O3B  O 0 1 N N N 46.365 53.680 -7.552 -0.573 -0.148 1.265   O3B  GP3 28 
GP3 PG   PG   P 0 1 N N R 45.720 52.279 -7.111 -1.501 0.305  2.500   PG   GP3 29 
GP3 O1G  O1G  O 0 1 N N N 46.786 51.503 -6.370 -2.926 0.165  2.123   O1G  GP3 30 
GP3 O2G  O2G  O 0 1 N N N 45.067 51.613 -8.279 -1.192 1.841  2.868   O2G  GP3 31 
GP3 O5E  BO5* O 0 1 N N N 44.602 52.756 -6.052 -1.190 -0.625 3.776   O5E  GP3 32 
GP3 C5E  BC5* C 0 1 N N N 44.977 53.492 -4.838 -2.041 -0.176 4.832   C5E  GP3 33 
GP3 C4E  BC4* C 0 1 N N R 43.800 54.157 -3.993 -1.793 -1.024 6.082   C4E  GP3 34 
GP3 O4E  BO4* O 0 1 N N N 42.681 53.287 -3.758 -0.432 -0.869 6.516   O4E  GP3 35 
GP3 C3E  BC3* C 0 1 N N S 44.220 54.592 -2.603 -2.701 -0.542 7.230   C3E  GP3 36 
GP3 O3E  BO3* O 0 1 N N N 44.978 55.813 -2.594 -3.567 -1.591 7.666   O3E  GP3 37 
GP3 C2E  BC2* C 0 1 N N R 42.959 54.761 -1.898 -1.708 -0.154 8.357   C2E  GP3 38 
GP3 O2E  BO2* O 0 1 N N N 42.514 56.096 -2.105 -2.194 -0.578 9.632   O2E  GP3 39 
GP3 C1E  BC1* C 0 1 N N R 41.977 53.763 -2.612 -0.438 -0.947 7.957   C1E  GP3 40 
GP3 N9B  BN9  N 0 1 Y N N 41.377 52.677 -1.761 0.762  -0.317 8.513   N9B  GP3 41 
GP3 C8B  BC8  C 0 1 Y N N 40.059 52.368 -1.601 1.473  0.701  7.949   C8B  GP3 42 
GP3 N7B  BN7  N 0 1 Y N N 39.751 51.455 -0.729 2.480  1.012  8.713   N7B  GP3 43 
GP3 C5B  BC5  C 0 1 Y N N 41.005 51.109 -0.228 2.475  0.214  9.808   C5B  GP3 44 
GP3 C6B  BC6  C 0 1 N N N 41.340 50.150 0.786  3.304  0.102  10.949  C6B  GP3 45 
GP3 O6B  BO6  O 0 1 N N N 40.543 49.461 1.439  4.271  0.830  11.092  O6B  GP3 46 
GP3 N1B  BN1  N 0 1 N N N 42.727 50.093 1.033  2.997  -0.832 11.875  N1B  GP3 47 
GP3 C2B  BC2  C 0 1 N N N 43.680 50.845 0.342  1.913  -1.640 11.705  C2B  GP3 48 
GP3 N2B  BN2  N 0 1 N N N 44.981 50.690 0.659  1.626  -2.580 12.663  N2B  GP3 49 
GP3 N3B  BN3  N 0 1 N N N 43.341 51.736 -0.616 1.135  -1.546 10.650  N3B  GP3 50 
GP3 C4B  BC4  C 0 1 Y N N 42.007 51.837 -0.838 1.373  -0.640 9.694   C4B  GP3 51 
GP3 H8A  AH8  H 0 1 N N N 46.122 62.517 -1.721 -1.557 -1.019 -7.432  H8A  GP3 52 
GP3 H1A  AH1  H 0 1 N N N 41.684 65.216 -5.476 1.219  -3.431 -12.749 H1A  GP3 53 
GP3 H21A AH21 H 0 0 N N N 41.228 61.997 -6.732 3.702  -1.041 -12.132 H21A GP3 54 
GP3 H22A AH22 H 0 0 N N N 41.489 63.560 -7.229 3.215  -2.282 -13.154 H22A GP3 55 
GP3 H51A AH51 H 0 0 N N N 44.518 58.823 -6.664 0.196  3.016  -4.432  H51A GP3 56 
GP3 H52A AH52 H 0 0 N N N 44.676 57.196 -6.203 -1.061 1.873  -4.959  H52A GP3 57 
GP3 H4D  AH4* H 0 1 N N N 45.713 57.871 -4.031 1.858  1.855  -5.874  H4D  GP3 58 
GP3 H3D  AH3* H 0 1 N N N 43.027 58.950 -5.123 -0.710 2.983  -7.002  H3D  GP3 59 
GP3 HO3A AHO3 H 0 0 N N N 42.234 57.264 -3.791 0.837  4.317  -8.037  HO3A GP3 60 
GP3 H2D  AH2* H 0 1 N N N 42.680 59.968 -2.953 -0.614 1.655  -8.892  H2D  GP3 61 
GP3 HO2A AHO2 H 0 0 N N N 43.719 59.015 -1.209 0.950  3.184  -9.644  HO2A GP3 62 
GP3 H1D  AH1* H 0 1 N N N 45.477 60.244 -2.297 1.965  0.331  -8.038  H1D  GP3 63 
GP3 HOA2 2HOA H 0 0 N N N 47.988 55.250 -5.928 -2.148 0.331  -3.028  HOA2 GP3 64 
GP3 HOB2 2HOB H 0 0 N N N 44.167 53.927 -9.064 0.306  2.400  0.653   HOB2 GP3 65 
GP3 HOG2 2HOG H 0 0 N N N 44.685 50.783 -8.017 -0.256 1.889  3.107   HOG2 GP3 66 
GP3 H51B BH51 H 0 0 N N N 45.579 52.828 -4.174 -1.824 0.868  5.054   H51B GP3 67 
GP3 H52B BH52 H 0 0 N N N 45.732 54.270 -5.095 -3.082 -0.274 4.527   H52B GP3 68 
GP3 H4E  BH4* H 0 1 N N N 43.522 55.021 -4.639 -1.996 -2.072 5.864   H4E  GP3 69 
GP3 H3E  BH3* H 0 1 N N N 44.899 53.843 -2.133 -3.282 0.325  6.918   H3E  GP3 70 
GP3 HO3B BHO3 H 0 0 N N N 45.241 56.085 -1.722 -4.064 -1.248 8.422   HO3B GP3 71 
GP3 H2E  BH2* H 0 1 N N N 43.030 54.571 -0.801 -1.514 0.918  8.354   H2E  GP3 72 
GP3 HO2B BHO2 H 0 0 N N N 41.690 56.206 -1.644 -2.981 -0.049 9.821   HO2B GP3 73 
GP3 H1E  BH1* H 0 1 N N N 41.045 54.307 -2.892 -0.513 -1.983 8.286   H1E  GP3 74 
GP3 H8B  BH8  H 0 1 N N N 39.249 52.852 -2.172 1.237  1.178  7.009   H8B  GP3 75 
GP3 H1B  BH1  H 0 1 N N N 43.064 49.464 1.762  3.551  -0.927 12.666  H1B  GP3 76 
GP3 H21B BH21 H 0 0 N N N 45.676 51.239 0.154  0.858  -3.163 12.555  H21B GP3 77 
GP3 H22B BH22 H 0 0 N N N 45.223 49.701 0.585  2.191  -2.662 13.447  H22B GP3 78 
# 
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 
GP3 N9A C8A  SING Y N 1  
GP3 N9A C4A  SING Y N 2  
GP3 N9A C1D  SING N N 3  
GP3 C8A N7A  DOUB Y N 4  
GP3 C8A H8A  SING N N 5  
GP3 N7A C5A  SING Y N 6  
GP3 C5A C6A  SING N N 7  
GP3 C5A C4A  DOUB Y N 8  
GP3 C6A O6A  DOUB N N 9  
GP3 C6A N1A  SING N N 10 
GP3 N1A C2A  SING N N 11 
GP3 N1A H1A  SING N N 12 
GP3 C2A N2A  SING N N 13 
GP3 C2A N3A  DOUB N N 14 
GP3 N2A H21A SING N N 15 
GP3 N2A H22A SING N N 16 
GP3 N3A C4A  SING N N 17 
GP3 O5D C5D  SING N N 18 
GP3 O5D PA   SING N N 19 
GP3 C5D C4D  SING N N 20 
GP3 C5D H51A SING N N 21 
GP3 C5D H52A SING N N 22 
GP3 C4D O4D  SING N N 23 
GP3 C4D C3D  SING N N 24 
GP3 C4D H4D  SING N N 25 
GP3 O4D C1D  SING N N 26 
GP3 C3D O3D  SING N N 27 
GP3 C3D C2D  SING N N 28 
GP3 C3D H3D  SING N N 29 
GP3 O3D HO3A SING N N 30 
GP3 C2D O2D  SING N N 31 
GP3 C2D C1D  SING N N 32 
GP3 C2D H2D  SING N N 33 
GP3 O2D HO2A SING N N 34 
GP3 C1D H1D  SING N N 35 
GP3 PA  O1A  DOUB N N 36 
GP3 PA  O2A  SING N N 37 
GP3 PA  O3A  SING N N 38 
GP3 O2A HOA2 SING N N 39 
GP3 O3A PB   SING N N 40 
GP3 PB  O1B  DOUB N N 41 
GP3 PB  O2B  SING N N 42 
GP3 PB  O3B  SING N N 43 
GP3 O2B HOB2 SING N N 44 
GP3 O3B PG   SING N N 45 
GP3 PG  O1G  DOUB N N 46 
GP3 PG  O2G  SING N N 47 
GP3 PG  O5E  SING N N 48 
GP3 O2G HOG2 SING N N 49 
GP3 O5E C5E  SING N N 50 
GP3 C5E C4E  SING N N 51 
GP3 C5E H51B SING N N 52 
GP3 C5E H52B SING N N 53 
GP3 C4E O4E  SING N N 54 
GP3 C4E C3E  SING N N 55 
GP3 C4E H4E  SING N N 56 
GP3 O4E C1E  SING N N 57 
GP3 C3E O3E  SING N N 58 
GP3 C3E C2E  SING N N 59 
GP3 C3E H3E  SING N N 60 
GP3 O3E HO3B SING N N 61 
GP3 C2E O2E  SING N N 62 
GP3 C2E C1E  SING N N 63 
GP3 C2E H2E  SING N N 64 
GP3 O2E HO2B SING N N 65 
GP3 C1E N9B  SING N N 66 
GP3 C1E H1E  SING N N 67 
GP3 N9B C8B  SING Y N 68 
GP3 N9B C4B  SING Y N 69 
GP3 C8B N7B  DOUB Y N 70 
GP3 C8B H8B  SING N N 71 
GP3 N7B C5B  SING Y N 72 
GP3 C5B C6B  SING N N 73 
GP3 C5B C4B  DOUB Y N 74 
GP3 C6B O6B  DOUB N N 75 
GP3 C6B N1B  SING N N 76 
GP3 N1B C2B  SING N N 77 
GP3 N1B H1B  SING N N 78 
GP3 C2B N2B  SING N N 79 
GP3 C2B N3B  DOUB N N 80 
GP3 N2B H21B SING N N 81 
GP3 N2B H22B SING N N 82 
GP3 N3B C4B  SING N N 83 
# 
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 
GP3 InChI            InChI                1.02b 
;InChI=1/C20H27N10O18P3/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(45-17)1-43-49(37,38)47-51(41,42)48-50(39,40)44-2-6-10(32)12(34)18(46-6)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)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1/f/h27-28,37,39,41H,21-22H2
;
GP3 InChIKey         InChI                1.02b AAXYAFFKOSNMEB-OCOKSQPWDO 
GP3 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)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)n5cnc6C(=O)NC(=Nc56)N)[C@@H](O)[C@H]3O 
GP3 SMILES           CACTVS               3.341 NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH](CO[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 
GP3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc2c(n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@@](=O)(O)OP(=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 
GP3 SMILES           "OpenEye OEToolkits" 1.5.0 c1nc2c(n1C3C(C(C(O3)COP(=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           GP3 
_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        
"[[[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl] [(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl hydrogen phosphate" 
# 
