data_GPG
# 
_chem_comp.id                                    GPG 
_chem_comp.name                                  "GUANYLYL-2',5'-PHOSPHOGUANOSINE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H25 N10 O12 P" 
_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                    2011-06-04 
_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                        628.446 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GPG 
_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        2RNT 
_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 
GPG N9A  AN9  N 0 1 Y N N 17.934 33.256 20.785 -4.541 -1.333 -0.055 N9A  GPG 1  
GPG C8A  AC8  C 0 1 Y N N 17.491 32.108 20.148 -5.227 -1.728 -1.167 C8A  GPG 2  
GPG N7A  AN7  N 0 1 Y N N 16.206 31.858 20.167 -4.613 -2.725 -1.734 N7A  GPG 3  
GPG C5A  AC5  C 0 1 Y N N 15.721 32.906 20.855 -3.500 -3.029 -1.022 C5A  GPG 4  
GPG C6A  AC6  C 0 1 N N N 14.441 33.382 21.299 -2.475 -3.994 -1.161 C6A  GPG 5  
GPG O6A  AO6  O 0 1 N N N 13.405 32.749 21.050 -2.485 -4.787 -2.087 O6A  GPG 6  
GPG N1A  AN1  N 0 1 N N N 14.292 34.597 22.053 -1.486 -4.016 -0.241 N1A  GPG 7  
GPG C2A  AC2  C 0 1 N N N 15.406 35.416 22.399 -1.485 -3.125 0.791  C2A  GPG 8  
GPG N2A  AN2  N 0 1 N N N 15.229 36.521 23.090 -0.467 -3.171 1.710  N2A  GPG 9  
GPG N3A  AN3  N 0 1 N N N 16.620 34.976 21.972 -2.431 -2.223 0.931  N3A  GPG 10 
GPG C4A  AC4  C 0 1 Y N N 16.756 33.786 21.249 -3.440 -2.138 0.056  C4A  GPG 11 
GPG O5D  AO5* O 0 1 N N N 18.236 34.156 24.504 -8.913 1.358  0.827  O5D  GPG 12 
GPG C5D  AC5* C 0 1 N N N 19.493 34.832 24.326 -7.689 2.018  0.501  C5D  GPG 13 
GPG C4D  AC4* C 0 1 N N R 19.871 34.932 22.889 -6.536 1.358  1.259  C4D  GPG 14 
GPG O4D  AO4* O 0 1 N N N 19.897 33.657 22.154 -6.330 0.021  0.775  O4D  GPG 15 
GPG C3D  AC3* C 0 1 N N R 18.831 35.740 22.027 -5.231 2.140  1.012  C3D  GPG 16 
GPG O3D  AO3* O 0 1 N N N 18.965 37.126 22.236 -4.702 2.638  2.243  O3D  GPG 17 
GPG C2D  AC2* C 0 1 N N R 19.468 35.287 20.679 -4.272 1.093  0.395  C2D  GPG 18 
GPG O2D  AO2* O 0 1 N N N 20.583 36.200 20.460 -2.953 1.233  0.927  O2D  GPG 19 
GPG C1D  AC1* C 0 1 N N R 19.333 33.790 20.887 -4.912 -0.243 0.851  C1D  GPG 20 
GPG P    P    P 0 1 N N R 20.931 37.385 19.426 -1.964 1.432  -0.328 P    GPG 21 
GPG O1P  O1P  O 0 1 N N N 19.817 37.187 18.418 -2.431 2.573  -1.148 O1P  GPG 22 
GPG O2P  O2P  O 0 1 N N N 22.348 37.389 18.957 -1.958 0.094  -1.224 O2P  GPG 23 
GPG O5E  BO5* O 0 1 N N N 20.892 38.850 19.995 -0.474 1.728  0.205  O5E  GPG 24 
GPG C5E  BC5* C 0 1 N N N 21.897 39.711 20.580 0.327  2.011  -0.944 C5E  GPG 25 
GPG C4E  BC4* C 0 1 N N R 22.562 40.758 19.726 1.763  2.303  -0.506 C4E  GPG 26 
GPG O4E  BO4* O 0 1 N N N 21.959 42.037 19.488 2.370  1.116  0.051  O4E  GPG 27 
GPG C3E  BC3* C 0 1 N N S 23.928 41.147 20.347 2.640  2.659  -1.727 C3E  GPG 28 
GPG O3E  BO3* O 0 1 N N N 24.950 40.965 19.408 2.771  4.076  -1.854 O3E  GPG 29 
GPG C2E  BC2* C 0 1 N N R 23.731 42.530 20.995 4.009  2.013  -1.409 C2E  GPG 30 
GPG O2E  BO2* O 0 1 N N N 24.731 43.511 20.725 5.028  3.012  -1.332 O2E  GPG 31 
GPG C1E  BC1* C 0 1 N N R 22.543 43.085 20.255 3.794  1.341  -0.034 C1E  GPG 32 
GPG N9B  BN9  N 0 1 Y N N 21.556 43.739 21.159 4.516  0.068  0.030  N9B  GPG 33 
GPG C8B  BC8  C 0 1 Y N N 20.824 43.304 22.245 4.008  -1.164 -0.265 C8B  GPG 34 
GPG N7B  BN7  N 0 1 Y N N 20.014 44.196 22.756 4.927  -2.070 -0.100 N7B  GPG 35 
GPG C5B  BC5  C 0 1 Y N N 20.219 45.312 21.971 6.074  -1.477 0.310  C5B  GPG 36 
GPG C6B  BC6  C 0 1 N N N 19.723 46.679 21.868 7.366  -1.952 0.636  C6B  GPG 37 
GPG O6B  BO6  O 0 1 N N N 18.872 47.174 22.609 7.629  -3.140 0.575  O6B  GPG 38 
GPG N1B  BN1  N 0 1 N N N 20.211 47.589 20.861 8.303  -1.054 1.013  N1B  GPG 39 
GPG C2B  BC2  C 0 1 N N N 21.190 47.219 19.886 7.997  0.273  1.084  C2B  GPG 40 
GPG N2B  BN2  N 0 1 N N N 21.580 48.114 19.003 8.967  1.161  1.476  N2B  GPG 41 
GPG N3B  BN3  N 0 1 N N N 21.641 45.933 19.984 6.800  0.726  0.783  N3B  GPG 42 
GPG C4B  BC4  C 0 1 Y N N 21.183 45.042 20.954 5.824  -0.103 0.397  C4B  GPG 43 
GPG H8A  AH8  H 0 1 N N N 18.182 31.442 19.653 -6.143 -1.280 -1.523 H8A  GPG 44 
GPG H1A  AH1  H 0 1 N N N 13.377 34.877 22.344 -0.772 -4.669 -0.315 H1A  GPG 45 
GPG H21A AH21 H 0 0 N N N 14.347 36.863 23.414 0.238  -3.831 1.621  H21A GPG 46 
GPG H22A AH22 H 0 0 N N N 16.111 36.967 23.242 -0.453 -2.543 2.450  H22A GPG 47 
GPG HO5A AHO5 H 0 0 N N N 18.084 34.007 25.430 -9.612 1.804  0.330  HO5A GPG 48 
GPG H51A AH51 H 0 0 N N N 20.270 34.252 24.845 -7.756 3.069  0.784  H51A GPG 49 
GPG H52A AH52 H 0 0 N N N 19.408 35.848 24.739 -7.509 1.942  -0.572 H52A GPG 50 
GPG H4D  AH4* H 0 1 N N N 20.864 35.397 22.980 -6.758 1.336  2.326  H4D  GPG 51 
GPG H3D  AH3* H 0 1 N N N 17.755 35.573 22.183 -5.403 2.958  0.313  H3D  GPG 52 
GPG HO3A AHO3 H 0 0 N N N 18.995 37.305 23.169 -5.339 3.283  2.580  HO3A GPG 53 
GPG H2D  AH2* H 0 1 N N N 19.140 35.372 19.633 -4.261 1.168  -0.692 H2D  GPG 54 
GPG H1D  AH1* H 0 1 N N N 19.821 33.194 20.102 -4.620 -0.479 1.874  H1D  GPG 55 
GPG HOP2 2HOP H 0 0 N N N 22.368 37.390 18.007 -1.649 -0.622 -0.653 HOP2 GPG 56 
GPG H51B BH51 H 0 0 N N N 22.715 39.024 20.843 -0.078 2.880  -1.464 H51B GPG 57 
GPG H52B BH52 H 0 0 N N N 21.401 40.251 21.400 0.319  1.151  -1.613 H52B GPG 58 
GPG H4E  BH4* H 0 1 N N N 22.539 40.222 18.766 1.780  3.114  0.222  H4E  GPG 59 
GPG H3E  BH3* H 0 1 N N N 24.278 40.498 21.163 2.217  2.232  -2.637 H3E  GPG 60 
GPG HO3B BHO3 H 0 0 N N N 24.576 40.924 18.536 3.325  4.237  -2.629 HO3B GPG 61 
GPG H2E  BH2* H 0 1 N N N 23.692 42.374 22.083 4.263  1.267  -2.162 H2E  GPG 62 
GPG HO2B BHO2 H 0 0 N N N 24.720 43.729 19.800 5.071  3.434  -2.201 HO2B GPG 63 
GPG H1E  BH1* H 0 1 N N N 22.884 43.885 19.582 4.122  2.004  0.767  H1E  GPG 64 
GPG H8B  BH8  H 0 1 N N N 20.913 42.304 22.643 2.996  -1.357 -0.588 H8B  GPG 65 
GPG H1B  BH1  H 0 1 N N N 19.848 48.521 20.844 9.196  -1.355 1.242  H1B  GPG 66 
GPG H21B BH21 H 0 0 N N N 21.247 49.055 18.948 8.765  2.108  1.527  H21B GPG 67 
GPG H22B BH22 H 0 0 N N N 22.261 47.705 18.396 9.853  0.841  1.705  H22B GPG 68 
# 
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 
GPG N9A C8A  SING Y N 1  
GPG N9A C4A  SING Y N 2  
GPG N9A C1D  SING N N 3  
GPG C8A N7A  DOUB Y N 4  
GPG C8A H8A  SING N N 5  
GPG N7A C5A  SING Y N 6  
GPG C5A C6A  SING N N 7  
GPG C5A C4A  DOUB Y N 8  
GPG C6A O6A  DOUB N N 9  
GPG C6A N1A  SING N N 10 
GPG N1A C2A  SING N N 11 
GPG N1A H1A  SING N N 12 
GPG C2A N2A  SING N N 13 
GPG C2A N3A  DOUB N N 14 
GPG N2A H21A SING N N 15 
GPG N2A H22A SING N N 16 
GPG N3A C4A  SING N N 17 
GPG O5D C5D  SING N N 18 
GPG O5D HO5A SING N N 19 
GPG C5D C4D  SING N N 20 
GPG C5D H51A SING N N 21 
GPG C5D H52A SING N N 22 
GPG C4D O4D  SING N N 23 
GPG C4D C3D  SING N N 24 
GPG C4D H4D  SING N N 25 
GPG O4D C1D  SING N N 26 
GPG C3D O3D  SING N N 27 
GPG C3D C2D  SING N N 28 
GPG C3D H3D  SING N N 29 
GPG O3D HO3A SING N N 30 
GPG C2D O2D  SING N N 31 
GPG C2D C1D  SING N N 32 
GPG C2D H2D  SING N N 33 
GPG O2D P    SING N N 34 
GPG C1D H1D  SING N N 35 
GPG P   O1P  DOUB N N 36 
GPG P   O2P  SING N N 37 
GPG P   O5E  SING N N 38 
GPG O2P HOP2 SING N N 39 
GPG O5E C5E  SING N N 40 
GPG C5E C4E  SING N N 41 
GPG C5E H51B SING N N 42 
GPG C5E H52B SING N N 43 
GPG C4E O4E  SING N N 44 
GPG C4E C3E  SING N N 45 
GPG C4E H4E  SING N N 46 
GPG O4E C1E  SING N N 47 
GPG C3E O3E  SING N N 48 
GPG C3E C2E  SING N N 49 
GPG C3E H3E  SING N N 50 
GPG O3E HO3B SING N N 51 
GPG C2E O2E  SING N N 52 
GPG C2E C1E  SING N N 53 
GPG C2E H2E  SING N N 54 
GPG O2E HO2B SING N N 55 
GPG C1E N9B  SING N N 56 
GPG C1E H1E  SING N N 57 
GPG N9B C8B  SING Y N 58 
GPG N9B C4B  SING Y N 59 
GPG C8B N7B  DOUB Y N 60 
GPG C8B H8B  SING N N 61 
GPG N7B C5B  SING Y N 62 
GPG C5B C6B  SING N N 63 
GPG C5B C4B  DOUB Y N 64 
GPG C6B O6B  DOUB N N 65 
GPG C6B N1B  SING N N 66 
GPG N1B C2B  SING N N 67 
GPG N1B H1B  SING N N 68 
GPG C2B N2B  SING N N 69 
GPG C2B N3B  DOUB N N 70 
GPG N2B H21B SING N N 71 
GPG N2B H22B SING N N 72 
GPG N3B C4B  SING N N 73 
# 
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 
GPG SMILES           ACDLabs              10.04 "O=C6NC(=Nc1c6ncn1C5OC(CO)C(O)C5OP(=O)(O)OCC4OC(n3cnc2c3N=C(N)NC2=O)C(O)C4O)N" 
GPG SMILES_CANONICAL CACTVS               3.341 "NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@H](CO[P@](O)(=O)O[C@@H]4[C@H](O)[C@@H](CO)O[C@H]4n5cnc6C(=O)NC(=Nc56)N)[C@@H](O)[C@H]3O" 
GPG SMILES           CACTVS               3.341 "NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH](CO[P](O)(=O)O[CH]4[CH](O)[CH](CO)O[CH]4n5cnc6C(=O)NC(=Nc56)N)[CH](O)[CH]3O" 
GPG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@@](=O)(O)O[C@@H]4[C@@H]([C@H](O[C@H]4n5cnc6c5N=C(NC6=O)N)CO)O)O)O)N=C(NC2=O)N" 
GPG SMILES           "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1C3C(C(C(O3)COP(=O)(O)OC4C(C(OC4n5cnc6c5N=C(NC6=O)N)CO)O)O)O)N=C(NC2=O)N" 
GPG InChI            InChI                1.03  
;InChI=1S/C20H25N10O12P/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(34)9(32)6(41-17)2-39-43(37,38)42-12-10(33)5(1-31)40-18(12)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)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1
;
GPG InChIKey         InChI                1.03  YYNDAHWXMRBBRC-MHARETSRSA-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 
GPG "SYSTEMATIC NAME" ACDLabs              10.04 
"[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3R,4R,5R)-2-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl hydrogen (R)-phosphate (non-preferred name)" 
GPG "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]methyl [(2R,3R,4R,5R)-2-(2-amino-6-oxo-1H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-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 
GPG "Create component"  1999-07-08 RCSB 
GPG "Modify descriptor" 2011-06-04 RCSB 
# 
