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 #