data_GFB # _chem_comp.id GFB _chem_comp.name "GUANOSINE-5'-DIPHOSPHATE-BETA-L-FUCOPYRANOSE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C16 H25 N5 O15 P2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2011-08-17 _chem_comp.pdbx_modified_date 2014-09-05 _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 589.342 _chem_comp.one_letter_code ? _chem_comp.three_letter_code GFB _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 3ZY5 _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 GFB O1P O1P O 0 1 N N N -12.884 -27.017 16.536 0.654 1.823 2.609 O1P GFB 1 GFB P P P 0 1 N N N -11.382 -26.857 16.482 1.029 1.967 1.049 P GFB 2 GFB O3P O3P O 0 1 N N N -10.829 -26.213 15.237 1.503 3.344 0.782 O3P GFB 3 GFB O2P O2P O 0 1 N N N -10.967 -26.010 17.813 2.191 0.918 0.677 O2P GFB 4 GFB "O5'" "O5'" O 0 1 N N N -10.693 -28.268 16.747 -0.274 1.665 0.154 "O5'" GFB 5 GFB P1 P1 P 0 1 N N N -9.557 -25.824 18.583 3.775 0.857 0.959 P1 GFB 6 GFB "C5'" "C5'" C 0 1 N N N -11.180 -29.032 17.850 -1.442 2.489 0.175 "C5'" GFB 7 GFB "C4'" "C4'" C 0 1 N N R -12.031 -30.144 17.241 -2.485 1.919 -0.788 "C4'" GFB 8 GFB "O4'" "O4'" O 0 1 N N N -11.942 -31.309 18.072 -2.951 0.647 -0.308 "O4'" GFB 9 GFB "C3'" "C3'" C 0 1 N N S -13.507 -29.788 17.158 -3.705 2.859 -0.854 "C3'" GFB 10 GFB "C1'" "C1'" C 0 1 N N R -13.246 -31.799 18.393 -4.344 0.543 -0.674 "C1'" GFB 11 GFB "O3'" "O3'" O 0 1 N N N -13.875 -29.167 15.910 -3.901 3.332 -2.188 "O3'" GFB 12 GFB "C2'" "C2'" C 0 1 N N R -14.177 -31.132 17.393 -4.893 1.968 -0.415 "C2'" GFB 13 GFB "O2'" "O2'" O 0 1 N N N -14.236 -31.910 16.192 -6.047 2.224 -1.220 "O2'" GFB 14 GFB N9 N9 N 0 1 Y N N -13.695 -31.303 19.719 -5.028 -0.436 0.175 N9 GFB 15 GFB C8 C8 C 0 1 Y N N -13.113 -30.413 20.547 -4.645 -0.828 1.425 C8 GFB 16 GFB C4 C4 C 0 1 Y N N -14.860 -31.667 20.249 -6.171 -1.120 -0.137 C4 GFB 17 GFB N7 N7 N 0 1 Y N N -13.919 -30.225 21.620 -5.482 -1.710 1.887 N7 GFB 18 GFB C5 C5 C 0 1 Y N N -15.005 -31.010 21.459 -6.451 -1.934 0.966 C5 GFB 19 GFB C6 C6 C 0 1 N N N -16.153 -31.256 22.199 -7.595 -2.765 0.921 C6 GFB 20 GFB O6 O6 O 0 1 N N N -16.303 -30.672 23.296 -7.877 -3.491 1.860 O6 GFB 21 GFB N1 N1 N 0 1 N N N -17.086 -32.107 21.707 -8.367 -2.735 -0.187 N1 GFB 22 GFB C2 C2 C 0 1 N N N -16.907 -32.724 20.519 -8.043 -1.920 -1.230 C2 GFB 23 GFB N2 N2 N 0 1 N N N -17.798 -33.592 19.997 -8.846 -1.909 -2.343 N2 GFB 24 GFB N3 N3 N 0 1 N N N -15.809 -32.510 19.793 -6.983 -1.143 -1.201 N3 GFB 25 GFB C1 C1 C 0 1 N N R -7.346 -26.108 17.135 5.883 -0.340 -0.166 C1 GFB 26 GFB C2A C2A C 0 1 N N S -7.594 -26.092 15.615 6.273 -0.697 -1.603 C2A GFB 27 GFB O1 O1 O 0 1 N N N -8.501 -26.673 17.731 4.469 -0.149 -0.090 O1 GFB 28 GFB O5 O5 O 0 1 N N N -6.307 -27.013 17.495 6.268 -1.403 0.709 O5 GFB 29 GFB C3 C3 C 0 1 N N R -6.326 -25.840 14.804 7.781 -0.959 -1.664 C3 GFB 30 GFB O2 O2 O 0 1 N N N -8.536 -25.069 15.304 5.941 0.388 -2.471 O2 GFB 31 GFB C4A C4A C 0 1 N N S -5.209 -26.767 15.289 8.136 -2.071 -0.672 C4A GFB 32 GFB O3 O3 O 0 1 N N N -6.600 -26.038 13.391 8.143 -1.363 -2.986 O3 GFB 33 GFB C5A C5A C 0 1 N N S -5.056 -26.800 16.816 7.674 -1.661 0.729 C5A GFB 34 GFB O4 O4 O 0 1 N N N -5.495 -28.097 14.838 7.479 -3.281 -1.056 O4 GFB 35 GFB C6A C6A C 0 1 N N N -4.113 -27.923 17.227 7.970 -2.792 1.716 C6A GFB 36 GFB O1X O1X O 0 1 N N N -9.263 -24.339 18.582 4.357 2.209 0.804 O1X GFB 37 GFB O2X O2X O 0 1 N N N -9.650 -26.488 19.929 4.034 0.330 2.459 O2X GFB 38 GFB "H5'" "H5'" H 0 1 N N N -11.791 -28.402 18.513 -1.853 2.511 1.184 "H5'" GFB 39 GFB "H5'A" "H5'A" H 0 0 N N N -10.342 -29.459 18.420 -1.178 3.501 -0.132 "H5'A" GFB 40 GFB "H4'" "H4'" H 0 1 N N N -11.658 -30.367 16.231 -2.050 1.804 -1.781 "H4'" GFB 41 GFB "H3'" "H3'" H 0 1 N N N -13.756 -29.118 17.994 -3.580 3.695 -0.166 "H3'" GFB 42 GFB "H1'" "H1'" H 0 1 N N N -13.313 -32.895 18.326 -4.445 0.274 -1.725 "H1'" GFB 43 GFB "HO3'" "HO3'" H 0 0 N N N -14.804 -28.968 15.916 -4.656 3.928 -2.287 "HO3'" GFB 44 GFB "H2'" "H2'" H 0 1 N N N -15.174 -30.990 17.835 -5.118 2.113 0.642 "H2'" GFB 45 GFB "HO2'" "HO2'" H 0 0 N N N -14.659 -32.741 16.373 -6.374 3.132 -1.160 "HO2'" GFB 46 GFB H8 H8 H 0 1 N N N -12.161 -29.929 20.383 -3.776 -0.461 1.952 H8 GFB 47 GFB HN1 HN1 H 0 1 N N N -17.920 -32.281 22.231 -9.156 -3.296 -0.241 HN1 GFB 48 GFB H1 H1 H 0 1 N N N -7.149 -25.089 17.499 6.390 0.577 0.131 H1 GFB 49 GFB H2A H2A H 0 1 N N N -8.002 -27.071 15.324 5.735 -1.592 -1.914 H2A GFB 50 GFB H3 H3 H 0 1 N N N -6.009 -24.800 14.971 8.320 -0.049 -1.400 H3 GFB 51 GFB HO2 HO2 H 0 1 N N N -9.409 -25.442 15.267 5.001 0.612 -2.479 HO2 GFB 52 GFB H4A H4A H 0 1 N N N -4.259 -26.424 14.853 9.215 -2.226 -0.669 H4A GFB 53 GFB HO3 HO3 H 0 1 N N N -5.809 -25.880 12.889 7.940 -0.706 -3.667 HO3 GFB 54 GFB H5A H5A H 0 1 N N N -4.620 -25.844 17.140 8.204 -0.761 1.038 H5A GFB 55 GFB HO4 HO4 H 0 1 N N N -4.810 -28.686 15.131 7.660 -4.029 -0.470 HO4 GFB 56 GFB H6A H6A H 0 1 N N N -3.144 -27.791 16.724 7.641 -2.500 2.713 H6A GFB 57 GFB H6AA H6AA H 0 0 N N N -3.967 -27.899 18.317 7.439 -3.692 1.407 H6AA GFB 58 GFB H6AB H6AB H 0 0 N N N -4.547 -28.891 16.937 9.042 -2.990 1.730 H6AB GFB 59 GFB HN2 HN2 H 0 1 N N N -17.613 -34.030 19.117 -8.628 -1.334 -3.093 HN2 GFB 60 GFB HN2A HN2A H 0 0 N N N -18.643 -33.798 20.490 -9.632 -2.477 -2.379 HN2A GFB 61 GFB HO1P HO1P H 0 0 N N N -13.269 -26.671 15.739 0.335 0.944 2.856 HO1P GFB 62 GFB HO2X HO2X H 0 0 N N N -9.503 -25.844 20.611 3.679 -0.553 2.632 HO2X GFB 63 # 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 GFB P O1P SING N N 1 GFB O1P HO1P SING N N 2 GFB O3P P DOUB N N 3 GFB P "O5'" SING N N 4 GFB P O2P SING N N 5 GFB O2P P1 SING N N 6 GFB "O5'" "C5'" SING N N 7 GFB O1 P1 SING N N 8 GFB O1X P1 DOUB N N 9 GFB P1 O2X SING N N 10 GFB "C4'" "C5'" SING N N 11 GFB "C5'" "H5'A" SING N N 12 GFB "C5'" "H5'" SING N N 13 GFB "H4'" "C4'" SING N N 14 GFB "C3'" "C4'" SING N N 15 GFB "C4'" "O4'" SING N N 16 GFB "O4'" "C1'" SING N N 17 GFB "O3'" "C3'" SING N N 18 GFB "C3'" "C2'" SING N N 19 GFB "C3'" "H3'" SING N N 20 GFB "C2'" "C1'" SING N N 21 GFB "H1'" "C1'" SING N N 22 GFB "C1'" N9 SING N N 23 GFB "HO3'" "O3'" SING N N 24 GFB "O2'" "C2'" SING N N 25 GFB "C2'" "H2'" SING N N 26 GFB "O2'" "HO2'" SING N N 27 GFB N9 C4 SING Y N 28 GFB N9 C8 SING Y N 29 GFB H8 C8 SING N N 30 GFB C8 N7 DOUB Y N 31 GFB N3 C4 SING N N 32 GFB C4 C5 DOUB Y N 33 GFB C5 N7 SING Y N 34 GFB C5 C6 SING N N 35 GFB N1 C6 SING N N 36 GFB C6 O6 DOUB N N 37 GFB C2 N1 SING N N 38 GFB N1 HN1 SING N N 39 GFB N3 C2 DOUB N N 40 GFB N2 C2 SING N N 41 GFB HN2 N2 SING N N 42 GFB N2 HN2A SING N N 43 GFB C2A C1 SING N N 44 GFB C1 O5 SING N N 45 GFB C1 H1 SING N N 46 GFB C1 O1 SING N N 47 GFB C3 C2A SING N N 48 GFB O2 C2A SING N N 49 GFB H2A C2A SING N N 50 GFB C5A O5 SING N N 51 GFB O3 C3 SING N N 52 GFB C3 H3 SING N N 53 GFB C3 C4A SING N N 54 GFB HO2 O2 SING N N 55 GFB H4A C4A SING N N 56 GFB O4 C4A SING N N 57 GFB C4A C5A SING N N 58 GFB HO3 O3 SING N N 59 GFB C5A H5A SING N N 60 GFB C5A C6A SING N N 61 GFB O4 HO4 SING N N 62 GFB H6A C6A SING N N 63 GFB H6AA C6A SING N N 64 GFB C6A H6AB SING N N 65 GFB O2X HO2X SING N N 66 # 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 GFB SMILES ACDLabs 12.01 "O=C4NC(=Nc1c4ncn1C2OC(C(O)C2O)COP(=O)(OP(=O)(OC3OC(C(O)C(O)C3O)C)O)O)N" GFB InChI InChI 1.03 "InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5+,7+,8+,9+,10+,11-,14+,15+/m0/s1" GFB InChIKey InChI 1.03 LQEBEXMHBLQMDB-JGQUBWHWSA-N GFB SMILES_CANONICAL CACTVS 3.385 "C[C@@H]1O[C@H](O[P](O)(=O)O[P](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n3cnc4C(=O)NC(=Nc34)N)[C@@H](O)[C@H](O)[C@@H]1O" GFB SMILES CACTVS 3.385 "C[CH]1O[CH](O[P](O)(=O)O[P](O)(=O)OC[CH]2O[CH]([CH](O)[CH]2O)n3cnc4C(=O)NC(=Nc34)N)[CH](O)[CH](O)[CH]1O" GFB SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "C[C@H]1[C@H]([C@H]([C@@H]([C@H](O1)OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)n3cnc4c3N=C(NC4=O)N)O)O)O)O)O" GFB SMILES "OpenEye OEToolkits" 1.9.2 "CC1C(C(C(C(O1)OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)n3cnc4c3N=C(NC4=O)N)O)O)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 GFB "SYSTEMATIC NAME" ACDLabs 12.01 "[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)" GFB "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "[[(2R,3S,4R,5R)-5-(2-azanyl-6-oxidanylidene-1H-purin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-oxidanyl-phosphoryl] [(2R,3S,4R,5S,6S)-6-methyl-3,4,5-tris(oxidanyl)oxan-2-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 GFB "Create component" 2011-08-17 EBI GFB "Modify descriptor" 2014-09-05 RCSB #