data_GBR # _chem_comp.id GBR _chem_comp.name "5'-O-[(R)-{[(S)-[(R)-bromo(phosphono)methyl](hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]-2'-deoxyguanosine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C11 H17 Br N5 O12 P3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-09-14 _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 584.104 _chem_comp.one_letter_code ? _chem_comp.three_letter_code GBR _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 3JPQ _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 GBR N1 N1 N 0 1 N N N 9.736 8.849 8.120 -8.419 2.101 0.154 N1 GBR 1 GBR C2 C2 C 0 1 N N N 8.476 9.010 7.571 -7.913 1.551 1.294 C2 GBR 2 GBR N2 N2 N 0 1 N N N 8.418 9.545 6.339 -8.590 1.727 2.475 N2 GBR 3 GBR N3 N3 N 0 1 N N N 7.352 8.669 8.198 -6.797 0.858 1.295 N3 GBR 4 GBR C4 C4 C 0 1 Y N N 7.586 8.158 9.434 -6.104 0.661 0.167 C4 GBR 5 GBR C5 C5 C 0 1 Y N N 8.796 7.964 10.075 -6.571 1.200 -1.036 C5 GBR 6 GBR C6 C6 C 0 1 N N N 10.000 8.317 9.387 -7.774 1.945 -1.023 C6 GBR 7 GBR O6 O6 O 0 1 N N N 11.172 8.193 9.773 -8.218 2.432 -2.048 O6 GBR 8 GBR N7 N7 N 0 1 Y N N 8.604 7.420 11.336 -5.688 0.852 -2.003 N7 GBR 9 GBR C8 C8 C 0 1 Y N N 7.309 7.284 11.433 -4.729 0.148 -1.477 C8 GBR 10 GBR N9 N9 N 0 1 Y N N 6.636 7.689 10.302 -4.943 0.003 -0.137 N9 GBR 11 GBR PA PA P 0 1 N N N 4.994 5.159 14.675 1.471 -1.851 -0.730 PA GBR 12 GBR PB PB P 0 1 N N N 3.969 2.770 13.812 4.157 -0.707 -0.214 PB GBR 13 GBR BRB BRB BR 0 0 N N N 5.007 -0.200 14.131 3.889 2.364 0.060 BRB GBR 14 GBR PG PG P 0 1 N N N 3.996 1.366 16.601 6.532 0.865 0.650 PG GBR 15 GBR "C1'" "C1'" C 0 1 N N R 5.204 7.592 10.034 -4.087 -0.723 0.804 "C1'" GBR 16 GBR O1A O1A O 0 1 N N N 3.726 5.169 15.837 1.258 -1.529 -2.293 O1A GBR 17 GBR O1B O1B O 0 1 N N N 4.011 2.149 12.209 4.585 -0.507 -1.753 O1B GBR 18 GBR O1G O1G O 0 1 N N N 3.269 2.856 17.058 6.960 1.065 -0.889 O1G GBR 19 GBR "C2'" "C2'" C 0 1 N N N 4.807 6.174 9.625 -4.609 -2.162 0.985 "C2'" GBR 20 GBR O2A O2A O 0 1 N N N 6.403 5.181 15.140 1.957 -3.240 -0.573 O2A GBR 21 GBR O2B O2B O 0 1 N N N 2.655 3.182 14.368 4.781 -1.941 0.315 O2B GBR 22 GBR O2G O2G O 0 1 N N N 5.092 0.621 17.697 7.028 2.130 1.514 O2G GBR 23 GBR "C3'" "C3'" C 0 1 N N S 4.435 5.565 10.961 -3.418 -3.054 0.559 "C3'" GBR 24 GBR "O3'" "O3'" O 0 1 N N N 3.563 4.445 10.779 -3.282 -4.175 1.435 "O3'" GBR 25 GBR O3A O3A O 0 1 N N N 4.808 4.014 13.708 2.555 -0.831 -0.115 O3A GBR 26 GBR C3B C3B C 0 1 N N R 4.793 1.574 14.963 4.718 0.725 0.763 C3B GBR 27 GBR O3G O3G O 0 1 N N N 2.862 0.419 16.494 7.156 -0.368 1.180 O3G GBR 28 GBR "C4'" "C4'" C 0 1 N N R 3.708 6.734 11.613 -2.217 -2.086 0.710 "C4'" GBR 29 GBR "O4'" "O4'" O 0 1 N N N 4.496 7.886 11.239 -2.752 -0.816 0.279 "O4'" GBR 30 GBR "C5'" "C5'" C 0 1 N N N 3.526 6.677 13.113 -1.060 -2.518 -0.194 "C5'" GBR 31 GBR "O5'" "O5'" O 0 1 N N N 4.776 6.454 13.769 0.072 -1.681 0.049 "O5'" GBR 32 GBR HN1 HN1 H 0 1 N N N 10.519 9.135 7.568 -9.247 2.605 0.188 HN1 GBR 33 GBR HN2 HN2 H 0 1 N N N 7.532 9.686 5.896 -9.415 2.236 2.491 HN2 GBR 34 GBR HN2A HN2A H 0 0 N N N 9.260 9.802 5.865 -8.242 1.341 3.295 HN2A GBR 35 GBR H8 H8 H 0 1 N N N 6.816 6.894 12.311 -3.889 -0.261 -2.019 H8 GBR 36 GBR "H1'" "H1'" H 0 1 N N N 4.963 8.293 9.221 -4.074 -0.210 1.766 "H1'" GBR 37 GBR "H2'" "H2'" H 0 1 N N N 3.966 6.166 8.916 -4.870 -2.345 2.027 "H2'" GBR 38 GBR "H2'A" "H2'A" H 0 0 N N N 5.633 5.635 9.138 -5.469 -2.339 0.339 "H2'A" GBR 39 GBR "H3'" "H3'" H 0 1 N N N 5.281 5.176 11.546 -3.527 -3.382 -0.474 "H3'" GBR 40 GBR "HO3'" "HO3'" H 0 0 N N N 3.340 4.076 11.625 -4.050 -4.763 1.444 "HO3'" GBR 41 GBR H3B H3B H 0 1 N N N 5.771 2.041 15.153 4.428 0.590 1.805 H3B GBR 42 GBR "H4'" "H4'" H 0 1 N N N 2.666 6.743 11.261 -1.894 -2.034 1.750 "H4'" GBR 43 GBR "H5'" "H5'" H 0 1 N N N 3.105 7.632 13.459 -0.799 -3.554 0.021 "H5'" GBR 44 GBR "H5'A" "H5'A" H 0 0 N N N 2.840 5.853 13.360 -1.362 -2.428 -1.238 "H5'A" GBR 45 GBR H14 H14 H 0 1 N N N 3.082 4.508 15.610 0.940 -0.633 -2.470 H14 GBR 46 GBR H15 H15 H 0 1 N N N 3.132 2.143 11.848 4.212 0.283 -2.166 H15 GBR 47 GBR H16 H16 H 0 1 N N N 2.329 2.739 17.137 6.587 1.856 -1.301 H16 GBR 48 GBR H17 H17 H 0 1 N N N 4.736 -0.212 17.984 7.985 2.266 1.499 H17 GBR 49 # 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 GBR N1 C2 SING N N 1 GBR N1 C6 SING N N 2 GBR N1 HN1 SING N N 3 GBR C2 N2 SING N N 4 GBR C2 N3 DOUB N N 5 GBR N2 HN2 SING N N 6 GBR N2 HN2A SING N N 7 GBR N3 C4 SING N N 8 GBR C4 C5 DOUB Y N 9 GBR C4 N9 SING Y N 10 GBR C5 C6 SING N N 11 GBR C5 N7 SING Y N 12 GBR C6 O6 DOUB N N 13 GBR N7 C8 DOUB Y N 14 GBR C8 N9 SING Y N 15 GBR C8 H8 SING N N 16 GBR N9 "C1'" SING N N 17 GBR PA O1A SING N N 18 GBR PA O2A DOUB N N 19 GBR PA O3A SING N N 20 GBR PA "O5'" SING N N 21 GBR PB O1B SING N N 22 GBR PB O2B DOUB N N 23 GBR PB O3A SING N N 24 GBR PB C3B SING N N 25 GBR BRB C3B SING N N 26 GBR PG O1G SING N N 27 GBR PG O2G SING N N 28 GBR PG C3B SING N N 29 GBR PG O3G DOUB N N 30 GBR "C1'" "C2'" SING N N 31 GBR "C1'" "O4'" SING N N 32 GBR "C1'" "H1'" SING N N 33 GBR "C2'" "C3'" SING N N 34 GBR "C2'" "H2'" SING N N 35 GBR "C2'" "H2'A" SING N N 36 GBR "C3'" "O3'" SING N N 37 GBR "C3'" "C4'" SING N N 38 GBR "C3'" "H3'" SING N N 39 GBR "O3'" "HO3'" SING N N 40 GBR C3B H3B SING N N 41 GBR "C4'" "O4'" SING N N 42 GBR "C4'" "C5'" SING N N 43 GBR "C4'" "H4'" SING N N 44 GBR "C5'" "O5'" SING N N 45 GBR "C5'" "H5'" SING N N 46 GBR "C5'" "H5'A" SING N N 47 GBR O1A H14 SING N N 48 GBR O1B H15 SING N N 49 GBR O1G H16 SING N N 50 GBR O2G H17 SING N N 51 # 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 GBR SMILES ACDLabs 11.02 "O=P(O)(O)C(Br)P(=O)(O)OP(=O)(O)OCC3OC(n2cnc1c2N=C(N)NC1=O)CC3O" GBR SMILES_CANONICAL CACTVS 3.352 "NC1=Nc2n(cnc2C(=O)N1)[C@H]3C[C@H](O)[C@@H](CO[P](O)(=O)O[P](O)(=O)[C@H](Br)[P](O)(O)=O)O3" GBR SMILES CACTVS 3.352 "NC1=Nc2n(cnc2C(=O)N1)[CH]3C[CH](O)[CH](CO[P](O)(=O)O[P](O)(=O)[CH](Br)[P](O)(O)=O)O3" GBR SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "c1nc2c(n1[C@H]3C[C@@H]([C@H](O3)CO[P@@](=O)(O)O[P@](=O)([C@@H](P(=O)(O)O)Br)O)O)N=C(NC2=O)N" GBR SMILES "OpenEye OEToolkits" 1.7.0 "c1nc2c(n1C3CC(C(O3)COP(=O)(O)OP(=O)(C(P(=O)(O)O)Br)O)O)N=C(NC2=O)N" GBR InChI InChI 1.03 "InChI=1S/C11H17BrN5O12P3/c12-10(30(20,21)22)31(23,24)29-32(25,26)27-2-5-4(18)1-6(28-5)17-3-14-7-8(17)15-11(13)16-9(7)19/h3-6,10,18H,1-2H2,(H,23,24)(H,25,26)(H2,20,21,22)(H3,13,15,16,19)/t4-,5+,6+,10+/m0/s1" GBR InChIKey InChI 1.03 NBJGMAKPACFZHS-AVAJSQPUSA-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 GBR "SYSTEMATIC NAME" ACDLabs 11.02 "5'-O-[(R)-{[(S)-[(R)-bromo(phosphono)methyl](hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]-2'-deoxyguanosine" GBR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "[(R)-[[[(2R,3S,5R)-5-(2-azanyl-6-oxo-1H-purin-9-yl)-3-hydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]-bromo-methyl]phosphonic acid" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site GBR "Create component" 2009-09-14 RCSB GBR "Modify descriptor" 2011-06-04 RCSB #