data_51O # _chem_comp.id 51O _chem_comp.name "Au(caffein-2-ylidene)2" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C18 H24 Au N8 O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge ? _chem_comp.pdbx_initial_date 2015-07-10 _chem_comp.pdbx_modified_date 2026-07-31 _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 613.401 _chem_comp.one_letter_code ? _chem_comp.three_letter_code ? _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details MetalCoord _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 5CCW _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site RCSB _chem_comp.pdbx_pcm ? _chem_comp.pdbx_comp_type "metal-containing ligand" # 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.pdbx_n_terminal_atom_flag _chem_comp_atom.pdbx_backbone_atom_flag _chem_comp_atom.pdbx_c_terminal_atom_flag _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 51O O4 O1 O 0 1 N N N N N N -5.234 0.052 -22.236 -5.287 0.235 -22.210 O4 51O 1 51O C15 C1 C 0 1 N N N N N N -4.595 0.081 -21.208 -4.666 0.242 -21.162 C15 51O 2 51O N7 N1 N 0 1 N N N N N N -3.209 0.200 -21.249 -3.274 0.337 -21.169 N7 51O 3 51O C17 C2 C 0 1 N N N N N N -2.477 0.298 -22.510 -2.653 0.432 -22.516 C17 51O 4 51O C16 C3 C 0 1 N N N N N N -2.515 0.226 -20.054 -2.423 0.354 -20.053 C16 51O 5 51O O3 O2 O 0 1 N N N N N N -1.304 0.324 -20.070 -1.209 0.442 -20.184 O3 51O 6 51O C13 C4 C 0 1 N N N N N N -3.205 0.135 -18.854 -3.160 0.256 -18.830 C13 51O 7 51O N5 N2 N 0 1 N N N N N N -2.748 0.140 -17.553 -2.679 0.241 -17.539 N5 51O 8 51O C11 C5 C 0 1 N N N N N N -1.349 0.249 -17.186 -1.298 0.321 -17.058 C11 51O 9 51O N8 N3 N 0 1 N N N N N N -5.266 -0.005 -19.989 -5.313 0.145 -19.938 N8 51O 10 51O C18 C6 C 0 1 N N N N N N -6.715 -0.141 -20.021 -6.782 0.047 -19.948 C18 51O 11 51O C14 C7 C 0 1 N N N N N N -4.545 0.024 -18.792 -4.537 0.157 -18.793 C14 51O 12 51O N6 N4 N 0 1 N N N N N N -4.888 -0.040 -17.424 -4.886 0.082 -17.429 N6 51O 13 51O C12 C8 C 0 1 N N N N N N -6.244 -0.170 -16.897 -6.172 -0.037 -16.730 C12 51O 14 51O C10 C9 C -2 1 N N N N N N -3.766 0.031 -16.709 -3.734 0.133 -16.700 C10 51O 15 51O AU AU1 AU ? 0 N N N N N N -3.613 0.001 -14.692 -3.552 0.023 -14.690 AU 51O 16 51O C1 C10 C -2 1 N N N N N N -3.446 -0.025 -12.672 -3.420 -0.012 -12.674 C1 51O 17 51O N2 N5 N 0 1 N N N N N N -2.293 0.076 -12.001 -2.255 0.117 -12.000 N2 51O 18 51O C5 C11 C 0 1 N N N N N N -2.504 0.017 -10.625 -2.526 0.010 -10.653 C5 51O 19 51O C3 C12 C 0 1 N N N N N N -0.993 0.215 -12.640 -0.974 0.329 -12.680 C3 51O 20 51O N1 N6 N 0 1 N N N N N N -4.411 -0.124 -11.745 -4.437 -0.200 -11.784 N1 51O 21 51O C2 C13 C 0 1 N N N N N N -5.851 -0.246 -11.958 -5.807 -0.362 -12.284 C2 51O 22 51O C4 C14 C 0 1 N N N N N N -3.836 -0.103 -10.470 -3.882 -0.188 -10.487 C4 51O 23 51O N4 N7 N 0 1 N N N N N N -4.392 -0.198 -9.204 -4.465 -0.331 -9.241 N4 51O 24 51O C8 C15 C 0 1 N N N N N N -5.842 -0.328 -9.037 -5.905 -0.545 -9.014 C8 51O 25 51O C7 C16 C 0 1 N N N N N N -3.572 -0.149 -8.080 -3.641 -0.273 -8.126 C7 51O 26 51O O2 O3 O 0 1 N N N N N N -4.059 -0.230 -6.961 -4.087 -0.393 -7.000 O2 51O 27 51O N3 N8 N 0 1 N N N N N N -2.188 -0.022 -8.233 -2.274 -0.069 -8.325 N3 51O 28 51O C9 C17 C 0 1 N N N N N N -1.312 0.015 -7.068 -1.455 -0.021 -7.086 C9 51O 29 51O C6 C18 C 0 1 N N N N N N -1.651 0.071 -9.512 -1.613 0.081 -9.554 C6 51O 30 51O O1 O4 O 0 1 N N N N N N -0.444 0.190 -9.617 -0.401 0.252 -9.603 O1 51O 31 51O H1 H1 H 0 1 N N N N N N -1.400 0.384 -22.304 -1.694 0.573 -22.499 H1 51O 32 51O H2 H2 H 0 1 N N N N N N -2.664 -0.603 -23.113 -3.037 1.180 -23.003 H2 51O 33 51O H3 H3 H 0 1 N N N N N N -2.816 1.187 -23.063 -2.827 -0.387 -23.008 H3 51O 34 51O H4 H4 H 0 1 N N N N N N -1.254 0.229 -16.090 -1.286 0.663 -16.152 H4 51O 35 51O H5 H5 H 0 1 N N N N N N -0.790 -0.594 -17.618 -0.789 0.915 -17.629 H5 51O 36 51O H6 H6 H 0 1 N N N N N N -0.942 1.195 -17.572 -0.899 -0.562 -17.074 H6 51O 37 51O H7 H7 H 0 1 N N N N N N -7.101 -0.197 -18.993 -7.054 -0.764 -19.485 H7 51O 38 51O H8 H8 H 0 1 N N N N N N -7.154 0.729 -20.531 -7.124 0.018 -20.857 H8 51O 39 51O H9 H9 H 0 1 N N N N N N -6.985 -1.059 -20.564 -7.159 0.819 -19.493 H9 51O 40 51O H10 H10 H 0 1 N N N N N N -6.210 -0.195 -15.798 -6.027 -0.100 -15.775 H10 51O 41 51O H11 H11 H 0 1 N N N N N N -6.849 0.688 -17.226 -6.631 -0.834 -17.034 H11 51O 42 51O H12 H12 H 0 1 N N N N N N -6.695 -1.101 -17.271 -6.716 0.741 -16.922 H12 51O 43 51O H13 H13 H 0 1 N N N N N N -0.210 0.278 -11.870 -0.419 0.919 -12.149 H13 51O 44 51O H14 H14 H 0 1 N N N N N N -0.805 -0.658 -13.283 -1.127 0.731 -13.548 H14 51O 45 51O H15 H15 H 0 1 N N N N N N -0.981 1.130 -13.251 -0.525 -0.522 -12.793 H15 51O 46 51O H16 H16 H 0 1 N N N N N N -6.362 -0.306 -10.986 -6.165 -1.208 -11.977 H16 51O 47 51O H17 H17 H 0 1 N N N N N N -6.216 0.633 -12.510 -5.813 -0.346 -13.252 H17 51O 48 51O H18 H18 H 0 1 N N N N N N -6.060 -1.156 -12.539 -6.359 0.361 -11.949 H18 51O 49 51O H19 H19 H 0 1 N N N N N N -6.084 -0.389 -7.966 -6.095 -0.665 -8.070 H19 51O 50 51O H20 H20 H 0 1 N N N N N N -6.342 0.548 -9.477 -6.191 -1.341 -9.494 H20 51O 51 51O H21 H21 H 0 1 N N N N N N -6.189 -1.241 -9.544 -6.400 0.225 -9.343 H21 51O 52 51O H22 H22 H 0 1 N N N N N N -1.915 -0.071 -6.152 -1.805 0.657 -6.484 H22 51O 53 51O H23 H23 H 0 1 N N N N N N -0.600 -0.822 -7.118 -0.520 0.185 -7.238 H23 51O 54 51O H24 H24 H 0 1 N N N N N N -0.759 0.966 -7.055 -1.499 -0.884 -6.642 H24 51O 55 # 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 _chem_comp_bond.pdbx_metal_coordination_flag _chem_comp_bond.pdbx_metal_pi_flag 51O C17 N7 SING N N 1 N N 51O O4 C15 DOUB N N 2 N N 51O N7 C15 SING N N 3 N N 51O N7 C16 SING N N 4 N N 51O C15 N8 SING N N 5 N N 51O O3 C16 DOUB N N 6 N N 51O C16 C13 SING N N 7 N N 51O C18 N8 SING N N 8 N N 51O N8 C14 SING N N 9 N N 51O C13 C14 DOUB N N 10 N N 51O C13 N5 SING N N 11 N N 51O C14 N6 SING N N 12 N N 51O N5 C11 SING N N 13 N N 51O N5 C10 SING N N 14 N N 51O N6 C12 SING N N 15 N N 51O N6 C10 SING N N 16 N N 51O C10 AU SING N N 17 Y N 51O AU C1 SING N N 18 Y N 51O C1 N2 SING N N 19 N N 51O C1 N1 SING N N 20 N N 51O C3 N2 SING N N 21 N N 51O N2 C5 SING N N 22 N N 51O C2 N1 SING N N 23 N N 51O N1 C4 SING N N 24 N N 51O C5 C4 DOUB N N 25 N N 51O C5 C6 SING N N 26 N N 51O C4 N4 SING N N 27 N N 51O O1 C6 DOUB N N 28 N N 51O C6 N3 SING N N 29 N N 51O N4 C8 SING N N 30 N N 51O N4 C7 SING N N 31 N N 51O N3 C7 SING N N 32 N N 51O N3 C9 SING N N 33 N N 51O C7 O2 DOUB N N 34 N N 51O C17 H1 SING N N 35 N N 51O C17 H2 SING N N 36 N N 51O C17 H3 SING N N 37 N N 51O C11 H4 SING N N 38 N N 51O C11 H5 SING N N 39 N N 51O C11 H6 SING N N 40 N N 51O C18 H7 SING N N 41 N N 51O C18 H8 SING N N 42 N N 51O C18 H9 SING N N 43 N N 51O C12 H10 SING N N 44 N N 51O C12 H11 SING N N 45 N N 51O C12 H12 SING N N 46 N N 51O C3 H13 SING N N 47 N N 51O C3 H14 SING N N 48 N N 51O C3 H15 SING N N 49 N N 51O C2 H16 SING N N 50 N N 51O C2 H17 SING N N 51 N N 51O C2 H18 SING N N 52 N N 51O C8 H19 SING N N 53 N N 51O C8 H20 SING N N 54 N N 51O C8 H21 SING N N 55 N N 51O C9 H22 SING N N 56 N N 51O C9 H23 SING N N 57 N N 51O C9 H24 SING N N 58 N N # 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 51O SMILES ACDLabs 14.52 "CN1C=2C(=O)N(C)C(=O)N(C)C=2N(C)C1[Au+]C1N(C)C=2C(=O)N(C)C(=O)N(C)C=2N1C" 51O InChI InChI 1.06 "InChI=1S/2C9H13N4O2.Au/c2*1-10-5-11(2)7-6(10)8(14)13(4)9(15)12(7)3;/h2*5H,1-4H3;/q;;+1" 51O InChIKey InChI 1.06 KFEAJSOESINENJ-UHFFFAOYSA-N 51O SMILES_CANONICAL CACTVS 3.385 "[Au+].CN1CN(C)C2=C1N(C)C(=O)N(C)C2=O.CN3CN(C)C4=C3N(C)C(=O)N(C)C4=O" 51O SMILES CACTVS 3.385 "[Au+].CN1CN(C)C2=C1N(C)C(=O)N(C)C2=O.CN3CN(C)C4=C3N(C)C(=O)N(C)C4=O" 51O SMILES_CANONICAL "OpenEye OEToolkits" 3.1.0.0 "CN1C2=C(N(C(=O)N(C2=O)C)C)N([C]1[Au+][C]3N(C4=C(N3C)N(C(=O)N(C4=O)C)C)C)C" 51O SMILES "OpenEye OEToolkits" 3.1.0.0 "CN1C2=C(N(C(=O)N(C2=O)C)C)N([C]1[Au+][C]3N(C4=C(N3C)N(C(=O)N(C4=O)C)C)C)C" # 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 51O "SYSTEMATIC NAME" ACDLabs 14.52 "[(8R)-1,3,7,9-tetramethyl-2,6-dioxo-2,3,6,7,8,9-hexahydro-1H-purin-8-yl][(8S)-1,3,7,9-tetramethyl-2,6-dioxo-2,3,6,7,8,9-hexahydro-1H-purin-8-yl]gold(1+)" 51O "SYSTEMATIC NAME" "OpenEye OEToolkits" 3.1.0.0 "bis[1,3,7,9-tetramethyl-2,6-bis(oxidanylidene)purin-8-yl]gold(1+)" # loop_ _pdbx_chem_comp_atom_coordination.geometry_id _pdbx_chem_comp_atom_coordination.comp_id _pdbx_chem_comp_atom_coordination.atom_id _pdbx_chem_comp_atom_coordination.number _pdbx_chem_comp_atom_coordination.geometry_calculated _pdbx_chem_comp_atom_coordination.geometry_generic _pdbx_chem_comp_atom_coordination.geometry_abbr _pdbx_chem_comp_atom_coordination.provenance _pdbx_chem_comp_atom_coordination.representative_entry_id 1 51O AU 2 linear linear LIN FindGeo 5CCW 1 51O AU 2 linear linear LIN MetalCoord 5CCW # _pdbx_chem_comp_atom_coordination_sphere.id 1 _pdbx_chem_comp_atom_coordination_sphere.geometry_id 1 _pdbx_chem_comp_atom_coordination_sphere.comp_id 51O _pdbx_chem_comp_atom_coordination_sphere.atom_id AU _pdbx_chem_comp_atom_coordination_sphere.descriptor "@LIN{Au,C,C}" _pdbx_chem_comp_atom_coordination_sphere.provenance MetalCoord _pdbx_chem_comp_atom_coordination_sphere.representative_entry_id 5CCW # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 51O "Create component" 2015-07-10 RCSB 51O "Initial release" 2016-03-16 RCSB 51O "Other modification" 2026-07-08 RCSB 51O "Other modification" 2026-07-17 RCSB 51O "Other modification" 2026-07-31 RCSB #