data_WPG # _chem_comp.id WPG _chem_comp.name ;(3-{(3R,4R)-3-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-4-[(2R)-2-hydroxy-2-phosphonoethoxy]pyrrolidin-1-yl}-3-oxopropy l)phosphonic acid ; _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C14 H22 N6 O10 P2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "[3R,4R]-4-guanin-9-yl-3-((R)-2-hydroxy-2-phosphonoethyl)oxy-1-N-(phosphonopropionyl)pyrrolidine" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2016-01-14 _chem_comp.pdbx_modified_date 2020-06-17 _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 496.306 _chem_comp.one_letter_code ? _chem_comp.three_letter_code WPG _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 5HIG _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 WPG C4 C1 C 0 1 Y N N -40.784 -10.095 25.155 3.329 1.655 -0.177 C4 WPG 1 WPG C5 C2 C 0 1 Y N N -41.371 -10.156 26.421 4.047 2.396 0.767 C5 WPG 2 WPG C6 C3 C 0 1 N N N -40.690 -9.519 27.503 5.437 2.572 0.575 C6 WPG 3 WPG C8 C4 C 0 1 Y N N -42.683 -11.306 25.032 1.978 2.368 1.412 C8 WPG 4 WPG N1 N1 N 0 1 N N N -39.530 -8.850 27.250 6.010 2.015 -0.515 N1 WPG 5 WPG N2 N2 N 0 1 N N N -37.741 -8.093 25.822 5.865 0.748 -2.498 N2 WPG 6 WPG N3 N3 N 0 1 N N N -39.592 -9.399 24.970 3.964 1.132 -1.233 N3 WPG 7 WPG OAI O1 O 0 1 N N N -45.738 -16.091 20.510 -0.684 -4.601 0.339 OAI WPG 8 WPG PBF P1 P 0 1 N N N -45.245 -15.553 21.909 0.718 -4.342 -0.059 PBF WPG 9 WPG OAJ O2 O 0 1 N N N -45.048 -16.682 22.955 1.463 -5.741 -0.343 OAJ WPG 10 WPG OAE O3 O 0 1 N N N -46.194 -14.498 22.430 0.740 -3.441 -1.393 OAE WPG 11 WPG CAZ C5 C 0 1 N N R -43.637 -14.704 21.557 1.577 -3.458 1.285 CAZ WPG 12 WPG OAF O4 O 0 1 N N N -43.931 -13.692 20.665 2.931 -3.208 0.901 OAF WPG 13 WPG CAN C6 C 0 1 N N N -43.002 -14.129 22.812 0.870 -2.129 1.555 CAN WPG 14 WPG OAT O5 O 0 1 N N N -41.887 -13.283 22.624 0.889 -1.330 0.371 OAT WPG 15 WPG CBA C7 C 0 1 N N R -42.090 -11.983 22.170 0.250 -0.060 0.516 CBA WPG 16 WPG CAO C8 C 0 1 N N N -41.489 -11.899 20.833 -1.201 -0.102 -0.025 CAO WPG 17 WPG NBC N4 N 0 1 N N N -40.762 -10.619 20.827 -1.510 1.293 -0.386 NBC WPG 18 WPG CAU C9 C 0 1 N N N -39.725 -10.193 19.918 -2.744 1.830 -0.461 CAU WPG 19 WPG OAB O6 O 0 1 N N N -39.224 -9.080 20.063 -2.881 2.995 -0.768 OAB WPG 20 WPG CAL C10 C 0 1 N N N -39.286 -11.081 18.786 -3.954 0.982 -0.162 CAL WPG 21 WPG CAM C11 C 0 1 N N N -38.121 -10.513 18.009 -5.220 1.827 -0.319 CAM WPG 22 WPG PBE P2 P 0 1 N N N -36.496 -10.703 18.871 -6.683 0.802 0.043 PBE WPG 23 WPG OAG O7 O 0 1 N N N -36.331 -9.624 19.986 -6.809 -0.363 -1.062 OAG WPG 24 WPG OAH O8 O 0 1 N N N -35.420 -10.499 17.733 -6.541 0.195 1.385 OAH WPG 25 WPG OAD O9 O 0 1 N N N -36.303 -12.100 19.467 -8.005 1.721 0.007 OAD WPG 26 WPG CAP C12 C 0 1 N N N -41.225 -9.810 21.967 -0.250 2.003 -0.650 CAP WPG 27 WPG CBB C13 C 0 1 N N R -41.320 -10.963 22.903 0.899 0.999 -0.415 CBB WPG 28 WPG N9 N5 N 0 1 Y N N -41.642 -10.809 24.330 2.029 1.651 0.251 N9 WPG 29 WPG C2 C14 C 0 1 N N N -38.980 -8.799 26.017 5.257 1.303 -1.401 C2 WPG 30 WPG O6 O10 O 0 1 N N N -41.215 -9.555 28.775 6.102 3.211 1.372 O6 WPG 31 WPG N7 N6 N 0 1 Y N N -42.558 -10.900 26.339 3.167 2.800 1.715 N7 WPG 32 WPG H1 H1 H 0 1 N N N -43.479 -11.918 24.634 1.086 2.544 1.994 H1 WPG 33 WPG H2 H2 H 0 1 N N N -37.331 -8.045 24.911 5.342 0.238 -3.136 H2 WPG 34 WPG H3 H3 H 0 1 N N N -37.290 -7.650 26.597 6.818 0.866 -2.636 H3 WPG 35 WPG H5 H5 H 0 1 N N N -45.263 -17.520 22.562 1.058 -6.265 -1.048 H5 WPG 36 WPG H6 H6 H 0 1 N N N -46.900 -14.371 21.807 1.628 -3.232 -1.712 H6 WPG 37 WPG H7 H7 H 0 1 N N N -42.976 -15.465 21.116 1.563 -4.068 2.188 H7 WPG 38 WPG H8 H8 H 0 1 N N N -43.136 -13.220 20.448 3.020 -2.670 0.102 H8 WPG 39 WPG H9 H9 H 0 1 N N N -43.774 -13.552 23.342 -0.163 -2.320 1.848 H9 WPG 40 WPG H10 H10 H 0 1 N N N -42.679 -14.973 23.440 1.383 -1.601 2.358 H10 WPG 41 WPG H11 H11 H 0 1 N N N -43.157 -11.718 22.137 0.271 0.269 1.555 H11 WPG 42 WPG H12 H12 H 0 1 N N N -42.268 -11.906 20.057 -1.259 -0.743 -0.905 H12 WPG 43 WPG H13 H13 H 0 1 N N N -40.798 -12.738 20.666 -1.883 -0.457 0.747 H13 WPG 44 WPG H14 H14 H 0 1 N N N -40.133 -11.217 18.098 -3.990 0.142 -0.856 H14 WPG 45 WPG H15 H15 H 0 1 N N N -38.990 -12.056 19.200 -3.891 0.607 0.859 H15 WPG 46 WPG H16 H16 H 0 1 N N N -38.064 -11.030 17.040 -5.184 2.667 0.375 H16 WPG 47 WPG H17 H17 H 0 1 N N N -38.303 -9.441 17.842 -5.282 2.202 -1.340 H17 WPG 48 WPG H18 H18 H 0 1 N N N -35.609 -9.047 19.765 -6.905 -0.037 -1.967 H18 WPG 49 WPG H19 H19 H 0 1 N N N -35.584 -12.536 19.026 -8.823 1.240 0.191 H19 WPG 50 WPG H20 H20 H 0 1 N N N -40.491 -9.056 22.286 -0.231 2.353 -1.682 H20 WPG 51 WPG H21 H21 H 0 1 N N N -42.194 -9.323 21.784 -0.150 2.847 0.032 H21 WPG 52 WPG H22 H22 H 0 1 N N N -40.298 -11.369 22.912 1.213 0.545 -1.355 H22 WPG 53 WPG H23 H23 H 0 1 N N N -39.070 -8.380 28.003 6.962 2.122 -0.668 H23 WPG 54 # # 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 WPG OAH PBE DOUB N N 1 WPG CAM CAL SING N N 2 WPG CAM PBE SING N N 3 WPG CAL CAU SING N N 4 WPG PBE OAD SING N N 5 WPG PBE OAG SING N N 6 WPG CAU OAB DOUB N N 7 WPG CAU NBC SING N N 8 WPG OAI PBF DOUB N N 9 WPG OAF CAZ SING N N 10 WPG NBC CAO SING N N 11 WPG NBC CAP SING N N 12 WPG CAO CBA SING N N 13 WPG CAZ PBF SING N N 14 WPG CAZ CAN SING N N 15 WPG PBF OAE SING N N 16 WPG PBF OAJ SING N N 17 WPG CAP CBB SING N N 18 WPG CBA OAT SING N N 19 WPG CBA CBB SING N N 20 WPG OAT CAN SING N N 21 WPG CBB N9 SING N N 22 WPG N9 C8 SING Y N 23 WPG N9 C4 SING Y N 24 WPG N3 C4 SING N N 25 WPG N3 C2 DOUB N N 26 WPG C8 N7 DOUB Y N 27 WPG C4 C5 DOUB Y N 28 WPG N2 C2 SING N N 29 WPG C2 N1 SING N N 30 WPG N7 C5 SING Y N 31 WPG C5 C6 SING N N 32 WPG N1 C6 SING N N 33 WPG C6 O6 DOUB N N 34 WPG C8 H1 SING N N 35 WPG N2 H2 SING N N 36 WPG N2 H3 SING N N 37 WPG OAJ H5 SING N N 38 WPG OAE H6 SING N N 39 WPG CAZ H7 SING N N 40 WPG OAF H8 SING N N 41 WPG CAN H9 SING N N 42 WPG CAN H10 SING N N 43 WPG CBA H11 SING N N 44 WPG CAO H12 SING N N 45 WPG CAO H13 SING N N 46 WPG CAL H14 SING N N 47 WPG CAL H15 SING N N 48 WPG CAM H16 SING N N 49 WPG CAM H17 SING N N 50 WPG OAG H18 SING N N 51 WPG OAD H19 SING N N 52 WPG CAP H20 SING N N 53 WPG CAP H21 SING N N 54 WPG CBB H22 SING N N 55 WPG N1 H23 SING N N 56 # # 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 WPG SMILES ACDLabs 12.01 "c12c(C(=O)NC(N)=N1)ncn2C3C(OCC(P(=O)(O)O)O)CN(C3)C(=O)CCP(O)(O)=O" WPG InChI InChI 1.03 "InChI=1S/C14H22N6O10P2/c15-14-17-12-11(13(23)18-14)16-6-20(12)7-3-19(9(21)1-2-31(24,25)26)4-8(7)30-5-10(22)32(27,28)29/h6-8,10,22H,1-5H2,(H2,24,25,26)(H2,27,28,29)(H3,15,17,18,23)/t7-,8-,10-/m1/s1" WPG InChIKey InChI 1.03 RBYFDIJTTUISNF-NQMVMOMDSA-N WPG SMILES_CANONICAL CACTVS 3.385 "NC1=Nc2n(cnc2C(=O)N1)[C@@H]3CN(C[C@H]3OC[C@H](O)[P](O)(O)=O)C(=O)CC[P](O)(O)=O" WPG SMILES CACTVS 3.385 "NC1=Nc2n(cnc2C(=O)N1)[CH]3CN(C[CH]3OC[CH](O)[P](O)(O)=O)C(=O)CC[P](O)(O)=O" WPG SMILES_CANONICAL "OpenEye OEToolkits" 2.0.4 "c1nc2c(n1[C@@H]3CN(C[C@H]3OC[C@H](O)P(=O)(O)O)C(=O)CCP(=O)(O)O)N=C(NC2=O)N" WPG SMILES "OpenEye OEToolkits" 2.0.4 "c1nc2c(n1C3CN(CC3OCC(O)P(=O)(O)O)C(=O)CCP(=O)(O)O)N=C(NC2=O)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 WPG "SYSTEMATIC NAME" ACDLabs 12.01 "(3-{(3R,4R)-3-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-4-[(2R)-2-hydroxy-2-phosphonoethoxy]pyrrolidin-1-yl}-3-oxopropyl)phosphonic acid" WPG "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.4 "[3-[(3~{R},4~{R})-3-(2-azanyl-6-oxidanylidene-1~{H}-purin-9-yl)-4-[(2~{R})-2-oxidanyl-2-phosphono-ethoxy]pyrrolidin-1-yl]-3-oxidanylidene-propyl]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 WPG "Create component" 2016-01-14 RCSB WPG "Initial release" 2017-12-06 RCSB WPG "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id WPG _pdbx_chem_comp_synonyms.name "[3R,4R]-4-guanin-9-yl-3-((R)-2-hydroxy-2-phosphonoethyl)oxy-1-N-(phosphonopropionyl)pyrrolidine" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##