data_DWN # _chem_comp.id DWN _chem_comp.name "(2R,4S,6R)-4-amino-6-methyl-5-oxotetrahydro-2H-pyran-2-yl [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl dihydrogen diphosphate" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C16 H25 N3 O13 P2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-03-12 _chem_comp.pdbx_modified_date 2012-05-16 _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 529.330 _chem_comp.one_letter_code ? _chem_comp.three_letter_code DWN _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 4E32 _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 DWN O4 O4 O 0 1 N N N 19.656 18.003 1.129 8.299 -2.822 -1.012 O4 DWN 1 DWN C4 C4 C 0 1 N N N 20.284 16.983 1.434 7.569 -1.963 -0.580 C4 DWN 2 DWN C5 C5 C 0 1 N N R 21.320 16.459 0.477 6.605 -2.251 0.552 C5 DWN 3 DWN C6 C6 C 0 1 N N N 22.587 17.314 0.353 7.082 -1.551 1.826 C6 DWN 4 DWN O5 O5 O 0 1 N N N 21.863 15.216 0.878 5.314 -1.755 0.182 O5 DWN 5 DWN C3 C3 C 0 1 N N S 20.139 16.250 2.737 7.590 -0.558 -1.148 C3 DWN 6 DWN N3 N3 N 0 1 N N N 18.957 16.738 3.410 8.365 -0.539 -2.396 N3 DWN 7 DWN C2 C2 C 0 1 N N N 20.296 14.734 2.718 6.141 -0.139 -1.429 C2 DWN 8 DWN C1 C1 C 0 1 N N R 20.895 14.290 1.380 5.301 -0.370 -0.167 C1 DWN 9 DWN O1 O1 O 0 1 N N N 19.828 14.174 0.446 3.955 0.047 -0.406 O1 DWN 10 DWN P2 P2 P 0 1 N N N 19.889 12.991 -0.650 2.999 0.630 0.751 P2 DWN 11 DWN O3P O3P O 0 1 N N N 20.012 11.685 0.122 2.710 -0.521 1.839 O3P DWN 12 DWN O4P O4P O 0 1 N N N 18.748 13.201 -1.616 3.664 1.776 1.410 O4P DWN 13 DWN OPP OPP O 0 1 N N N 21.287 13.276 -1.383 1.608 1.116 0.102 OPP DWN 14 DWN P P P 0 1 N N N 22.030 12.644 -2.676 0.441 2.117 0.580 P DWN 15 DWN O1P O1P O 0 1 N N N 23.391 13.307 -2.694 0.891 3.638 0.302 O1P DWN 16 DWN O2P O2P O 0 1 N N N 21.189 12.829 -3.891 0.195 1.933 2.028 O2P DWN 17 DWN O5X O5X O 0 1 N N N 22.121 11.110 -2.226 -0.909 1.798 -0.238 O5X DWN 18 DWN C5X C5X C 0 1 N N N 22.748 10.211 -3.137 -2.153 2.447 0.030 C5X DWN 19 DWN C4X C4X C 0 1 N N R 22.596 8.823 -2.536 -3.223 1.912 -0.924 C4X DWN 20 DWN O4X O4X O 0 1 N N N 22.997 7.959 -3.598 -3.548 0.543 -0.600 O4X DWN 21 DWN C3X C3X C 0 1 N N S 23.568 8.624 -1.380 -4.546 2.687 -0.737 C3X DWN 22 DWN O3X O3X O 0 1 N N N 22.931 7.723 -0.456 -4.678 3.701 -1.735 O3X DWN 23 DWN C2X C2X C 0 1 N N N 24.725 7.940 -2.071 -5.640 1.610 -0.912 C2X DWN 24 DWN C1X C1X C 0 1 N N R 24.142 7.193 -3.261 -4.848 0.312 -1.184 C1X DWN 25 DWN N11 N11 N 0 1 N N N 25.103 7.272 -4.369 -5.502 -0.829 -0.539 N11 DWN 26 DWN C21 C21 C 0 1 N N N 25.545 6.123 -4.897 -5.635 -0.851 0.800 C21 DWN 27 DWN O21 O21 O 0 1 N N N 25.099 5.028 -4.506 -5.210 0.078 1.460 O21 DWN 28 DWN N31 N31 N 0 1 N N N 26.397 6.122 -5.949 -6.232 -1.886 1.419 N31 DWN 29 DWN C61 C61 C 0 1 N N N 25.562 8.471 -4.776 -5.977 -1.860 -1.303 C61 DWN 30 DWN C51 C51 C 0 1 N N N 26.490 8.559 -5.801 -6.580 -2.911 -0.708 C51 DWN 31 DWN C5A C5A C 0 1 N N N 27.032 9.881 -6.280 -7.109 -4.056 -1.533 C5A DWN 32 DWN C41 C41 C 0 1 N N N 26.953 7.273 -6.385 -6.708 -2.924 0.702 C41 DWN 33 DWN O41 O41 O 0 1 N N N 27.774 7.245 -7.329 -7.249 -3.861 1.261 O41 DWN 34 DWN H1 H1 H 0 1 N N N 20.865 16.366 -0.520 6.550 -3.326 0.722 H1 DWN 35 DWN H2 H2 H 0 1 N N N 22.313 18.333 0.040 6.375 -1.745 2.633 H2 DWN 36 DWN H3 H3 H 0 1 N N N 23.099 17.354 1.326 8.064 -1.931 2.104 H3 DWN 37 DWN H4 H4 H 0 1 N N N 23.258 16.868 -0.396 7.144 -0.477 1.648 H4 DWN 38 DWN H5 H5 H 0 1 N N N 20.983 16.603 3.348 8.038 0.124 -0.426 H5 DWN 39 DWN H6 H6 H 0 1 N N N 18.847 16.259 4.281 9.316 -0.836 -2.236 H6 DWN 40 DWN H7 H7 H 0 1 N N N 19.051 17.719 3.579 7.923 -1.107 -3.104 H7 DWN 41 DWN H9 H9 H 0 1 N N N 19.311 14.263 2.851 6.113 0.916 -1.701 H9 DWN 42 DWN H10 H10 H 0 1 N N N 20.963 14.426 3.537 5.742 -0.737 -2.249 H10 DWN 43 DWN H11 H11 H 0 1 N N N 21.367 13.307 1.525 5.719 0.214 0.653 H11 DWN 44 DWN H12 H12 H 0 1 N N N 19.296 11.108 -0.115 2.274 -1.305 1.477 H12 DWN 45 DWN H13 H13 H 0 1 N N N 23.510 13.764 -3.518 1.069 3.831 -0.628 H13 DWN 46 DWN H14 H14 H 0 1 N N N 23.813 10.463 -3.250 -2.453 2.247 1.059 H14 DWN 47 DWN H15 H15 H 0 1 N N N 22.254 10.257 -4.119 -2.042 3.521 -0.114 H15 DWN 48 DWN H16 H16 H 0 1 N N N 21.559 8.643 -2.215 -2.881 1.988 -1.957 H16 DWN 49 DWN H17 H17 H 0 1 N N N 23.864 9.579 -0.922 -4.595 3.125 0.260 H17 DWN 50 DWN H18 H18 H 0 1 N N N 23.506 7.570 0.285 -5.492 4.219 -1.665 H18 DWN 51 DWN H19 H19 H 0 1 N N N 25.214 7.235 -1.383 -6.230 1.514 -0.001 H19 DWN 52 DWN H20 H20 H 0 1 N N N 25.457 8.686 -2.413 -6.283 1.852 -1.759 H20 DWN 53 DWN H21 H21 H 0 1 N N N 23.899 6.153 -2.999 -4.757 0.141 -2.257 H21 DWN 54 DWN H22 H22 H 0 1 N N N 26.617 5.261 -6.408 -6.319 -1.886 2.385 H22 DWN 55 DWN H23 H23 H 0 1 N N N 25.204 9.371 -4.299 -5.871 -1.832 -2.378 H23 DWN 56 DWN H24 H24 H 0 1 N N N 26.557 10.698 -5.717 -6.329 -4.807 -1.654 H24 DWN 57 DWN H25 H25 H 0 1 N N N 28.120 9.910 -6.121 -7.967 -4.501 -1.030 H25 DWN 58 DWN H26 H26 H 0 1 N N N 26.815 9.999 -7.352 -7.413 -3.687 -2.513 H26 DWN 59 # 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 DWN O41 C41 DOUB N N 1 DWN C41 N31 SING N N 2 DWN C41 C51 SING N N 3 DWN C5A C51 SING N N 4 DWN N31 C21 SING N N 5 DWN C51 C61 DOUB N N 6 DWN C21 O21 DOUB N N 7 DWN C21 N11 SING N N 8 DWN C61 N11 SING N N 9 DWN N11 C1X SING N N 10 DWN O2P P DOUB N N 11 DWN O4X C1X SING N N 12 DWN O4X C4X SING N N 13 DWN C1X C2X SING N N 14 DWN C5X C4X SING N N 15 DWN C5X O5X SING N N 16 DWN O1P P SING N N 17 DWN P O5X SING N N 18 DWN P OPP SING N N 19 DWN C4X C3X SING N N 20 DWN C2X C3X SING N N 21 DWN O4P P2 DOUB N N 22 DWN OPP P2 SING N N 23 DWN C3X O3X SING N N 24 DWN P2 O3P SING N N 25 DWN P2 O1 SING N N 26 DWN C6 C5 SING N N 27 DWN O1 C1 SING N N 28 DWN C5 O5 SING N N 29 DWN C5 C4 SING N N 30 DWN O5 C1 SING N N 31 DWN O4 C4 DOUB N N 32 DWN C1 C2 SING N N 33 DWN C4 C3 SING N N 34 DWN C2 C3 SING N N 35 DWN C3 N3 SING N N 36 DWN C5 H1 SING N N 37 DWN C6 H2 SING N N 38 DWN C6 H3 SING N N 39 DWN C6 H4 SING N N 40 DWN C3 H5 SING N N 41 DWN N3 H6 SING N N 42 DWN N3 H7 SING N N 43 DWN C2 H9 SING N N 44 DWN C2 H10 SING N N 45 DWN C1 H11 SING N N 46 DWN O3P H12 SING N N 47 DWN O1P H13 SING N N 48 DWN C5X H14 SING N N 49 DWN C5X H15 SING N N 50 DWN C4X H16 SING N N 51 DWN C3X H17 SING N N 52 DWN O3X H18 SING N N 53 DWN C2X H19 SING N N 54 DWN C2X H20 SING N N 55 DWN C1X H21 SING N N 56 DWN N31 H22 SING N N 57 DWN C61 H23 SING N N 58 DWN C5A H24 SING N N 59 DWN C5A H25 SING N N 60 DWN C5A H26 SING N N 61 # 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 DWN SMILES ACDLabs 12.01 "O=C1C(=CN(C(=O)N1)C2OC(C(O)C2)COP(=O)(OP(=O)(OC3OC(C(=O)C(N)C3)C)O)O)C" DWN InChI InChI 1.03 "InChI=1S/C16H25N3O13P2/c1-7-5-19(16(23)18-15(7)22)12-4-10(20)11(30-12)6-28-33(24,25)32-34(26,27)31-13-3-9(17)14(21)8(2)29-13/h5,8-13,20H,3-4,6,17H2,1-2H3,(H,24,25)(H,26,27)(H,18,22,23)/t8-,9+,10+,11-,12-,13-/m1/s1" DWN InChIKey InChI 1.03 IVWGOICUSBJICO-KISRQWFGSA-N DWN SMILES_CANONICAL CACTVS 3.370 "C[C@H]1O[C@@H](C[C@H](N)C1=O)O[P](O)(=O)O[P](O)(=O)OC[C@H]2O[C@H](C[C@@H]2O)N3C=C(C)C(=O)NC3=O" DWN SMILES CACTVS 3.370 "C[CH]1O[CH](C[CH](N)C1=O)O[P](O)(=O)O[P](O)(=O)OC[CH]2O[CH](C[CH]2O)N3C=C(C)C(=O)NC3=O" DWN SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "C[C@@H]1C(=O)[C@H](C[C@H](O1)OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H](C[C@@H](O2)N3C=C(C(=O)NC3=O)C)O)N" DWN SMILES "OpenEye OEToolkits" 1.7.6 "CC1C(=O)C(CC(O1)OP(=O)(O)OP(=O)(O)OCC2C(CC(O2)N3C=C(C(=O)NC3=O)C)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 DWN "SYSTEMATIC NAME" ACDLabs 12.01 "(2R,4S,6R)-4-amino-6-methyl-5-oxotetrahydro-2H-pyran-2-yl [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl dihydrogen diphosphate (non-preferred name)" DWN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "[(2R,4S,6R)-4-azanyl-6-methyl-5-oxidanylidene-oxan-2-yl] [[(2R,3S,5R)-5-[5-methyl-2,4-bis(oxidanylidene)pyrimidin-1-yl]-3-oxidanyl-oxolan-2-yl]methoxy-oxidanyl-phosphoryl] 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 DWN "Create component" 2012-03-12 RCSB DWN "Modify atom id" 2012-05-16 RCSB #