data_WS2 # _chem_comp.id WS2 _chem_comp.name "6-(1-beta-D-Galactopyranosyloxymethyl)-N-(5'-deoxyluridine-5'-yl)picolinamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H28 N4 O12" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-08-16 _chem_comp.pdbx_modified_date 2015-02-25 _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 540.477 _chem_comp.one_letter_code ? _chem_comp.three_letter_code WS2 _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 ? _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 WS2 O4 O4 O 0 1 N N N -6.016 -4.476 2.491 -6.016 -4.476 2.491 O4 WS2 1 WS2 C4 C4 C 0 1 N N N -5.720 -3.555 1.752 -5.720 -3.555 1.752 C4 WS2 2 WS2 N3 N3 N 0 1 N N N -5.321 -3.798 0.487 -5.321 -3.798 0.487 N3 WS2 3 WS2 C2 C2 C 0 1 N N N -4.995 -2.779 -0.329 -4.995 -2.779 -0.329 C2 WS2 4 WS2 O2 O2 O 0 1 N N N -4.637 -3.013 -1.467 -4.637 -3.013 -1.467 O2 WS2 5 WS2 C5 C5 C 0 1 N N N -5.797 -2.217 2.211 -5.797 -2.217 2.211 C5 WS2 6 WS2 C6 C6 C 0 1 N N N -5.463 -1.214 1.371 -5.463 -1.214 1.371 C6 WS2 7 WS2 N1 N1 N 0 1 N N N -5.058 -1.504 0.097 -5.058 -1.504 0.097 N1 WS2 8 WS2 "C1'" "C1'" C 0 1 N N R -4.696 -0.415 -0.814 -4.696 -0.415 -0.814 "C1'" WS2 9 WS2 "O4'" "O4'" O 0 1 N N N -3.721 0.453 -0.198 -3.721 0.453 -0.198 "O4'" WS2 10 WS2 "C2'" "C2'" C 0 1 N N R -5.919 0.489 -1.085 -5.919 0.489 -1.085 "C2'" WS2 11 WS2 "O2'" "O2'" O 0 1 N N N -6.536 0.140 -2.326 -6.536 0.140 -2.326 "O2'" WS2 12 WS2 "C3'" "C3'" C 0 1 N N S -5.324 1.913 -1.157 -5.324 1.913 -1.157 "C3'" WS2 13 WS2 "O3'" "O3'" O 0 1 N N N -5.558 2.488 -2.444 -5.558 2.488 -2.444 "O3'" WS2 14 WS2 "C4'" "C4'" C 0 1 N N R -3.810 1.700 -0.922 -3.810 1.700 -0.922 "C4'" WS2 15 WS2 "C5'" "C5'" C 0 1 N N N -3.234 2.844 -0.086 -3.234 2.844 -0.086 "C5'" WS2 16 WS2 N11 N11 N 0 1 N N N -1.782 2.687 0.024 -1.782 2.687 0.024 N11 WS2 17 WS2 C12 C12 C 0 1 N N N -1.057 3.585 0.720 -1.057 3.585 0.720 C12 WS2 18 WS2 O13 O13 O 0 1 N N N -1.608 4.525 1.256 -1.608 4.525 1.256 O13 WS2 19 WS2 C14 C14 C 0 1 Y N N 0.412 3.425 0.831 0.412 3.425 0.831 C14 WS2 20 WS2 C15 C15 C 0 1 Y N N 1.155 4.357 1.552 1.155 4.357 1.552 C15 WS2 21 WS2 C16 C16 C 0 1 Y N N 2.528 4.194 1.647 2.528 4.194 1.647 C16 WS2 22 WS2 C17 C17 C 0 1 Y N N 3.110 3.104 1.018 3.110 3.104 1.018 C17 WS2 23 WS2 C18 C18 C 0 1 Y N N 2.309 2.217 0.317 2.309 2.217 0.317 C18 WS2 24 WS2 N19 N19 N 0 1 Y N N 1.008 2.392 0.247 1.008 2.392 0.247 N19 WS2 25 WS2 C20 C20 C 0 1 N N N 2.937 1.031 -0.368 2.937 1.031 -0.368 C20 WS2 26 WS2 "O1'" "O1'" O 0 1 N N N 4.349 1.046 -0.150 4.349 1.046 -0.150 "O1'" WS2 27 WS2 H1 H1 H 0 1 N N N -5.267 -4.739 0.154 -5.270 -4.711 0.164 H1 WS2 28 WS2 H2 H2 H 0 1 N N N -6.119 -2.002 3.219 -6.118 -2.003 3.220 H2 WS2 29 WS2 H3 H3 H 0 1 N N N -5.515 -0.188 1.703 -5.515 -0.188 1.704 H3 WS2 30 WS2 H4 H4 H 0 1 N N N -4.318 -0.816 -1.766 -4.308 -0.818 -1.750 H4 WS2 31 WS2 H5 H5 H 0 1 N N N -6.628 0.421 -0.247 -6.636 0.415 -0.267 H5 WS2 32 WS2 H6 H6 H 0 1 N N N -6.896 -0.737 -2.265 -7.273 0.715 -2.574 H6 WS2 33 WS2 H7 H7 H 0 1 N N N -5.744 2.535 -0.353 -5.748 2.544 -0.375 H7 WS2 34 WS2 H8 H8 H 0 1 N N N -5.187 3.362 -2.473 -6.494 2.588 -2.667 H8 WS2 35 WS2 H9 H9 H 0 1 N N N -3.288 1.639 -1.888 -3.285 1.625 -1.875 H9 WS2 36 WS2 H10 H10 H 0 1 N N N -3.463 3.804 -0.572 -3.461 3.796 -0.568 H10 WS2 37 WS2 H11 H11 H 0 1 N N N -3.682 2.825 0.919 -3.678 2.826 0.909 H11 WS2 38 WS2 H12 H12 H 0 1 N N N -1.328 1.913 -0.418 -1.342 1.936 -0.405 H12 WS2 39 WS2 H13 H13 H 0 1 N N N 0.668 5.194 2.030 0.669 5.194 2.029 H13 WS2 40 WS2 H14 H14 H 0 1 N N N 3.131 4.900 2.199 3.131 4.900 2.199 H14 WS2 41 WS2 H15 H15 H 0 1 N N N 4.177 2.948 1.074 4.177 2.949 1.072 H15 WS2 42 WS2 H16 H16 H 0 1 N N N 2.732 1.081 -1.448 2.517 0.111 0.039 H16 WS2 43 WS2 H17 H17 H 0 1 N N N 2.513 0.103 0.043 2.734 1.080 -1.438 H17 WS2 44 WS2 C11 C11 C 0 1 N N R 5.044 -0.042 -0.762 5.044 -0.042 -0.762 C11 WS2 45 WS2 C22 C22 C 0 1 N N S 6.552 0.143 -0.570 6.552 0.143 -0.570 C22 WS2 46 WS2 C33 C33 C 0 1 N N S 7.286 -1.057 -1.175 7.286 -1.057 -1.175 C33 WS2 47 WS2 C44 C44 C 0 1 N N R 6.770 -2.342 -0.519 6.770 -2.342 -0.519 C44 WS2 48 WS2 C55 C55 C 0 1 N N R 5.254 -2.431 -0.713 5.254 -2.431 -0.713 C55 WS2 49 WS2 O66 O66 O 0 1 N N N 4.635 -1.270 -0.155 4.635 -1.270 -0.155 O66 WS2 50 WS2 H18 H18 H 0 1 N N N 4.828 -0.066 -1.840 4.814 -0.068 -1.827 H18 WS2 51 WS2 H19 H19 H 0 1 N N N 6.871 1.059 -1.089 6.873 1.057 -1.069 H19 WS2 52 WS2 H21 H21 H 0 1 N N N 7.081 -1.097 -2.255 7.100 -1.095 -2.248 H21 WS2 53 WS2 H23 H23 H 0 1 N N N 7.246 -3.208 -1.003 7.248 -3.205 -0.983 H23 WS2 54 WS2 H25 H25 H 0 1 N N N 5.034 -2.504 -1.788 5.026 -2.488 -1.778 H25 WS2 55 WS2 C77 C77 C 0 1 N N N 4.722 -3.681 -0.009 4.722 -3.681 -0.009 C77 WS2 56 WS2 O70 O70 O 0 1 N N N 3.328 -3.826 -0.287 3.328 -3.826 -0.287 O70 WS2 57 WS2 H26 H26 H 0 1 N N N 5.263 -4.566 -0.375 5.259 -4.557 -0.371 H26 WS2 58 WS2 H27 H27 H 0 1 N N N 4.871 -3.582 1.076 4.870 -3.583 1.066 H27 WS2 59 WS2 H28 H28 H 0 1 N N N 2.997 -4.602 0.150 2.923 -4.600 0.128 H28 WS2 60 WS2 O71 O71 O 0 1 N N N 7.073 -2.320 0.877 7.073 -2.320 0.877 O71 WS2 61 WS2 O72 O72 O 0 1 N N N 8.689 -0.929 -0.936 8.689 -0.929 -0.936 O72 WS2 62 WS2 O73 O73 O 0 1 N N N 6.848 0.230 0.825 6.848 0.230 0.825 O73 WS2 63 WS2 H20 H20 H 0 1 N N N 6.753 -3.117 1.284 8.017 -2.260 1.074 H20 WS2 64 WS2 H22 H22 H 0 1 N N N 9.144 -1.674 -1.312 9.082 -0.132 -1.318 H22 WS2 65 WS2 H24 H24 H 0 1 N N N 7.783 0.345 0.944 6.412 0.967 1.275 H24 WS2 66 # 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 WS2 "O2'" "C2'" SING N N 1 WS2 "O3'" "C3'" SING N N 2 WS2 "C2'" "C3'" SING N N 3 WS2 "C2'" "C1'" SING N N 4 WS2 "C4'" "C3'" SING N N 5 WS2 "C4'" "C5'" SING N N 6 WS2 "C4'" "O4'" SING N N 7 WS2 "C5'" N11 SING N N 8 WS2 O13 C12 DOUB N N 9 WS2 "O4'" "C1'" SING N N 10 WS2 "C1'" N1 SING N N 11 WS2 O2 C2 DOUB N N 12 WS2 C12 N11 SING N N 13 WS2 C12 C14 SING N N 14 WS2 "O1'" C20 SING N N 15 WS2 N1 C2 SING N N 16 WS2 N1 C6 SING N N 17 WS2 C2 N3 SING N N 18 WS2 N19 C14 DOUB Y N 19 WS2 N19 C18 SING Y N 20 WS2 C14 C15 SING Y N 21 WS2 C6 C5 DOUB N N 22 WS2 C20 C18 SING N N 23 WS2 N3 C4 SING N N 24 WS2 C18 C17 DOUB Y N 25 WS2 C15 C16 DOUB Y N 26 WS2 C5 C4 SING N N 27 WS2 C4 O4 DOUB N N 28 WS2 C17 C16 SING Y N 29 WS2 N3 H1 SING N N 30 WS2 C5 H2 SING N N 31 WS2 C6 H3 SING N N 32 WS2 "C1'" H4 SING N N 33 WS2 "C2'" H5 SING N N 34 WS2 "O2'" H6 SING N N 35 WS2 "C3'" H7 SING N N 36 WS2 "O3'" H8 SING N N 37 WS2 "C4'" H9 SING N N 38 WS2 "C5'" H10 SING N N 39 WS2 "C5'" H11 SING N N 40 WS2 N11 H12 SING N N 41 WS2 C15 H13 SING N N 42 WS2 C16 H14 SING N N 43 WS2 C17 H15 SING N N 44 WS2 C20 H16 SING N N 45 WS2 C20 H17 SING N N 46 WS2 "O1'" C11 SING N N 47 WS2 C11 C22 SING N N 48 WS2 C22 C33 SING N N 49 WS2 C33 C44 SING N N 50 WS2 C44 C55 SING N N 51 WS2 C55 O66 SING N N 52 WS2 O66 C11 SING N N 53 WS2 C11 H18 SING N N 54 WS2 C22 H19 SING N N 55 WS2 C33 H21 SING N N 56 WS2 C44 H23 SING N N 57 WS2 C55 H25 SING N N 58 WS2 C55 C77 SING N N 59 WS2 C77 O70 SING N N 60 WS2 C77 H26 SING N N 61 WS2 C77 H27 SING N N 62 WS2 O70 H28 SING N N 63 WS2 C44 O71 SING N N 64 WS2 C33 O72 SING N N 65 WS2 C22 O73 SING N N 66 WS2 O71 H20 SING N N 67 WS2 O72 H22 SING N N 68 WS2 O73 H24 SING N N 69 # 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 WS2 SMILES ACDLabs 12.01 "O=C1C=CN(C(=O)N1)C2OC(C(O)C2O)CNC(=O)c3nc(ccc3)COC4OC(C(O)C(O)C4O)CO" WS2 InChI InChI 1.03 "InChI=1S/C22H28N4O12/c27-7-12-15(30)16(31)18(33)21(38-12)36-8-9-2-1-3-10(24-9)19(34)23-6-11-14(29)17(32)20(37-11)26-5-4-13(28)25-22(26)35/h1-5,11-12,14-18,20-21,27,29-33H,6-8H2,(H,23,34)(H,25,28,35)/t11-,12-,14-,15+,16+,17-,18+,20-,21-/m1/s1" WS2 InChIKey InChI 1.03 KPOTWZYLDCHCIG-GBMKPDNQSA-N WS2 SMILES_CANONICAL CACTVS 3.385 "OC[C@H]1O[C@@H](OCc2cccc(n2)C(=O)NC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N4C=CC(=O)NC4=O)[C@@H](O)[C@@H](O)[C@H]1O" WS2 SMILES CACTVS 3.385 "OC[CH]1O[CH](OCc2cccc(n2)C(=O)NC[CH]3O[CH]([CH](O)[CH]3O)N4C=CC(=O)NC4=O)[CH](O)[CH](O)[CH]1O" WS2 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1cc(nc(c1)C(=O)NC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)CO[C@H]4[C@H]([C@H]([C@H]([C@H](O4)CO)O)O)O" WS2 SMILES "OpenEye OEToolkits" 1.7.6 "c1cc(nc(c1)C(=O)NCC2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)COC4C(C(C(C(O4)CO)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 WS2 "SYSTEMATIC NAME" ACDLabs 12.01 "5'-deoxy-5'-[({6-[(beta-D-talopyranosyloxy)methyl]pyridin-2-yl}carbonyl)amino]uridine" WS2 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "N-[[(2R,3S,4R,5R)-5-[2,4-bis(oxidanylidene)pyrimidin-1-yl]-3,4-bis(oxidanyl)oxolan-2-yl]methyl]-6-[[(2R,3S,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxymethyl]pyridine-2-carboxamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site WS2 "Create component" 2013-08-16 RCSB WS2 "Other modification" 2013-08-29 RCSB WS2 "Initial release" 2013-09-11 RCSB WS2 "Other modification" 2015-02-25 RCSB #