data_FNF # _chem_comp.id FNF _chem_comp.name "(2R,3R,4S,5R,6R)-4-(formylamino)-3,5-dihydroxy-6-methyltetrahydro-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)" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C17 H27 N3 O15 P2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-08-01 _chem_comp.pdbx_modified_date 2013-08-09 _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 575.355 _chem_comp.one_letter_code ? _chem_comp.three_letter_code FNF _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 4LXX _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 FNF O1F O1F O 0 1 N N N -23.880 0.786 17.953 5.566 -0.554 3.337 O1F FNF 1 FNF C1F C1F C 0 1 N N N -24.687 1.677 18.257 6.465 0.260 3.351 C1F FNF 2 FNF N3Q N3Q N 0 1 N N N -25.208 2.695 17.387 6.566 1.170 2.363 N3Q FNF 3 FNF C3Q C3Q C 0 1 N N S -24.562 3.991 17.098 5.589 1.177 1.271 C3Q FNF 4 FNF C2Q C2Q C 0 1 N N R -24.562 4.956 18.285 6.019 0.177 0.193 C2Q FNF 5 FNF O2Q O2Q O 0 1 N N N -23.608 4.442 19.229 6.017 -1.143 0.738 O2Q FNF 6 FNF C4Q C4Q C 0 1 N N R -25.280 4.675 15.930 5.519 2.578 0.654 C4Q FNF 7 FNF O4Q O4Q O 0 1 N N N -26.678 4.814 16.259 6.820 2.968 0.208 O4Q FNF 8 FNF C5Q C5Q C 0 1 N N R -24.682 6.046 15.587 4.556 2.556 -0.535 C5Q FNF 9 FNF C6Q C6Q C 0 1 N N N -25.521 6.694 14.472 4.527 3.937 -1.194 C6Q FNF 10 FNF O5Q O5Q O 0 1 N N N -24.847 6.873 16.756 4.997 1.584 -1.486 O5Q FNF 11 FNF C1Q C1Q C 0 1 N N R -24.176 6.395 17.929 5.036 0.248 -0.979 C1Q FNF 12 FNF O3B O3B O 0 1 N N N -22.787 6.367 17.696 3.733 -0.130 -0.531 O3B FNF 13 FNF PB PB P 0 1 N N N -21.928 7.748 17.634 2.649 -0.839 -1.488 PB FNF 14 FNF O2B O2B O 0 1 N N N -20.529 7.301 17.953 3.239 -2.057 -2.085 O2B FNF 15 FNF O1B O1B O 0 1 N N N -22.694 8.772 18.415 2.220 0.180 -2.659 O1B FNF 16 FNF O3A O3A O 0 1 N N N -22.113 8.101 16.051 1.351 -1.239 -0.623 O3A FNF 17 FNF PA PA P 0 1 N N N -22.238 9.432 15.144 0.144 -2.283 -0.837 PA FNF 18 FNF O1A O1A O 0 1 N N N -22.101 8.894 13.736 -0.278 -2.266 -2.256 O1A FNF 19 FNF O2A O2A O 0 1 N N N -23.318 10.405 15.434 0.637 -3.763 -0.441 O2A FNF 20 FNF "O5'" "O5'" O 0 1 N N N -20.827 10.134 15.475 -1.099 -1.864 0.097 "O5'" FNF 21 FNF "C5'" "C5'" C 0 1 N N N -19.597 9.453 15.205 -2.362 -2.532 0.059 "C5'" FNF 22 FNF "C4'" "C4'" C 0 1 N N R -18.539 10.134 16.069 -3.312 -1.885 1.068 "C4'" FNF 23 FNF "O4'" "O4'" O 0 1 N N N -18.389 11.519 15.650 -3.686 -0.561 0.628 "O4'" FNF 24 FNF "C3'" "C3'" C 0 1 N N S -18.942 10.239 17.520 -4.641 -2.669 1.134 "C3'" FNF 25 FNF "O3'" "O3'" O 0 1 N N N -18.479 9.137 18.303 -4.642 -3.560 2.251 "O3'" FNF 26 FNF "C2'" "C2'" C 0 1 N N N -18.145 11.447 18.030 -5.715 -1.573 1.314 "C2'" FNF 27 FNF "C1'" "C1'" C 0 1 N N R -18.140 12.334 16.796 -4.908 -0.256 1.336 "C1'" FNF 28 FNF N1 N1 N 0 1 N N N -19.108 13.440 16.793 -5.646 0.806 0.647 N1 FNF 29 FNF C2 C2 C 0 1 N N N -18.674 14.651 17.207 -5.940 0.673 -0.659 C2 FNF 30 FNF O2 O2 O 0 1 N N N -17.422 14.789 17.609 -5.590 -0.329 -1.254 O2 FNF 31 FNF C6 C6 C 0 1 N N N -20.385 13.268 16.371 -6.033 1.921 1.339 C6 FNF 32 FNF C5 C5 C 0 1 N N N -21.303 14.305 16.358 -6.713 2.899 0.703 C5 FNF 33 FNF C5M C5M C 0 1 N N N -22.734 14.144 15.888 -7.148 4.135 1.449 C5M FNF 34 FNF C4 C4 C 0 1 N N N -20.767 15.610 16.804 -7.011 2.749 -0.673 C4 FNF 35 FNF N3 N3 N 0 1 N N N -19.498 15.714 17.220 -6.616 1.633 -1.317 N3 FNF 36 FNF O4 O4 O 0 1 N N N -21.559 16.682 16.795 -7.623 3.618 -1.267 O4 FNF 37 FNF H1 H1 H 0 1 N N N -25.034 1.689 19.280 7.182 0.258 4.159 H1 FNF 38 FNF H2 H2 H 0 1 N N N -26.083 2.510 16.939 7.285 1.821 2.375 H2 FNF 39 FNF H3 H3 H 0 1 N N N -23.518 3.811 16.801 4.609 0.898 1.657 H3 FNF 40 FNF H4 H4 H 0 1 N N N -25.566 4.962 18.733 7.021 0.426 -0.156 H4 FNF 41 FNF H5 H5 H 0 1 N N N -23.574 5.013 19.988 6.280 -1.829 0.109 H5 FNF 42 FNF H6 H6 H 0 1 N N N -25.180 4.030 15.045 5.162 3.287 1.401 H6 FNF 43 FNF H7 H7 H 0 1 N N N -27.040 3.962 16.470 6.850 3.847 -0.194 H7 FNF 44 FNF H8 H8 H 0 1 N N N -23.629 5.953 15.284 3.556 2.297 -0.188 H8 FNF 45 FNF H9 H9 H 0 1 N N N -25.099 7.678 14.220 5.527 4.195 -1.541 H9 FNF 46 FNF H10 H10 H 0 1 N N N -25.506 6.049 13.581 3.841 3.921 -2.040 H10 FNF 47 FNF H11 H11 H 0 1 N N N -26.558 6.818 14.818 4.191 4.678 -0.468 H11 FNF 48 FNF H12 H12 H 0 1 N N N -24.408 7.044 18.786 5.361 -0.430 -1.768 H12 FNF 49 FNF H13 H13 H 0 1 N N N -22.159 9.088 19.134 1.825 1.003 -2.339 H13 FNF 50 FNF H14 H14 H 0 1 N N N -23.815 10.573 14.642 0.929 -3.848 0.477 H14 FNF 51 FNF H15 H15 H 0 1 N N N -19.682 8.390 15.473 -2.785 -2.452 -0.942 H15 FNF 52 FNF H16 H16 H 0 1 N N N -19.336 9.543 14.140 -2.224 -3.583 0.312 H16 FNF 53 FNF H17 H17 H 0 1 N N N -17.584 9.595 15.982 -2.847 -1.842 2.053 H17 FNF 54 FNF H18 H18 H 0 1 N N N -20.024 10.408 17.624 -4.808 -3.218 0.207 H18 FNF 55 FNF H19 H19 H 0 1 N N N -19.112 8.430 18.260 -5.454 -4.078 2.341 H19 FNF 56 FNF H20 H20 H 0 1 N N N -17.125 11.162 18.326 -6.413 -1.580 0.477 H20 FNF 57 FNF H21 H21 H 0 1 N N N -18.650 11.936 18.876 -6.249 -1.712 2.255 H21 FNF 58 FNF H22 H22 H 0 1 N N N -17.132 12.765 16.706 -4.689 0.038 2.362 H22 FNF 59 FNF H23 H23 H 0 1 N N N -20.697 12.290 16.034 -5.797 2.017 2.388 H23 FNF 60 FNF H24 H24 H 0 1 N N N -23.259 15.107 15.974 -6.366 4.891 1.386 H24 FNF 61 FNF H25 H25 H 0 1 N N N -22.740 13.816 14.838 -8.065 4.522 1.005 H25 FNF 62 FNF H26 H26 H 0 1 N N N -23.242 13.392 16.510 -7.328 3.884 2.494 H26 FNF 63 FNF H27 H27 H 0 1 N N N -19.158 16.596 17.545 -6.821 1.520 -2.259 H27 FNF 64 # 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 FNF O1A PA DOUB N N 1 FNF C6Q C5Q SING N N 2 FNF PA O2A SING N N 3 FNF PA "O5'" SING N N 4 FNF PA O3A SING N N 5 FNF "C5'" "O5'" SING N N 6 FNF "C5'" "C4'" SING N N 7 FNF C5Q C4Q SING N N 8 FNF C5Q O5Q SING N N 9 FNF "O4'" "C4'" SING N N 10 FNF "O4'" "C1'" SING N N 11 FNF C5M C5 SING N N 12 FNF C4Q O4Q SING N N 13 FNF C4Q C3Q SING N N 14 FNF O3A PB SING N N 15 FNF "C4'" "C3'" SING N N 16 FNF C5 C6 DOUB N N 17 FNF C5 C4 SING N N 18 FNF C6 N1 SING N N 19 FNF O5Q C1Q SING N N 20 FNF N1 "C1'" SING N N 21 FNF N1 C2 SING N N 22 FNF O4 C4 DOUB N N 23 FNF "C1'" "C2'" SING N N 24 FNF C4 N3 SING N N 25 FNF C3Q N3Q SING N N 26 FNF C3Q C2Q SING N N 27 FNF C2 N3 SING N N 28 FNF C2 O2 DOUB N N 29 FNF N3Q C1F SING N N 30 FNF "C3'" "C2'" SING N N 31 FNF "C3'" "O3'" SING N N 32 FNF PB O3B SING N N 33 FNF PB O2B DOUB N N 34 FNF PB O1B SING N N 35 FNF O3B C1Q SING N N 36 FNF C1Q C2Q SING N N 37 FNF O1F C1F DOUB N N 38 FNF C2Q O2Q SING N N 39 FNF C1F H1 SING N N 40 FNF N3Q H2 SING N N 41 FNF C3Q H3 SING N N 42 FNF C2Q H4 SING N N 43 FNF O2Q H5 SING N N 44 FNF C4Q H6 SING N N 45 FNF O4Q H7 SING N N 46 FNF C5Q H8 SING N N 47 FNF C6Q H9 SING N N 48 FNF C6Q H10 SING N N 49 FNF C6Q H11 SING N N 50 FNF C1Q H12 SING N N 51 FNF O1B H13 SING N N 52 FNF O2A H14 SING N N 53 FNF "C5'" H15 SING N N 54 FNF "C5'" H16 SING N N 55 FNF "C4'" H17 SING N N 56 FNF "C3'" H18 SING N N 57 FNF "O3'" H19 SING N N 58 FNF "C2'" H20 SING N N 59 FNF "C2'" H21 SING N N 60 FNF "C1'" H22 SING N N 61 FNF C6 H23 SING N N 62 FNF C5M H24 SING N N 63 FNF C5M H25 SING N N 64 FNF C5M H26 SING N N 65 FNF N3 H27 SING N N 66 # 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 FNF SMILES ACDLabs 12.01 "O=C1C(=CN(C(=O)N1)C2OC(C(O)C2)COP(=O)(OP(=O)(OC3OC(C(O)C(NC=O)C3O)C)O)O)C" FNF InChI InChI 1.03 "InChI=1S/C17H27N3O15P2/c1-7-4-20(17(26)19-15(7)25)11-3-9(22)10(33-11)5-31-36(27,28)35-37(29,30)34-16-14(24)12(18-6-21)13(23)8(2)32-16/h4,6,8-14,16,22-24H,3,5H2,1-2H3,(H,18,21)(H,27,28)(H,29,30)(H,19,25,26)/t8-,9+,10-,11-,12+,13+,14-,16-/m1/s1" FNF InChIKey InChI 1.03 XDTNOGIJZRWAPO-KYQZRJCOSA-N FNF SMILES_CANONICAL CACTVS 3.385 "C[C@H]1O[C@H](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)[C@H](O)[C@@H](NC=O)[C@H]1O" FNF SMILES CACTVS 3.385 "C[CH]1O[CH](O[P](O)(=O)O[P](O)(=O)OC[CH]2O[CH](C[CH]2O)N3C=C(C)C(=O)NC3=O)[CH](O)[CH](NC=O)[CH]1O" FNF SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "C[C@@H]1[C@@H]([C@@H]([C@H]([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)O)NC=O)O" FNF SMILES "OpenEye OEToolkits" 1.7.6 "CC1C(C(C(C(O1)OP(=O)(O)OP(=O)(O)OCC2C(CC(O2)N3C=C(C(=O)NC3=O)C)O)O)NC=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 FNF "SYSTEMATIC NAME" ACDLabs 12.01 "(2R,3R,4S,5R,6R)-4-(formylamino)-3,5-dihydroxy-6-methyltetrahydro-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)" FNF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "[(2R,3R,4S,5R,6R)-4-formamido-6-methyl-3,5-bis(oxidanyl)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 FNF "Create component" 2013-08-01 RCSB FNF "Initial release" 2013-08-14 RCSB #