data_DAU
# 
_chem_comp.id                                    DAU 
_chem_comp.name                                  "2'DEOXY-THYMIDINE-5'-DIPHOSPHO-ALPHA-D-GLUCOSE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H26 N2 O16 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-11-16 
_chem_comp.pdbx_modified_date                    2008-10-14 
_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                        564.329 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DAU 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1G1L 
_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 
DAU O6   O6   O 0 1 N N N 47.805 16.783 19.152 3.240  -1.890 3.945  O6   DAU 1  
DAU C6   C6   C 0 1 N N N 48.107 16.991 20.534 3.257  -1.122 5.150  C6   DAU 2  
DAU C5   C5   C 0 1 N N R 47.813 18.385 21.062 1.956  -0.326 5.266  C5   DAU 3  
DAU O5   O5   O 0 1 N N N 46.425 18.650 20.987 0.850  -1.226 5.291  O5   DAU 4  
DAU C4   C4   C 0 1 N N S 48.326 18.480 22.512 1.980  0.500  6.554  C4   DAU 5  
DAU O4   O4   O 0 1 N N N 49.769 18.450 22.548 3.106  1.380  6.535  O4   DAU 6  
DAU C3   C3   C 0 1 N N S 47.837 19.754 23.161 0.687  1.319  6.645  C3   DAU 7  
DAU O3   O3   O 0 1 N N N 48.179 19.731 24.529 0.629  1.982  7.910  O3   DAU 8  
DAU C2   C2   C 0 1 N N R 46.362 19.912 23.036 -0.504 0.369  6.503  C2   DAU 9  
DAU O2   O2   O 0 1 N N N 45.956 21.146 23.573 -1.714 1.126  6.438  O2   DAU 10 
DAU C1   C1   C 0 1 N N R 45.928 19.796 21.581 -0.342 -0.447 5.219  C1   DAU 11 
DAU O1   O1   O 0 1 N N N 46.500 20.867 20.851 -0.265 0.436  4.099  O1   DAU 12 
DAU P2   P2   P 0 1 N N R 45.813 21.446 19.521 -0.884 -0.351 2.840  P2   DAU 13 
DAU O3P  O3P  O 0 1 N N N 44.286 21.602 19.953 -0.099 -1.581 2.593  O3P  DAU 14 
DAU O4P  O4P  O 0 1 N N N 46.622 22.673 18.957 -2.414 -0.745 3.153  O4P  DAU 15 
DAU OPP  OPP  O 0 1 N N N 45.566 20.364 18.427 -0.829 0.591  1.536  OPP  DAU 16 
DAU P    P    P 0 1 N N S 44.235 20.603 17.491 -1.461 -0.255 0.322  P    DAU 17 
DAU O1P  O1P  O 0 1 N N N 43.798 22.126 17.528 -0.667 -1.487 0.113  O1P  DAU 18 
DAU O2P  O2P  O 0 1 N N N 44.786 19.749 16.252 -2.980 -0.650 0.677  O2P  DAU 19 
DAU O5,  O5,  O 0 1 N N N 42.924 19.924 18.176 -1.437 0.631  -1.020 O5,  DAU 20 
DAU C5,  C5,  C 0 1 N N N 42.973 18.560 18.544 -2.007 -0.170 -2.056 C5,  DAU 21 
DAU C4,  C4,  C 0 1 N N R 41.748 17.844 18.033 -2.014 0.618  -3.367 C4,  DAU 22 
DAU O4,  O4,  O 0 1 N N N 40.585 18.231 18.751 -0.665 0.872  -3.820 O4,  DAU 23 
DAU C3,  C3,  C 0 1 N N S 41.472 18.145 16.576 -2.629 -0.228 -4.510 C3,  DAU 24 
DAU O3,  O3,  O 0 1 N N N 40.918 16.932 16.011 -4.052 -0.097 -4.535 O3,  DAU 25 
DAU C2,  C2,  C 0 1 N N N 40.530 19.310 16.744 -1.994 0.413  -5.767 C2,  DAU 26 
DAU C1,  C1,  C 0 1 N N R 39.634 18.880 17.893 -0.742 1.134  -5.231 C1,  DAU 27 
DAU N11  N11  N 0 1 N N N 38.990 19.885 18.768 0.454  0.617  -5.900 N11  DAU 28 
DAU C61  C61  C 0 1 N N N 39.700 20.926 19.249 1.250  1.467  -6.618 C61  DAU 29 
DAU C51  C51  C 0 1 N N N 39.096 21.833 20.102 2.353  0.990  -7.234 C51  DAU 30 
DAU C5A  C5A  C 0 1 N N N 39.892 23.008 20.676 3.242  1.911  -8.030 C5A  DAU 31 
DAU C21  C21  C 0 1 N N N 37.690 19.754 19.133 0.760  -0.689 -5.801 C21  DAU 32 
DAU O21  O21  O 0 1 N N N 36.971 18.766 18.681 0.039  -1.427 -5.158 O21  DAU 33 
DAU N31  N31  N 0 1 N N N 37.090 20.611 19.985 1.853  -1.191 -6.405 N31  DAU 34 
DAU C41  C41  C 0 1 N N N 37.783 21.635 20.467 2.661  -0.387 -7.126 C41  DAU 35 
DAU O41  O41  O 0 1 N N N 37.219 22.468 21.295 3.650  -0.840 -7.673 O41  DAU 36 
DAU HO6  HO6  H 0 1 N N N 47.988 15.911 18.821 4.076  -2.375 3.911  HO6  DAU 37 
DAU HC61 1HC6 H 0 0 N N N 47.586 16.227 21.158 4.103  -0.434 5.131  HC61 DAU 38 
DAU HC62 2HC6 H 0 0 N N N 49.169 16.720 20.738 3.352  -1.790 6.006  HC62 DAU 39 
DAU HC5  HC5  H 0 1 N N N 48.334 19.151 20.442 1.861  0.340  4.409  HC5  DAU 40 
DAU HC4  HC4  H 0 1 N N N 47.930 17.601 23.073 2.052  -0.165 7.413  HC4  DAU 41 
DAU HO4  HO4  H 0 1 N N N 50.085 18.508 23.441 3.082  1.881  7.362  HO4  DAU 42 
DAU HC3  HC3  H 0 1 N N N 48.321 20.612 22.640 0.665  2.058  5.844  HC3  DAU 43 
DAU HO3  HO3  H 0 1 N N N 47.871 20.531 24.937 -0.197 2.484  7.925  HO3  DAU 44 
DAU HC2  HC2  H 0 1 N N N 45.871 19.093 23.612 -0.540 -0.302 7.361  HC2  DAU 45 
DAU HO2  HO2  H 0 1 N N N 45.014 21.246 23.493 -2.437 0.491  6.349  HO2  DAU 46 
DAU HC1  HC1  H 0 1 N N N 44.813 19.792 21.569 -1.200 -1.109 5.100  HC1  DAU 47 
DAU H4PO OH4P H 0 0 N N N 46.215 23.015 18.169 -2.889 0.082  3.307  H4PO DAU 48 
DAU H2PO OH2P H 0 0 N N N 44.017 19.887 15.711 -3.462 0.177  0.804  H2PO DAU 49 
DAU HC51 1HC5 H 0 0 N N N 43.915 18.069 18.205 -3.029 -0.437 -1.787 HC51 DAU 50 
DAU HC52 2HC5 H 0 0 N N N 43.106 18.428 19.643 -1.415 -1.077 -2.181 HC52 DAU 51 
DAU H4,C CH4, H 0 0 N N N 41.964 16.758 18.169 -2.560 1.554  -3.247 H4,C DAU 52 
DAU H3,C CH3, H 0 0 N N N 42.305 18.411 15.884 -2.338 -1.275 -4.419 H3,C DAU 53 
DAU H3,O OH3, H 0 0 N N N 40.744 17.121 15.096 -4.363 -0.570 -5.319 H3,O DAU 54 
DAU HC21 1HC2 H 0 0 N N N 41.033 20.293 16.894 -2.681 1.128  -6.219 HC21 DAU 55 
DAU HC22 2HC2 H 0 0 N N N 39.983 19.599 15.816 -1.713 -0.354 -6.488 HC22 DAU 56 
DAU H1,C CH1, H 0 0 N N N 38.771 18.341 17.436 -0.828 2.207  -5.405 H1,C DAU 57 
DAU H61C CH61 H 0 0 N N N 40.756 21.033 18.950 0.998  2.514  -6.692 H61C DAU 58 
DAU H5A1 1H5A H 0 0 N N N 39.405 23.738 21.363 4.074  1.343  -8.446 H5A1 DAU 59 
DAU H5A2 2H5A H 0 0 N N N 40.798 22.601 21.182 2.667  2.360  -8.839 H5A2 DAU 60 
DAU H5A3 3H5A H 0 0 N N N 40.342 23.573 19.826 3.627  2.696  -7.379 H5A3 DAU 61 
DAU H31N NH31 H 0 0 N N N 36.116 20.485 20.263 2.059  -2.135 -6.324 H31N DAU 62 
# 
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 
DAU O6  C6   SING N N 1  
DAU O6  HO6  SING N N 2  
DAU C6  C5   SING N N 3  
DAU C6  HC61 SING N N 4  
DAU C6  HC62 SING N N 5  
DAU C5  O5   SING N N 6  
DAU C5  C4   SING N N 7  
DAU C5  HC5  SING N N 8  
DAU O5  C1   SING N N 9  
DAU C4  O4   SING N N 10 
DAU C4  C3   SING N N 11 
DAU C4  HC4  SING N N 12 
DAU O4  HO4  SING N N 13 
DAU C3  O3   SING N N 14 
DAU C3  C2   SING N N 15 
DAU C3  HC3  SING N N 16 
DAU O3  HO3  SING N N 17 
DAU C2  O2   SING N N 18 
DAU C2  C1   SING N N 19 
DAU C2  HC2  SING N N 20 
DAU O2  HO2  SING N N 21 
DAU C1  O1   SING N N 22 
DAU C1  HC1  SING N N 23 
DAU O1  P2   SING N N 24 
DAU P2  O3P  DOUB N N 25 
DAU P2  O4P  SING N N 26 
DAU P2  OPP  SING N N 27 
DAU O4P H4PO SING N N 28 
DAU OPP P    SING N N 29 
DAU P   O1P  DOUB N N 30 
DAU P   O2P  SING N N 31 
DAU P   O5,  SING N N 32 
DAU O2P H2PO SING N N 33 
DAU O5, C5,  SING N N 34 
DAU C5, C4,  SING N N 35 
DAU C5, HC51 SING N N 36 
DAU C5, HC52 SING N N 37 
DAU C4, O4,  SING N N 38 
DAU C4, C3,  SING N N 39 
DAU C4, H4,C SING N N 40 
DAU O4, C1,  SING N N 41 
DAU C3, O3,  SING N N 42 
DAU C3, C2,  SING N N 43 
DAU C3, H3,C SING N N 44 
DAU O3, H3,O SING N N 45 
DAU C2, C1,  SING N N 46 
DAU C2, HC21 SING N N 47 
DAU C2, HC22 SING N N 48 
DAU C1, N11  SING N N 49 
DAU C1, H1,C SING N N 50 
DAU N11 C61  SING N N 51 
DAU N11 C21  SING N N 52 
DAU C61 C51  DOUB N N 53 
DAU C61 H61C SING N N 54 
DAU C51 C5A  SING N N 55 
DAU C51 C41  SING N N 56 
DAU C5A H5A1 SING N N 57 
DAU C5A H5A2 SING N N 58 
DAU C5A H5A3 SING N N 59 
DAU C21 O21  DOUB N N 60 
DAU C21 N31  SING N N 61 
DAU N31 C41  SING N N 62 
DAU N31 H31N SING N N 63 
DAU C41 O41  DOUB N N 64 
# 
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 
DAU SMILES           ACDLabs              10.04 O=P(OC1OC(C(O)C(O)C1O)CO)(O)OP(=O)(O)OCC3OC(N2C=C(C(=O)NC2=O)C)CC3O 
DAU InChI            InChI                1.02b 
InChI=1/C16H26N2O16P2/c1-6-3-18(16(25)17-14(6)24)10-2-7(20)9(31-10)5-30-35(26,27)34-36(28,29)33-15-13(23)12(22)11(21)8(4-19)32-15/h3,7-13,15,19-23H,2,4-5H2,1H3,(H,26,27)(H,28,29)(H,17,24,25)/t7-,8+,9+,10+,11+,12-,13+,15+/m0/s1/f/h17,26,28H 
DAU InChIKey         InChI                1.02b YSYKRGRSMLTJNL-ORBAVMPSDL 
DAU SMILES_CANONICAL CACTVS               3.341 CC1=CN([C@H]2C[C@H](O)[C@@H](CO[P@@](O)(=O)O[P@@](O)(=O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)O2)C(=O)NC1=O 
DAU SMILES           CACTVS               3.341 CC1=CN([CH]2C[CH](O)[CH](CO[P](O)(=O)O[P](O)(=O)O[CH]3O[CH](CO)[CH](O)[CH](O)[CH]3O)O2)C(=O)NC1=O 
DAU SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO[P@](=O)(O)O[P@](=O)(O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O 
DAU SMILES           "OpenEye OEToolkits" 1.5.0 CC1=CN(C(=O)NC1=O)C2CC(C(O2)COP(=O)(O)OP(=O)(O)OC3C(C(C(C(O3)CO)O)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 
DAU "SYSTEMATIC NAME" ACDLabs              10.04 
"[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl (2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)" 
DAU "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate" 
# 
