data_UPF
# 
_chem_comp.id                                    UPF 
_chem_comp.name                                  "URIDINE-5'-DIPHOSPHATE-2-DEOXY-2-FLUOROGALACTOSE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C15 H23 F N2 O16 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         
;URIDINE-5'-MONOPHOSPHATE 2-DEOXY-2-FLUORO-GALACTOPYRANOSYL-MONOPHOSPHATE ESTER
;
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-11-30 
_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                        568.293 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     UPF 
_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        1GA8 
_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 
UPF N1     N1     N 0 1 N N N 27.246 44.476 57.859 0.858  -0.674 5.805  N1     UPF 1  
UPF C2     C2     C 0 1 N N N 27.632 43.844 56.664 1.590  0.372  5.383  C2     UPF 2  
UPF N3     N3     N 0 1 N N N 26.736 44.095 55.610 2.870  0.523  5.772  N3     UPF 3  
UPF C4     C4     C 0 1 N N N 25.543 44.905 55.653 3.444  -0.383 6.588  C4     UPF 4  
UPF C5     C5     C 0 1 N N N 25.233 45.520 56.910 2.686  -1.493 7.036  C5     UPF 5  
UPF C6     C6     C 0 1 N N N 26.052 45.309 57.942 1.403  -1.617 6.634  C6     UPF 6  
UPF O2     O2     O 0 1 N N N 28.633 43.138 56.565 1.086  1.198  4.647  O2     UPF 7  
UPF O4     O4     O 0 1 N N N 24.868 45.022 54.645 4.603  -0.250 6.936  O4     UPF 8  
UPF C1D    C1*    C 0 1 N N R 27.946 44.427 59.222 -0.533 -0.809 5.369  C1D    UPF 9  
UPF C2D    C2*    C 0 1 N N R 29.213 45.245 59.123 -1.346 0.460  5.726  C2D    UPF 10 
UPF "O2'"  O2*    O 0 1 N N N 30.325 44.490 59.591 -1.858 0.381  7.058  "O2'"  UPF 11 
UPF C3D    C3*    C 0 1 N N S 28.928 46.470 59.974 -2.497 0.412  4.687  C3D    UPF 12 
UPF C4D    C4*    C 0 1 N N R 28.177 45.825 61.135 -1.951 -0.493 3.566  C4D    UPF 13 
UPF O4D    O4*    O 0 1 N N N 27.357 44.776 60.451 -0.611 -0.866 3.929  O4D    UPF 14 
UPF O3D    O3*    O 0 1 N N N 30.009 47.247 60.450 -3.673 -0.155 5.270  O3D    UPF 15 
UPF C5D    C5*    C 0 1 N N N 26.869 46.225 61.745 -1.938 0.270  2.241  C5D    UPF 16 
UPF O5D    O5*    O 0 1 N N N 26.298 47.578 61.483 -1.424 -0.574 1.209  O5D    UPF 17 
UPF PA     PA     P 0 1 N N R 26.766 49.099 61.249 -1.438 0.288  -0.149 PA     UPF 18 
UPF O1A    O1A    O 0 1 N N N 28.222 49.272 61.261 -2.825 0.704  -0.454 O1A    UPF 19 
UPF O2A    O2A    O 0 1 N N N 26.106 49.694 60.059 -0.514 1.593  0.033  O2A    UPF 20 
UPF O3A    O3A    O 0 1 N N N 26.011 49.279 62.643 -0.869 -0.607 -1.359 O3A    UPF 21 
UPF PB     PB     P 0 1 N N S 25.737 50.507 63.615 -0.912 0.313  -2.680 PB     UPF 22 
UPF O1B    O1B    O 0 1 N N N 27.073 51.140 63.723 -2.307 0.729  -2.946 O1B    UPF 23 
UPF O2B    O2B    O 0 1 N N N 24.752 51.397 62.959 0.003  1.618  -2.454 O2B    UPF 24 
UPF O3B    O3B    O 0 1 N N N 25.283 49.976 64.989 -0.352 -0.523 -3.936 O3B    UPF 25 
UPF "C1'"  "C1'"  C 0 1 N N R 25.663 49.782 66.526 -0.416 0.342  -5.071 "C1'"  UPF 26 
UPF "C2'"  "C2'"  C 0 1 N N R 27.142 49.349 66.499 -0.643 -0.491 -6.334 "C2'"  UPF 27 
UPF "C3'"  "C3'"  C 0 1 N N S 27.570 48.162 65.500 0.503  -1.496 -6.482 "C3'"  UPF 28 
UPF "C4'"  "C4'"  C 0 1 N N R 26.580 46.942 65.687 1.832  -0.733 -6.435 "C4'"  UPF 29 
UPF "C5'"  "C5'"  C 0 1 N N R 25.091 47.558 65.670 1.873  0.117  -5.163 "C5'"  UPF 30 
UPF "C6'"  "C6'"  C 0 1 N N N 24.067 46.500 66.124 3.210  0.856  -5.089 "C6'"  UPF 31 
UPF "F2'"  "F2'"  F 0 1 N N N 28.007 50.445 66.303 -1.858 -1.177 -6.229 "F2'"  UPF 32 
UPF "O3'"  "O3'"  O 0 1 N N N 28.862 47.756 65.870 0.383  -2.180 -7.731 "O3'"  UPF 33 
UPF "O4'"  "O4'"  O 0 1 N N N 26.878 46.287 66.949 1.939  0.110  -7.583 "O4'"  UPF 34 
UPF "O5'"  "O5'"  O 0 1 N N N 24.823 48.627 66.707 0.808  1.065  -5.184 "O5'"  UPF 35 
UPF "O6'"  "O6'"  O 0 1 N N N 23.780 45.249 65.553 3.251  1.649  -3.901 "O6'"  UPF 36 
UPF HN3    HN3    H 0 1 N N N 26.975 43.644 54.726 3.382  1.285  5.461  HN3    UPF 37 
UPF H5     H5     H 0 1 N N N 24.354 46.163 57.085 3.129  -2.229 7.690  H5     UPF 38 
UPF H6     H6     H 0 1 N N N 25.741 45.824 58.866 0.810  -2.456 6.966  H6     UPF 39 
UPF H1D    H1*    H 0 1 N N N 27.995 43.318 59.331 -0.989 -1.694 5.814  H1D    UPF 40 
UPF H2D    H2*    H 0 1 N N N 29.480 45.534 58.080 -0.741 1.358  5.596  H2D    UPF 41 
UPF "HO2'" *HO2   H 0 0 N N N 31.121 45.004 59.528 -2.351 1.198  7.216  "HO2'" UPF 42 
UPF H3D    H3*    H 0 1 N N N 28.405 47.242 59.363 -2.707 1.410  4.303  H3D    UPF 43 
UPF H4D    H4*    H 0 1 N N N 29.017 45.834 61.868 -2.572 -1.384 3.474  H4D    UPF 44 
UPF "HO3'" *HO3   H 0 0 N N N 29.830 48.013 60.982 -3.930 0.423  6.000  "HO3'" UPF 45 
UPF "H5'1" 1H5*   H 0 0 N N N 26.104 45.462 61.466 -1.306 1.152  2.336  "H5'1" UPF 46 
UPF "H5'2" 2H5*   H 0 0 N N N 26.938 46.081 62.848 -2.953 0.576  1.987  "H5'2" UPF 47 
UPF HOA2   2HOA   H 0 0 N N N 26.382 50.592 59.920 0.378  1.278  0.230  HOA2   UPF 48 
UPF HOB2   2HOB   H 0 0 N N N 24.588 52.130 63.539 0.902  1.303  -2.284 HOB2   UPF 49 
UPF "H1'"  "H1'"  H 0 1 N N N 25.544 50.610 67.262 -1.241 1.043  -4.946 "H1'"  UPF 50 
UPF "H2'"  "H2'"  H 0 1 N N N 27.251 48.908 67.517 -0.669 0.164  -7.204 "H2'"  UPF 51 
UPF "H3'"  "H3'"  H 0 1 N N N 27.539 48.503 64.439 0.465  -2.218 -5.666 "H3'"  UPF 52 
UPF "H4'"  "H4'"  H 0 1 N N N 26.681 46.177 64.881 2.659  -1.442 -6.424 "H4'"  UPF 53 
UPF "H5'"  "H5'"  H 0 1 N N N 25.004 47.940 64.626 1.767  -0.528 -4.292 "H5'"  UPF 54 
UPF "H6'1" "1H6'" H 0 0 N N N 24.310 46.290 67.191 3.317  1.502  -5.960 "H6'1" UPF 55 
UPF "H6'2" "2H6'" H 0 0 N N N 23.089 47.034 66.173 4.025  0.132  -5.071 "H6'2" UPF 56 
UPF HO3A   "'HO3" H 0 0 N N N 29.114 47.055 65.280 -0.469 -2.634 -7.721 HO3A   UPF 57 
UPF "HO4'" "'HO4" H 0 0 N N N 26.283 45.554 67.061 1.903  -0.466 -8.358 "HO4'" UPF 58 
UPF "HO6'" "'HO6" H 0 0 N N N 23.148 44.596 65.832 4.108  2.096  -3.893 "HO6'" UPF 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 
UPF N1    C2     SING N N 1  
UPF N1    C6     SING N N 2  
UPF N1    C1D    SING N N 3  
UPF C2    N3     SING N N 4  
UPF C2    O2     DOUB N N 5  
UPF N3    C4     SING N N 6  
UPF N3    HN3    SING N N 7  
UPF C4    C5     SING N N 8  
UPF C4    O4     DOUB N N 9  
UPF C5    C6     DOUB N N 10 
UPF C5    H5     SING N N 11 
UPF C6    H6     SING N N 12 
UPF C1D   C2D    SING N N 13 
UPF C1D   O4D    SING N N 14 
UPF C1D   H1D    SING N N 15 
UPF C2D   "O2'"  SING N N 16 
UPF C2D   C3D    SING N N 17 
UPF C2D   H2D    SING N N 18 
UPF "O2'" "HO2'" SING N N 19 
UPF C3D   C4D    SING N N 20 
UPF C3D   O3D    SING N N 21 
UPF C3D   H3D    SING N N 22 
UPF C4D   O4D    SING N N 23 
UPF C4D   C5D    SING N N 24 
UPF C4D   H4D    SING N N 25 
UPF O3D   "HO3'" SING N N 26 
UPF C5D   O5D    SING N N 27 
UPF C5D   "H5'1" SING N N 28 
UPF C5D   "H5'2" SING N N 29 
UPF O5D   PA     SING N N 30 
UPF PA    O1A    DOUB N N 31 
UPF PA    O2A    SING N N 32 
UPF PA    O3A    SING N N 33 
UPF O2A   HOA2   SING N N 34 
UPF O3A   PB     SING N N 35 
UPF PB    O1B    DOUB N N 36 
UPF PB    O2B    SING N N 37 
UPF PB    O3B    SING N N 38 
UPF O2B   HOB2   SING N N 39 
UPF O3B   "C1'"  SING N N 40 
UPF "C1'" "C2'"  SING N N 41 
UPF "C1'" "O5'"  SING N N 42 
UPF "C1'" "H1'"  SING N N 43 
UPF "C2'" "C3'"  SING N N 44 
UPF "C2'" "F2'"  SING N N 45 
UPF "C2'" "H2'"  SING N N 46 
UPF "C3'" "C4'"  SING N N 47 
UPF "C3'" "O3'"  SING N N 48 
UPF "C3'" "H3'"  SING N N 49 
UPF "C4'" "C5'"  SING N N 50 
UPF "C4'" "O4'"  SING N N 51 
UPF "C4'" "H4'"  SING N N 52 
UPF "C5'" "C6'"  SING N N 53 
UPF "C5'" "O5'"  SING N N 54 
UPF "C5'" "H5'"  SING N N 55 
UPF "C6'" "O6'"  SING N N 56 
UPF "C6'" "H6'1" SING N N 57 
UPF "C6'" "H6'2" SING N N 58 
UPF "O3'" HO3A   SING N N 59 
UPF "O4'" "HO4'" SING N N 60 
UPF "O6'" "HO6'" 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 
UPF SMILES           ACDLabs              10.04 O=P(OC1OC(C(O)C(O)C1F)CO)(O)OP(=O)(O)OCC3OC(N2C=CC(=O)NC2=O)C(O)C3O 
UPF InChI            InChI                1.02b 
InChI=1/C15H23FN2O16P2/c16-8-11(23)9(21)5(3-19)32-14(8)33-36(28,29)34-35(26,27)30-4-6-10(22)12(24)13(31-6)18-2-1-7(20)17-15(18)25/h1-2,5-6,8-14,19,21-24H,3-4H2,(H,26,27)(H,28,29)(H,17,20,25)/t5-,6-,8-,9+,10-,11-,12-,13-,14-/m1/s1/f/h17,26,28H 
UPF InChIKey         InChI                1.02b NGTCPFGWXMBZEP-DLMCISTEDB 
UPF SMILES_CANONICAL CACTVS               3.341 OC[C@H]1O[C@H](O[P@@](O)(=O)O[P@@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=O)NC3=O)[C@H](F)[C@@H](O)[C@H]1O 
UPF SMILES           CACTVS               3.341 OC[CH]1O[CH](O[P](O)(=O)O[P](O)(=O)OC[CH]2O[CH]([CH](O)[CH]2O)N3C=CC(=O)NC3=O)[CH](F)[CH](O)[CH]1O 
UPF SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([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)F)O)O 
UPF SMILES           "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OC3C(C(C(C(O3)CO)O)O)F)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 
UPF "SYSTEMATIC NAME" ACDLabs              10.04 
"[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3R,4S,5R,6R)-3-fluoro-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)" 
UPF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methyl [[(2R,3R,4S,5R,6R)-3-fluoro-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl] hydrogen phosphate" 
# 
