data_U2F
# 
_chem_comp.id                                    U2F 
_chem_comp.name                                  "URIDINE-5'-DIPHOSPHATE-2-DEOXY-2-FLUORO-ALPHA-D-GLUCOSE" 
_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                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-10-20 
_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                     U2F 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1UQT 
_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 
U2F C1     C1     C 0 1 N N R 36.379 25.672 14.627 6.957  2.761  -5.048 C1     U2F 1  
U2F O1     O1     O 0 1 N N N 35.007 24.869 14.537 6.982  1.513  -5.737 O1     U2F 2  
U2F PB     PB     P 0 1 N N R 34.271 24.121 15.744 6.790  0.139  -4.913 PB     U2F 3  
U2F O1B    O1B    O 0 1 N N N 33.864 22.753 15.262 6.835  -1.107 -5.748 O1B    U2F 4  
U2F O2B    O2B    O 0 1 N N N 35.512 23.768 16.530 7.903  0.198  -3.740 O2B    U2F 5  
U2F O3A    O3A    O 0 1 N N N 33.206 24.597 16.791 5.396  0.374  -4.128 O3A    U2F 6  
U2F PA     PA     P 0 1 N N R 32.010 25.602 16.518 4.636  -0.528 -3.023 PA     U2F 7  
U2F O1A    O1A    O 0 1 N N N 32.540 26.905 16.243 5.422  -0.774 -1.769 O1A    U2F 8  
U2F O2A    O2A    O 0 1 N N N 31.145 25.510 17.757 4.237  -1.859 -3.852 O2A    U2F 9  
U2F "O5'"  "O5'"  O 0 1 N N N 31.275 25.113 15.183 3.228  0.245  -2.828 "O5'"  U2F 10 
U2F "C5'"  "C5'"  C 0 1 N N N 30.558 23.901 15.258 3.242  1.544  -2.262 "C5'"  U2F 11 
U2F "C4'"  "C4'"  C 0 1 N N R 29.541 24.033 14.120 1.814  2.065  -2.179 "C4'"  U2F 12 
U2F "O4'"  "O4'"  O 0 1 N N N 29.072 22.750 13.718 1.855  3.410  -1.654 "O4'"  U2F 13 
U2F "C1'"  "C1'"  C 0 1 N N R 27.650 22.725 13.868 1.528  4.335  -2.703 "C1'"  U2F 14 
U2F "C2'"  "C2'"  C 0 1 N N R 27.339 23.649 14.994 1.551  3.545  -4.000 "C2'"  U2F 15 
U2F "C3'"  "C3'"  C 0 1 N N S 28.314 24.752 14.654 1.130  2.167  -3.536 "C3'"  U2F 16 
U2F "O3'"  "O3'"  O 0 1 N N N 27.779 25.605 13.673 -0.280 2.126  -3.322 "O3'"  U2F 17 
U2F "O2'"  "O2'"  O 0 1 N N N 26.024 24.071 14.948 0.676  4.073  -4.975 "O2'"  U2F 18 
U2F N1     N1     N 0 1 N N N 27.357 21.329 14.136 2.484  5.405  -2.696 N1     U2F 19 
U2F "C6'"  "C6'"  C 0 1 N N N 26.320 20.741 13.419 2.120  6.719  -3.075 "C6'"  U2F 20 
U2F "O6'"  "O6'"  O 0 1 N N N 25.769 21.338 12.539 0.984  7.039  -3.432 "O6'"  U2F 21 
U2F N3     N3     N 0 1 N N N 26.038 19.394 13.603 3.155  7.663  -3.021 N3     U2F 22 
U2F "C7'"  "C7'"  C 0 1 N N N 26.713 18.660 14.534 4.468  7.434  -2.640 "C7'"  U2F 23 
U2F "O7'"  "O7'"  O 0 1 N N N 26.416 17.603 14.679 5.342  8.295  -2.609 "O7'"  U2F 24 
U2F "C8'"  "C8'"  C 0 1 N N N 27.695 19.271 15.309 4.765  6.038  -2.260 "C8'"  U2F 25 
U2F "C9'"  "C9'"  C 0 1 N N N 28.036 20.608 15.102 3.789  5.128  -2.306 "C9'"  U2F 26 
U2F C2     C2     C 0 1 N N R 36.988 26.374 15.780 5.815  3.655  -5.517 C2     U2F 27 
U2F F1     F1     F 0 1 N N N 37.493 25.417 16.691 4.661  2.935  -5.523 F1     U2F 28 
U2F C3     C3     C 0 1 N N S 35.936 27.231 16.670 6.057  4.219  -6.911 C3     U2F 29 
U2F O3     O3     O 0 1 N N N 36.299 27.727 18.113 5.072  5.224  -7.152 O3     U2F 30 
U2F C4     C4     C 0 1 N N S 35.436 28.438 15.809 7.452  4.842  -6.999 C4     U2F 31 
U2F O4     O4     O 0 1 N N N 34.176 29.006 16.498 7.751  5.150  -8.358 O4     U2F 32 
U2F C5     C5     C 0 1 N N R 35.068 27.864 14.263 8.522  3.884  -6.460 C5     U2F 33 
U2F C6     C6     C 0 1 N N N 34.825 29.128 13.332 9.894  4.550  -6.405 C6     U2F 34 
U2F O6     O6     O 0 1 N N N 35.769 30.193 13.418 10.827 3.617  -5.891 O6     U2F 35 
U2F O5     O5     O 0 1 N N N 36.183 27.019 13.860 8.204  3.453  -5.133 O5     U2F 36 
U2F H1     H1     H 0 1 N N N 37.172 25.081 14.111 6.797  2.514  -3.994 H1     U2F 37 
U2F "H5'1" "1H5'" H 0 0 N N N 30.113 23.684 16.257 3.689  1.489  -1.265 "H5'1" U2F 38 
U2F "H5'2" "2H5'" H 0 0 N N N 31.189 22.983 15.214 3.853  2.197  -2.893 "H5'2" U2F 39 
U2F "H4'"  "H4'"  H 0 1 N N N 29.980 24.584 13.256 1.244  1.450  -1.474 "H4'"  U2F 40 
U2F "H1'"  "H1'"  H 0 1 N N N 27.148 23.061 12.931 0.546  4.774  -2.496 "H1'"  U2F 41 
U2F "H2'"  "H2'"  H 0 1 N N N 27.581 23.184 15.978 2.563  3.508  -4.422 "H2'"  U2F 42 
U2F "H3'"  "H3'"  H 0 1 N N N 28.575 25.332 15.570 1.386  1.365  -4.234 "H3'"  U2F 43 
U2F HB     HB     H 0 1 N N N 27.012 26.055 14.007 -0.683 2.615  -4.055 HB     U2F 44 
U2F HA     HA     H 0 1 N N N 25.411 23.378 15.162 1.227  4.445  -5.686 HA     U2F 45 
U2F H3     H3     H 0 1 N N N 25.317 18.948 13.035 2.917  8.614  -3.289 H3     U2F 46 
U2F "H8'"  "H8'"  H 0 1 N N N 28.209 18.692 16.095 5.771  5.785  -1.951 "H8'"  U2F 47 
U2F "H9'"  "H9'"  H 0 1 N N N 28.833 21.082 15.698 3.986  4.097  -2.031 "H9'"  U2F 48 
U2F H2     H2     H 0 1 N N N 37.814 27.035 15.428 5.677  4.483  -4.811 H2     U2F 49 
U2F HC     HC     H 0 1 N N N 35.048 26.569 16.798 5.916  3.448  -7.677 HC     U2F 50 
U2F HD     HD     H 0 1 N N N 35.683 28.229 18.634 4.742  5.498  -6.283 HD     U2F 51 
U2F H4     H4     H 0 1 N N N 36.227 29.221 15.750 7.466  5.785  -6.439 H4     U2F 52 
U2F HE     HE     H 0 1 N N N 33.872 29.739 15.975 7.869  4.302  -8.814 HE     U2F 53 
U2F H5     H5     H 0 1 N N N 34.137 27.252 14.307 8.615  3.008  -7.114 H5     U2F 54 
U2F H6C1   1H6C   H 0 0 N N N 33.799 29.527 13.510 9.858  5.421  -5.751 H6C1   U2F 55 
U2F H6C2   2H6C   H 0 0 N N N 34.737 28.795 12.271 10.201 4.853  -7.406 H6C2   U2F 56 
U2F H6     H6     H 0 1 N N N 35.624 30.949 12.861 10.720 3.610  -4.924 H6     U2F 57 
U2F HO1    HO1    H 0 1 N N N 31.698 25.491 18.529 3.836  -2.615 -3.373 HO1    U2F 58 
U2F HO2    HO2    H 0 1 N N N 36.252 23.694 15.938 8.039  -0.592 -3.176 HO2    U2F 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 
U2F C1    O1     SING N N 1  
U2F C1    C2     SING N N 2  
U2F C1    O5     SING N N 3  
U2F C1    H1     SING N N 4  
U2F O1    PB     SING N N 5  
U2F PB    O1B    DOUB N N 6  
U2F PB    O2B    SING N N 7  
U2F PB    O3A    SING N N 8  
U2F O3A   PA     SING N N 9  
U2F PA    O1A    DOUB N N 10 
U2F PA    O2A    SING N N 11 
U2F PA    "O5'"  SING N N 12 
U2F "O5'" "C5'"  SING N N 13 
U2F "C5'" "C4'"  SING N N 14 
U2F "C5'" "H5'1" SING N N 15 
U2F "C5'" "H5'2" SING N N 16 
U2F "C4'" "O4'"  SING N N 17 
U2F "C4'" "C3'"  SING N N 18 
U2F "C4'" "H4'"  SING N N 19 
U2F "O4'" "C1'"  SING N N 20 
U2F "C1'" "C2'"  SING N N 21 
U2F "C1'" N1     SING N N 22 
U2F "C1'" "H1'"  SING N N 23 
U2F "C2'" "C3'"  SING N N 24 
U2F "C2'" "O2'"  SING N N 25 
U2F "C2'" "H2'"  SING N N 26 
U2F "C3'" "O3'"  SING N N 27 
U2F "C3'" "H3'"  SING N N 28 
U2F "O3'" HB     SING N N 29 
U2F "O2'" HA     SING N N 30 
U2F N1    "C6'"  SING N N 31 
U2F N1    "C9'"  SING N N 32 
U2F "C6'" "O6'"  DOUB N N 33 
U2F "C6'" N3     SING N N 34 
U2F N3    "C7'"  SING N N 35 
U2F N3    H3     SING N N 36 
U2F "C7'" "O7'"  DOUB N N 37 
U2F "C7'" "C8'"  SING N N 38 
U2F "C8'" "C9'"  DOUB N N 39 
U2F "C8'" "H8'"  SING N N 40 
U2F "C9'" "H9'"  SING N N 41 
U2F C2    F1     SING N N 42 
U2F C2    C3     SING N N 43 
U2F C2    H2     SING N N 44 
U2F C3    O3     SING N N 45 
U2F C3    C4     SING N N 46 
U2F C3    HC     SING N N 47 
U2F O3    HD     SING N N 48 
U2F C4    O4     SING N N 49 
U2F C4    C5     SING N N 50 
U2F C4    H4     SING N N 51 
U2F O4    HE     SING N N 52 
U2F C5    C6     SING N N 53 
U2F C5    O5     SING N N 54 
U2F C5    H5     SING N N 55 
U2F C6    O6     SING N N 56 
U2F C6    H6C1   SING N N 57 
U2F C6    H6C2   SING N N 58 
U2F O6    H6     SING N N 59 
U2F HO1   O2A    SING N N 60 
U2F HO2   O2B    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 
U2F 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 
U2F 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 
U2F InChIKey         InChI                1.02b NGTCPFGWXMBZEP-IDUGYYQMDT 
U2F 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 
U2F 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 
U2F 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 
U2F 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 
U2F "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,5S,6R)-3-fluoro-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)" 
U2F "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl] [(2R,3R,4S,5S,6R)-3-fluoro-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate" 
# 
