data_DUX
# 
_chem_comp.id                                    DUX 
_chem_comp.name                                  2,3-DEOXY-3-FLUORO-5-O-TRITYLURIDINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C28 H25 F N2 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         1-{(2S,5S)-4-FLUORO-5-[(TRITYLOXY)METHYL]TETRAHYDROFURAN-2-YL}PYRIMIDINE-2,4(1H,3H)-DIONE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-05-05 
_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                        472.508 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DUX 
_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        1VYQ 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
DUX "F3'"  "F3'"  F 0 1 N N N 37.829 -8.962  -12.615 4.088  -0.520 -1.486 "F3'"  DUX 1  
DUX "C3'"  "C3'"  C 0 1 N N S 37.380 -9.638  -11.556 2.848  0.127  -1.494 "C3'"  DUX 2  
DUX "C2'"  "C2'"  C 0 1 N N N 36.218 -10.547 -11.964 2.346  0.319  -2.945 "C2'"  DUX 3  
DUX "C1'"  "C1'"  C 0 1 N N R 36.522 -11.802 -11.163 1.376  -0.877 -3.114 "C1'"  DUX 4  
DUX N1     N1     N 0 1 N N N 35.940 -11.840 -9.817  0.380  -0.592 -4.150 N1     DUX 5  
DUX C2     C2     C 0 1 N N N 35.849 -13.104 -9.174  -0.448 0.457  -4.006 C2     DUX 6  
DUX N3     N3     N 0 1 N N N 35.303 -13.186 -7.936  -1.369 0.744  -4.944 N3     DUX 7  
DUX C4     C4     C 0 1 N N N 34.865 -12.083 -7.278  -1.482 -0.026 -6.045 C4     DUX 8  
DUX C5     C5     C 0 1 N N N 34.951 -10.821 -7.863  -0.620 -1.137 -6.206 C5     DUX 9  
DUX C6     C6     C 0 1 N N N 35.494 -10.732 -9.149  0.298  -1.400 -5.252 C6     DUX 10 
DUX O4     O4     O 0 1 N N N 34.402 -12.157 -6.131  -2.319 0.230  -6.892 O4     DUX 11 
DUX O2     O2     O 0 1 N N N 36.272 -14.117 -9.780  -0.358 1.161  -3.019 O2     DUX 12 
DUX "O4'"  "O4'"  O 0 1 N N N 37.944 -11.828 -10.984 0.749  -0.988 -1.818 "O4'"  DUX 13 
DUX "C4'"  "C4'"  C 0 1 N N R 38.522 -10.505 -11.094 1.774  -0.757 -0.832 "C4'"  DUX 14 
DUX "C5'"  "C5'"  C 0 1 N N N 39.152 -9.953  -9.822  1.176  -0.042 0.380  "C5'"  DUX 15 
DUX "O5'"  "O5'"  O 0 1 N N N 40.521 -10.439 -9.666  0.170  -0.868 0.971  "O5'"  DUX 16 
DUX C17    C17    C 0 1 N N N 41.140 -10.542 -8.348  -0.272 -0.197 2.153  C17    DUX 17 
DUX C30    C30    C 0 1 Y N N 41.722 -9.167  -8.013  0.853  -0.144 3.153  C30    DUX 18 
DUX C31    C31    C 0 1 Y N N 41.558 -8.049  -8.870  1.894  -1.049 3.070  C31    DUX 19 
DUX C32    C32    C 0 1 Y N N 42.112 -6.810  -8.539  2.927  -1.000 3.987  C32    DUX 20 
DUX C33    C33    C 0 1 Y N N 42.872 -6.658  -7.374  2.919  -0.045 4.987  C33    DUX 21 
DUX C34    C34    C 0 1 Y N N 43.066 -7.753  -6.536  1.878  0.859  5.069  C34    DUX 22 
DUX C35    C35    C 0 1 Y N N 42.493 -8.999  -6.843  0.847  0.813  4.149  C35    DUX 23 
DUX C24    C24    C 0 1 Y N N 40.038 -11.031 -7.431  -0.701 1.204  1.803  C24    DUX 24 
DUX C25    C25    C 0 1 Y N N 39.548 -10.275 -6.365  -2.028 1.472  1.526  C25    DUX 25 
DUX C26    C26    C 0 1 Y N N 38.509 -10.752 -5.564  -2.421 2.758  1.205  C26    DUX 26 
DUX C27    C27    C 0 1 Y N N 37.909 -11.971 -5.842  -1.487 3.776  1.163  C27    DUX 27 
DUX C28    C28    C 0 1 Y N N 38.369 -12.744 -6.904  -0.160 3.508  1.442  C28    DUX 28 
DUX C29    C29    C 0 1 Y N N 39.422 -12.275 -7.704  0.231  2.223  1.766  C29    DUX 29 
DUX C18    C18    C 0 1 Y N N 42.287 -11.539 -8.474  -1.437 -0.945 2.748  C18    DUX 30 
DUX C19    C19    C 0 1 Y N N 43.101 -11.563 -9.624  -2.131 -1.865 1.984  C19    DUX 31 
DUX C20    C20    C 0 1 Y N N 44.174 -12.479 -9.729  -3.199 -2.552 2.530  C20    DUX 32 
DUX C21    C21    C 0 1 Y N N 44.440 -13.407 -8.711  -3.575 -2.318 3.840  C21    DUX 33 
DUX C22    C22    C 0 1 Y N N 43.647 -13.385 -7.564  -2.881 -1.398 4.604  C22    DUX 34 
DUX C23    C23    C 0 1 Y N N 42.593 -12.466 -7.456  -1.809 -0.715 4.059  C23    DUX 35 
DUX "H3'"  "H3'"  H 0 1 N N N 37.066 -8.938  -10.747 2.918  1.088  -0.984 "H3'"  DUX 36 
DUX "H2'1" "1H2'" H 0 0 N N N 36.096 -10.700 -13.062 1.817  1.266  -3.052 "H2'1" DUX 37 
DUX "H2'2" "2H2'" H 0 0 N N N 35.201 -10.118 -11.809 3.171  0.254  -3.654 "H2'2" DUX 38 
DUX "H1'"  "H1'"  H 0 1 N N N 36.199 -12.701 -11.737 1.927  -1.787 -3.353 "H1'"  DUX 39 
DUX H3     H3     H 0 1 N N N 35.219 -14.099 -7.488  -1.957 1.507  -4.827 H3     DUX 40 
DUX H5     H5     H 0 1 N N N 34.602 -9.921  -7.329  -0.695 -1.766 -7.081 H5     DUX 41 
DUX H6     H6     H 0 1 N N N 35.564 -9.745  -9.636  0.965  -2.243 -5.357 H6     DUX 42 
DUX "H4'"  "H4'"  H 0 1 N N N 39.298 -10.524 -11.894 2.213  -1.706 -0.525 "H4'"  DUX 43 
DUX "H5'1" "1H5'" H 0 0 N N N 38.530 -10.177 -8.924  1.961  0.152  1.111  "H5'1" DUX 44 
DUX "H5'2" "2H5'" H 0 0 N N N 39.104 -8.840  -9.788  0.731  0.900  0.064  "H5'2" DUX 45 
DUX H31    H31    H 0 1 N N N 40.987 -8.159  -9.807  1.901  -1.795 2.289  H31    DUX 46 
DUX H32    H32    H 0 1 N N N 41.949 -5.944  -9.202  3.741  -1.708 3.923  H32    DUX 47 
DUX H33    H33    H 0 1 N N N 43.314 -5.679  -7.122  3.726  -0.008 5.704  H33    DUX 48 
DUX H34    H34    H 0 1 N N N 43.675 -7.641  -5.623  1.871  1.605  5.851  H34    DUX 49 
DUX H35    H35    H 0 1 N N N 42.647 -9.854  -6.163  0.034  1.521  4.214  H35    DUX 50 
DUX H25    H25    H 0 1 N N N 39.988 -9.286  -6.152  -2.758 0.676  1.559  H25    DUX 51 
DUX H26    H26    H 0 1 N N N 38.163 -10.155 -4.704  -3.458 2.967  0.988  H26    DUX 52 
DUX H27    H27    H 0 1 N N N 37.069 -12.327 -5.223  -1.794 4.780  0.912  H27    DUX 53 
DUX H28    H28    H 0 1 N N N 37.907 -13.723 -7.116  0.569  4.303  1.408  H28    DUX 54 
DUX H29    H29    H 0 1 N N N 39.773 -12.883 -8.555  1.268  2.014  1.984  H29    DUX 55 
DUX H19    H19    H 0 1 N N N 42.900 -10.861 -10.450 -1.838 -2.048 0.961  H19    DUX 56 
DUX H20    H20    H 0 1 N N N 44.813 -12.463 -10.628 -3.742 -3.270 1.933  H20    DUX 57 
DUX H21    H21    H 0 1 N N N 45.259 -14.139 -8.816  -4.410 -2.853 4.266  H21    DUX 58 
DUX H22    H22    H 0 1 N N N 43.849 -14.091 -6.741  -3.174 -1.215 5.627  H22    DUX 59 
DUX H23    H23    H 0 1 N N N 41.980 -12.468 -6.539  -1.267 0.002  4.656  H23    DUX 60 
# 
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 
DUX "F3'" "C3'"  SING N N 1  
DUX "C3'" "C2'"  SING N N 2  
DUX "C3'" "C4'"  SING N N 3  
DUX "C3'" "H3'"  SING N N 4  
DUX "C2'" "C1'"  SING N N 5  
DUX "C2'" "H2'1" SING N N 6  
DUX "C2'" "H2'2" SING N N 7  
DUX "C1'" N1     SING N N 8  
DUX "C1'" "O4'"  SING N N 9  
DUX "C1'" "H1'"  SING N N 10 
DUX N1    C2     SING N N 11 
DUX N1    C6     SING N N 12 
DUX C2    N3     SING N N 13 
DUX C2    O2     DOUB N N 14 
DUX N3    C4     SING N N 15 
DUX N3    H3     SING N N 16 
DUX C4    C5     SING N N 17 
DUX C4    O4     DOUB N N 18 
DUX C5    C6     DOUB N N 19 
DUX C5    H5     SING N N 20 
DUX C6    H6     SING N N 21 
DUX "O4'" "C4'"  SING N N 22 
DUX "C4'" "C5'"  SING N N 23 
DUX "C4'" "H4'"  SING N N 24 
DUX "C5'" "O5'"  SING N N 25 
DUX "C5'" "H5'1" SING N N 26 
DUX "C5'" "H5'2" SING N N 27 
DUX "O5'" C17    SING N N 28 
DUX C17   C30    SING N N 29 
DUX C17   C24    SING N N 30 
DUX C17   C18    SING N N 31 
DUX C30   C31    DOUB Y N 32 
DUX C30   C35    SING Y N 33 
DUX C31   C32    SING Y N 34 
DUX C31   H31    SING N N 35 
DUX C32   C33    DOUB Y N 36 
DUX C32   H32    SING N N 37 
DUX C33   C34    SING Y N 38 
DUX C33   H33    SING N N 39 
DUX C34   C35    DOUB Y N 40 
DUX C34   H34    SING N N 41 
DUX C35   H35    SING N N 42 
DUX C24   C25    DOUB Y N 43 
DUX C24   C29    SING Y N 44 
DUX C25   C26    SING Y N 45 
DUX C25   H25    SING N N 46 
DUX C26   C27    DOUB Y N 47 
DUX C26   H26    SING N N 48 
DUX C27   C28    SING Y N 49 
DUX C27   H27    SING N N 50 
DUX C28   C29    DOUB Y N 51 
DUX C28   H28    SING N N 52 
DUX C29   H29    SING N N 53 
DUX C18   C19    DOUB Y N 54 
DUX C18   C23    SING Y N 55 
DUX C19   C20    SING Y N 56 
DUX C19   H19    SING N N 57 
DUX C20   C21    DOUB Y N 58 
DUX C20   H20    SING N N 59 
DUX C21   C22    SING Y N 60 
DUX C21   H21    SING N N 61 
DUX C22   C23    DOUB Y N 62 
DUX C22   H22    SING N N 63 
DUX C23   H23    SING 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 
DUX SMILES           ACDLabs              10.04 O=C1NC(=O)N(C=C1)C2OC(C(F)C2)COC(c3ccccc3)(c4ccccc4)c5ccccc5                                                                                                                                       
DUX InChI            InChI                1.02b InChI=1/C28H25FN2O4/c29-23-18-26(31-17-16-25(32)30-27(31)33)35-24(23)19-34-28(20-10-4-1-5-11-20,21-12-6-2-7-13-21)22-14-8-3-9-15-22/h1-17,23-24,26H,18-19H2,(H,30,32,33)/t23-,24+,26+/m0/s1/f/h30H 
DUX InChIKey         InChI                1.02b GJNIPWYJQUGERM-LWLWAZKTDN                                                                                                                                                                          
DUX SMILES_CANONICAL CACTVS               3.341 F[C@H]1C[C@@H](O[C@@H]1COC(c2ccccc2)(c3ccccc3)c4ccccc4)N5C=CC(=O)NC5=O                                                                                                                             
DUX SMILES           CACTVS               3.341 F[CH]1C[CH](O[CH]1COC(c2ccccc2)(c3ccccc3)c4ccccc4)N5C=CC(=O)NC5=O                                                                                                                                  
DUX SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)C(c2ccccc2)(c3ccccc3)OC[C@@H]4[C@H](C[C@@H](O4)N5C=CC(=O)NC5=O)F                                                                                                                         
DUX SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)C(c2ccccc2)(c3ccccc3)OCC4C(CC(O4)N5C=CC(=O)NC5=O)F                                                                                                                                       
# 
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 
DUX "SYSTEMATIC NAME" ACDLabs              10.04 "2',3'-dideoxy-3'-fluoro-5'-O-trityluridine"                               
DUX "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 1-[(2R,4S,5R)-4-fluoro-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione 
# 
