data_TFE
# 
_chem_comp.id                                    TFE 
_chem_comp.name                                  
;2'-O-[2-(TRIFLUORO)ETHYL] THYMIDINE-5'-MONOPHOSPHATE
;
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C12 H16 F3 N2 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               DT 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-12-17 
_chem_comp.pdbx_modified_date                    2009-01-07 
_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                        420.232 
_chem_comp.one_letter_code                       T 
_chem_comp.three_letter_code                     TFE 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1Y8L 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
TFE P      P      P 0 1 N N N -4.643 6.001  7.252  2.787  0.324  -4.407 P      TFE 1  
TFE OP1    O1P    O 0 1 N N N -5.860 6.727  6.783  3.659  1.172  -5.286 OP1    TFE 2  
TFE OP2    O2P    O 0 1 N N N -4.804 4.743  8.007  1.198  0.588  -4.548 OP2    TFE 3  
TFE "O5'"  O5*    O 0 1 N N N -3.698 5.763  6.003  3.063  0.476  -2.819 "O5'"  TFE 4  
TFE "C5'"  C5*    C 0 1 N N N -3.406 6.846  5.122  2.282  -0.292 -1.921 "C5'"  TFE 5  
TFE "C4'"  C4*    C 0 1 N N R -2.360 6.432  4.141  2.725  0.023  -0.498 "C4'"  TFE 6  
TFE "O4'"  O4*    O 0 1 N N N -1.083 6.257  4.812  2.470  1.422  -0.246 "O4'"  TFE 7  
TFE "C1'"  C1*    C 0 1 N N R -0.360 5.221  4.168  1.373  1.543  0.675  "C1'"  TFE 8  
TFE N1     N1     N 0 1 N N N -0.135 4.119  5.124  0.452  2.524  0.177  N1     TFE 9  
TFE C6     C6     C 0 1 N N N -0.959 3.879  6.205  0.309  2.663  -1.199 C6     TFE 10 
TFE C2     C2     C 0 1 N N N 0.953  3.328  4.860  -0.300 3.336  1.055  C2     TFE 11 
TFE O2     O2     O 0 1 N N N 1.642  3.481  3.866  -0.225 3.269  2.283  O2     TFE 12 
TFE N3     N3     N 0 1 N N N 1.179  2.334  5.773  -1.159 4.248  0.431  N3     TFE 13 
TFE C4     C4     C 0 1 N N N 0.401  2.028  6.871  -1.338 4.427  -0.932 C4     TFE 14 
TFE O4     O4     O 0 1 N N N 0.704  1.086  7.583  -2.112 5.251  -1.413 O4     TFE 15 
TFE C5     C5     C 0 1 N N N -0.761 2.885  7.071  -0.514 3.537  -1.792 C5     TFE 16 
TFE C5M    C5M    C 0 1 N N N -1.677 2.619  8.225  -0.651 3.669  -3.275 C5M    TFE 17 
TFE "C2'"  C2*    C 0 1 N N R -1.200 4.721  2.995  0.748  0.163  0.786  "C2'"  TFE 18 
TFE "O2'"  O2*    O 0 1 N N N -0.950 5.530  1.850  0.137  -0.058 2.041  "O2'"  TFE 19 
TFE "CB'"  "CB'"  C 0 1 N N N 0.370  5.493  1.338  -0.332 -1.396 2.174  "CB'"  TFE 20 
TFE "CC'"  "CC'"  C 0 1 N N N 0.386  6.251  0.083  -0.983 -1.558 3.522  "CC'"  TFE 21 
TFE "FD'"  "FD'"  F 0 1 N N N 1.565  6.125  -0.494 -0.103 -1.289 4.511  "FD'"  TFE 22 
TFE "FE'"  "FE'"  F 0 1 N N N -0.532 5.806  -0.757 -1.431 -2.818 3.702  "FE'"  TFE 23 
TFE "FF'"  "FF'"  F 0 1 N N N 0.123  7.537  0.259  -2.029 -0.717 3.665  "FF'"  TFE 24 
TFE "C3'"  C3*    C 0 1 N N R -2.596 5.092  3.466  1.940  -0.742 0.560  "C3'"  TFE 25 
TFE "O3'"  O3*    O 0 1 N N N -3.552 5.156  2.418  2.742  -0.809 1.739  "O3'"  TFE 26 
TFE OP3    O3P    O 0 1 N Y N ?      ?      ?      2.921  -1.270 -4.647 OP3    TFE 27 
TFE HOP2   2HOP   H 0 0 N N N -4.029 4.281  8.306  0.799  0.616  -5.443 HOP2   TFE 28 
TFE "H5'"  1H5*   H 0 1 N N N -3.119 7.771  5.675  1.229  -0.035 -2.051 "H5'"  TFE 29 
TFE "H5''" 2H5*   H 0 0 N N N -4.322 7.236  4.619  2.428  -1.352 -2.133 "H5''" TFE 30 
TFE "H4'"  H4*    H 0 1 N N N -2.385 7.248  3.382  3.804  -0.139 -0.410 "H4'"  TFE 31 
TFE "H1'"  H1*    H 0 1 N N N 0.626  5.594  3.806  1.754  1.910  1.633  "H1'"  TFE 32 
TFE H6     H6     H 0 1 N N N -1.834 4.525  6.389  0.928  1.995  -1.790 H6     TFE 33 
TFE HN3    HN3    H 0 1 N N N 2.011  1.764  5.620  -1.709 4.843  1.045  HN3    TFE 34 
TFE H71    1H5M   H 0 1 N N N -2.707 2.505  7.815  -1.057 2.748  -3.690 H71    TFE 35 
TFE H72    2H5M   H 0 1 N N N -1.511 1.788  8.949  0.324  3.866  -3.719 H72    TFE 36 
TFE H73    3H5M   H 0 1 N N N -1.758 3.563  8.812  -1.320 4.497  -3.510 H73    TFE 37 
TFE "H2'"  H2*    H 0 1 N N N -1.019 3.651  2.738  -0.000 0.004  -0.000 "H2'"  TFE 38 
TFE "HB'1" "1HB'" H 0 0 N N N 0.760  4.455  1.221  0.518  -2.078 2.073  "HB'1" TFE 39 
TFE "HB'2" "2HB'" H 0 0 N N N 1.129  5.854  2.071  -1.049 -1.598 1.373  "HB'2" TFE 40 
TFE "H3'"  H3*    H 0 1 N N N -3.045 4.327  4.142  1.675  -1.764 0.277  "H3'"  TFE 41 
TFE "HO3'" H3T    H 0 0 N Y N -3.700 4.318  1.996  3.447  -0.153 1.628  "HO3'" TFE 42 
TFE HOP3   3HOP   H 0 0 N N N 0.775  -0.462 0.299  2.886  -1.617 -5.563 HOP3   TFE 43 
# 
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 
TFE P     OP1    DOUB N N 1  
TFE P     OP2    SING N N 2  
TFE P     "O5'"  SING N N 3  
TFE P     OP3    SING N N 4  
TFE OP2   HOP2   SING N N 5  
TFE "O5'" "C5'"  SING N N 6  
TFE "C5'" "C4'"  SING N N 7  
TFE "C5'" "H5'"  SING N N 8  
TFE "C5'" "H5''" SING N N 9  
TFE "C4'" "O4'"  SING N N 10 
TFE "C4'" "C3'"  SING N N 11 
TFE "C4'" "H4'"  SING N N 12 
TFE "O4'" "C1'"  SING N N 13 
TFE "C1'" N1     SING N N 14 
TFE "C1'" "C2'"  SING N N 15 
TFE "C1'" "H1'"  SING N N 16 
TFE N1    C6     SING N N 17 
TFE N1    C2     SING N N 18 
TFE C6    C5     DOUB N N 19 
TFE C6    H6     SING N N 20 
TFE C2    O2     DOUB N N 21 
TFE C2    N3     SING N N 22 
TFE N3    C4     SING N N 23 
TFE N3    HN3    SING N N 24 
TFE C4    O4     DOUB N N 25 
TFE C4    C5     SING N N 26 
TFE C5    C5M    SING N N 27 
TFE C5M   H71    SING N N 28 
TFE C5M   H72    SING N N 29 
TFE C5M   H73    SING N N 30 
TFE "C2'" "O2'"  SING N N 31 
TFE "C2'" "C3'"  SING N N 32 
TFE "C2'" "H2'"  SING N N 33 
TFE "O2'" "CB'"  SING N N 34 
TFE "CB'" "CC'"  SING N N 35 
TFE "CB'" "HB'1" SING N N 36 
TFE "CB'" "HB'2" SING N N 37 
TFE "CC'" "FD'"  SING N N 38 
TFE "CC'" "FE'"  SING N N 39 
TFE "CC'" "FF'"  SING N N 40 
TFE "C3'" "O3'"  SING N N 41 
TFE "C3'" "H3'"  SING N N 42 
TFE "O3'" "HO3'" SING N N 43 
TFE OP3   HOP3   SING N N 44 
# 
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 
TFE SMILES           ACDLabs              10.04 "FC(F)(F)COC2C(O)C(OC2N1C(=O)NC(=O)C(=C1)C)COP(=O)(O)O"                                                                                                                                  
TFE InChI            InChI                1.02b "InChI=1/C12H16F3N2O9P/c1-5-2-17(11(20)16-9(5)19)10-8(24-4-12(13,14)15)7(18)6(26-10)3-25-27(21,22)23/h2,6-8,10,18H,3-4H2,1H3,(H,16,19,20)(H2,21,22,23)/t6-,7-,8-,10-/m1/s1/f/h16,21-22H" 
TFE InChIKey         InChI                1.02b YTGJEPUSXBDJRJ-HMQQKWOJDB                                                                                                                                                                
TFE SMILES_CANONICAL CACTVS               3.341 "CC1=CN([C@@H]2O[C@H](CO[P](O)(O)=O)[C@@H](O)[C@H]2OCC(F)(F)F)C(=O)NC1=O"                                                                                                                
TFE SMILES           CACTVS               3.341 "CC1=CN([CH]2O[CH](CO[P](O)(O)=O)[CH](O)[CH]2OCC(F)(F)F)C(=O)NC1=O"                                                                                                                      
TFE SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)OCC(F)(F)F"                                                                                                                
TFE SMILES           "OpenEye OEToolkits" 1.5.0 "CC1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)O)O)OCC(F)(F)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 
TFE "SYSTEMATIC NAME" ACDLabs              10.04 
;5-methyl-2'-O-(2,2,2-trifluoroethyl)uridine 5'-(dihydrogen phosphate)
;
TFE "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3R,4R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-4-(2,2,2-trifluoroethoxy)oxolan-2-yl]methyl dihydrogen phosphate" 
# 
