data_TPE
# 
_chem_comp.id                                    TPE 
_chem_comp.name                                  
;3'-O-ACETYLTHYMIDINE-(5' DIPHOSPHATE PHENYL ESTER)
;
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H22 N2 O12 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-03-09 
_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                        520.321 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TPE 
_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        1DZT 
_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 
TPE C1B    C1B  C 0 1 Y N N 24.190 23.431 17.202 -1.116 0.476  -6.421 C1B    TPE 1  
TPE C2B    C2B  C 0 1 Y N N 23.059 23.027 17.977 -2.016 -0.534 -6.727 C2B    TPE 2  
TPE C3B    C3B  C 0 1 Y N N 23.203 21.975 18.952 -1.910 -1.211 -7.926 C3B    TPE 3  
TPE C4B    C4B  C 0 1 Y N N 24.477 21.331 19.149 -0.909 -0.882 -8.822 C4B    TPE 4  
TPE C5B    C5B  C 0 1 Y N N 25.607 21.745 18.366 -0.011 0.124  -8.519 C5B    TPE 5  
TPE C6B    C6B  C 0 1 Y N N 25.463 22.792 17.394 -0.116 0.808  -7.323 C6B    TPE 6  
TPE PA     PA   P 0 1 N N R 22.522 27.107 18.347 0.522  0.227  -1.732 PA     TPE 7  
TPE O1A    O1A  O 0 1 N N N 21.280 26.453 17.887 1.913  0.194  -2.234 O1A    TPE 8  
TPE O2A    O2A  O 0 1 N N N 22.341 28.561 18.530 -0.046 -1.275 -1.628 O2A    TPE 9  
TPE O3A    O3A  O 0 1 N N N 23.689 26.950 17.228 -0.394 1.079  -2.745 O3A    TPE 10 
TPE PB     PB   P 0 1 N N S 24.532 25.927 16.386 -0.319 0.340  -4.173 PB     TPE 11 
TPE O1B    O1B  O 0 1 N N N 24.234 26.713 15.037 1.085  0.305  -4.638 O1B    TPE 12 
TPE O2B    O2B  O 0 1 N N N 25.987 25.970 16.739 -0.874 -1.164 -4.029 O2B    TPE 13 
TPE O3B    O3B  O 0 1 N N N 24.030 24.503 16.193 -1.218 1.143  -5.241 O3B    TPE 14 
TPE "O5'"  O5*  O 0 1 N N N 23.079 26.484 19.693 0.493  0.914  -0.276 "O5'"  TPE 15 
TPE "C5'"  C5*  C 0 1 N N N 24.275 26.952 20.336 1.320  0.116  0.573  "C5'"  TPE 16 
TPE "C4'"  C4*  C 0 1 N N R 24.488 26.054 21.541 1.336  0.717  1.980  "C4'"  TPE 17 
TPE "O4'"  O4*  O 0 1 N N N 23.594 26.448 22.607 0.002  0.724  2.539  "O4'"  TPE 18 
TPE "C3'"  C3*  C 0 1 N N S 24.233 24.547 21.265 2.160  -0.167 2.941  "C3'"  TPE 19 
TPE "O3'"  O3*  O 0 1 N N N 25.218 23.693 21.915 3.501  0.364  3.100  "O3'"  TPE 20 
TPE CR     CR   C 0 1 N N N 26.469 23.684 21.286 4.520  -0.459 3.389  CR     TPE 21 
TPE OR     OR   O 0 1 N N N 26.899 24.514 20.404 4.322  -1.644 3.517  OR     TPE 22 
TPE CHR    CHR  C 0 1 N N N 27.441 22.631 21.717 5.913  0.093  3.553  CHR    TPE 23 
TPE "C2'"  C2*  C 0 1 N N N 22.832 24.345 21.895 1.387  -0.096 4.277  "C2'"  TPE 24 
TPE "C1'"  C1*  C 0 1 N N R 22.799 25.364 23.026 0.187  0.826  3.968  "C1'"  TPE 25 
TPE N1     N1   N 0 1 Y N N 21.474 25.855 23.462 -1.008 0.360  4.674  N1     TPE 26 
TPE C2     C2   C 0 1 Y N N 21.072 25.695 24.787 -1.490 -0.871 4.427  C2     TPE 27 
TPE O2     O2   O 0 1 N N N 21.748 25.149 25.650 -0.924 -1.586 3.624  O2     TPE 28 
TPE N3     N3   N 0 1 Y N N 19.831 26.229 25.057 -2.585 -1.326 5.065  N3     TPE 29 
TPE C4     C4   C 0 1 Y N N 18.940 26.891 24.191 -3.224 -0.545 5.959  C4     TPE 30 
TPE O4     O4   O 0 1 N N N 17.883 27.298 24.620 -4.218 -0.954 6.533  O4     TPE 31 
TPE C5     C5   C 0 1 Y N N 19.427 27.001 22.840 -2.731 0.754  6.224  C5     TPE 32 
TPE C5M    C5M  C 0 1 N N N 18.630 27.647 21.745 -3.427 1.648  7.218  C5M    TPE 33 
TPE C6     C6   C 0 1 Y N N 20.630 26.503 22.532 -1.628 1.184  5.574  C6     TPE 34 
TPE H2B    H2B  H 0 1 N N N 22.085 23.521 17.824 -2.797 -0.792 -6.027 H2B    TPE 35 
TPE H3B    H3B  H 0 1 N N N 22.332 21.660 19.551 -2.610 -1.998 -8.165 H3B    TPE 36 
TPE H4B    H4B  H 0 1 N N N 24.586 20.525 19.894 -0.829 -1.412 -9.759 H4B    TPE 37 
TPE H5B    H5B  H 0 1 N N N 26.586 21.258 18.511 0.769  0.379  -9.220 H5B    TPE 38 
TPE H6B    H6B  H 0 1 N N N 26.332 23.106 16.793 0.584  1.594  -7.087 H6B    TPE 39 
TPE HPA2   2HPA H 0 0 N N N 23.139 28.981 18.825 -0.953 -1.208 -1.298 HPA2   TPE 40 
TPE HPB2   2HPB H 0 0 N N N 26.497 25.351 16.229 -1.789 -1.096 -3.725 HPB2   TPE 41 
TPE "H5'2" 2H5* H 0 0 N N N 25.156 26.995 19.654 2.334  0.094  0.176  "H5'2" TPE 42 
TPE "H5'1" 1H5* H 0 0 N N N 24.245 28.036 20.591 0.924  -0.898 0.616  "H5'1" TPE 43 
TPE "H4'"  H4*  H 0 1 N N N 25.562 26.177 21.813 1.742  1.728  1.955  "H4'"  TPE 44 
TPE "H3'"  H3*  H 0 1 N N N 24.300 24.281 20.184 2.198  -1.194 2.577  "H3'"  TPE 45 
TPE HHR3   3HHR H 0 0 N N N 28.437 22.623 21.216 6.601  -0.719 3.783  HHR3   TPE 46 
TPE HHR2   2HHR H 0 0 N N N 27.581 22.685 22.821 6.222  0.580  2.628  HHR2   TPE 47 
TPE HHR1   1HHR H 0 0 N N N 26.968 21.626 21.617 5.922  0.818  4.366  HHR1   TPE 48 
TPE "H2'2" 2H2* H 0 0 N N N 21.985 24.428 21.174 1.042  -1.086 4.573  "H2'2" TPE 49 
TPE "H2'1" 1H2* H 0 0 N N N 22.614 23.298 22.210 2.012  0.339  5.057  "H2'1" TPE 50 
TPE "H1'"  H1*  H 0 1 N N N 23.176 24.837 23.933 0.416  1.854  4.249  "H1'"  TPE 51 
TPE H3     H3   H 0 1 N N N 19.532 26.119 26.026 -2.917 -2.218 4.878  H3     TPE 52 
TPE H5M3   3H5M H 0 0 N N N 19.007 27.732 20.699 -4.290 1.126  7.634  H5M3   TPE 53 
TPE H5M2   2H5M H 0 0 N N N 17.638 27.137 21.705 -2.737 1.905  8.022  H5M2   TPE 54 
TPE H5M1   1H5M H 0 0 N N N 18.355 28.671 22.088 -3.759 2.558  6.719  H5M1   TPE 55 
TPE H6     H6   H 0 1 N N N 20.935 26.630 21.479 -1.237 2.172  5.763  H6     TPE 56 
# 
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 
TPE C1B   C2B    DOUB Y N 1  
TPE C1B   C6B    SING Y N 2  
TPE C1B   O3B    SING N N 3  
TPE C2B   C3B    SING Y N 4  
TPE C2B   H2B    SING N N 5  
TPE C3B   C4B    DOUB Y N 6  
TPE C3B   H3B    SING N N 7  
TPE C4B   C5B    SING Y N 8  
TPE C4B   H4B    SING N N 9  
TPE C5B   C6B    DOUB Y N 10 
TPE C5B   H5B    SING N N 11 
TPE C6B   H6B    SING N N 12 
TPE PA    O1A    DOUB N N 13 
TPE PA    O2A    SING N N 14 
TPE PA    O3A    SING N N 15 
TPE PA    "O5'"  SING N N 16 
TPE O2A   HPA2   SING N N 17 
TPE O3A   PB     SING N N 18 
TPE PB    O1B    DOUB N N 19 
TPE PB    O2B    SING N N 20 
TPE PB    O3B    SING N N 21 
TPE O2B   HPB2   SING N N 22 
TPE "O5'" "C5'"  SING N N 23 
TPE "C5'" "C4'"  SING N N 24 
TPE "C5'" "H5'2" SING N N 25 
TPE "C5'" "H5'1" SING N N 26 
TPE "C4'" "O4'"  SING N N 27 
TPE "C4'" "C3'"  SING N N 28 
TPE "C4'" "H4'"  SING N N 29 
TPE "O4'" "C1'"  SING N N 30 
TPE "C3'" "O3'"  SING N N 31 
TPE "C3'" "C2'"  SING N N 32 
TPE "C3'" "H3'"  SING N N 33 
TPE "O3'" CR     SING N N 34 
TPE CR    OR     DOUB N N 35 
TPE CR    CHR    SING N N 36 
TPE CHR   HHR3   SING N N 37 
TPE CHR   HHR2   SING N N 38 
TPE CHR   HHR1   SING N N 39 
TPE "C2'" "C1'"  SING N N 40 
TPE "C2'" "H2'2" SING N N 41 
TPE "C2'" "H2'1" SING N N 42 
TPE "C1'" N1     SING N N 43 
TPE "C1'" "H1'"  SING N N 44 
TPE N1    C2     SING Y N 45 
TPE N1    C6     SING Y N 46 
TPE C2    O2     DOUB N N 47 
TPE C2    N3     SING Y N 48 
TPE N3    C4     SING Y N 49 
TPE N3    H3     SING N N 50 
TPE C4    O4     DOUB N N 51 
TPE C4    C5     SING Y N 52 
TPE C5    C5M    SING N N 53 
TPE C5    C6     DOUB Y N 54 
TPE C5M   H5M3   SING N N 55 
TPE C5M   H5M2   SING N N 56 
TPE C5M   H5M1   SING N N 57 
TPE C6    H6     SING N N 58 
# 
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 
TPE SMILES           ACDLabs              10.04 O=P(O)(Oc1ccccc1)OP(=O)(O)OCC3OC(N2C(=O)NC(=O)C(=C2)C)CC3OC(=O)C 
TPE InChI            InChI                1.02b 
InChI=1/C18H22N2O12P2/c1-11-9-20(18(23)19-17(11)22)16-8-14(29-12(2)21)15(30-16)10-28-33(24,25)32-34(26,27)31-13-6-4-3-5-7-13/h3-7,9,14-16H,8,10H2,1-2H3,(H,24,25)(H,26,27)(H,19,22,23)/t14-,15+,16+/m0/s1/f/h19,24,26H 
TPE InChIKey         InChI                1.02b FBXZTUIVKSOQAY-ZMTSGXNRDJ 
TPE SMILES_CANONICAL CACTVS               3.341 CC(=O)O[C@H]1C[C@@H](O[C@@H]1CO[P@](O)(=O)O[P@](O)(=O)Oc2ccccc2)N3C=C(C)C(=O)NC3=O 
TPE SMILES           CACTVS               3.341 CC(=O)O[CH]1C[CH](O[CH]1CO[P](O)(=O)O[P](O)(=O)Oc2ccccc2)N3C=C(C)C(=O)NC3=O 
TPE 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)Oc3ccccc3)OC(=O)C 
TPE SMILES           "OpenEye OEToolkits" 1.5.0 CC1=CN(C(=O)NC1=O)C2CC(C(O2)COP(=O)(O)OP(=O)(O)Oc3ccccc3)OC(=O)C 
# 
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 
TPE "SYSTEMATIC NAME" ACDLabs              10.04 "3'-O-acetyl-5'-O-[(R)-hydroxy{[(S)-hydroxy(phenoxy)phosphoryl]oxy}phosphoryl]thymidine"                                                    
TPE "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-2-[[hydroxy-(hydroxy-phenoxy-phosphoryl)oxy-phosphoryl]oxymethyl]-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolan-3-yl] ethanoate" 
# 
