data_THW
# 
_chem_comp.id                                    THW 
_chem_comp.name                                  "C2-1-HYDROXYPHENYL-THIAMIN DIPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H24 N4 O8 P2 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-11-30 
_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                        530.428 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     THW 
_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   Y 
_chem_comp.pdbx_model_coordinates_db_code        2BEW 
_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 
THW C10    C10  C 0  1 Y N N 77.151 6.104  6.447  5.178  -2.996 -0.759 C10    THW 1  
THW C12    C12  C 0  1 Y N N 77.316 7.388  5.966  6.003  -3.701 0.090  C12    THW 2  
THW C14    C14  C 0  1 Y N N 77.956 7.559  4.764  5.731  -3.744 1.447  C14    THW 3  
THW C13    C13  C 0  1 Y N N 78.473 6.464  4.071  4.630  -3.081 1.963  C13    THW 4  
THW C11    C11  C 0  1 Y N N 78.334 5.167  4.528  3.798  -2.367 1.128  C11    THW 5  
THW C9     C9   C 0  1 Y N N 77.659 5.026  5.725  4.062  -2.322 -0.247 C9     THW 6  
THW C8     C8   C -1 1 N N N 77.459 3.655  6.291  3.178  -1.568 -1.144 C8     THW 7  
THW O9     O9   O 0  1 N N N 78.706 3.045  6.506  3.403  -1.577 -2.488 O9     THW 8  
THW C2     C2   C 0  1 Y N N 76.112 3.022  6.554  2.136  -0.861 -0.635 C2     THW 9  
THW S1     S1   S 0  1 Y N N 74.518 3.542  6.250  0.801  -1.410 0.418  S1     THW 10 
THW C5     C5   C 0  1 Y N N 73.661 2.108  6.734  -0.053 0.151  0.564  C5     THW 11 
THW C5A    C5A  C 0  1 N N N 72.119 1.925  6.611  -1.315 0.471  1.324  C5A    THW 12 
THW C5B    C5B  C 0  1 N N N 71.333 2.860  7.511  -2.526 0.259  0.412  C5B    THW 13 
THW O5G    O5G  O 0  1 N N N 69.986 2.499  7.182  -3.722 0.563  1.132  O5G    THW 14 
THW PA     PA   P 0  1 N N S 68.880 3.537  7.705  -4.949 0.319  0.118  PA     THW 15 
THW O1A    O1A  O 0  1 N N N 69.172 3.982  9.048  -4.862 1.376  -1.093 O1A    THW 16 
THW O2A    O2A  O 0  1 N N N 67.552 2.902  7.414  -4.878 -1.057 -0.421 O2A    THW 17 
THW O3A    O3A  O 0  1 N N N 68.974 4.859  6.769  -6.341 0.516  0.903  O3A    THW 18 
THW PB     PB   P 0  1 N N N 68.777 5.028  5.139  -7.473 -0.234 0.039  PB     THW 19 
THW O1B    O1B  O 0  1 N N N 68.316 6.455  5.012  -7.417 -1.815 0.337  O1B    THW 20 
THW O2B    O2B  O 0  1 N N N 70.177 4.914  4.473  -8.924 0.337  0.443  O2B    THW 21 
THW O3B    O3B  O 0  1 N N N 67.657 4.033  4.760  -7.233 0.006  -1.402 O3B    THW 22 
THW C4     C4   C 0  1 Y N N 74.670 1.289  7.196  0.710  0.962  -0.169 C4     THW 23 
THW C4A    C4A  C 0  1 N N N 74.436 -0.138 7.739  0.336  2.414  -0.317 C4A    THW 24 
THW N3     N3   N 1  1 Y N N 75.921 1.775  7.094  1.827  0.481  -0.788 N3     THW 25 
THW C35    C35  C 0  1 N N N 77.022 1.057  7.671  2.674  1.360  -1.598 C35    THW 26 
THW "C5'"  C5*  C 0  1 Y N N 77.059 1.407  9.280  3.764  1.941  -0.735 "C5'"  THW 27 
THW "C6'"  C6*  C 0  1 Y N N 76.932 0.350  10.224 3.568  3.122  -0.046 "C6'"  THW 28 
THW "N1'"  N1*  N 0  1 Y N N 76.980 0.540  11.568 4.550  3.604  0.703  "N1'"  THW 29 
THW "C2'"  C2*  C 0  1 Y N N 77.197 1.752  12.118 5.703  2.975  0.798  "C2'"  THW 30 
THW C2A    C2A  C 0  1 N N N 77.220 1.951  13.647 6.789  3.562  1.662  C2A    THW 31 
THW "N3'"  N3*  N 0  1 Y N N 77.260 2.806  11.316 5.936  1.849  0.154  "N3'"  THW 32 
THW "C4'"  C4*  C 0  1 Y N N 77.193 2.665  9.947  4.998  1.300  -0.613 "C4'"  THW 33 
THW "N4'"  N4*  N 0  1 N N N 77.388 3.813  9.277  5.244  0.113  -1.284 "N4'"  THW 34 
THW H10    H10  H 0  1 N N N 76.631 5.936  7.378  5.391  -2.963 -1.818 H10    THW 35 
THW H12    H12  H 0  1 N N N 76.950 8.238  6.523  6.863  -4.221 -0.303 H12    THW 36 
THW H14    H14  H 0  1 N N N 78.060 8.551  4.350  6.382  -4.298 2.108  H14    THW 37 
THW H13    H13  H 0  1 N N N 79.001 6.636  3.144  4.425  -3.121 3.022  H13    THW 38 
THW H11    H11  H 0  1 N N N 78.727 4.320  3.985  2.940  -1.850 1.531  H11    THW 39 
THW H9     H9   H 0  1 N N N 79.140 2.907  5.672  2.762  -0.970 -2.883 H9     THW 40 
THW H5A1   1H5A H 0  0 N N N 71.884 0.896  6.920  -1.394 -0.185 2.191  H5A1   THW 41 
THW H5A2   2H5A H 0  0 N N N 71.830 2.126  5.569  -1.287 1.509  1.655  H5A2   THW 42 
THW H5B1   1H5B H 0  0 N N N 71.561 3.925  7.358  -2.447 0.915  -0.455 H5B1   THW 43 
THW H5B2   2H5B H 0  0 N N N 71.559 2.702  8.576  -2.554 -0.779 0.081  H5B2   THW 44 
THW H2A    H2A  H 0  1 N N N 67.080 2.768  8.227  ?      ?      ?      H2A    THW 45 
THW H2B    H2B  H 0  1 N N N 70.078 4.891  3.528  -9.571 -0.137 -0.096 H2B    THW 46 
THW H3B    H3B  H 0  1 N N N 67.140 3.829  5.530  ?      ?      ?      H3B    THW 47 
THW H4A1   1H4A H 0  0 N N N 73.493 -0.165 8.304  -0.377 2.525  -1.133 H4A1   THW 48 
THW H4A2   2H4A H 0  0 N N N 75.268 -0.419 8.401  -0.114 2.769  0.610  H4A2   THW 49 
THW H4A3   3H4A H 0  0 N N N 74.380 -0.846 6.899  1.230  2.999  -0.534 H4A3   THW 50 
THW H351   1H35 H 0  0 N N N 77.967 1.352  7.191  2.069  2.167  -2.012 H351   THW 51 
THW H352   2H35 H 0  0 N N N 76.887 -0.025 7.523  3.120  0.787  -2.410 H352   THW 52 
THW "H6'"  H6*  H 0  1 N N N 76.790 -0.654 9.853  2.626  3.646  -0.116 "H6'"  THW 53 
THW H2A1   1H2A H 0  0 N N N 76.327 2.514  13.957 6.696  3.174  2.677  H2A1   THW 54 
THW H2A2   2H2A H 0  0 N N N 78.124 2.511  13.930 7.764  3.289  1.257  H2A2   THW 55 
THW H2A3   3H2A H 0  0 N N N 77.225 0.970  14.145 6.694  4.648  1.678  H2A3   THW 56 
THW "H4'1" 1H4* H 0  0 N N N 78.244 3.758  8.763  4.612  -0.210 -1.945 "H4'1" THW 57 
THW "H4'2" 2H4* H 0  0 N N N 77.436 4.573  9.925  6.049  -0.395 -1.093 "H4'2" THW 58 
# 
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 
THW C10   C12    SING Y N 1  
THW C10   C9     DOUB Y N 2  
THW C10   H10    SING N N 3  
THW C12   C14    DOUB Y N 4  
THW C12   H12    SING N N 5  
THW C14   C13    SING Y N 6  
THW C14   H14    SING N N 7  
THW C13   C11    DOUB Y N 8  
THW C13   H13    SING N N 9  
THW C11   C9     SING Y N 10 
THW C11   H11    SING N N 11 
THW C9    C8     SING N N 12 
THW C8    O9     SING N N 13 
THW C8    C2     SING N N 14 
THW O9    H9     SING N N 15 
THW C2    S1     SING Y N 16 
THW C2    N3     DOUB Y N 17 
THW S1    C5     SING Y N 18 
THW C5    C5A    SING N N 19 
THW C5    C4     DOUB Y N 20 
THW C5A   C5B    SING N N 21 
THW C5A   H5A1   SING N N 22 
THW C5A   H5A2   SING N N 23 
THW C5B   O5G    SING N N 24 
THW C5B   H5B1   SING N N 25 
THW C5B   H5B2   SING N N 26 
THW O5G   PA     SING N N 27 
THW PA    O1A    DOUB N N 28 
THW PA    O2A    SING N N 29 
THW PA    O3A    SING N N 30 
THW O2A   H2A    SING N N 31 
THW O3A   PB     SING N N 32 
THW PB    O1B    DOUB N N 33 
THW PB    O2B    SING N N 34 
THW PB    O3B    SING N N 35 
THW O2B   H2B    SING N N 36 
THW O3B   H3B    SING N N 37 
THW C4    C4A    SING N N 38 
THW C4    N3     SING Y N 39 
THW C4A   H4A1   SING N N 40 
THW C4A   H4A2   SING N N 41 
THW C4A   H4A3   SING N N 42 
THW N3    C35    SING N N 43 
THW C35   "C5'"  SING N N 44 
THW C35   H351   SING N N 45 
THW C35   H352   SING N N 46 
THW "C5'" "C6'"  DOUB Y N 47 
THW "C5'" "C4'"  SING Y N 48 
THW "C6'" "N1'"  SING Y N 49 
THW "C6'" "H6'"  SING N N 50 
THW "N1'" "C2'"  DOUB Y N 51 
THW "C2'" C2A    SING N N 52 
THW "C2'" "N3'"  SING Y N 53 
THW C2A   H2A1   SING N N 54 
THW C2A   H2A2   SING N N 55 
THW C2A   H2A3   SING N N 56 
THW "N3'" "C4'"  DOUB Y N 57 
THW "C4'" "N4'"  SING N N 58 
THW "N4'" "H4'1" SING N N 59 
THW "N4'" "H4'2" SING N N 60 
# 
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 
THW SMILES           ACDLabs              10.04 O=P(O)(O)OP(=O)(O)OCCc2sc([C-](O)c1ccccc1)[n+](c2C)Cc3cnc(nc3N)C                                                                                                                                              
THW InChI            InChI                1.02b InChI=1/C19H24N4O8P2S/c1-12-16(8-9-30-33(28,29)31-32(25,26)27)34-19(17(24)14-6-4-3-5-7-14)23(12)11-15-10-21-13(2)22-18(15)20/h3-7,10,24H,8-9,11H2,1-2H3,(H,28,29)(H2,20,21,22)(H2,25,26,27)/f/h25-26,28H,20H2 
THW InChIKey         InChI                1.02b ZOLUTNQCUQSPSG-RHUBMAKMCR                                                                                                                                                                                     
THW SMILES_CANONICAL CACTVS               3.341 Cc1ncc(C[n+]2c(C)c(CCO[P@@](O)(=O)O[P](O)(O)=O)sc2[C-](O)c3ccccc3)c(N)n1                                                                                                                                      
THW SMILES           CACTVS               3.341 Cc1ncc(C[n+]2c(C)c(CCO[P](O)(=O)O[P](O)(O)=O)sc2[C-](O)c3ccccc3)c(N)n1                                                                                                                                        
THW SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c(sc([n+]1Cc2cnc(nc2N)C)[C-](c3ccccc3)O)CCO[P@](=O)(O)OP(=O)(O)O                                                                                                                                           
THW SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c(sc([n+]1Cc2cnc(nc2N)C)[C-](c3ccccc3)O)CCOP(=O)(O)OP(=O)(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 
THW "SYSTEMATIC NAME" ACDLabs              10.04 {3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[(S)-hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium-2-yl}(hydroxy)phenylmethanide 
THW "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-2-(hydroxy-phenyl-methyl)-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate"              
# 
