data_THD
# 
_chem_comp.id                                    THD 
_chem_comp.name                                  "2-[3-[(4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL]-2-(1,2-DIHYDROXYETHYL)-4-METHYL-1,3-THIAZOL-3-IUM-5-YL]ETHYL TRIHYDROGEN DIPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H22 N4 O9 P2 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "({ALPHA,BETA}-DIHYDROXYETHYL)-THIAMIN DIPHOSPHATE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-11-09 
_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                        484.358 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     THD 
_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        1GPU 
_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 
THD "N1'"  "N1'"  N 0 1 Y N N -3.041 61.454 19.848 1.428  1.481  5.541  "N1'"  THD 1  
THD "C2'"  "C2'"  C 0 1 Y N N -2.184 60.470 20.188 2.050  0.833  6.505  "C2'"  THD 2  
THD CM2    CM2    C 0 1 N N N -0.873 60.838 20.682 2.653  1.615  7.643  CM2    THD 3  
THD "N3'"  "N3'"  N 0 1 Y N N -2.532 59.196 20.071 2.164  -0.479 6.498  "N3'"  THD 4  
THD "C4'"  "C4'"  C 0 1 Y N N -3.803 58.840 19.598 1.639  -1.201 5.512  "C4'"  THD 5  
THD "N4'"  "N4'"  N 0 1 N N N -4.019 57.528 19.535 1.757  -2.581 5.511  "N4'"  THD 6  
THD "C5'"  "C5'"  C 0 1 Y N N -4.775 59.864 19.219 0.974  -0.545 4.475  "C5'"  THD 7  
THD "C6'"  "C6'"  C 0 1 Y N N -4.314 61.147 19.373 0.884  0.832  4.522  "C6'"  THD 8  
THD "C7'"  "C7'"  C 0 1 N N N -6.195 59.594 18.689 0.369  -1.320 3.333  "C7'"  THD 9  
THD N3     N3     N 0 1 N N N -6.112 58.680 17.427 -0.262 -0.391 2.393  N3     THD 10 
THD C2     C2     C 0 1 N N N -6.228 57.285 17.358 -1.577 0.052  2.586  C2     THD 11 
THD S1     S1     S 0 1 N N N -5.973 56.722 15.756 -1.793 1.127  1.176  S1     THD 12 
THD C5     C5     C 0 1 N N N -5.752 58.299 15.189 -0.178 0.909  0.448  C5     THD 13 
THD C4     C4     C 0 1 N N N -5.856 59.211 16.208 0.409  0.067  1.292  C4     THD 14 
THD CM4    CM4    C 0 1 N N N -5.708 60.684 16.020 1.823  -0.385 1.035  CM4    THD 15 
THD C6     C6     C 0 1 N N N -5.468 58.595 13.730 0.379  1.526  -0.809 C6     THD 16 
THD C7     C7     C 0 1 N N N -5.621 57.464 12.801 0.070  0.619  -2.002 C7     THD 17 
THD O7     O7     O 0 1 N N N -4.798 57.778 11.677 0.598  1.203  -3.194 O7     THD 18 
THD PA     PA     P 0 1 N N R -3.699 56.763 11.303 0.239  0.202  -4.402 PA     THD 19 
THD O1A    O1A    O 0 1 N N N -2.538 56.617 12.250 -1.358 0.038  -4.506 O1A    THD 20 
THD O2A    O2A    O 0 1 N N N -3.433 57.289 9.996  0.855  -1.119 -4.147 O2A    THD 21 
THD O3A    O3A    O 0 1 N N N -4.402 55.393 10.820 0.808  0.801  -5.783 O3A    THD 22 
THD PB     PB     P 0 1 N N N -5.639 54.735 10.025 0.415  -0.244 -6.942 PB     THD 23 
THD O1B    O1B    O 0 1 N N N -4.978 54.712 8.730  -1.056 -0.388 -6.998 O1B    THD 24 
THD O2B    O2B    O 0 1 N N N -5.798 53.395 10.573 0.957  0.294  -8.359 O2B    THD 25 
THD O3B    O3B    O 0 1 N N N -6.849 55.575 10.209 1.082  -1.674 -6.622 O3B    THD 26 
THD C8     C8     C 0 1 N N N -6.621 56.702 18.419 -2.436 -0.242 3.566  C8     THD 27 
THD O9     O9     O 0 1 N N N -6.947 57.126 19.553 -2.030 -1.006 4.622  O9     THD 28 
THD C9     C9     C 0 1 N N N -6.659 55.276 18.152 -3.852 0.268  3.505  C9     THD 29 
THD O10    O10    O 0 1 N N N -5.679 54.612 18.927 -4.757 -0.837 3.499  O10    THD 30 
THD HM21   1HM2   H 0 0 N N N -0.164 60.024 20.963 1.915  1.728  8.438  HM21   THD 31 
THD HM22   2HM2   H 0 0 N N N -0.993 61.530 21.548 3.523  1.083  8.029  HM22   THD 32 
THD HM23   3HM2   H 0 0 N N N -0.380 61.508 19.939 2.957  2.599  7.287  HM23   THD 33 
THD "H4'1" "1H4'" H 0 0 N N N -5.019 57.248 19.163 2.221  -3.029 6.236  "H4'1" THD 34 
THD "H4'2" "2H4'" H 0 0 N N N -3.286 56.755 19.821 1.375  -3.100 4.786  "H4'2" THD 35 
THD "H6'"  "H6'"  H 0 1 N N N -4.987 61.979 19.107 0.376  1.373  3.737  "H6'"  THD 36 
THD "H7'1" "1H7'" H 0 0 N N N -6.758 60.536 18.491 1.150  -1.881 2.821  "H7'1" THD 37 
THD "H7'2" "2H7'" H 0 0 N N N -6.865 59.170 19.473 -0.379 -2.011 3.720  "H7'2" THD 38 
THD HM41   1HM4   H 0 0 N N N -5.497 61.121 15.016 2.193  0.079  0.121  HM41   THD 39 
THD HM42   2HM4   H 0 0 N N N -4.922 61.044 16.724 2.456  -0.092 1.873  HM42   THD 40 
THD HM43   3HM4   H 0 0 N N N -6.623 61.176 16.425 1.844  -1.469 0.926  HM43   THD 41 
THD H6C1   1H6C   H 0 0 N N N -4.450 59.036 13.625 -0.077 2.503  -0.967 H6C1   THD 42 
THD H6C2   2H6C   H 0 0 N N N -6.094 59.452 13.389 1.458  1.640  -0.709 H6C2   THD 43 
THD H7C1   1H7C   H 0 0 N N N -6.681 57.245 12.533 0.526  -0.357 -1.843 H7C1   THD 44 
THD H7C2   2H7C   H 0 0 N N N -5.394 56.473 13.260 -1.009 0.504  -2.101 H7C2   THD 45 
THD HO1A   HO1A   H 0 0 N N N -1.861 55.992 12.020 -1.719 0.919  -4.672 HO1A   THD 46 
THD HO2B   HO2B   H 0 0 N N N -6.527 53.007 10.104 0.701  -0.359 -9.023 HO2B   THD 47 
THD HO3B   HO3B   H 0 0 N N N -7.578 55.187 9.740  2.039  -1.537 -6.594 HO3B   THD 48 
THD H9     H9     H 0 1 N N N -7.240 56.691 20.345 -2.075 -0.443 5.407  H9     THD 49 
THD H9C1   1H9C   H 0 0 N N N -6.555 55.051 17.065 -4.050 0.894  4.375  H9C1   THD 50 
THD H9C2   2H9C   H 0 0 N N N -7.677 54.848 18.310 -3.989 0.854  2.596  H9C2   THD 51 
THD H10    H10    H 0 1 N N N -5.704 53.679 18.752 -5.650 -0.468 3.460  H10    THD 52 
# 
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 
THD "N1'" "C2'"  DOUB Y N 1  
THD "N1'" "C6'"  SING Y N 2  
THD "C2'" CM2    SING N N 3  
THD "C2'" "N3'"  SING Y N 4  
THD CM2   HM21   SING N N 5  
THD CM2   HM22   SING N N 6  
THD CM2   HM23   SING N N 7  
THD "N3'" "C4'"  DOUB Y N 8  
THD "C4'" "N4'"  SING N N 9  
THD "C4'" "C5'"  SING Y N 10 
THD "N4'" "H4'1" SING N N 11 
THD "N4'" "H4'2" SING N N 12 
THD "C5'" "C6'"  DOUB Y N 13 
THD "C5'" "C7'"  SING N N 14 
THD "C6'" "H6'"  SING N N 15 
THD "C7'" N3     SING N N 16 
THD "C7'" "H7'1" SING N N 17 
THD "C7'" "H7'2" SING N N 18 
THD N3    C2     SING N N 19 
THD N3    C4     SING N N 20 
THD C2    S1     SING N N 21 
THD C2    C8     DOUB N E 22 
THD S1    C5     SING N N 23 
THD C5    C4     DOUB N N 24 
THD C5    C6     SING N N 25 
THD C4    CM4    SING N N 26 
THD CM4   HM41   SING N N 27 
THD CM4   HM42   SING N N 28 
THD CM4   HM43   SING N N 29 
THD C6    C7     SING N N 30 
THD C6    H6C1   SING N N 31 
THD C6    H6C2   SING N N 32 
THD C7    O7     SING N N 33 
THD C7    H7C1   SING N N 34 
THD C7    H7C2   SING N N 35 
THD O7    PA     SING N N 36 
THD PA    O1A    SING N N 37 
THD PA    O2A    DOUB N N 38 
THD PA    O3A    SING N N 39 
THD O1A   HO1A   SING N N 40 
THD O3A   PB     SING N N 41 
THD PB    O1B    DOUB N N 42 
THD PB    O2B    SING N N 43 
THD PB    O3B    SING N N 44 
THD O2B   HO2B   SING N N 45 
THD O3B   HO3B   SING N N 46 
THD C8    O9     SING N N 47 
THD C8    C9     SING N N 48 
THD O9    H9     SING N N 49 
THD C9    O10    SING N N 50 
THD C9    H9C1   SING N N 51 
THD C9    H9C2   SING N N 52 
THD O10   H10    SING N N 53 
# 
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 
THD SMILES           ACDLabs              10.04 O=P(O)(O)OP(=O)(O)OCCC=1S\C(=C(\O)CO)N(C=1C)Cc2cnc(nc2N)C                                                                                                                                            
THD InChI            InChI                1.02b InChI=1/C14H22N4O9P2S/c1-8-12(3-4-26-29(24,25)27-28(21,22)23)30-14(11(20)7-19)18(8)6-10-5-16-9(2)17-13(10)15/h5,19-20H,3-4,6-7H2,1-2H3,(H,24,25)(H2,15,16,17)(H2,21,22,23)/b14-11+/f/h21-22,24H,15H2 
THD InChIKey         InChI                1.02b LXZUEFPJZTWGEL-GXHYSZLUDP                                                                                                                                                                            
THD SMILES_CANONICAL CACTVS               3.341 Cc1ncc(CN\2C(=C(CCO[P@](O)(=O)O[P](O)(O)=O)SC\2=C(/O)CO)C)c(N)n1                                                                                                                                     
THD SMILES           CACTVS               3.341 Cc1ncc(CN2C(=C(CCO[P](O)(=O)O[P](O)(O)=O)SC2=C(O)CO)C)c(N)n1                                                                                                                                         
THD SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1ncc(c(n1)N)CN\2C(=C(S/C2=C(\CO)/O)CCO[P@@](=O)(O)OP(=O)(O)O)C                                                                                                                                     
THD SMILES           "OpenEye OEToolkits" 1.5.0 Cc1ncc(c(n1)N)CN2C(=C(SC2=C(CO)O)CCOP(=O)(O)OP(=O)(O)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 
THD "SYSTEMATIC NAME" ACDLabs              10.04 "2-[(2E)-3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-(1,2-dihydroxyethylidene)-4-methyl-2,3-dihydro-1,3-thiazol-5-yl]ethyl trihydrogen diphosphate" 
THD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[(2E)-3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-2-(1,2-dihydroxyethylidene)-4-methyl-1,3-thiazol-5-yl]ethyl phosphono hydrogen phosphate"       
# 
