data_THV
# 
_chem_comp.id                                    THV 
_chem_comp.name                                  "C2-1-HYDROXY-3-METHYL-PROPYL-THIAMIN DIPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H26 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                        496.412 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     THV 
_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        ? 
_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 
THV O2B    O2B  O 0  1 N N N 70.453 4.999  4.489  8.437  0.610  -0.378 O2B    THV 1  
THV PB     PB   P 0  1 N N N 69.101 5.238  5.253  6.968  0.426  0.257  PB     THV 2  
THV O3B    O3B  O 0  1 N N N 68.070 4.161  4.777  6.697  1.596  1.329  O3B    THV 3  
THV O1B    O1B  O 0  1 N N N 68.529 6.593  5.087  6.883  -0.889 0.930  O1B    THV 4  
THV O3A    O3A  O 0  1 N N N 69.366 4.993  6.790  5.865  0.503  -0.913 O3A    THV 5  
THV PA     PA   P 0  1 N N R 69.148 3.602  7.745  4.494  -0.075 -0.298 PA     THV 6  
THV O1A    O1A  O 0  1 N N N 69.499 4.021  9.095  4.588  -1.678 -0.188 O1A    THV 7  
THV O2A    O2A  O 0  1 N N N 67.818 3.125  7.447  4.276  0.500  1.049  O2A    THV 8  
THV O5G    O5G  O 0  1 N N N 70.258 2.652  7.174  3.264  0.326  -1.257 O5G    THV 9  
THV C5B    C5B  C 0  1 N N N 71.612 2.851  7.567  2.071  -0.109 -0.602 C5B    THV 10 
THV C5A    C5A  C 0  1 N N N 72.413 2.104  6.505  0.858  0.243  -1.466 C5A    THV 11 
THV C5     C5   C 0  1 Y N N 73.911 2.289  6.681  -0.400 -0.215 -0.776 C5     THV 12 
THV C4     C4   C 0  1 Y N N 74.921 1.450  7.205  -1.170 0.450  0.083  C4     THV 13 
THV C4A    C4A  C 0  1 N N N 74.645 0.027  7.809  -0.809 1.859  0.477  C4A    THV 14 
THV S1     S1   S 0  1 Y N N 74.697 3.717  6.112  -1.237 -1.787 -0.903 S1     THV 15 
THV C2     C2   C 0  1 Y N N 76.300 3.238  6.527  -2.583 -1.443 0.220  C2     THV 16 
THV C8     C8   C -1 1 N N N 77.583 4.067  6.312  -3.602 -2.227 0.588  C8     THV 17 
THV O9     O9   O 0  1 N N N 78.700 3.604  6.678  -3.932 -2.343 1.904  O9     THV 18 
THV C9     C9   C 0  1 N N N 77.452 5.475  5.623  -4.386 -2.983 -0.455 C9     THV 19 
THV C10    C10  C 0  1 N N N 77.496 6.607  6.662  -3.449 -3.926 -1.213 C10    THV 20 
THV C11    C11  C 0  1 N N N 78.496 5.717  4.525  -5.487 -3.798 0.227  C11    THV 21 
THV N3     N3   N 1  1 Y N N 76.200 1.991  7.115  -2.289 -0.137 0.606  N3     THV 22 
THV C35    C35  C 0  1 N N N 77.394 1.317  7.691  -3.146 0.581  1.552  C35    THV 23 
THV "C5'"  C5*  C 0  1 Y N N 77.411 1.547  9.252  -4.107 1.459  0.793  "C5'"  THV 24 
THV "C6'"  C6*  C 0  1 Y N N 77.279 0.427  10.125 -3.776 2.761  0.476  "C6'"  THV 25 
THV "N1'"  N1*  N 0  1 Y N N 77.312 0.504  11.454 -4.647 3.505  -0.193 "N1'"  THV 26 
THV "C2'"  C2*  C 0  1 Y N N 77.450 1.698  12.100 -5.817 3.019  -0.556 "C2'"  THV 27 
THV C2A    C2A  C 0  1 N N N 77.474 1.884  13.635 -6.773 3.903  -1.315 C2A    THV 28 
THV "N3'"  N3*  N 0  1 Y N N 77.579 2.851  11.327 -6.173 1.783  -0.275 "N3'"  THV 29 
THV "C4'"  C4*  C 0  1 Y N N 77.603 2.803  9.914  -5.352 0.974  0.388  "C4'"  THV 30 
THV "N4'"  N4*  N 0  1 N N N 77.683 3.991  9.298  -5.731 -0.326 0.682  "N4'"  THV 31 
THV H2B    H2B  H 0  1 N N N 70.285 4.951  3.555  9.066  0.557  0.355  H2B    THV 32 
THV H3B    H3B  H 0  1 N N N 67.861 4.305  3.861  6.762  2.434  0.850  H3B    THV 33 
THV H1A    H1A  H 0  1 N N N 69.575 3.257  9.654  4.730  -2.012 -1.085 H1A    THV 34 
THV H5B1   1H5B H 0  0 N N N 71.815 2.486  8.585  1.985  0.388  0.364  H5B1   THV 35 
THV H5B2   2H5B H 0  0 N N N 71.871 3.920  7.587  2.110  -1.188 -0.454 H5B2   THV 36 
THV H5A1   1H5A H 0  0 N N N 72.134 2.510  5.521  0.944  -0.253 -2.433 H5A1   THV 37 
THV H5A2   2H5A H 0  0 N N N 72.181 1.031  6.581  0.819  1.323  -1.614 H5A2   THV 38 
THV H4A1   1H4A H 0  0 N N N 73.696 0.043  8.365  -1.283 2.561  -0.210 H4A1   THV 39 
THV H4A2   2H4A H 0  0 N N N 75.465 -0.248 8.489  -1.158 2.053  1.491  H4A2   THV 40 
THV H4A3   3H4A H 0  0 N N N 74.580 -0.711 6.996  0.273  1.983  0.434  H4A3   THV 41 
THV H9     H9   H 0  1 N N N 79.259 3.488  5.919  -3.268 -1.848 2.403  H9     THV 42 
THV HA     HA   H 0  1 N N N 76.469 5.476  5.129  -4.835 -2.277 -1.153 HA     THV 43 
THV H101   1H10 H 0  0 N N N 76.609 7.246  6.545  -3.000 -4.631 -0.514 H101   THV 44 
THV H102   2H10 H 0  0 N N N 78.404 7.209  6.510  -4.016 -4.472 -1.967 H102   THV 45 
THV H103   3H10 H 0  0 N N N 77.507 6.176  7.674  -2.665 -3.345 -1.698 H103   THV 46 
THV H111   1H11 H 0  0 N N N 79.219 4.888  4.517  -5.038 -4.503 0.926  H111   THV 47 
THV H112   2H11 H 0  0 N N N 79.024 6.662  4.723  -6.155 -3.126 0.767  H112   THV 48 
THV H113   3H11 H 0  0 N N N 77.994 5.775  3.548  -6.054 -4.344 -0.527 H113   THV 49 
THV H351   1H35 H 0  0 N N N 78.308 1.735  7.244  -3.706 -0.137 2.152  H351   THV 50 
THV H352   2H35 H 0  0 N N N 77.349 0.239  7.477  -2.529 1.197  2.205  H352   THV 51 
THV "H6'"  H6*  H 0  1 N N N 77.143 -0.547 9.679  -2.821 3.170  0.769  "H6'"  THV 52 
THV H2A1   1H2A H 0  0 N N N 76.581 2.444  13.950 -6.595 3.796  -2.385 H2A1   THV 53 
THV H2A2   2H2A H 0  0 N N N 78.378 2.441  13.923 -7.798 3.611  -1.086 H2A2   THV 54 
THV H2A3   3H2A H 0  0 N N N 77.480 0.899  14.124 -6.617 4.942  -1.023 H2A3   THV 55 
THV "H4'1" 1H4* H 0  0 N N N 78.518 4.026  8.749  -6.471 -0.735 0.207  "H4'1" THV 56 
THV "H4'2" 2H4* H 0  0 N N N 77.703 4.721  9.981  -5.255 -0.828 1.363  "H4'2" THV 57 
# 
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 
THV O2B   PB     SING N N 1  
THV O2B   H2B    SING N N 2  
THV PB    O3B    SING N N 3  
THV PB    O1B    DOUB N N 4  
THV PB    O3A    SING N N 5  
THV O3B   H3B    SING N N 6  
THV O3A   PA     SING N N 7  
THV PA    O1A    SING N N 8  
THV PA    O2A    DOUB N N 9  
THV PA    O5G    SING N N 10 
THV O1A   H1A    SING N N 11 
THV O5G   C5B    SING N N 12 
THV C5B   C5A    SING N N 13 
THV C5B   H5B1   SING N N 14 
THV C5B   H5B2   SING N N 15 
THV C5A   C5     SING N N 16 
THV C5A   H5A1   SING N N 17 
THV C5A   H5A2   SING N N 18 
THV C5    C4     DOUB Y N 19 
THV C5    S1     SING Y N 20 
THV C4    C4A    SING N N 21 
THV C4    N3     SING Y N 22 
THV C4A   H4A1   SING N N 23 
THV C4A   H4A2   SING N N 24 
THV C4A   H4A3   SING N N 25 
THV S1    C2     SING Y N 26 
THV C2    C8     SING N N 27 
THV C2    N3     DOUB Y N 28 
THV C8    O9     SING N N 29 
THV C8    C9     SING N N 30 
THV O9    H9     SING N N 31 
THV C9    C10    SING N N 32 
THV C9    C11    SING N N 33 
THV C9    HA     SING N N 34 
THV C10   H101   SING N N 35 
THV C10   H102   SING N N 36 
THV C10   H103   SING N N 37 
THV C11   H111   SING N N 38 
THV C11   H112   SING N N 39 
THV C11   H113   SING N N 40 
THV N3    C35    SING N N 41 
THV C35   "C5'"  SING N N 42 
THV C35   H351   SING N N 43 
THV C35   H352   SING N N 44 
THV "C5'" "C6'"  DOUB Y N 45 
THV "C5'" "C4'"  SING Y N 46 
THV "C6'" "N1'"  SING Y N 47 
THV "C6'" "H6'"  SING N N 48 
THV "N1'" "C2'"  DOUB Y N 49 
THV "C2'" C2A    SING N N 50 
THV "C2'" "N3'"  SING Y N 51 
THV C2A   H2A1   SING N N 52 
THV C2A   H2A2   SING N N 53 
THV C2A   H2A3   SING N N 54 
THV "N3'" "C4'"  DOUB Y N 55 
THV "C4'" "N4'"  SING N N 56 
THV "N4'" "H4'1" SING N N 57 
THV "N4'" "H4'2" 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 
THV SMILES           ACDLabs              10.04 O=P(O)(O)OP(=O)(O)OCCc1sc([C-](O)C(C)C)[n+](c1C)Cc2cnc(nc2N)C                                                                                                                                 
THV InChI            InChI                1.02b InChI=1/C16H26N4O8P2S/c1-9(2)14(21)16-20(8-12-7-18-11(4)19-15(12)17)10(3)13(31-16)5-6-27-30(25,26)28-29(22,23)24/h7,9,21H,5-6,8H2,1-4H3,(H,25,26)(H2,17,18,19)(H2,22,23,24)/f/h22-23,25H,17H2 
THV InChIKey         InChI                1.02b VBABUKBBNKNHAI-QLOJNKACCY                                                                                                                                                                     
THV SMILES_CANONICAL CACTVS               3.341 CC(C)[C-](O)c1sc(CCO[P@](O)(=O)O[P](O)(O)=O)c(C)[n+]1Cc2cnc(C)nc2N                                                                                                                            
THV SMILES           CACTVS               3.341 CC(C)[C-](O)c1sc(CCO[P](O)(=O)O[P](O)(O)=O)c(C)[n+]1Cc2cnc(C)nc2N                                                                                                                             
THV SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c(sc([n+]1Cc2cnc(nc2N)C)[C-](C(C)C)O)CCO[P@@](=O)(O)OP(=O)(O)O                                                                                                                             
THV SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c(sc([n+]1Cc2cnc(nc2N)C)[C-](C(C)C)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 
THV "SYSTEMATIC NAME" ACDLabs              10.04 1-{3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[(R)-hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium-2-yl}-1-hydroxy-2-methylpropan-1-ide 
THV "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-2-(1-hydroxy-2-methyl-propyl)-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate"                   
# 
