data_HTL
# 
_chem_comp.id                                    HTL 
_chem_comp.name                                  "2-ACETYL-THIAMINE DIPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H21 N4 O8 P2 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         
;2-ACETYL-3-[(4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL]-4-METHYL-5-(4,6,6-TRIHYDROXY-3,5-DIOXA-4,6-DIPHOSPHAHEX-1-YL)THIAZOLIUM INNER SALT P,P'-DIOXIDE
;
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     2001-11-26 
_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                        467.351 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     HTL 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1KEK 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
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 
HTL "N1'"  N1*    N 0 1 Y N N -27.307 -64.040 24.764 4.450  5.604  1.056  "N1'"  HTL 1  
HTL "C2'"  C2*    C 0 1 Y N N -25.993 -64.198 25.403 4.976  6.807  0.757  "C2'"  HTL 2  
HTL C2A    C2A    C 0 1 N N N -25.424 -63.174 26.151 6.115  7.264  1.604  C2A    HTL 3  
HTL "N3'"  N3*    N 0 1 Y N N -25.260 -65.408 25.276 4.583  7.641  -0.224 "N3'"  HTL 4  
HTL "C4'"  C4*    C 0 1 Y N N -25.802 -66.527 24.499 3.551  7.196  -0.970 "C4'"  HTL 5  
HTL "N4'"  N4*    N 0 1 N N N -24.969 -67.714 24.436 3.084  8.023  -2.021 "N4'"  HTL 6  
HTL "C5'"  C5*    C 0 1 Y N N -27.195 -66.399 23.802 2.938  5.990  -0.757 "C5'"  HTL 7  
HTL "C6'"  C6*    C 0 1 Y N N -27.858 -65.169 23.977 3.421  5.222  0.271  "C6'"  HTL 8  
HTL C35    C35    C 0 1 N N N -27.799 -67.521 22.988 1.787  5.498  -1.590 C35    HTL 9  
HTL N3     N3     N 1 1 Y N N -27.013 -67.782 21.798 1.364  4.198  -1.117 N3     HTL 10 
HTL C2     C2     C 0 1 Y N N -26.231 -69.056 21.568 0.444  4.059  -0.188 C2     HTL 11 
HTL S1     S1     S 0 1 Y N N -26.614 -69.552 20.078 0.159  2.409  0.160  S1     HTL 12 
HTL C5     C5     C 0 1 Y N N -26.793 -67.856 19.597 1.327  1.942  -0.996 C5     HTL 13 
HTL C4     C4     C 0 1 Y N N -27.453 -67.264 20.583 1.889  3.020  -1.601 C4     HTL 14 
HTL C4A    C4A    C 0 1 N N N -28.486 -66.335 20.269 2.924  3.091  -2.643 C4A    HTL 15 
HTL C5A    C5A    C 0 1 N N N -27.595 -67.951 18.307 1.601  0.481  -1.216 C5A    HTL 16 
HTL C5B    C5B    C 0 1 N N N -26.542 -67.438 17.346 0.713  -0.131 -2.295 C5B    HTL 17 
HTL O5G    O5G    O 0 1 N N N -26.802 -66.753 16.028 0.955  0.511  -3.536 O5G    HTL 18 
HTL P1     P1     P 0 1 N N R -25.866 -66.395 14.838 0.140  0.051  -4.856 P1     HTL 19 
HTL O11    O11    O 0 1 N N N -25.277 -67.823 14.566 -1.416 0.155  -4.431 O11    HTL 20 
HTL O12    O12    O 0 1 N N N -26.572 -65.883 13.643 0.488  0.809  -6.105 O12    HTL 21 
HTL O13    O13    O 0 1 N N N -24.815 -65.583 15.432 0.393  -1.544 -4.952 O13    HTL 22 
HTL P2     P2     P 0 1 N N N -25.867 -69.177 13.790 -2.330 1.434  -4.056 P2     HTL 23 
HTL O21    O21    O 0 1 N N N -24.777 -69.648 12.836 -1.846 2.224  -2.875 O21    HTL 24 
HTL O22    O22    O 0 1 N N N -26.391 -70.031 14.843 -3.807 0.797  -3.900 O22    HTL 25 
HTL O23    O23    O 0 1 N N N -27.002 -68.568 12.936 -2.415 2.253  -5.447 O23    HTL 26 
HTL "C1'"  "C1'"  C 0 1 N N N -26.029 -70.529 22.865 -0.268 5.090  0.489  "C1'"  HTL 27 
HTL "O2'"  "O2'"  O 0 1 N N N -26.080 -70.358 24.089 0.156  6.241  0.734  "O2'"  HTL 28 
HTL "C3'"  "C3'"  C 0 1 N N N -25.571 -71.942 22.345 -1.676 4.802  0.971  "C3'"  HTL 29 
HTL H2A1   1H2A   H 0 0 N N N -24.427 -63.293 26.635 7.009  7.425  0.989  H2A1   HTL 30 
HTL H2A2   2H2A   H 0 0 N N N -25.388 -62.260 25.512 5.876  8.203  2.121  H2A2   HTL 31 
HTL H2A3   3H2A   H 0 0 N N N -26.155 -62.875 26.938 6.356  6.526  2.381  H2A3   HTL 32 
HTL "H4'1" 1H4*   H 0 0 N N N -25.346 -68.492 23.895 2.454  7.640  -2.692 "H4'1" HTL 33 
HTL "H4'2" 2H4*   H 0 0 N N N -24.736 -68.026 25.379 3.467  8.939  -2.120 "H4'2" HTL 34 
HTL "H6'"  H6*    H 0 1 N N N -28.840 -65.087 23.481 3.000  4.251  0.514  "H6'"  HTL 35 
HTL H351   1H35   H 0 0 N N N -27.938 -68.443 23.599 0.943  6.196  -1.542 H351   HTL 36 
HTL H352   2H35   H 0 0 N N N -28.867 -67.319 22.739 2.071  5.427  -2.647 H352   HTL 37 
HTL H4A1   1H4A   H 0 0 N N N -28.838 -65.920 19.295 3.822  2.514  -2.358 H4A1   HTL 38 
HTL H4A2   2H4A   H 0 0 N N N -29.401 -66.765 20.737 2.570  2.695  -3.612 H4A2   HTL 39 
HTL H4A3   3H4A   H 0 0 N N N -28.252 -65.437 20.887 3.247  4.129  -2.843 H4A3   HTL 40 
HTL H5A1   1H5A   H 0 0 N N N -28.038 -68.946 18.071 2.656  0.342  -1.485 H5A1   HTL 41 
HTL H5A2   2H5A   H 0 0 N N N -28.577 -67.423 18.294 1.443  -0.059 -0.274 H5A2   HTL 42 
HTL H5B1   1H5B   H 0 0 N N N -25.887 -66.752 17.933 0.954  -1.192 -2.415 H5B1   HTL 43 
HTL H5B2   2H5B   H 0 0 N N N -25.871 -68.300 17.125 -0.350 -0.037 -2.050 H5B2   HTL 44 
HTL H22O   OH22   H 0 0 N N N -26.726 -70.802 14.401 -4.539 1.368  -3.585 H22O   HTL 45 
HTL H23O   OH23   H 0 0 N N N -27.337 -69.339 12.494 -2.862 3.126  -5.458 H23O   HTL 46 
HTL "H3'1" "1H3'" H 0 0 N N N -25.456 -72.774 23.078 -1.739 3.915  1.620  "H3'1" HTL 47 
HTL "H3'2" "2H3'" H 0 0 N N N -26.263 -72.268 21.534 -2.390 4.659  0.145  "H3'2" HTL 48 
HTL "H3'3" "3H3'" H 0 0 N N N -24.616 -71.825 21.781 -2.121 5.609  1.580  "H3'3" HTL 49 
HTL HO1    HO1    H 0 1 N N N -24.145 -65.406 14.782 1.237  -1.868 -5.332 HO1    HTL 50 
# 
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 
HTL "N1'" "C2'"  DOUB Y N 1  
HTL "N1'" "C6'"  SING Y N 2  
HTL "C2'" C2A    SING N N 3  
HTL "C2'" "N3'"  SING Y N 4  
HTL C2A   H2A1   SING N N 5  
HTL C2A   H2A2   SING N N 6  
HTL C2A   H2A3   SING N N 7  
HTL "N3'" "C4'"  DOUB Y N 8  
HTL "C4'" "N4'"  SING N N 9  
HTL "C4'" "C5'"  SING Y N 10 
HTL "N4'" "H4'1" SING N N 11 
HTL "N4'" "H4'2" SING N N 12 
HTL "C5'" "C6'"  DOUB Y N 13 
HTL "C5'" C35    SING N N 14 
HTL "C6'" "H6'"  SING N N 15 
HTL C35   N3     SING N N 16 
HTL C35   H351   SING N N 17 
HTL C35   H352   SING N N 18 
HTL N3    C2     DOUB Y N 19 
HTL N3    C4     SING Y N 20 
HTL C2    S1     SING Y N 21 
HTL C2    "C1'"  SING N N 22 
HTL S1    C5     SING Y N 23 
HTL C5    C4     DOUB Y N 24 
HTL C5    C5A    SING N N 25 
HTL C4    C4A    SING N N 26 
HTL C4A   H4A1   SING N N 27 
HTL C4A   H4A2   SING N N 28 
HTL C4A   H4A3   SING N N 29 
HTL C5A   C5B    SING N N 30 
HTL C5A   H5A1   SING N N 31 
HTL C5A   H5A2   SING N N 32 
HTL C5B   O5G    SING N N 33 
HTL C5B   H5B1   SING N N 34 
HTL C5B   H5B2   SING N N 35 
HTL O5G   P1     SING N N 36 
HTL P1    O11    SING N N 37 
HTL P1    O12    DOUB N N 38 
HTL P1    O13    SING N N 39 
HTL O11   P2     SING N N 40 
HTL P2    O21    DOUB N N 41 
HTL P2    O22    SING N N 42 
HTL P2    O23    SING N N 43 
HTL O22   H22O   SING N N 44 
HTL O23   H23O   SING N N 45 
HTL "C1'" "O2'"  DOUB N N 46 
HTL "C1'" "C3'"  SING N N 47 
HTL "C3'" "H3'1" SING N N 48 
HTL "C3'" "H3'2" SING N N 49 
HTL "C3'" "H3'3" SING N N 50 
HTL HO1   O13    SING N N 51 
# 
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 
HTL SMILES           ACDLabs              10.04 O=C(c1sc(c([n+]1Cc2cnc(nc2N)C)C)CCOP(=O)(O)OP(=O)(O)O)C                                                                                                                                          
HTL InChI            InChI                1.02b InChI=1/C14H20N4O8P2S/c1-8-12(4-5-25-28(23,24)26-27(20,21)22)29-14(9(2)19)18(8)7-11-6-16-10(3)17-13(11)15/h6H,4-5,7H2,1-3H3,(H4-,15,16,17,20,21,22,23,24)/p+1/fC14H21N4O8P2S/h20-21,23H,15H2/q+1 
HTL InChIKey         InChI                1.02b GYRGKLZCJRVYRV-HNSMEJINCT                                                                                                                                                                        
HTL SMILES_CANONICAL CACTVS               3.341 CC(=O)c1sc(CCO[P@](O)(=O)O[P](O)(O)=O)c(C)[n+]1Cc2cnc(C)nc2N                                                                                                                                     
HTL SMILES           CACTVS               3.341 CC(=O)c1sc(CCO[P](O)(=O)O[P](O)(O)=O)c(C)[n+]1Cc2cnc(C)nc2N                                                                                                                                      
HTL SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c(sc([n+]1Cc2cnc(nc2N)C)C(=O)C)CCO[P@@](=O)(O)OP(=O)(O)O                                                                                                                                      
HTL SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c(sc([n+]1Cc2cnc(nc2N)C)C(=O)C)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 
HTL "SYSTEMATIC NAME" ACDLabs              10.04 2-acetyl-3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[(R)-hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium 
HTL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-2-ethanoyl-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate"       
# 
