data_TDL
# 
_chem_comp.id                                    TDL 
_chem_comp.name                                  3-[(4-AMINO-2-METHYLPYRIMIDIN-5-YL)METHYL]-2-(1-CARBOXY-1-HYDROXYETHYL)-5-(2-{[HYDROXY(PHOSPHONOOXY)PHOSPHORYL]OXY}ETHYL)-4-METHYL-1,3-THIAZOL-3-IUM 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C15 H23 N4 O10 P2 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "2-LACTYLTHIAMIN DIPHOSPHATE" 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     2005-12-01 
_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                        513.376 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TDL 
_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        2EZ8 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
TDL O1B    O1B  O 0 1 N N N 83.082 59.127 0.917  8.177  -0.277 -0.151 O1B    TDL 1  
TDL PB     PB   P 0 1 N N N 84.265 60.053 1.026  6.599  -0.596 -0.154 PB     TDL 2  
TDL O2B    O2B  O 0 1 N N N 85.126 59.830 2.246  6.284  -1.757 0.917  O2B    TDL 3  
TDL O3B    O3B  O 0 1 N N N 85.013 60.260 -0.269 6.189  -1.045 -1.503 O3B    TDL 4  
TDL O3A    O3A  O 0 1 N N N 83.639 61.517 1.430  5.782  0.734  0.241  O3A    TDL 5  
TDL PA     PA   P 0 1 N N R 83.520 62.877 0.554  4.246  0.473  -0.162 PA     TDL 6  
TDL O1A    O1A  O 0 1 N N N 84.738 63.087 -0.282 4.084  0.581  -1.760 O1A    TDL 7  
TDL O2A    O2A  O 0 1 N N N 83.153 63.999 1.505  3.841  -0.879 0.285  O2A    TDL 8  
TDL O7     O7   O 0 1 N N N 82.261 62.581 -0.370 3.310  1.575  0.547  O7     TDL 9  
TDL C7     C7   C 0 1 N N N 80.960 62.607 0.218  1.958  1.222  0.250  C7     TDL 10 
TDL C6     C6   C 0 1 N N N 80.075 62.005 -0.863 1.012  2.235  0.898  C6     TDL 11 
TDL C5     C5   C 0 1 Y N N 78.573 62.109 -0.725 -0.414 1.862  0.584  C5     TDL 12 
TDL S1     S1   S 0 1 Y N N 77.801 61.124 0.482  -1.446 2.352  -0.790 S1     TDL 13 
TDL C4     C4   C 0 1 Y N N 77.606 62.843 -1.447 -1.272 1.062  1.267  C4     TDL 14 
TDL CM4    CM4  C 0 1 N N N 78.035 63.793 -2.552 -0.846 0.387  2.545  CM4    TDL 15 
TDL N3     N3   N 1 1 Y N N 76.304 62.646 -1.050 -2.484 0.888  0.784  N3     TDL 16 
TDL C2     C2   C 0 1 Y N N 76.224 61.728 -0.006 -2.866 1.464  -0.332 C2     TDL 17 
TDL CLA    CLA  C 0 1 N N S 74.900 61.167 0.531  -4.199 1.383  -1.032 CLA    TDL 18 
TDL OL1    OL1  O 0 1 N N N 73.885 62.144 0.712  -4.302 0.131  -1.714 OL1    TDL 19 
TDL CLB    CLB  C 0 1 N N N 75.028 60.362 1.841  -4.314 2.525  -2.043 CLB    TDL 20 
TDL CLC    CLC  C 0 1 N N N 74.357 60.183 -0.580 -5.307 1.495  -0.017 CLC    TDL 21 
TDL OL2    OL2  O 0 1 N N N 74.349 58.913 -0.415 -6.438 0.790  -0.177 OL2    TDL 22 
TDL OL3    OL3  O 0 1 N N N 73.887 60.597 -1.705 -5.178 2.221  0.940  OL3    TDL 23 
TDL "C7'"  C7*  C 0 1 N N N 75.185 63.405 -1.689 -3.425 0.027  1.504  "C7'"  TDL 24 
TDL "C5'"  C5*  C 0 1 Y N N 75.232 64.880 -1.178 -3.535 -1.300 0.798  "C5'"  TDL 25 
TDL "C6'"  C6*  C 0 1 Y N N 75.473 65.928 -2.101 -4.744 -1.735 0.292  "C6'"  TDL 26 
TDL "N1'"  N1*  N 0 1 Y N N 75.531 67.226 -1.719 -4.803 -2.908 -0.323 "N1'"  TDL 27 
TDL "C2'"  C2*  C 0 1 Y N N 75.371 67.559 -0.417 -3.729 -3.659 -0.457 "C2'"  TDL 28 
TDL CM2    CM2  C 0 1 N N N 75.446 68.995 0.049  -3.845 -4.985 -1.164 CM2    TDL 29 
TDL "N3'"  N3*  N 0 1 Y N N 75.142 66.608 0.503  -2.556 -3.286 0.015  "N3'"  TDL 30 
TDL "C4'"  C4*  C 0 1 Y N N 75.068 65.282 0.170  -2.416 -2.120 0.639  "C4'"  TDL 31 
TDL "N4'"  N4*  N 0 1 N N N 74.816 64.429 1.209  -1.181 -1.729 1.129  "N4'"  TDL 32 
TDL H2B    H2B  H 0 1 N N N 86.038 59.783 1.986  6.566  -1.424 1.780  H2B    TDL 33 
TDL H3B    H3B  H 0 1 N N N 84.395 60.303 -0.989 ?      ?      ?      H3B    TDL 34 
TDL H2A    H2A  H 0 1 N N N 83.076 63.655 2.387  ?      ?      ?      H2A    TDL 35 
TDL H71    1H7  H 0 1 N N N 80.645 63.618 0.515  1.748  0.226  0.641  H71    TDL 36 
TDL H72    2H7  H 0 1 N N N 80.923 62.017 1.146  1.810  1.227  -0.830 H72    TDL 37 
TDL H61    1H6  H 0 1 N N N 80.276 60.925 -0.805 1.222  3.230  0.507  H61    TDL 38 
TDL H62    2H6  H 0 1 N N N 80.337 62.518 -1.800 1.159  2.230  1.978  H62    TDL 39 
TDL HM41   1HM4 H 0 0 N N N 77.277 63.794 -3.349 0.045  -0.213 2.361  HM41   TDL 40 
TDL HM42   2HM4 H 0 0 N N N 79.000 63.464 -2.964 -0.625 1.144  3.299  HM42   TDL 41 
TDL HM43   3HM4 H 0 0 N N N 78.139 64.809 -2.143 -1.650 -0.256 2.902  HM43   TDL 42 
TDL HL1    HL1  H 0 1 N N N 73.816 62.362 1.634  -4.026 -0.552 -1.087 HL1    TDL 43 
TDL HLB1   1HLB H 0 0 N N N 74.163 60.574 2.487  -3.513 2.443  -2.777 HLB1   TDL 44 
TDL HLB2   2HLB H 0 0 N N N 75.954 60.652 2.360  -5.278 2.466  -2.549 HLB2   TDL 45 
TDL HLB3   3HLB H 0 0 N N N 75.058 59.287 1.610  -4.235 3.480  -1.523 HLB3   TDL 46 
TDL HL2    HL2  H 0 1 N N N 73.982 58.495 -1.186 -7.177 0.916  0.434  HL2    TDL 47 
TDL "H7'1" 1H7* H 0 0 N N N 74.220 62.946 -1.426 -4.405 0.504  1.534  "H7'1" TDL 48 
TDL "H7'2" 2H7* H 0 0 N N N 75.299 63.386 -2.783 -3.067 -0.132 2.522  "H7'2" TDL 49 
TDL "H6'"  H6*  H 0 1 N N N 75.615 65.684 -3.143 -5.630 -1.127 0.396  "H6'"  TDL 50 
TDL HM21   1HM2 H 0 0 N N N 74.567 69.545 -0.317 -3.664 -4.845 -2.230 HM21   TDL 51 
TDL HM22   2HM2 H 0 0 N N N 76.361 69.461 -0.345 -3.110 -5.679 -0.758 HM22   TDL 52 
TDL HM23   3HM2 H 0 0 N N N 75.464 69.024 1.148  -4.847 -5.389 -1.016 HM23   TDL 53 
TDL "H4'1" 1H4* H 0 0 N N N 75.557 64.490 1.878  -1.113 -1.328 2.010  "H4'1" TDL 54 
TDL "H4'2" 2H4* H 0 0 N N N 74.755 63.492 0.864  -0.383 -1.856 0.592  "H4'2" TDL 55 
# 
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 
TDL O1B   PB     DOUB N N 1  
TDL PB    O2B    SING N N 2  
TDL PB    O3B    SING N N 3  
TDL PB    O3A    SING N N 4  
TDL O2B   H2B    SING N N 5  
TDL O3B   H3B    SING N N 6  
TDL O3A   PA     SING N N 7  
TDL PA    O1A    DOUB N N 8  
TDL PA    O2A    SING N N 9  
TDL PA    O7     SING N N 10 
TDL O2A   H2A    SING N N 11 
TDL O7    C7     SING N N 12 
TDL C7    C6     SING N N 13 
TDL C7    H71    SING N N 14 
TDL C7    H72    SING N N 15 
TDL C6    C5     SING N N 16 
TDL C6    H61    SING N N 17 
TDL C6    H62    SING N N 18 
TDL C5    S1     SING Y N 19 
TDL C5    C4     DOUB Y N 20 
TDL S1    C2     SING Y N 21 
TDL C4    CM4    SING N N 22 
TDL C4    N3     SING Y N 23 
TDL CM4   HM41   SING N N 24 
TDL CM4   HM42   SING N N 25 
TDL CM4   HM43   SING N N 26 
TDL N3    C2     DOUB Y N 27 
TDL N3    "C7'"  SING N N 28 
TDL C2    CLA    SING N N 29 
TDL CLA   OL1    SING N N 30 
TDL CLA   CLB    SING N N 31 
TDL CLA   CLC    SING N N 32 
TDL OL1   HL1    SING N N 33 
TDL CLB   HLB1   SING N N 34 
TDL CLB   HLB2   SING N N 35 
TDL CLB   HLB3   SING N N 36 
TDL CLC   OL2    SING N N 37 
TDL CLC   OL3    DOUB N N 38 
TDL OL2   HL2    SING N N 39 
TDL "C7'" "C5'"  SING N N 40 
TDL "C7'" "H7'1" SING N N 41 
TDL "C7'" "H7'2" SING N N 42 
TDL "C5'" "C6'"  SING Y N 43 
TDL "C5'" "C4'"  DOUB Y N 44 
TDL "C6'" "N1'"  DOUB Y N 45 
TDL "C6'" "H6'"  SING N N 46 
TDL "N1'" "C2'"  SING Y N 47 
TDL "C2'" CM2    SING N N 48 
TDL "C2'" "N3'"  DOUB Y N 49 
TDL CM2   HM21   SING N N 50 
TDL CM2   HM22   SING N N 51 
TDL CM2   HM23   SING N N 52 
TDL "N3'" "C4'"  SING Y N 53 
TDL "C4'" "N4'"  SING N N 54 
TDL "N4'" "H4'1" SING N N 55 
TDL "N4'" "H4'2" SING N N 56 
# 
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 
TDL SMILES           ACDLabs              10.04 O=P(O)(O)OP(=O)(O)OCCc1sc([n+](c1C)Cc2cnc(nc2N)C)C(O)(C(=O)O)C 
TDL InChI            InChI                1.02b 
InChI=1/C15H22N4O10P2S/c1-8-11(4-5-28-31(26,27)29-30(23,24)25)32-13(15(3,22)14(20)21)19(8)7-10-6-17-9(2)18-12(10)16/h6,22H,4-5,7H2,1-3H3,(H5-,16,17,18,20,21,23,24,25,26,27)/p+1/t15-/m1/s1/fC15H23N4O10P2S/h20,23-24,26H,16H2/q+1 
TDL InChIKey         InChI                1.02b TVDSMGSBVYONNB-UOTLSGGBDB 
TDL SMILES_CANONICAL CACTVS               3.341 Cc1ncc(C[n+]2c(C)c(CCO[P@](O)(=O)O[P](O)(O)=O)sc2[C@@](C)(O)C(O)=O)c(N)n1 
TDL SMILES           CACTVS               3.341 Cc1ncc(C[n+]2c(C)c(CCO[P](O)(=O)O[P](O)(O)=O)sc2[C](C)(O)C(O)=O)c(N)n1 
TDL SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c(sc([n+]1Cc2cnc(nc2N)C)[C@](C)(C(=O)O)O)CCO[P@@](=O)(O)OP(=O)(O)O 
TDL SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c(sc([n+]1Cc2cnc(nc2N)C)C(C)(C(=O)O)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 
TDL "SYSTEMATIC NAME" ACDLabs              10.04 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-[(1S)-1-carboxy-1-hydroxyethyl]-5-(2-{[(R)-hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium   
TDL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-5-[2-(hydroxy-phosphonooxy-phosphoryl)oxyethyl]-4-methyl-1,3-thiazol-3-ium-2-yl]-2-hydroxy-propanoic acid" 
# 
