data_TP8
# 
_chem_comp.id                                    TP8 
_chem_comp.name                                  5-(2-{[HYDROXY(PHOSPHONOOXY)PHOSPHORYL]OXY}ETHYL)-2-[(1Z)-1-HYDROXY-3-(PHOSPHONOOXY)PROP-1-EN-1-YL]-3-{[(4Z)-4-IMINO-2-METHYL-4,5-DIHYDROPYRIMIDIN-5-YL]METHYL}-4-METHYL-1,3-THIAZOL-3-IUM 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C15 H21 N4 O12 P3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "PUTATIVE ENOL(ATE)-THDP REACTION INTERMEDIATE" 
_chem_comp.pdbx_formal_charge                    -2 
_chem_comp.pdbx_initial_date                     2006-10-13 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        574.333 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TP8 
_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 
TP8 C8   C8   C 0  1 N N N 19.825 108.817 41.443 4.321  -1.570 -1.049 C8   TP8 1  
TP8 C5   C5   C 0  1 Y N N 21.967 111.537 43.388 6.902  -2.284 -3.801 C5   TP8 2  
TP8 C4   C4   C 0  1 Y N N 22.535 110.284 43.613 7.115  -3.134 -2.742 C4   TP8 3  
TP8 N3   N3   N 1  1 Y N N 21.886 109.260 42.980 6.218  -2.923 -1.724 N3   TP8 4  
TP8 C2   C2   C 0  1 Y N N 20.805 109.620 42.243 5.337  -1.973 -1.932 C2   TP8 5  
TP8 C6   C6   C 0  1 N N N 22.379 112.889 43.911 7.623  -2.169 -5.085 C6   TP8 6  
TP8 O3C  O3C  O -1 1 N N N 14.797 108.115 40.668 0.090  -4.310 2.143  O3C  TP8 7  
TP8 PC   PC   P 0  1 N N N 15.702 108.070 39.461 0.267  -2.935 1.535  PC   TP8 8  
TP8 O1C  O1C  O 0  1 N N N 15.809 106.713 38.810 -0.902 -2.232 0.879  O1C  TP8 9  
TP8 O2C  O2C  O 0  1 N N N 15.507 109.217 38.488 0.890  -1.950 2.680  O2C  TP8 10 
TP8 O10  O10  O 0  1 N N N 17.188 108.331 40.032 1.532  -2.990 0.505  O10  TP8 11 
TP8 C10  C10  C 0  1 N N N 17.619 107.965 41.370 1.906  -1.813 -0.201 C10  TP8 12 
TP8 C9   C9   C 0  1 N N N 18.589 108.663 41.961 3.082  -2.132 -1.069 C9   TP8 13 
TP8 O8   O8   O 0  1 N N N 20.139 108.287 40.388 4.684  -0.569 -0.157 O8   TP8 14 
TP8 C7,  C7,  C 0  1 N N N 22.342 107.877 43.090 6.243  -3.703 -0.495 C7,  TP8 15 
TP8 C5,  C5,  C 0  1 N N R 23.567 107.606 42.230 7.137  -3.049 0.551  C5,  TP8 16 
TP8 C4,  C4,  C 0  1 N N N 23.656 107.928 40.874 7.220  -3.915 1.778  C4,  TP8 17 
TP8 N4,  N4,  N 0  1 N N N 22.648 108.528 40.202 7.977  -4.961 1.828  N4,  TP8 18 
TP8 N3,  N3,  N 0  1 N N N 24.783 107.635 40.184 6.446  -3.597 2.861  N3,  TP8 19 
TP8 C2,  C2,  C 0  1 N N N 25.825 107.033 40.796 5.900  -2.422 2.921  C2,  TP8 20 
TP8 CM2  CM2  C 0  1 N N N 27.071 106.705 40.018 5.054  -2.069 4.112  CM2  TP8 21 
TP8 N1,  N1,  N 0  1 N N N 25.754 106.720 42.108 6.017  -1.414 1.994  N1,  TP8 22 
TP8 C6,  C6,  C 0  1 N N N 24.660 106.993 42.828 6.601  -1.689 0.875  C6,  TP8 23 
TP8 CM4  CM4  C 0  1 N N N 23.763 110.116 44.482 8.132  -4.184 -2.580 CM4  TP8 24 
TP8 S1   S1   S 0  1 Y N N 20.537 111.390 42.328 5.570  -1.249 -3.464 S1   TP8 25 
TP8 C7   C7   C 0  1 N N N 22.065 114.039 42.982 8.800  -1.184 -5.045 C7   TP8 26 
TP8 O7   O7   O 0  1 N N N 22.355 115.200 43.747 9.756  -1.626 -4.089 O7   TP8 27 
TP8 PA   PA   P 0  1 N N N 22.850 116.549 43.036 11.111 -0.743 -3.856 PA   TP8 28 
TP8 O1A  O1A  O -1 1 N N N 23.480 117.412 44.104 11.945 -1.431 -2.797 O1A  TP8 29 
TP8 O2A  O2A  O 0  1 N N N 23.656 116.182 41.818 11.714 -0.380 -5.196 O2A  TP8 30 
TP8 O3A  O3A  O 0  1 N N N 21.451 117.173 42.531 10.453 0.602  -3.203 O3A  TP8 31 
TP8 PB   PB   P 0  1 N N N 20.100 117.281 43.415 9.569  0.805  -1.846 PB   TP8 32 
TP8 O2B  O2B  O -1 1 N N N 19.495 115.898 43.495 8.235  0.113  -2.020 O2B  TP8 33 
TP8 O3B  O3B  O 0  1 N N N 20.589 117.815 44.744 10.438 0.523  -0.640 O3B  TP8 34 
TP8 O1B  O1B  O 0  1 N N N 19.272 118.237 42.596 9.332  2.417  -1.946 O1B  TP8 35 
TP8 HO8  HO8  H 0  1 N N N 20.221 108.950 39.712 4.390  -0.807 0.725  HO8  TP8 36 
TP8 H9   H9   H 0  1 N N N 18.373 109.132 42.909 2.891  -2.918 -1.801 H9   TP8 37 
TP8 H101 1H10 H 0  0 N N N 16.734 108.061 42.016 2.098  -1.026 0.530  H101 TP8 38 
TP8 H102 2H10 H 0  0 N N N 18.054 106.963 41.243 1.063  -1.505 -0.828 H102 TP8 39 
TP8 H2C  H2C  H 0  1 N N N 15.466 110.036 38.967 0.890  -0.983 2.517  H2C  TP8 40 
TP8 H61  1H6  H 0  1 N N N 21.844 113.063 44.856 8.003  -3.156 -5.411 H61  TP8 41 
TP8 H62  2H6  H 0  1 N N N 23.473 112.864 44.027 6.933  -1.841 -5.884 H62  TP8 42 
TP8 H71  1H7  H 0  1 N N N 22.683 113.997 42.073 9.297  -1.138 -6.019 H71  TP8 43 
TP8 H72  2H7  H 0  1 N N N 21.022 114.020 42.632 8.467  -0.177 -4.772 H72  TP8 44 
TP8 H1B  H1B  H 0  1 N N N 19.098 119.021 43.104 8.650  2.751  -2.568 H1B  TP8 45 
TP8 HM41 1HM4 H 0  0 N N N 24.660 110.075 43.846 9.001  -4.007 -3.238 HM41 TP8 46 
TP8 HM42 2HM4 H 0  0 N N N 23.842 110.968 45.173 8.510  -4.245 -1.543 HM42 TP8 47 
TP8 HM43 3HM4 H 0  0 N N N 23.679 109.183 45.058 7.738  -5.189 -2.816 HM43 TP8 48 
TP8 H7,1 1H7, H 0  0 N N N 22.600 107.675 44.140 5.225  -3.797 -0.109 H7,1 TP8 49 
TP8 H7,2 2H7, H 0  0 N N N 21.530 107.223 42.739 6.604  -4.710 -0.718 H7,2 TP8 50 
TP8 H5,  H5,  H 0  1 N N N 22.752 108.192 41.781 8.145  -2.919 0.140  H5,  TP8 51 
TP8 H6,  H6,  H 0  1 N N N 24.627 106.736 43.876 6.697  -0.903 0.109  H6,  TP8 52 
TP8 H4,  H4,  H 0  1 N N N 21.881 108.686 40.824 8.465  -5.065 0.933  H4,  TP8 53 
TP8 HM21 1HM2 H 0  0 N N N 26.826 106.625 38.949 5.646  -2.174 5.017  HM21 TP8 54 
TP8 HM22 2HM2 H 0  0 N N N 27.815 107.502 40.165 4.196  -2.735 4.155  HM22 TP8 55 
TP8 HM23 3HM2 H 0  0 N N N 27.483 105.748 40.372 4.707  -1.043 4.016  HM23 TP8 56 
# 
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 
TP8 C8  O8   SING N N 1  
TP8 C8  C9   DOUB N Z 2  
TP8 C8  C2   SING N N 3  
TP8 C5  C4   DOUB Y N 4  
TP8 C5  S1   SING Y N 5  
TP8 C5  C6   SING N N 6  
TP8 C4  N3   SING Y N 7  
TP8 C4  CM4  SING N N 8  
TP8 N3  C2   DOUB Y N 9  
TP8 N3  C7,  SING N N 10 
TP8 C2  S1   SING Y N 11 
TP8 C6  H61  SING N N 12 
TP8 C6  H62  SING N N 13 
TP8 C6  C7   SING N N 14 
TP8 O3C PC   SING N N 15 
TP8 PC  O10  SING N N 16 
TP8 PC  O1C  DOUB N N 17 
TP8 PC  O2C  SING N N 18 
TP8 O2C H2C  SING N N 19 
TP8 O10 C10  SING N N 20 
TP8 C10 C9   SING N N 21 
TP8 C10 H101 SING N N 22 
TP8 C10 H102 SING N N 23 
TP8 C9  H9   SING N N 24 
TP8 O8  HO8  SING N N 25 
TP8 C7, H7,1 SING N N 26 
TP8 C7, H7,2 SING N N 27 
TP8 C7, C5,  SING N N 28 
TP8 C5, H5,  SING N N 29 
TP8 C5, C6,  SING N N 30 
TP8 C5, C4,  SING N N 31 
TP8 C4, N3,  SING N N 32 
TP8 C4, N4,  DOUB N N 33 
TP8 N4, H4,  SING N N 34 
TP8 N3, C2,  DOUB N N 35 
TP8 C2, N1,  SING N N 36 
TP8 C2, CM2  SING N N 37 
TP8 CM2 HM21 SING N N 38 
TP8 CM2 HM22 SING N N 39 
TP8 CM2 HM23 SING N N 40 
TP8 N1, C6,  DOUB N N 41 
TP8 C6, H6,  SING N N 42 
TP8 CM4 HM41 SING N N 43 
TP8 CM4 HM42 SING N N 44 
TP8 CM4 HM43 SING N N 45 
TP8 C7  H71  SING N N 46 
TP8 C7  H72  SING N N 47 
TP8 C7  O7   SING N N 48 
TP8 O7  PA   SING N N 49 
TP8 PA  O1A  SING N N 50 
TP8 PA  O2A  DOUB N N 51 
TP8 PA  O3A  SING N N 52 
TP8 O3A PB   SING N N 53 
TP8 PB  O2B  SING N N 54 
TP8 PB  O3B  DOUB N N 55 
TP8 PB  O1B  SING N N 56 
TP8 O1B H1B  SING N N 57 
# 
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 
TP8 InChI            InChI                1.02b 
InChI=1/C15H23N4O12P3S/c1-9-13(4-6-30-34(27,28)31-33(24,25)26)35-15(12(20)3-5-29-32(21,22)23)19(9)8-11-7-17-10(2)18-14(11)16/h3,7,11,16H,4-6,8H2,1-2H3,(H5-,20,21,22,23,24,25,26,27,28)/p-2/b12-3-,16-14+/fC15H21N4O12P3S/h20-21,24H/q-2 
TP8 InChIKey         InChI                1.02b IYJJFPCOWJABBY-ADFGLLFVDD 
TP8 SMILES_CANONICAL CACTVS               3.341 CC1=NC(=N)[C@@H](C[n+]2c(C)c(CCO[P]([O-])(=O)O[P](O)([O-])=O)sc2\C(O)=C\CO[P](O)([O-])=O)C=N1 
TP8 SMILES           CACTVS               3.341 CC1=NC(=N)[CH](C[n+]2c(C)c(CCO[P]([O-])(=O)O[P](O)([O-])=O)sc2C(O)=CCO[P](O)([O-])=O)C=N1 
TP8 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C/1\[C@H](C=NC(=N1)C)C[n+]2c(c(sc2/C(=C/CO[P@](=O)(O)[O-])/O)CCO[P@](=O)([O-])O[P@@](=O)(O)[O-])C 
TP8 SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C1C(C=NC(=N1)C)C[n+]2c(c(sc2C(=CCOP(=O)(O)[O-])O)CCOP(=O)([O-])OP(=O)(O)[O-])C 
# 
_pdbx_chem_comp_identifier.comp_id           TP8 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   1.5.0 
_pdbx_chem_comp_identifier.identifier        "[(Z)-3-hydroxy-3-[5-[2-[(hydroxy-oxido-phosphoryl)oxy-oxido-phosphoryl]oxyethyl]-3-[[(5S)-4-imino-2-methyl-5H-pyrimidin-5-yl]methyl]-4-methyl-1,3-thiazol-3-ium-2-yl]prop-2-enyl] hydrogen phosphate" 
# 
