data_TAP
# 
_chem_comp.id                                    TAP 
_chem_comp.name                                  "7-THIONICOTINAMIDE-ADENINE-DINUCLEOTIDE PHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H28 N7 O16 P3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         TATP 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        759.471 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TAP 
_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        1DR3 
_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 
TAP PA   AP   P 0  1 N N R 21.945 5.238  17.955 -0.318  -1.061 0.687  PA   TAP 1  
TAP O1A  AO1  O 0  1 N N N 21.158 3.995  18.042 0.196   -0.446 1.931  O1A  TAP 2  
TAP O2A  AO2  O 0  1 N N N 21.275 6.284  17.084 -1.026  -2.465 1.036  O2A  TAP 3  
TAP O5B  AO5* O 0  1 N N N 22.304 5.950  19.398 -1.391  -0.074 0.004  O5B  TAP 4  
TAP C5B  AC5* C 0  1 N N N 22.730 5.102  20.500 -2.384  0.205  0.993  C5B  TAP 5  
TAP C4B  AC4* C 0  1 N N R 22.253 5.575  21.834 -3.439  1.144  0.405  C4B  TAP 6  
TAP O4B  AO4* O 0  1 N N N 21.094 5.688  21.888 -4.171  0.469  -0.632 O4B  TAP 7  
TAP C3B  AC3* C 0  1 N N R 22.732 4.602  22.968 -4.450  1.545  1.497  C3B  TAP 8  
TAP O3B  AO3* O 0  1 N N N 24.074 5.165  23.392 -4.454  2.962  1.688  O3B  TAP 9  
TAP C2B  AC2* C 0  1 N N R 21.647 5.034  24.004 -5.816  1.069  0.938  C2B  TAP 10 
TAP O2B  AO2* O 0  1 N N N 21.889 6.357  24.443 -6.837  2.036  1.196  O2B  TAP 11 
TAP C1B  AC1* C 0  1 N N R 20.467 5.166  23.088 -5.527  0.963  -0.581 C1B  TAP 12 
TAP N9A  AN9  N 0  1 Y N N 19.823 3.874  22.807 -6.445  0.017  -1.220 N9A  TAP 13 
TAP C8A  AC8  C 0  1 Y N N 20.058 3.149  21.695 -6.237  -1.320 -1.389 C8A  TAP 14 
TAP N7A  AN7  N 0  1 Y N N 19.305 2.064  21.686 -7.257  -1.856 -1.993 N7A  TAP 15 
TAP C5A  AC5  C 0  1 Y N N 18.632 2.165  22.969 -8.182  -0.900 -2.250 C5A  TAP 16 
TAP C6A  AC6  C 0  1 Y N N 17.552 1.327  23.712 -9.446  -0.887 -2.863 C6A  TAP 17 
TAP N6A  AN6  N 0  1 N N N 17.054 0.166  23.223 -10.000 -2.051 -3.367 N6A  TAP 18 
TAP N1A  AN1  N 0  1 Y N N 17.086 1.770  24.889 -10.098 0.268  -2.947 N1A  TAP 19 
TAP C2A  AC2  C 0  1 Y N N 17.617 2.941  25.292 -9.578  1.383  -2.468 C2A  TAP 20 
TAP N3A  AN3  N 0  1 Y N N 18.498 3.772  24.742 -8.397  1.419  -1.887 N3A  TAP 21 
TAP C4A  AC4  C 0  1 Y N N 18.983 3.292  23.574 -7.674  0.312  -1.752 C4A  TAP 22 
TAP O3   O3   O 0  1 N N N 23.370 5.059  17.360 0.903   -1.315 -0.331 O3   TAP 23 
TAP PN   NP   P 0  1 N N N 24.125 4.263  16.206 2.101   -1.959 0.530  PN   TAP 24 
TAP O1N  NO1  O 0  1 N N N 23.751 2.874  16.038 1.835   -3.467 0.734  O1N  TAP 25 
TAP O2N  NO2  O -1 1 N N N 25.531 4.439  16.333 2.181   -1.260 1.905  O2N  TAP 26 
TAP O5D  NO5* O 0  1 N N N 23.545 5.028  14.881 3.493   -1.761 -0.255 O5D  TAP 27 
TAP C5D  NC5* C 0  1 N N N 23.820 6.412  14.547 4.525   -2.244 0.607  C5D  TAP 28 
TAP C4D  NC4* C 0  1 N N R 24.819 6.273  13.363 5.881   -2.083 -0.082 C4D  TAP 29 
TAP O4D  NO4* O 0  1 N N N 24.093 5.429  12.422 6.199   -0.684 -0.247 O4D  TAP 30 
TAP C3D  NC3* C 0  1 N N S 25.070 7.632  12.548 7.011   -2.642 0.811  C3D  TAP 31 
TAP O3D  NO3* O 0  1 N N N 26.242 7.424  11.692 7.363   -3.966 0.404  O3D  TAP 32 
TAP C2D  NC2* C 0  1 N N R 23.773 7.684  11.719 8.191   -1.670 0.578  C2D  TAP 33 
TAP O2D  NO2* O 0  1 N N N 24.064 8.449  10.523 9.309   -2.364 0.021  O2D  TAP 34 
TAP C1D  NC1* C 0  1 N N R 23.544 6.254  11.363 7.632   -0.638 -0.427 C1D  TAP 35 
TAP N1N  NN1  N 1  1 Y N N 22.142 5.960  10.863 8.141   0.701  -0.120 N1N  TAP 36 
TAP C2N  NC2  C 0  1 Y N N 21.839 5.528  9.564  9.125   1.192  -0.844 C2N  TAP 37 
TAP C3N  NC3  C 0  1 Y N N 20.589 5.240  9.187  9.638   2.462  -0.575 C3N  TAP 38 
TAP C7N  NC7  C 0  1 N N N 20.361 4.762  7.824  10.744  3.012  -1.384 C7N  TAP 39 
TAP S7N  NS7  S 0  1 N N N 18.859 4.848  7.255  11.971  1.973  -1.973 S7N  TAP 40 
TAP N7N  NN7  N 0  1 N N N 21.276 4.213  7.046  10.789  4.330  -1.658 N7N  TAP 41 
TAP C4N  NC4  C 0  1 Y N N 19.369 5.306  10.151 9.082   3.209  0.471  C4N  TAP 42 
TAP C5N  NC5  C 0  1 Y N N 19.857 5.718  11.528 8.047   2.649  1.198  C5N  TAP 43 
TAP C6N  NC6  C 0  1 Y N N 21.115 5.990  11.804 7.598   1.381  0.872  C6N  TAP 44 
TAP P2B  AP2* P 0  1 N N N 22.621 6.612  25.840 -8.043  1.257  1.924  P2B  TAP 45 
TAP O1X  AOP1 O 0  1 N N N 22.359 8.049  26.228 -7.526  0.560  3.124  O1X  TAP 46 
TAP O2X  AOP2 O 0  1 N N N 21.873 5.644  26.711 -9.176  2.313  2.363  O2X  TAP 47 
TAP O3X  AOP3 O 0  1 N N N 24.057 6.246  25.653 -8.677  0.180  0.909  O3X  TAP 48 
TAP HOA2 2HOA H 0  0 N N N 21.782 7.085  17.027 -1.347  -2.831 0.200  HOA2 TAP 49 
TAP H51A AH51 H 0  0 N N N 22.425 4.043  20.324 -2.858  -0.725 1.304  H51A TAP 50 
TAP H52A AH52 H 0  0 N N N 23.838 4.978  20.497 -1.914  0.680  1.854  H52A TAP 51 
TAP H4B  AH4* H 0  1 N N N 22.698 6.586  21.983 -2.959  2.034  -0.001 H4B  TAP 52 
TAP H3B  AH3* H 0  1 N N N 22.831 3.507  22.777 -4.222  1.036  2.433  H3B  TAP 53 
TAP HO3A AHO3 H 0  0 N N N 24.364 4.575  24.078 -3.583  3.199  2.035  HO3A TAP 54 
TAP H2B  AH2* H 0  1 N N N 21.574 4.352  24.883 -6.090  0.098  1.351  H2B  TAP 55 
TAP H1B  AH1* H 0  1 N N N 19.652 5.798  23.512 -5.596  1.942  -1.055 H1B  TAP 56 
TAP H8A  AH8  H 0  1 N N N 20.773 3.409  20.896 -5.356  -1.855 -1.068 H8A  TAP 57 
TAP H61A AH61 H 0  0 N N N 16.346 -0.383 23.710 -9.515  -2.888 -3.300 H61A TAP 58 
TAP H62A AH62 H 0  0 N N N 17.844 -0.451 23.037 -10.874 -2.029 -3.788 H62A TAP 59 
TAP H2A  AH2  H 0  1 N N N 17.256 3.291  26.273 -10.141 2.300  -2.558 H2A  TAP 60 
TAP H51N NH51 H 0  0 N N N 22.918 7.032  14.332 4.352   -3.297 0.827  H51N TAP 61 
TAP H52N NH52 H 0  0 N N N 24.180 7.038  15.396 4.520   -1.673 1.535  H52N TAP 62 
TAP H4D  NH4* H 0  1 N N N 25.800 5.916  13.754 5.877   -2.588 -1.049 H4D  TAP 63 
TAP H3D  NH3* H 0  1 N N N 25.262 8.555  13.141 6.709   -2.634 1.858  H3D  TAP 64 
TAP HO3N NHO3 H 0  0 N N N 26.390 8.228  11.209 8.070   -4.261 0.994  HO3N TAP 65 
TAP H2D  NH2* H 0  1 N N N 22.897 8.141  12.236 8.473   -1.180 1.510  H2D  TAP 66 
TAP HO2N NHO2 H 0  0 N N N 23.264 8.481  10.011 9.573   -3.033 0.668  HO2N TAP 67 
TAP H1D  NH1* H 0  1 N N N 24.107 5.971  10.443 7.896   -0.919 -1.446 H1D  TAP 68 
TAP H2N  NH2  H 0  1 N N N 22.624 5.408  8.799  9.543   0.605  -1.648 H2N  TAP 69 
TAP H71N NH71 H 0  0 N N N 22.228 4.158  7.406  11.515  4.691  -2.189 H71N TAP 70 
TAP H72N NH72 H 0  0 N N N 21.117 3.879  6.095  10.091  4.918  -1.327 H72N TAP 71 
TAP H4N  NH4  H 0  1 N N N 18.317 5.092  9.896  9.452   4.196  0.705  H4N  TAP 72 
TAP H5N  NH5  H 0  1 N N N 19.228 5.832  12.427 7.594   3.195  2.012  H5N  TAP 73 
TAP H6N  NH6  H 0  1 N N N 21.314 6.251  12.856 6.791   0.941  1.438  H6N  TAP 74 
TAP HOP2 2HOP H 0  0 N N N 22.308 5.795  27.541 -9.878  1.807  2.795  HOP2 TAP 75 
TAP HOP3 3HOP H 0  0 N N N 24.492 6.397  26.483 -9.000  0.675  0.144  HOP3 TAP 76 
# 
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 
TAP PA  O1A  DOUB N N 1  
TAP PA  O2A  SING N N 2  
TAP PA  O5B  SING N N 3  
TAP PA  O3   SING N N 4  
TAP O2A HOA2 SING N N 5  
TAP O5B C5B  SING N N 6  
TAP C5B C4B  SING N N 7  
TAP C5B H51A SING N N 8  
TAP C5B H52A SING N N 9  
TAP C4B O4B  SING N N 10 
TAP C4B C3B  SING N N 11 
TAP C4B H4B  SING N N 12 
TAP O4B C1B  SING N N 13 
TAP C3B O3B  SING N N 14 
TAP C3B C2B  SING N N 15 
TAP C3B H3B  SING N N 16 
TAP O3B HO3A SING N N 17 
TAP C2B O2B  SING N N 18 
TAP C2B C1B  SING N N 19 
TAP C2B H2B  SING N N 20 
TAP O2B P2B  SING N N 21 
TAP C1B N9A  SING N N 22 
TAP C1B H1B  SING N N 23 
TAP N9A C8A  SING Y N 24 
TAP N9A C4A  SING Y N 25 
TAP C8A N7A  DOUB Y N 26 
TAP C8A H8A  SING N N 27 
TAP N7A C5A  SING Y N 28 
TAP C5A C6A  SING Y N 29 
TAP C5A C4A  DOUB Y N 30 
TAP C6A N6A  SING N N 31 
TAP C6A N1A  DOUB Y N 32 
TAP N6A H61A SING N N 33 
TAP N6A H62A SING N N 34 
TAP N1A C2A  SING Y N 35 
TAP C2A N3A  DOUB Y N 36 
TAP C2A H2A  SING N N 37 
TAP N3A C4A  SING Y N 38 
TAP O3  PN   SING N N 39 
TAP PN  O1N  DOUB N N 40 
TAP PN  O2N  SING N N 41 
TAP PN  O5D  SING N N 42 
TAP O5D C5D  SING N N 43 
TAP C5D C4D  SING N N 44 
TAP C5D H51N SING N N 45 
TAP C5D H52N SING N N 46 
TAP C4D O4D  SING N N 47 
TAP C4D C3D  SING N N 48 
TAP C4D H4D  SING N N 49 
TAP O4D C1D  SING N N 50 
TAP C3D O3D  SING N N 51 
TAP C3D C2D  SING N N 52 
TAP C3D H3D  SING N N 53 
TAP O3D HO3N SING N N 54 
TAP C2D O2D  SING N N 55 
TAP C2D C1D  SING N N 56 
TAP C2D H2D  SING N N 57 
TAP O2D HO2N SING N N 58 
TAP C1D N1N  SING N N 59 
TAP C1D H1D  SING N N 60 
TAP N1N C2N  SING Y N 61 
TAP N1N C6N  DOUB Y N 62 
TAP C2N C3N  DOUB Y N 63 
TAP C2N H2N  SING N N 64 
TAP C3N C7N  SING N N 65 
TAP C3N C4N  SING Y N 66 
TAP C7N S7N  DOUB N N 67 
TAP C7N N7N  SING N N 68 
TAP N7N H71N SING N N 69 
TAP N7N H72N SING N N 70 
TAP C4N C5N  DOUB Y N 71 
TAP C4N H4N  SING N N 72 
TAP C5N C6N  SING Y N 73 
TAP C5N H5N  SING N N 74 
TAP C6N H6N  SING N N 75 
TAP P2B O1X  DOUB N N 76 
TAP P2B O2X  SING N N 77 
TAP P2B O3X  SING N N 78 
TAP O2X HOP2 SING N N 79 
TAP O3X HOP3 SING N N 80 
# 
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 
TAP InChI            InChI                1.02b 
;InChI=1/C21H28N7O16P3S/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(43-45(32,33)34)14(30)11(42-21)6-40-47(37,38)44-46(35,36)39-5-10-13(29)15(31)20(41-10)27-3-1-2-9(4-27)18(23)48/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,48)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1/f/h32-33,37H,22-23H2
;
TAP InChIKey         InChI                1.02b OJNFDOAQUXJWED-SVCSVJLVDG 
TAP SMILES_CANONICAL CACTVS               3.341 NC(=S)c1ccc[n+](c1)[C@@H]2O[C@H](CO[P]([O-])(=O)O[P@@](O)(=O)OC[C@H]3O[C@H]([C@H](O[P](O)(O)=O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@@H](O)[C@H]2O 
TAP SMILES           CACTVS               3.341 NC(=S)c1ccc[n+](c1)[CH]2O[CH](CO[P]([O-])(=O)O[P](O)(=O)OC[CH]3O[CH]([CH](O[P](O)(O)=O)[CH]3O)n4cnc5c(N)ncnc45)[CH](O)[CH]2O 
TAP SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(c[n+](c1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO[P@@](=O)([O-])O[P@](=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)n4cnc5c4ncnc5N)OP(=O)(O)O)O)O)O)C(=S)N 
TAP SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(c[n+](c1)C2C(C(C(O2)COP(=O)([O-])OP(=O)(O)OCC3C(C(C(O3)n4cnc5c4ncnc5N)OP(=O)(O)O)O)O)O)C(=S)N 
# 
_pdbx_chem_comp_identifier.comp_id           TAP 
_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        "[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl] [(2R,3S,4R,5R)-5-(3-carbamothioylpyridin-1-ium-1-yl)-3,4-dihydroxy-oxolan-2-yl]methyl phosphate" 
# 
