data_PYI
# 
_chem_comp.id                                    PYI 
_chem_comp.name                                  1-[(4-AMINO-2-METHYLPYRIMIDIN-5-YL)METHYL]-3-(2-{[HYDROXY(PHOSPHONOOXY)PHOSPHORYL]OXY}ETHYL)-2-METHYLPYRIDINIUM 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H21 N4 O7 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "PYRITHIAMIN PYROPHOSPHATE" 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     2005-11-17 
_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                        419.287 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     PYI 
_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        2F17 
_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 
PYI CM2  CM2  C 0 1 N N N 6.847 69.455 25.418 7.607  2.557  1.324  CM2  PYI 1  
PYI C2A  C2A  C 0 1 Y N N 6.831 69.863 23.969 6.561  1.803  0.544  C2A  PYI 2  
PYI N1A  N1A  N 0 1 Y N N 7.958 69.791 23.262 5.415  2.394  0.272  N1A  PYI 3  
PYI C6A  C6A  C 0 1 Y N N 7.996 70.145 21.964 4.468  1.766  -0.411 C6A  PYI 4  
PYI C5A  C5A  C 0 1 Y N N 6.830 70.601 21.334 4.693  0.473  -0.841 C5A  PYI 5  
PYI C7A  C7A  C 0 1 N N N 6.862 71.008 19.868 3.643  -0.276 -1.621 C7A  PYI 6  
PYI N3   N3   N 1 1 Y N N 6.222 70.048 18.906 2.846  -1.096 -0.705 N3   PYI 7  
PYI C2   C2   C 0 1 Y N N 5.941 68.776 19.293 3.171  -2.363 -0.531 C2   PYI 8  
PYI C1   C1   C 0 1 Y N N 5.356 67.853 18.430 2.443  -3.167 0.325  C1   PYI 9  
PYI C6   C6   C 0 1 Y N N 5.055 68.250 17.125 1.362  -2.627 1.005  C6   PYI 10 
PYI C5   C5   C 0 1 Y N N 5.341 69.567 16.706 1.051  -1.292 0.796  C5   PYI 11 
PYI CM6  CM6  C 0 1 N N N 5.013 69.959 15.286 -0.114 -0.659 1.511  CM6  PYI 12 
PYI CM7  CM7  C 0 1 N N N 6.208 69.575 14.405 -1.351 -0.706 0.612  CM7  PYI 13 
PYI OM7  OM7  O 0 1 N N N 5.794 68.604 13.443 -2.456 -0.105 1.290  OM7  PYI 14 
PYI PA   PA   P 0 1 N N R 6.337 69.077 11.999 -3.716 -0.189 0.292  PA   PYI 15 
PYI O1A  O1A  O 0 1 N N N 6.229 67.879 11.047 -4.109 -1.732 0.051  O1A  PYI 16 
PYI O2A  O2A  O 0 1 N N N 5.452 70.231 11.458 -3.363 0.437  -1.002 O2A  PYI 17 
PYI O3A  O3A  O 0 1 N N N 7.914 69.496 12.155 -4.968 0.588  0.941  O3A  PYI 18 
PYI PB   PB   P 0 1 N N N 8.353 70.714 11.179 -6.039 0.814  -0.240 PB   PYI 19 
PYI O1B  O1B  O 0 1 N N N 9.823 70.456 10.717 -6.876 -0.542 -0.472 O1B  PYI 20 
PYI O2B  O2B  O 0 1 N N N 7.444 70.792 9.907  -7.045 2.003  0.167  O2B  PYI 21 
PYI O3B  O3B  O 0 1 N N N 8.300 72.081 11.952 -5.328 1.175  -1.488 O3B  PYI 22 
PYI C4   C4   C 0 1 Y N N 5.938 70.477 17.636 1.828  -0.548 -0.072 C4   PYI 23 
PYI CM4  CM4  C 0 1 N N N 6.262 71.915 17.212 1.500  0.904  -0.306 CM4  PYI 24 
PYI C4A  C4A  C 0 1 Y N N 5.644 70.667 22.116 5.918  -0.124 -0.536 C4A  PYI 25 
PYI N4A  N4A  N 0 1 N N N 4.457 71.108 21.556 6.191  -1.419 -0.945 N4A  PYI 26 
PYI N3A  N3A  N 0 1 Y N N 5.692 70.292 23.414 6.820  0.573  0.149  N3A  PYI 27 
PYI HM21 1HM2 H 0 0 N N N 7.638 70.037 25.945 7.465  2.379  2.390  HM21 PYI 28 
PYI HM22 2HM2 H 0 0 N N N 5.904 69.515 26.010 8.598  2.215  1.027  HM22 PYI 29 
PYI HM23 3HM2 H 0 0 N N N 7.252 68.419 25.494 7.514  3.624  1.119  HM23 PYI 30 
PYI H6A  H6A  H 0 1 N N N 8.958 70.064 21.430 3.533  2.259  -0.629 H6A  PYI 31 
PYI H7A1 1H7A H 0 0 N N N 7.912 71.215 19.555 2.992  0.436  -2.130 H7A1 PYI 32 
PYI H7A2 2H7A H 0 0 N N N 6.414 72.022 19.746 4.125  -0.918 -2.358 H7A2 PYI 33 
PYI H2   H2   H 0 1 N N N 6.193 68.487 20.327 4.014  -2.776 -1.064 H2   PYI 34 
PYI H1   H1   H 0 1 N N N 5.136 66.828 18.773 2.713  -4.204 0.464  H1   PYI 35 
PYI H6   H6   H 0 1 N N N 4.594 67.528 16.430 0.775  -3.232 1.680  H6   PYI 36 
PYI HM61 1HM6 H 0 0 N N N 4.731 71.033 15.188 -0.314 -1.204 2.434  HM61 PYI 37 
PYI HM62 2HM6 H 0 0 N N N 4.053 69.521 14.927 0.124  0.379  1.747  HM62 PYI 38 
PYI HM71 1HM7 H 0 0 N N N 7.081 69.229 15.006 -1.151 -0.160 -0.310 HM71 PYI 39 
PYI HM72 2HM7 H 0 0 N N N 6.685 70.464 13.930 -1.589 -1.743 0.376  HM72 PYI 40 
PYI H2A  H2A  H 0 1 N N N 5.772 70.510 10.608 ?      ?      ?      H2A  PYI 41 
PYI H2B  H2B  H 0 1 N N N 7.701 71.506 9.335  -7.668 2.105  -0.565 H2B  PYI 42 
PYI H3B  H3B  H 0 1 N N N 8.557 72.795 11.380 ?      ?      ?      H3B  PYI 43 
PYI HM41 1HM4 H 0 0 N N N 7.343 72.104 17.412 2.111  1.525  0.350  HM41 PYI 44 
PYI HM42 2HM4 H 0 0 N N N 6.031 72.264 16.179 1.708  1.161  -1.345 HM42 PYI 45 
PYI HM43 3HM4 H 0 0 N N N 5.775 72.611 17.934 0.446  1.078  -0.093 HM43 PYI 46 
PYI H4A1 1H4A H 0 0 N N N 4.264 70.542 20.729 5.530  -1.919 -1.448 H4A1 PYI 47 
PYI H4A2 2H4A H 0 0 N N N 3.606 71.155 22.117 7.045  -1.826 -0.729 H4A2 PYI 48 
# 
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 
PYI CM2 C2A  SING N N 1  
PYI CM2 HM21 SING N N 2  
PYI CM2 HM22 SING N N 3  
PYI CM2 HM23 SING N N 4  
PYI C2A N1A  DOUB Y N 5  
PYI C2A N3A  SING Y N 6  
PYI N1A C6A  SING Y N 7  
PYI C6A C5A  DOUB Y N 8  
PYI C6A H6A  SING N N 9  
PYI C5A C7A  SING N N 10 
PYI C5A C4A  SING Y N 11 
PYI C7A N3   SING N N 12 
PYI C7A H7A1 SING N N 13 
PYI C7A H7A2 SING N N 14 
PYI N3  C2   DOUB Y N 15 
PYI N3  C4   SING Y N 16 
PYI C2  C1   SING Y N 17 
PYI C2  H2   SING N N 18 
PYI C1  C6   DOUB Y N 19 
PYI C1  H1   SING N N 20 
PYI C6  C5   SING Y N 21 
PYI C6  H6   SING N N 22 
PYI C5  CM6  SING N N 23 
PYI C5  C4   DOUB Y N 24 
PYI CM6 CM7  SING N N 25 
PYI CM6 HM61 SING N N 26 
PYI CM6 HM62 SING N N 27 
PYI CM7 OM7  SING N N 28 
PYI CM7 HM71 SING N N 29 
PYI CM7 HM72 SING N N 30 
PYI OM7 PA   SING N N 31 
PYI PA  O1A  DOUB N N 32 
PYI PA  O2A  SING N N 33 
PYI PA  O3A  SING N N 34 
PYI O2A H2A  SING N N 35 
PYI O3A PB   SING N N 36 
PYI PB  O1B  DOUB N N 37 
PYI PB  O2B  SING N N 38 
PYI PB  O3B  SING N N 39 
PYI O2B H2B  SING N N 40 
PYI O3B H3B  SING N N 41 
PYI C4  CM4  SING N N 42 
PYI CM4 HM41 SING N N 43 
PYI CM4 HM42 SING N N 44 
PYI CM4 HM43 SING N N 45 
PYI C4A N4A  SING N N 46 
PYI C4A N3A  DOUB Y N 47 
PYI N4A H4A1 SING N N 48 
PYI N4A H4A2 SING N N 49 
# 
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 
PYI SMILES           ACDLabs              10.04 O=P(O)(O)OP(=O)(O)OCCc1ccc[n+](c1C)Cc2cnc(nc2N)C                                                                                                                                                
PYI InChI            InChI                1.02b InChI=1/C14H20N4O7P2/c1-10-12(5-7-24-27(22,23)25-26(19,20)21)4-3-6-18(10)9-13-8-16-11(2)17-14(13)15/h3-4,6,8H,5,7,9H2,1-2H3,(H4-,15,16,17,19,20,21,22,23)/p+1/fC14H21N4O7P2/h19-20,22H,15H2/q+1 
PYI InChIKey         InChI                1.02b ZHKSTKOYQKNDSJ-PLSYZFMQCX                                                                                                                                                                       
PYI SMILES_CANONICAL CACTVS               3.341 Cc1ncc(C[n+]2cccc(CCO[P@](O)(=O)O[P](O)(O)=O)c2C)c(N)n1                                                                                                                                         
PYI SMILES           CACTVS               3.341 Cc1ncc(C[n+]2cccc(CCO[P](O)(=O)O[P](O)(O)=O)c2C)c(N)n1                                                                                                                                          
PYI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c(ccc[n+]1Cc2cnc(nc2N)C)CCO[P@@](=O)(O)OP(=O)(O)O                                                                                                                                            
PYI SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c(ccc[n+]1Cc2cnc(nc2N)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 
PYI "SYSTEMATIC NAME" ACDLabs              10.04 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]-3-(2-{[(R)-hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-methylpyridinium 
PYI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[1-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-2-methyl-pyridin-1-ium-3-yl]ethyl phosphono hydrogen phosphate"     
# 
