data_8PA
# 
_chem_comp.id                                    8PA 
_chem_comp.name                                  3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[(S)-hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-[(1S,2E)-1-hydroxy-3-pyridin-3-ylprop-2-en-1-yl]-4-methyl-1,3-thiazol-3-ium 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H26 N5 O8 P2 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     2008-11-07 
_chem_comp.pdbx_modified_date                    2008-12-05 
_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                        558.462 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     8PA 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_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                  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 
8PA C1I  C1I  C 0 1 Y N N 64.675 57.924 157.606 -5.340 -4.445 1.086  C1  8PA 1  
8PA C1G  C1G  C 0 1 Y N N 64.255 59.261 157.505 -5.338 -5.821 1.230  C2  8PA 2  
8PA C1H  C1H  C 0 1 Y N N 64.666 60.205 158.464 -4.418 -6.574 0.522  C3  8PA 3  
8PA N1K  N1K  N 0 1 Y N N 65.448 59.854 159.507 -3.547 -6.002 -0.286 N1  8PA 4  
8PA C1J  C1J  C 0 1 Y N N 65.848 58.585 159.635 -3.511 -4.696 -0.456 C4  8PA 5  
8PA C1N  C1N  C 0 1 Y N N 65.464 57.605 158.719 -4.404 -3.866 0.222  C5  8PA 6  
8PA C1F  C1F  C 0 1 N N N 66.036 56.346 159.002 -4.367 -2.402 0.026  C6  8PA 7  
8PA C1E  C1E  C 0 1 N N N 65.473 55.130 158.942 -3.475 -1.866 -0.796 C7  8PA 8  
8PA C1M  C1M  C 0 1 N N S 66.201 53.945 159.220 -3.515 -0.388 -1.090 C8  8PA 9  
8PA O1D  O1D  O 0 1 N N N 66.076 52.962 158.243 -3.826 -0.186 -2.470 O1  8PA 10 
8PA C1Q  C1Q  C 0 1 Y N N 66.786 53.502 160.554 -2.171 0.221  -0.783 C9  8PA 11 
8PA S1   S1   S 0 1 Y N N 66.321 54.378 162.022 -0.778 0.064  -1.763 S1  8PA 12 
8PA C5   C5   C 0 1 Y N N 66.814 53.011 163.004 0.143  1.046  -0.626 C10 8PA 13 
8PA C6   C6   C 0 1 N N N 66.625 53.053 164.505 1.595  1.425  -0.756 C11 8PA 14 
8PA C7   C7   C 0 1 N N N 67.625 53.948 165.283 2.462  0.363  -0.076 C12 8PA 15 
8PA O7   O7   O 0 1 N N N 67.259 53.777 166.700 3.840  0.723  -0.200 O2  8PA 16 
8PA P1A  P1A  P 0 1 N N S 67.830 54.765 167.756 5.037  -0.170 0.402  P1  8PA 17 
8PA O2A  O2A  O 0 1 N N N 67.642 54.091 169.104 4.932  -0.194 2.009  O3  8PA 18 
8PA O1A  O1A  O 0 1 N N N 69.192 55.270 167.418 4.933  -1.551 -0.120 O4  8PA 19 
8PA O3A  O3A  O 0 1 N N N 66.908 56.019 167.689 6.451  0.464  -0.034 O5  8PA 20 
8PA P1B  P1B  P 0 1 N N N 65.249 56.191 167.851 7.952  -0.111 -0.129 P2  8PA 21 
8PA O2B  O2B  O 0 1 N N N 64.685 55.837 166.476 7.931  -1.442 -0.775 O6  8PA 22 
8PA O1B  O1B  O 0 1 N N N 64.793 55.232 168.946 8.857  0.896  -1.001 O7  8PA 23 
8PA O3B  O3B  O 0 1 N N N 65.054 57.627 168.199 8.571  -0.243 1.352  O8  8PA 24 
8PA C4   C4   C 0 1 Y N N 67.334 51.998 162.208 -0.675 1.395  0.372  C13 8PA 25 
8PA C4M  C4M  C 0 1 N N N 67.904 50.688 162.784 -0.226 2.244  1.534  C14 8PA 26 
8PA N3   N3   N 1 1 Y N N 67.305 52.269 160.889 -1.906 0.942  0.254  N2  8PA 27 
8PA C7S  C7S  C 0 1 N N N 67.873 51.305 159.931 -2.930 1.239  1.259  C15 8PA 28 
8PA C5S  C5S  C 0 1 Y N N 69.386 51.431 159.720 -3.724 2.444  0.825  C16 8PA 29 
8PA C6S  C6S  C 0 1 Y N N 70.128 50.290 159.912 -3.113 3.670  0.652  C17 8PA 30 
8PA N1S  N1S  N 0 1 Y N N 71.471 50.240 159.685 -3.843 4.709  0.270  N3  8PA 31 
8PA C2S  C2S  C 0 1 Y N N 72.076 51.384 159.333 -5.137 4.586  0.055  C18 8PA 32 
8PA C2M  C2M  C 0 1 N N N 73.595 51.350 159.049 -5.926 5.795  -0.378 C19 8PA 33 
8PA N3S  N3S  N 0 1 Y N N 71.406 52.504 159.087 -5.761 3.436  0.207  N4  8PA 34 
8PA C4S  C4S  C 0 1 Y N N 70.086 52.556 159.276 -5.096 2.348  0.583  C20 8PA 35 
8PA N4S  N4S  N 0 1 N N N 69.483 53.690 158.996 -5.756 1.140  0.743  N5  8PA 36 
8PA H1I  H1I  H 0 1 N N N 64.405 57.184 156.867 -6.050 -3.833 1.624  H1  8PA 37 
8PA H1G  H1G  H 0 1 N N N 63.615 59.565 156.690 -6.045 -6.302 1.889  H2  8PA 38 
8PA H1H  H1H  H 0 1 N N N 64.349 61.233 158.364 -4.414 -7.648 0.633  H3  8PA 39 
8PA H1J  H1J  H 0 1 N N N 66.482 58.312 160.466 -2.783 -4.264 -1.127 H4  8PA 40 
8PA H1F  H1F  H 0 1 N N N 67.071 56.364 159.310 -5.066 -1.769 0.552  H5  8PA 41 
8PA H1E  H1E  H 0 1 N N N 64.430 55.051 158.673 -2.721 -2.488 -1.255 H6  8PA 42 
8PA H6   H6   H 0 1 N N N 65.614 53.441 164.700 1.861  1.489  -1.811 H7  8PA 43 
8PA H6A  H6A  H 0 1 N N N 66.795 52.026 164.862 1.763  2.391  -0.280 H8  8PA 44 
8PA H7   H7   H 0 1 N N N 68.663 53.631 165.102 2.197  0.299  0.979  H9  8PA 45 
8PA H7A  H7A  H 0 1 N N N 67.571 55.000 164.966 2.295  -0.603 -0.553 H10 8PA 46 
8PA HO2A HO2A H 0 0 N N N 67.603 53.149 168.985 4.993  0.678  2.420  H11 8PA 47 
8PA HO1B HO1B H 0 0 N N N 64.698 54.359 168.584 9.777  0.612  -1.100 H12 8PA 48 
8PA HO3B HO3B H 0 0 N N N 65.013 57.722 169.143 8.615  0.594  1.836  H13 8PA 49 
8PA H4M  H4M  H 0 1 N N N 68.040 49.958 161.972 -0.307 3.297  1.267  H14 8PA 50 
8PA H4MA H4MA H 0 0 N N N 68.874 50.889 163.262 -0.858 2.039  2.398  H15 8PA 51 
8PA H4MB H4MB H 0 0 N N N 67.205 50.281 163.529 0.810  2.009  1.777  H16 8PA 52 
8PA H7S  H7S  H 0 1 N N N 67.670 50.293 160.312 -3.596 0.383  1.363  H17 8PA 53 
8PA H7SA H7SA H 0 0 N N N 67.401 51.512 158.959 -2.450 1.445  2.216  H18 8PA 54 
8PA H6S  H6S  H 0 1 N N N 69.627 49.397 160.256 -2.053 3.782  0.826  H19 8PA 55 
8PA H2M  H2M  H 0 1 N N N 73.765 51.342 157.962 -5.930 5.856  -1.467 H20 8PA 56 
8PA H2MA H2MA H 0 0 N N N 74.070 52.240 159.488 -6.950 5.711  -0.015 H21 8PA 57 
8PA H2MB H2MB H 0 0 N N N 74.031 50.444 159.495 -5.467 6.695  0.033  H22 8PA 58 
8PA HN4S HN4S H 0 0 N N N 69.330 54.204 159.840 -6.677 1.048  0.454  H23 8PA 59 
8PA HN4A HN4A H 0 0 N N N 70.056 54.228 158.378 -5.296 0.385  1.143  H24 8PA 60 
8PA H25  H25  H 0 1 N N N 67.083 54.597 159.308 -4.278 0.085  -0.473 H25 8PA 61 
8PA H26  H26  H 0 1 N N N 66.048 53.369 157.385 -3.187 -0.581 -3.079 H26 8PA 62 
# 
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 
8PA C1I C1N  SING Y N 1  
8PA C1I H1I  SING N N 2  
8PA C1G C1I  DOUB Y N 3  
8PA C1G C1H  SING Y N 4  
8PA C1G H1G  SING N N 5  
8PA C1H N1K  DOUB Y N 6  
8PA C1H H1H  SING N N 7  
8PA N1K C1J  SING Y N 8  
8PA C1J H1J  SING N N 9  
8PA C1N C1J  DOUB Y N 10 
8PA C1N C1F  SING N N 11 
8PA C1F H1F  SING N N 12 
8PA C1E C1F  DOUB N E 13 
8PA C1E C1M  SING N N 14 
8PA C1E H1E  SING N N 15 
8PA C1M C1Q  SING N N 16 
8PA O1D C1M  SING N N 17 
8PA C1Q N3   DOUB N N 18 
8PA C1Q S1   SING N N 19 
8PA S1  C5   SING Y N 20 
8PA C5  C6   SING Y N 21 
8PA C6  C7   SING Y N 22 
8PA C6  H6   SING N N 23 
8PA C6  H6A  SING N N 24 
8PA C7  O7   SING N N 25 
8PA C7  H7   SING N N 26 
8PA C7  H7A  SING N N 27 
8PA O7  P1A  SING N N 28 
8PA P1A O2A  SING N N 29 
8PA O2A HO2A SING N N 30 
8PA O1A P1A  DOUB N N 31 
8PA O3A P1A  SING N N 32 
8PA O3A P1B  SING N N 33 
8PA P1B O3B  SING N N 34 
8PA P1B O1B  SING N N 35 
8PA O2B P1B  DOUB N N 36 
8PA O1B HO1B SING N N 37 
8PA O3B HO3B SING N N 38 
8PA C4  C5   DOUB N N 39 
8PA C4  C4M  SING N N 40 
8PA C4M H4M  SING Y N 41 
8PA C4M H4MA SING N N 42 
8PA C4M H4MB SING N N 43 
8PA N3  C4   SING N N 44 
8PA C7S N3   SING N N 45 
8PA C7S H7S  SING Y N 46 
8PA C7S H7SA SING N N 47 
8PA C5S C7S  SING N N 48 
8PA C5S C6S  SING N N 49 
8PA C6S H6S  SING N N 50 
8PA N1S C6S  DOUB Y N 51 
8PA C2S N1S  SING N N 52 
8PA C2M C2S  SING Y N 53 
8PA C2M H2M  SING Y N 54 
8PA C2M H2MA SING N N 55 
8PA C2M H2MB SING N N 56 
8PA N3S C2S  DOUB N N 57 
8PA N3S C4S  SING N N 58 
8PA C4S C5S  DOUB Y N 59 
8PA N4S C4S  SING Y N 60 
8PA N4S HN4S SING Y N 61 
8PA N4S HN4A SING N N 62 
8PA C1M H25  SING N N 63 
8PA O1D H26  SING N N 64 
# 
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 
8PA SMILES           ACDLabs              10.04 O=P(O)(O)OP(=O)(O)OCCc1sc([n+](c1C)Cc2cnc(nc2N)C)C(O)\C=C\c3cccnc3 
8PA InChI            InChI                1.02b 
InChI=1/C20H25N5O8P2S/c1-13-18(7-9-32-35(30,31)33-34(27,28)29)36-20(17(26)6-5-15-4-3-8-22-10-15)25(13)12-16-11-23-14(2)24-19(16)21/h3-6,8,10-11,17,26H,7,9,12H2,1-2H3,(H4-,21,23,24,27,28,29,30,31)/p+1/b6-5+/t17-/m0/s1/fC20H26N5O8P2S/h27-28,30H,21H2/q+1 
8PA InChIKey         InChI                1.02b HUCLASQGRJZNFE-XJXITZPUDL 
8PA SMILES_CANONICAL CACTVS               3.341 Cc1ncc(C[n+]2c(C)c(CCO[P@@](O)(=O)O[P](O)(O)=O)sc2[C@@H](O)\C=C\c3cccnc3)c(N)n1 
8PA SMILES           CACTVS               3.341 Cc1ncc(C[n+]2c(C)c(CCO[P](O)(=O)O[P](O)(O)=O)sc2[CH](O)C=Cc3cccnc3)c(N)n1 
8PA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c(sc([n+]1Cc2cnc(nc2N)C)[C@H](\C=C\c3cccnc3)O)CCO[P@](=O)(O)OP(=O)(O)O 
8PA SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c(sc([n+]1Cc2cnc(nc2N)C)C(C=Cc3cccnc3)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 
8PA "SYSTEMATIC NAME" ACDLabs              10.04 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[(S)-hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-[(1S,2E)-1-hydroxy-3-pyridin-3-ylprop-2-en-1-yl]-4-methyl-1,3-thiazol-3-ium 
8PA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-2-[(E,1S)-1-hydroxy-3-pyridin-3-yl-prop-2-enyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate"            
# 
