data_PUA
# 
_chem_comp.id                                    PUA 
_chem_comp.name                                  "ADENYLATE-3'-PHOSPHATE-[[2'-DEOXY-URIDINE-5'-PHOSPHATE]-3'-PHOSPHATE]" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H27 N7 O20 P4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         U-PI-A-PI 
_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                        797.348 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     PUA 
_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        1QHC 
_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 
PUA PA     PA   P 0 1 N N S 9.177  9.853  2.100  -0.420 0.018  0.501   PA     PUA 1  
PUA O1A    O1A  O 0 1 N N N 9.684  11.138 2.755  -1.964 0.226  0.094   O1A    PUA 2  
PUA O2A    O2A  O 0 1 N N N 7.721  9.884  1.608  0.257  1.333  0.549   O2A    PUA 3  
PUA "O5'"  O5*  O 0 1 N N N 10.149 9.539  0.881  -0.336 -0.681 1.948   "O5'"  PUA 4  
PUA PB     PB   P 0 1 N N R 8.926  7.139  3.235  0.179  -0.160 -2.006  PB     PUA 5  
PUA O1B    O1B  O 0 1 N N N 8.880  6.614  1.849  -1.374 0.050  -2.371  O1B    PUA 6  
PUA O2B    O2B  O 0 1 N N N 9.764  6.440  4.235  0.848  1.156  -1.920  O2B    PUA 7  
PUA O3A    O3A  O 0 1 N N N 9.399  8.659  3.136  0.300  -0.918 -0.591  O3A    PUA 8  
PUA PG     PG   P 0 1 N N N 13.137 13.708 1.076  -3.850 1.427  5.159   PG     PUA 9  
PUA O1G    O1G  O 0 1 N N N 13.831 12.514 1.733  -5.396 1.074  5.439   O1G    PUA 10 
PUA O2G    O2G  O 0 1 N N N 14.119 14.669 0.409  -3.427 2.713  6.030   O2G    PUA 11 
PUA O3G    O3G  O 0 1 N N N 12.137 14.385 2.014  -3.665 1.724  3.720   O3G    PUA 12 
PUA N9A    N9A  N 0 1 Y N N 11.263 10.464 -3.412 1.654  -0.347 6.741   N9A    PUA 13 
PUA C4A    C4A  C 0 1 Y N N 9.995  10.007 -3.658 2.133  -0.802 7.943   C4A    PUA 14 
PUA N3A    N3A  N 0 1 Y N N 8.936  10.058 -2.818 1.666  -1.600 8.898   N3A    PUA 15 
PUA C2A    C2A  C 0 1 Y N N 7.848  9.531  -3.391 2.385  -1.856 9.970   C2A    PUA 16 
PUA N1A    N1A  N 0 1 Y N N 7.717  8.993  -4.627 3.588  -1.343 10.155  N1A    PUA 17 
PUA C6A    C6A  C 0 1 Y N N 8.806  8.959  -5.449 4.137  -0.534 9.255   C6A    PUA 18 
PUA N6A    N6A  N 0 1 N N N 8.670  8.429  -6.667 5.399  -0.001 9.458   N6A    PUA 19 
PUA C5A    C5A  C 0 1 Y N N 10.024 9.492  -4.954 3.405  -0.226 8.096   C5A    PUA 20 
PUA N7A    N7A  N 0 1 Y N N 11.295 9.621  -5.509 3.637  0.528  6.995   N7A    PUA 21 
PUA C8A    C8A  C 0 1 Y N N 11.992 10.197 -4.556 2.609  0.461  6.200   C8A    PUA 22 
PUA "C5'"  C5*  C 0 1 N N N 11.544 9.688  1.052  -0.990 0.193  2.869   "C5'"  PUA 23 
PUA "C4'"  C4*  C 0 1 N N R 12.099 10.687 0.068  -0.945 -0.416 4.272   "C4'"  PUA 24 
PUA "O4'"  O4*  O 0 1 N N N 12.147 10.133 -1.277 0.422  -0.575 4.707   "O4'"  PUA 25 
PUA "C1'"  C1*  C 0 1 N N R 11.712 11.116 -2.184 0.354  -0.671 6.147   "C1'"  PUA 26 
PUA "C2'"  C2*  C 0 1 N N R 10.649 11.881 -1.399 -0.703 0.374  6.565   "C2'"  PUA 27 
PUA "O2'"  O2*  O 0 1 N N N 10.397 13.130 -2.002 -1.490 -0.109 7.655   "O2'"  PUA 28 
PUA "C3'"  C3*  C 0 1 N N S 11.332 12.008 -0.042 -1.577 0.546  5.300   "C3'"  PUA 29 
PUA "O3'"  O3*  O 0 1 N N N 12.258 13.105 -0.163 -2.930 0.173  5.571   "O3'"  PUA 30 
PUA O5     O5   O 0 1 N N N 3.588  6.425  2.036  -2.133 -1.543 -6.508  O5     PUA 31 
PUA C5     C5   C 0 1 N N N 3.818  7.388  3.086  -1.482 -0.791 -5.481  C5     PUA 32 
PUA C4     C4   C 0 1 N N R 4.998  6.958  3.936  -0.003 -1.178 -5.425  C4     PUA 33 
PUA O4     O4   O 0 1 N N N 4.717  5.660  4.521  0.645  -0.869 -6.680  O4     PUA 34 
PUA C1     C1   C 0 1 N N R 5.678  4.699  4.100  2.055  -0.796 -6.374  C1     PUA 35 
PUA C2     C2   C 0 1 N N N 6.374  5.300  2.891  2.126  -0.067 -5.015  C2     PUA 36 
PUA C3     C3   C 0 1 N N S 6.304  6.794  3.151  0.743  -0.324 -4.377  C3     PUA 37 
PUA O3     O3   O 0 1 N N N 7.448  7.248  3.893  0.883  -1.046 -3.151  O3     PUA 38 
PUA PD     PD   P 0 1 N N N 2.961  6.862  0.596  -3.677 -1.088 -6.511  PD     PUA 39 
PUA O1D    O1D  O 0 1 N N N 1.456  6.894  0.835  -4.474 -1.900 -7.649  O1D    PUA 40 
PUA O2D    O2D  O 0 1 N N N 3.398  5.769  -0.381 -4.331 -1.399 -5.073  O2D    PUA 41 
PUA O3D    O3D  O 0 1 N N N 3.517  8.246  0.269  -3.763 0.362  -6.788  O3D    PUA 42 
PUA N1U    N1U  N 0 1 N N N 4.973  3.443  3.785  2.763  -0.030 -7.402  N1U    PUA 43 
PUA C6U    C6U  C 0 1 N N N 3.826  3.434  2.981  3.825  -0.594 -8.057  C6U    PUA 44 
PUA C2U    C2U  C 0 1 N N N 5.502  2.255  4.294  2.361  1.218  -7.698  C2U    PUA 45 
PUA O2U    O2U  O 0 1 N N N 6.474  2.217  5.009  1.416  1.700  -7.104  O2U    PUA 46 
PUA N3U    N3U  N 0 1 N N N 4.831  1.113  3.917  2.997  1.946  -8.635  N3U    PUA 47 
PUA C4U    C4U  C 0 1 N N N 3.699  1.028  3.094  4.047  1.427  -9.302  C4U    PUA 48 
PUA O4U    O4U  O 0 1 N N N 3.264  -0.087 2.775  4.620  2.083  -10.154 O4U    PUA 49 
PUA C5U    C5U  C 0 1 N N N 3.191  2.299  2.626  4.477  0.111  -9.005  C5U    PUA 50 
PUA H1A    H1A  H 0 1 N N N 10.583 11.118 3.059  -2.369 -0.651 0.075   H1A    PUA 51 
PUA H1B    H1B  H 0 1 N N N 8.342  7.062  1.207  -1.772 -0.830 -2.417  H1B    PUA 52 
PUA H1G    H1G  H 0 1 N N N 13.220 11.916 2.147  -5.912 1.849  5.179   H1G    PUA 53 
PUA H2G    H2G  H 0 1 N N N 13.687 15.410 0.000  -3.563 2.478  6.959   H2G    PUA 54 
PUA H2A    H2A  H 0 1 N N N 6.941  9.541  -2.762 1.977  -2.509 10.727  H2A    PUA 55 
PUA H6A1   1H6A H 0 0 N N N 9.483  8.403  -7.281 5.893  -0.218 10.265  H6A1   PUA 56 
PUA H6A2   2H6A H 0 0 N N N 7.905  8.900  -7.149 5.790  0.584  8.792   H6A2   PUA 57 
PUA H8A    H8A  H 0 1 N N N 13.060 10.428 -4.699 2.524  0.971  5.252   H8A    PUA 58 
PUA "H5'1" 1H5* H 0 0 N N N 11.805 9.954  2.102  -2.028 0.330  2.566   "H5'1" PUA 59 
PUA "H5'2" 2H5* H 0 0 N N N 12.074 8.709  0.990  -0.482 1.158  2.876   "H5'2" PUA 60 
PUA "H4'"  H4*  H 0 1 N N N 13.110 10.905 0.483  -1.461 -1.376 4.284   "H4'"  PUA 61 
PUA "H1'"  H1*  H 0 1 N N N 12.486 11.834 -2.539 0.040  -1.670 6.446   "H1'"  PUA 62 
PUA "H2'"  H2*  H 0 1 N N N 9.647  11.394 -1.345 -0.223 1.316  6.829   "H2'"  PUA 63 
PUA "HO2'" HO2* H 0 0 N N N 9.735  13.606 -1.513 -0.894 -0.197 8.412   "HO2'" PUA 64 
PUA "H3'"  H3*  H 0 1 N N N 10.660 12.186 0.829  -1.531 1.574  4.940   "H3'"  PUA 65 
PUA H51    1H5  H 0 1 N N N 3.946  8.420  2.685  -1.951 -1.006 -4.521  H51    PUA 66 
PUA H52    2H5  H 0 1 N N N 2.903  7.563  3.699  -1.572 0.272  -5.699  H52    PUA 67 
PUA H4     H4   H 0 1 N N N 5.132  7.767  4.690  0.102  -2.238 -5.194  H4     PUA 68 
PUA H1     H1   H 0 1 N N N 6.438  4.459  4.879  2.477  -1.798 -6.290  H1     PUA 69 
PUA H21    1H2  H 0 1 N N N 7.402  4.910  2.708  2.286  1.001  -5.163  H21    PUA 70 
PUA H22    2H2  H 0 1 N N N 5.952  4.981  1.909  2.917  -0.490 -4.395  H22    PUA 71 
PUA H3     H3   H 0 1 N N N 6.314  7.404  2.218  0.219  0.616  -4.207  H3     PUA 72 
PUA HD1    HD1  H 0 1 N N N 1.090  7.148  -0.004 -5.392 -1.599 -7.617  HD1    PUA 73 
PUA HD2    HD2  H 0 1 N N N 3.032  6.023  -1.220 -4.255 -2.353 -4.931  HD2    PUA 74 
PUA H6U    H6U  H 0 1 N N N 3.396  4.377  2.604  4.139  -1.599 -7.816  H6U    PUA 75 
PUA H3U    H3U  H 0 1 N N N 5.211  0.241  4.284  2.696  2.847  -8.833  H3U    PUA 76 
PUA H5U    H5U  H 0 1 N N N 2.300  2.405  1.984  5.317  -0.321 -9.529  H5U    PUA 77 
# 
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 
PUA PA    O1A    SING N N 1  
PUA PA    O2A    DOUB N N 2  
PUA PA    "O5'"  SING N N 3  
PUA PA    O3A    SING N N 4  
PUA O1A   H1A    SING N N 5  
PUA "O5'" "C5'"  SING N N 6  
PUA PB    O1B    SING N N 7  
PUA PB    O2B    DOUB N N 8  
PUA PB    O3A    SING N N 9  
PUA PB    O3     SING N N 10 
PUA O1B   H1B    SING N N 11 
PUA PG    O1G    SING N N 12 
PUA PG    O2G    SING N N 13 
PUA PG    O3G    DOUB N N 14 
PUA PG    "O3'"  SING N N 15 
PUA O1G   H1G    SING N N 16 
PUA O2G   H2G    SING N N 17 
PUA N9A   C4A    SING Y N 18 
PUA N9A   C8A    SING Y N 19 
PUA N9A   "C1'"  SING N N 20 
PUA C4A   N3A    SING Y N 21 
PUA C4A   C5A    DOUB Y N 22 
PUA N3A   C2A    DOUB Y N 23 
PUA C2A   N1A    SING Y N 24 
PUA C2A   H2A    SING N N 25 
PUA N1A   C6A    DOUB Y N 26 
PUA C6A   N6A    SING N N 27 
PUA C6A   C5A    SING Y N 28 
PUA N6A   H6A1   SING N N 29 
PUA N6A   H6A2   SING N N 30 
PUA C5A   N7A    SING Y N 31 
PUA N7A   C8A    DOUB Y N 32 
PUA C8A   H8A    SING N N 33 
PUA "C5'" "C4'"  SING N N 34 
PUA "C5'" "H5'1" SING N N 35 
PUA "C5'" "H5'2" SING N N 36 
PUA "C4'" "O4'"  SING N N 37 
PUA "C4'" "C3'"  SING N N 38 
PUA "C4'" "H4'"  SING N N 39 
PUA "O4'" "C1'"  SING N N 40 
PUA "C1'" "C2'"  SING N N 41 
PUA "C1'" "H1'"  SING N N 42 
PUA "C2'" "O2'"  SING N N 43 
PUA "C2'" "C3'"  SING N N 44 
PUA "C2'" "H2'"  SING N N 45 
PUA "O2'" "HO2'" SING N N 46 
PUA "C3'" "O3'"  SING N N 47 
PUA "C3'" "H3'"  SING N N 48 
PUA O5    C5     SING N N 49 
PUA O5    PD     SING N N 50 
PUA C5    C4     SING N N 51 
PUA C5    H51    SING N N 52 
PUA C5    H52    SING N N 53 
PUA C4    O4     SING N N 54 
PUA C4    C3     SING N N 55 
PUA C4    H4     SING N N 56 
PUA O4    C1     SING N N 57 
PUA C1    C2     SING N N 58 
PUA C1    N1U    SING N N 59 
PUA C1    H1     SING N N 60 
PUA C2    C3     SING N N 61 
PUA C2    H21    SING N N 62 
PUA C2    H22    SING N N 63 
PUA C3    O3     SING N N 64 
PUA C3    H3     SING N N 65 
PUA PD    O1D    SING N N 66 
PUA PD    O2D    SING N N 67 
PUA PD    O3D    DOUB N N 68 
PUA O1D   HD1    SING N N 69 
PUA O2D   HD2    SING N N 70 
PUA N1U   C6U    SING N N 71 
PUA N1U   C2U    SING N N 72 
PUA C6U   C5U    DOUB N N 73 
PUA C6U   H6U    SING N N 74 
PUA C2U   O2U    DOUB N N 75 
PUA C2U   N3U    SING N N 76 
PUA N3U   C4U    SING N N 77 
PUA N3U   H3U    SING N N 78 
PUA C4U   O4U    DOUB N N 79 
PUA C4U   C5U    SING N N 80 
PUA C5U   H5U    SING N N 81 
# 
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 
PUA SMILES           ACDLabs              10.04 O=C1C=CN(C(=O)N1)C5OC(COP(=O)(O)O)C(OP(=O)(O)OP(=O)(O)OCC4OC(n3cnc2c(ncnc23)N)C(O)C4OP(=O)(O)O)C5 
PUA InChI            InChI                1.02b 
;InChI=1/C19H27N7O20P4/c20-16-13-17(22-6-21-16)26(7-23-13)18-14(28)15(45-48(33,34)35)10(43-18)5-41-49(36,37)46-50(38,39)44-8-3-12(25-2-1-11(27)24-19(25)29)42-9(8)4-40-47(30,31)32/h1-2,6-10,12,14-15,18,28H,3-5H2,(H,36,37)(H,38,39)(H2,20,21,22)(H,24,27,29)(H2,30,31,32)(H2,33,34,35)/t8-,9+,10+,12+,14+,15+,18+/m0/s1/f/h24,30-31,33-34,36,38H,20H2
;
PUA InChIKey         InChI                1.02b JIAJERGOUFOENU-PCTGOLIFDL 
PUA SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P@@](O)(=O)O[P@@](O)(=O)O[C@H]4C[C@@H](O[C@@H]4CO[P](O)(O)=O)N5C=CC(=O)NC5=O)[C@@H](O[P](O)(O)=O)[C@H]3O 
PUA SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)O[P](O)(=O)O[CH]4C[CH](O[CH]4CO[P](O)(O)=O)N5C=CC(=O)NC5=O)[CH](O[P](O)(O)=O)[CH]3O 
PUA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@](=O)(O)O[P@](=O)(O)O[C@H]4C[C@@H](O[C@@H]4COP(=O)(O)O)N5C=CC(=O)NC5=O)OP(=O)(O)O)O)N 
PUA SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OC4CC(OC4COP(=O)(O)O)N5C=CC(=O)NC5=O)OP(=O)(O)O)O)N 
# 
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 
PUA "SYSTEMATIC NAME" ACDLabs              10.04 
"[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (2R,3S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-[(phosphonooxy)methyl]tetrahydrofuran-3-yl dihydrogen diphosphate (non-preferred name)" 
PUA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-oxolan-2-yl]methyl [[(2R,3S,5R)-5-(2,4-dioxopyrimidin-1-yl)-2-(phosphonooxymethyl)oxolan-3-yl]oxy-hydroxy-phosphoryl] hydrogen phosphate" 
# 
