data_APX
# 
_chem_comp.id                                    APX 
_chem_comp.name                                  "2'-MONOPHOSPHOADENOSINE-5'-DIPHOSPHORIBOSE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C15 H29 N5 O17 P3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     1999-09-29 
_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                        644.335 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     APX 
_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        1QMG 
_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 
APX PM   PM   P 0 1 N N R 11.240 3.297  72.727 -4.228  -0.903 0.040  PM   APX 1  
APX O6M  O6M  O 0 1 N N N 10.293 2.153  72.608 -3.774  -0.493 1.388  O6M  APX 2  
APX O7M  O7M  O 0 1 N N N 11.880 3.508  74.049 -4.890  -2.369 0.120  O7M  APX 3  
APX O3N  O3N  O 0 1 N N N 10.538 4.662  72.366 -2.970  -0.936 -0.963 O3N  APX 4  
APX O5M  O5M  O 0 1 N N N 12.393 3.160  71.603 -5.320  0.149  -0.502 O5M  APX 5  
APX C5M  C5M  C 0 1 N N N 13.574 3.990  71.575 -6.351  0.220  0.485  C5M  APX 6  
APX C4M  C4M  C 0 1 N N R 14.554 3.399  70.576 -7.426  1.208  0.029  C4M  APX 7  
APX O4M  O4M  O 0 1 N N N 14.886 2.065  71.038 -8.100  0.696  -1.132 O4M  APX 8  
APX C3M  C3M  C 0 1 N N S 13.962 3.247  69.179 -8.482  1.381  1.137  C3M  APX 9  
APX O3M  O3M  O 0 1 N N N 15.018 3.526  68.252 -8.548  2.743  1.566  O3M  APX 10 
APX C2M  C2M  C 0 1 N N R 13.468 1.791  69.175 -9.812  0.961  0.458  C2M  APX 11 
APX O2M  O2M  O 0 1 N N N 13.334 1.224  67.852 -10.877 1.834  0.841  O2M  APX 12 
APX C1M  C1M  C 0 1 N N R 14.533 1.128  70.017 -9.476  1.127  -1.046 C1M  APX 13 
APX O1N  O1N  O 0 1 N N N 14.102 -0.051 70.629 -10.315 0.294  -1.848 O1N  APX 14 
APX PA   PA   P 0 1 N N S 9.051  4.966  71.974 -1.772  -1.677 -0.183 PA   APX 15 
APX O6B  O6B  O 0 1 N N N 8.866  4.440  70.606 -1.760  -1.240 1.231  O6B  APX 16 
APX O7B  O7B  O 0 1 N N N 8.168  4.399  73.018 -1.992  -3.270 -0.251 O7B  APX 17 
APX O5B  O5B  O 0 1 N N N 9.041  6.543  71.932 -0.367  -1.299 -0.874 O5B  APX 18 
APX C5B  C5B  C 0 1 N N N 8.527  7.340  73.002 0.659   -1.886 -0.071 C5B  APX 19 
APX C4B  C4B  C 0 1 N N R 9.625  8.313  73.427 2.027   -1.563 -0.676 C4B  APX 20 
APX O4B  O4B  O 0 1 N N N 9.888  9.167  72.297 2.293   -0.146 -0.589 O4B  APX 21 
APX C3B  C3B  C 0 1 N N R 9.119  9.213  74.554 3.152   -2.227 0.149  C3B  APX 22 
APX O3B  O3B  O 0 1 N N N 10.118 9.448  75.537 3.568   -3.448 -0.466 O3B  APX 23 
APX C2B  C2B  C 0 1 N N R 8.724  10.493 73.856 4.298   -1.189 0.125  C2B  APX 24 
APX O2B  O2B  O 0 1 N N N 8.761  11.668 74.707 5.459   -1.739 -0.502 O2B  APX 25 
APX C1B  C1B  C 0 1 N N R 9.776  10.525 72.755 3.727   -0.020 -0.708 C1B  APX 26 
APX N9A  N9A  N 0 1 Y N N 9.387  11.386 71.632 4.173   1.263  -0.159 N9A  APX 27 
APX C4A  C4A  C 0 1 Y N N 10.019 12.514 71.319 5.332   1.909  -0.456 C4A  APX 28 
APX N3A  N3A  N 1 1 N N N 11.095 13.155 71.833 6.363   1.534  -1.320 N3A  APX 29 
APX C2A  C2A  C 0 1 N N N 11.496 14.315 71.285 7.562   2.318  -0.984 C2A  APX 30 
APX N1A  N1A  N 0 1 N N N 10.846 14.897 70.260 7.259   3.754  -1.011 N1A  APX 31 
APX C6A  C6A  C 0 1 N N R 9.751  14.312 69.722 6.469   4.054  0.197  C6A  APX 32 
APX C5A  C5A  C 0 1 Y N N 9.295  13.075 70.262 5.341   3.054  0.266  C5A  APX 33 
APX N7A  N7A  N 0 1 Y N N 8.286  12.254 69.984 4.220   3.100  0.984  N7A  APX 34 
APX C8A  C8A  C 0 1 Y N N 8.345  11.220 70.822 3.510   2.029  0.737  C8A  APX 35 
APX N6A  N6A  N 0 1 N N N 9.110  14.884 68.700 5.923   5.415  0.111  N6A  APX 36 
APX P2   P2   P 0 1 N N N 7.813  11.850 75.868 6.650   -1.665 0.578  P2   APX 37 
APX OP1  OP1  O 0 1 N N N 6.474  11.446 75.549 6.800   -0.272 1.054  OP1  APX 38 
APX OP2  OP2  O 0 1 N N N 7.804  13.242 76.139 6.305   -2.624 1.825  OP2  APX 39 
APX OP3  OP3  O 0 1 N N N 8.363  11.088 76.966 8.025   -2.149 -0.106 OP3  APX 40 
APX HC2A HC2A H 0 0 N N N 12.561 14.192 70.980 7.907   2.042  0.012  HC2A APX 41 
APX HOM7 7HOM H 0 0 N N N 12.483 4.237  74.124 -5.171  -2.598 -0.777 HOM7 APX 42 
APX H5M2 2H5M H 0 0 N N N 13.340 5.059  71.364 -5.926  0.556  1.431  H5M2 APX 43 
APX H5M1 1H5M H 0 0 N N N 14.024 4.128  72.585 -6.796  -0.766 0.617  H5M1 APX 44 
APX H4M  H4M  H 0 1 N N N 15.430 4.085  70.510 -6.970  2.171  -0.202 H4M  APX 45 
APX H3M  H3M  H 0 1 N N N 13.123 3.927  68.901 -8.261  0.727  1.980  H3M  APX 46 
APX H3O1 1H3O H 0 0 N N N 14.649 3.431  67.381 -9.265  2.798  2.213  H3O1 APX 47 
APX H2M  H2M  H 0 1 N N N 12.432 1.662  69.569 -10.059 -0.075 0.690  H2M  APX 48 
APX H2O1 1H2O H 0 0 N N N 13.028 0.324  67.849 -11.649 1.579  0.317  H2O1 APX 49 
APX H1M  H1M  H 0 1 N N N 15.386 0.850  69.355 -9.570  2.170  -1.348 H1M  APX 50 
APX H1N  H1N  H 0 1 N N N 13.867 -0.673 69.950 -10.012 0.388  -2.761 H1N  APX 51 
APX HOB7 7HOB H 0 0 N N N 7.266  4.583  72.780 -1.993  -3.513 -1.187 HOB7 APX 52 
APX H5B2 2H5B H 0 0 N N N 7.572  7.852  72.740 0.604   -1.483 0.940  H5B2 APX 53 
APX H5B1 1H5B H 0 0 N N N 8.138  6.728  73.849 0.521   -2.967 -0.040 H5B1 APX 54 
APX H4B  H4B  H 0 1 N N N 10.525 7.747  73.764 2.070   -1.894 -1.713 H4B  APX 55 
APX H3B  H3B  H 0 1 N N N 8.272  8.748  75.110 2.820   -2.409 1.171  H3B  APX 56 
APX H3O2 2H3O H 0 0 N N N 9.803  10.007 76.237 2.798   -4.032 -0.478 H3O2 APX 57 
APX H2B  H2B  H 0 1 N N N 7.666  10.511 73.503 4.533   -0.857 1.136  H2B  APX 58 
APX H1B  H1B  H 0 1 N N N 10.733 10.938 73.148 4.031   -0.113 -1.750 H1B  APX 59 
APX H3A  H3A  H 0 1 N N N 10.941 13.302 72.831 6.091   1.721  -2.273 H3A  APX 60 
APX HN3A HN3A H 0 0 N N N 11.885 12.509 71.844 6.560   0.550  -1.211 HN3A APX 61 
APX H2A  H2A  H 0 1 N N N 11.570 15.066 72.106 8.348   2.102  -1.707 H2A  APX 62 
APX H1A  H1A  H 0 1 N N N 11.517 15.068 69.511 8.138   4.238  -0.910 H1A  APX 63 
APX HC6A HC6A H 0 0 N N N 9.126  14.825 68.955 7.099   3.964  1.082  HC6A APX 64 
APX H8A  H8A  H 0 1 N N N 7.646  10.366 70.841 2.551   1.796  1.177  H8A  APX 65 
APX H6A2 2H6A H 0 0 N N N 8.284  14.443 68.294 5.438   5.478  -0.771 H6A2 APX 66 
APX H6A1 1H6A H 0 0 N N N 9.783  15.049 67.952 6.713   6.041  0.052  H6A1 APX 67 
APX HOP2 2HOP H 0 0 N N N 7.207  13.356 76.869 6.216   -3.520 1.472  HOP2 APX 68 
APX HOP3 3HOP H 0 0 N N N 7.766  11.202 77.696 8.711   -2.090 0.573  HOP3 APX 69 
# 
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 
APX PM  O6M  DOUB N N 1  
APX PM  O7M  SING N N 2  
APX PM  O3N  SING N N 3  
APX PM  O5M  SING N N 4  
APX O7M HOM7 SING N N 5  
APX O3N PA   SING N N 6  
APX O5M C5M  SING N N 7  
APX C5M C4M  SING N N 8  
APX C5M H5M2 SING N N 9  
APX C5M H5M1 SING N N 10 
APX C4M O4M  SING N N 11 
APX C4M C3M  SING N N 12 
APX C4M H4M  SING N N 13 
APX O4M C1M  SING N N 14 
APX C3M O3M  SING N N 15 
APX C3M C2M  SING N N 16 
APX C3M H3M  SING N N 17 
APX O3M H3O1 SING N N 18 
APX C2M O2M  SING N N 19 
APX C2M C1M  SING N N 20 
APX C2M H2M  SING N N 21 
APX O2M H2O1 SING N N 22 
APX C1M O1N  SING N N 23 
APX C1M H1M  SING N N 24 
APX O1N H1N  SING N N 25 
APX PA  O6B  DOUB N N 26 
APX PA  O7B  SING N N 27 
APX PA  O5B  SING N N 28 
APX O7B HOB7 SING N N 29 
APX O5B C5B  SING N N 30 
APX C5B C4B  SING N N 31 
APX C5B H5B2 SING N N 32 
APX C5B H5B1 SING N N 33 
APX C4B O4B  SING N N 34 
APX C4B C3B  SING N N 35 
APX C4B H4B  SING N N 36 
APX O4B C1B  SING N N 37 
APX C3B O3B  SING N N 38 
APX C3B C2B  SING N N 39 
APX C3B H3B  SING N N 40 
APX O3B H3O2 SING N N 41 
APX C2B O2B  SING N N 42 
APX C2B C1B  SING N N 43 
APX C2B H2B  SING N N 44 
APX O2B P2   SING N N 45 
APX C1B N9A  SING N N 46 
APX C1B H1B  SING N N 47 
APX N9A C4A  SING Y N 48 
APX N9A C8A  SING Y N 49 
APX C4A N3A  SING N N 50 
APX C4A C5A  DOUB Y N 51 
APX N3A C2A  SING N N 52 
APX N3A H3A  SING N N 53 
APX N3A HN3A SING N N 54 
APX C2A N1A  SING N N 55 
APX C2A HC2A SING N N 56 
APX C2A H2A  SING N N 57 
APX N1A C6A  SING N N 58 
APX N1A H1A  SING N N 59 
APX C6A C5A  SING N N 60 
APX C6A N6A  SING N N 61 
APX C6A HC6A SING N N 62 
APX C5A N7A  SING Y N 63 
APX N7A C8A  DOUB Y N 64 
APX C8A H8A  SING N N 65 
APX N6A H6A2 SING N N 66 
APX N6A H6A1 SING N N 67 
APX P2  OP1  DOUB N N 68 
APX P2  OP2  SING N N 69 
APX P2  OP3  SING N N 70 
APX OP2 HOP2 SING N N 71 
APX OP3 HOP3 SING N N 72 
# 
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 
APX SMILES           ACDLabs              10.04 O=P(O)(O)OC3C(O)C(OC3n1c2c(nc1)C(N)NC[NH2+]2)COP(=O)(O)OP(=O)(O)OCC4OC(O)C(O)C4O 
APX InChI            InChI                1.02b 
;InChI=1/C15H28N5O17P3/c16-12-7-13(18-3-17-12)20(4-19-7)14-11(36-38(25,26)27)9(22)6(34-14)2-33-40(30,31)37-39(28,29)32-1-5-8(21)10(23)15(24)35-5/h4-6,8-12,14-15,17-18,21-24H,1-3,16H2,(H,28,29)(H,30,31)(H2,25,26,27)/p+1/t5-,6-,8-,9-,10-,11-,12-,14-,15-/m1/s1/fC15H29N5O17P3/h18,25-26,28,30H/q+1
;
APX InChIKey         InChI                1.02b QHNQLFGTVLWISK-IALONEHGDU 
APX SMILES_CANONICAL CACTVS               3.341 N[C@@H]1NC[NH2+]c2n(cnc12)[C@@H]3O[C@H](CO[P@@](O)(=O)O[P@@](O)(=O)OC[C@H]4O[C@@H](O)[C@H](O)[C@@H]4O)[C@@H](O)[C@H]3O[P](O)(O)=O 
APX SMILES           CACTVS               3.341 N[CH]1NC[NH2+]c2n(cnc12)[CH]3O[CH](CO[P](O)(=O)O[P](O)(=O)OC[CH]4O[CH](O)[CH](O)[CH]4O)[CH](O)[CH]3O[P](O)(O)=O 
APX SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc2c(n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@](=O)(O)O[P@](=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)O)O)O)O)OP(=O)(O)O)[NH2+]CNC2N 
APX SMILES           "OpenEye OEToolkits" 1.5.0 c1nc2c(n1C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OCC4C(C(C(O4)O)O)O)O)OP(=O)(O)O)[NH2+]CNC2N 
# 
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 
APX "SYSTEMATIC NAME" ACDLabs              10.04 
;(6R)-6-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-({[(S)-hydroxy{[(R)-hydroxy{[(2R,3S,4R,5R)-3,4,5-trihydroxytetrahydrofuran-2-yl]methoxy}phosphoryl]oxy}phosphoryl]oxy}methyl)-3-(phosphonooxy)tetrahydrofuran-2-yl]-2,3,6,9-tetrahydro-1H-purin-3-ium (non-preferred name)
;
APX "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[[(2R,3R,4R,5R)-5-(6-amino-2,6-dihydro-1H-purin-3-ium-9-yl)-3-hydroxy-4-phosphonooxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl] [(2R,3S,4R,5R)-3,4,5-trihydroxyoxolan-2-yl]methyl hydrogen phosphate" 
# 
