data_ARX
# 
_chem_comp.id                                    ARX 
_chem_comp.name                                  (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-(6-{[(1R)-4-carbamimidamido-1-{[(1R)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}butyl]amino}-6-oxohexyl)-3,4-dihydroxytetrahydrofuran-2-carboxamide 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C28 H47 N15 O7" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-01-30 
_chem_comp.pdbx_modified_date                    2009-01-30 
_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                        705.769 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     ARX 
_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        3BWJ 
_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 
ARX C5     C5   C 0 1 Y N N 25.013 24.841 8.020  -12.048 -1.114 -0.803 C5     ARX 1  
ARX O77    O77  O 0 1 N N N 35.406 21.360 13.500 9.266   1.363  -2.690 O77    ARX 2  
ARX C75    C75  C 0 1 N N N 36.322 21.996 12.965 9.690   0.228  -2.709 C75    ARX 3  
ARX N76    N76  N 0 1 N N N 37.473 22.224 13.637 10.694  -0.103 -3.546 N76    ARX 4  
ARX C32    C32  C 0 1 N N R 36.113 22.514 11.527 9.096   -0.815 -1.798 C32    ARX 5  
ARX C78    C78  C 0 1 N N N 36.707 23.910 11.219 10.183  -1.363 -0.872 C78    ARX 6  
ARX C79    C79  C 0 1 N N N 38.228 23.925 11.012 9.610   -2.507 -0.033 C79    ARX 7  
ARX C85    C85  C 0 1 N N N 38.789 25.325 10.768 10.698  -3.056 0.892  C85    ARX 8  
ARX N77    N77  N 0 1 N N N 40.001 25.304 9.965  10.149  -4.151 1.696  N77    ARX 9  
ARX C86    C86  C 0 1 N N N 40.269 26.209 9.007  10.947  -4.803 2.606  C86    ARX 10 
ARX N94    N94  N 0 1 N N N 40.551 25.820 7.754  12.192  -4.447 2.754  N94    ARX 11 
ARX N93    N93  N 0 1 N N N 40.277 27.444 9.282  10.432  -5.831 3.359  N93    ARX 12 
ARX N31    N31  N 0 1 N N N 36.350 21.533 10.437 8.030   -0.210 -0.994 N31    ARX 13 
ARX C30    C30  C 0 1 N N N 37.390 20.716 10.189 6.781   -0.119 -1.492 C30    ARX 14 
ARX O35    O35  O 0 1 N N N 38.571 21.028 10.321 6.539   -0.536 -2.604 O35    ARX 15 
ARX C29    C29  C 0 1 N N R 37.035 19.332 9.692  5.685   0.503  -0.666 C29    ARX 16 
ARX C37    C37  C 0 1 N N N 36.803 18.372 10.875 6.056   1.949  -0.331 C37    ARX 17 
ARX C38    C38  C 0 1 N N N 38.034 18.083 11.741 5.005   2.541  0.610  C38    ARX 18 
ARX C39    C39  C 0 1 N N N 38.024 18.842 13.085 5.377   3.987  0.945  C39    ARX 19 
ARX N40    N40  N 0 1 N N N 37.400 18.134 14.202 4.370   4.554  1.847  N40    ARX 20 
ARX C41    C41  C 0 1 N N N 36.153 18.392 14.626 4.494   5.850  2.287  C41    ARX 21 
ARX N42    N42  N 0 1 N N N 35.153 18.026 13.931 5.506   6.575  1.903  N42    ARX 22 
ARX N43    N43  N 0 1 N N N 35.959 19.023 15.793 3.549   6.382  3.133  N43    ARX 23 
ARX N27    N27  N 0 1 N N N 35.827 19.374 8.872  4.431   0.484  -1.424 N27    ARX 24 
ARX C26    C26  C 0 1 N N N 35.764 19.764 7.601  3.250   0.501  -0.774 C26    ARX 25 
ARX O28    O28  O 0 1 N N N 36.726 20.106 6.922  3.225   0.532  0.438  O28    ARX 26 
ARX C25    C25  C 0 1 N N N 34.401 19.765 6.955  1.961   0.482  -1.554 C25    ARX 27 
ARX C24    C24  C 0 1 N N N 34.094 21.160 6.405  0.778   0.507  -0.584 C24    ARX 28 
ARX C23    C23  C 0 1 N N N 33.571 22.092 7.487  -0.531  0.487  -1.376 C23    ARX 29 
ARX C22    C22  C 0 1 N N N 32.440 21.435 8.283  -1.714  0.512  -0.406 C22    ARX 30 
ARX C21    C21  C 0 1 N N N 32.231 22.029 9.672  -3.023  0.492  -1.198 C21    ARX 31 
ARX N20    N20  N 0 1 N N N 31.846 23.418 9.594  -4.156  0.516  -0.269 N20    ARX 32 
ARX "C5'"  C5*  C 0 1 N N N 30.539 23.715 9.538  -5.417  0.504  -0.744 "C5'"  ARX 33 
ARX "O5'"  O5*  O 0 1 N N N 29.663 22.845 9.492  -5.615  0.474  -1.940 "O5'"  ARX 34 
ARX "C4'"  C4*  C 0 1 N N S 30.197 25.185 9.559  -6.583  0.528  0.211  "C4'"  ARX 35 
ARX "O4'"  O4*  O 0 1 N N N 29.484 25.521 8.344  -7.830  0.519  -0.517 "O4'"  ARX 36 
ARX "C1'"  C1*  C 0 1 N N R 28.328 26.321 8.635  -8.818  0.051  0.427  "C1'"  ARX 37 
ARX "C2'"  C2*  C 0 1 N N R 28.391 26.648 10.103 -8.115  -1.084 1.204  "C2'"  ARX 38 
ARX "O2'"  O2*  O 0 1 N N N 29.007 27.910 10.137 -8.501  -1.063 2.579  "O2'"  ARX 39 
ARX "C3'"  C3*  C 0 1 N N S 29.282 25.603 10.742 -6.611  -0.763 1.059  "C3'"  ARX 40 
ARX "O3'"  O3*  O 0 1 N N N 29.964 26.152 11.903 -6.022  -0.534 2.340  "O3'"  ARX 41 
ARX N9     N9   N 0 1 Y N N 27.096 25.519 8.428  -9.993  -0.466 -0.279 N9     ARX 42 
ARX C4     C4   C 0 1 Y N N 25.884 26.006 8.128  -11.264 -0.568 0.227  C4     ARX 43 
ARX N7     N7   N 0 1 Y N N 25.780 23.763 8.272  -11.231 -1.313 -1.865 N7     ARX 44 
ARX C8     C8   C 0 1 Y N N 27.027 24.186 8.513  -10.024 -0.933 -1.559 C8     ARX 45 
ARX N3     N3   N 0 1 Y N N 25.355 27.237 7.945  -11.837 -0.278 1.390  N3     ARX 46 
ARX C2     C2   C 0 1 Y N N 24.043 27.381 7.662  -13.121 -0.498 1.579  C2     ARX 47 
ARX N1     N1   N 0 1 Y N N 23.171 26.369 7.556  -13.898 -1.009 0.642  N1     ARX 48 
ARX C6     C6   C 0 1 Y N N 23.581 25.069 7.713  -13.413 -1.334 -0.552 C6     ARX 49 
ARX N6     N6   N 0 1 N N N 22.743 23.995 7.609  -14.235 -1.869 -1.529 N6     ARX 50 
ARX HN76   HN76 H 0 0 N N N 37.407 21.809 14.544 11.077  0.568  -4.133 HN76   ARX 51 
ARX HN7A   HN7A H 0 0 N N N 38.262 22.726 13.284 11.034  -1.011 -3.562 HN7A   ARX 52 
ARX H32    H32  H 0 1 N N N 35.023 22.666 11.528 8.683   -1.628 -2.395 H32    ARX 53 
ARX H78    H78  H 0 1 N N N 36.238 24.279 10.295 11.017  -1.733 -1.469 H78    ARX 54 
ARX H78A   H78A H 0 0 N N N 36.502 24.540 12.097 10.533  -0.569 -0.212 H78A   ARX 55 
ARX H79    H79  H 0 1 N N N 38.703 23.517 11.916 8.777   -2.138 0.564  H79    ARX 56 
ARX H79A   H79A H 0 0 N N N 38.444 23.324 10.117 9.260   -3.301 -0.693 H79A   ARX 57 
ARX H85    H85  H 0 1 N N N 38.029 25.918 10.238 11.531  -3.425 0.295  H85    ARX 58 
ARX H85A   H85A H 0 0 N N N 39.040 25.763 11.745 11.048  -2.262 1.552  H85A   ARX 59 
ARX HN77   HN77 H 0 0 N N N 40.669 24.580 10.134 9.222   -4.417 1.585  HN77   ARX 60 
ARX HN94   HN94 H 0 0 N N N 40.724 26.615 7.172  12.755  -4.907 3.396  HN94   ARX 61 
ARX HN93   HN93 H 0 0 N N N 40.058 27.588 10.247 9.505   -6.096 3.249  HN93   ARX 62 
ARX HN9A   HN9A H 0 0 N N N 40.474 28.173 8.627  10.995  -6.291 4.001  HN9A   ARX 63 
ARX HN31   HN31 H 0 0 N N N 35.607 21.469 9.771  8.224   0.124  -0.105 HN31   ARX 64 
ARX H29    H29  H 0 1 N N N 37.878 18.968 9.086  5.560   -0.063 0.257  H29    ARX 65 
ARX H37    H37  H 0 1 N N N 36.040 18.826 11.525 7.032   1.970  0.155  H37    ARX 66 
ARX H37A   H37A H 0 0 N N N 36.507 17.409 10.434 6.094   2.537  -1.248 H37A   ARX 67 
ARX H38    H38  H 0 1 N N N 38.059 17.004 11.955 4.029   2.520  0.125  H38    ARX 68 
ARX H38A   H38A H 0 0 N N N 38.918 18.420 11.179 4.967   1.954  1.528  H38A   ARX 69 
ARX H39    H39  H 0 1 N N N 39.070 19.040 13.361 6.352   4.008  1.431  H39    ARX 70 
ARX H39A   H39A H 0 0 N N N 37.420 19.747 12.921 5.415   4.574  0.028  H39A   ARX 71 
ARX HN40   HN40 H 0 0 N N N 37.926 17.425 14.671 3.616   4.014  2.132  HN40   ARX 72 
ARX HN42   HN42 H 0 0 N N N 34.291 18.284 14.368 5.594   7.490  2.214  HN42   ARX 73 
ARX HN43   HN43 H 0 0 N N N 36.828 19.247 16.235 2.795   5.842  3.418  HN43   ARX 74 
ARX HN4A   HN4A H 0 0 N N N 35.060 19.242 16.173 3.636   7.297  3.443  HN4A   ARX 75 
ARX HN27   HN27 H 0 0 N N N 34.973 19.084 9.303  4.451   0.460  -2.393 HN27   ARX 76 
ARX H25    H25  H 0 1 N N N 34.386 19.036 6.132  1.916   1.355  -2.204 H25    ARX 77 
ARX H25A   H25A H 0 0 N N N 33.642 19.492 7.703  1.916   -0.424 -2.159 H25A   ARX 78 
ARX H24    H24  H 0 1 N N N 35.019 21.586 5.989  0.822   -0.367 0.066  H24    ARX 79 
ARX H24A   H24A H 0 0 N N N 33.317 21.061 5.633  0.823   1.412  0.021  H24A   ARX 80 
ARX H23    H23  H 0 1 N N N 34.394 22.338 8.174  -0.576  1.361  -2.026 H23    ARX 81 
ARX H23A   H23A H 0 0 N N N 33.179 23.000 7.006  -0.576  -0.419 -1.981 H23A   ARX 82 
ARX H22    H22  H 0 1 N N N 31.507 21.563 7.715  -1.670  -0.362 0.244  H22    ARX 83 
ARX H22A   H22A H 0 0 N N N 32.719 20.380 8.424  -1.669  1.417  0.199  H22A   ARX 84 
ARX H21    H21  H 0 1 N N N 31.436 21.467 10.184 -3.068  1.366  -1.848 H21    ARX 85 
ARX H21A   H21A H 0 0 N N N 33.178 21.960 10.227 -3.068  -0.414 -1.803 H21A   ARX 86 
ARX HN20   HN20 H 0 0 N N N 32.537 24.141 9.582  -3.998  0.540  0.688  HN20   ARX 87 
ARX "H4'"  H4*  H 0 1 N N N 31.156 25.715 9.661  -6.525  1.405  0.857  "H4'"  ARX 88 
ARX "H1'"  H1*  H 0 1 N N N 28.311 27.214 7.993  -9.105  0.854  1.106  "H1'"  ARX 89 
ARX "H2'"  H2*  H 0 1 N N N 27.422 26.657 10.624 -8.346  -2.052 0.758  "H2'"  ARX 90 
ARX "HO2'" HO2* H 0 0 N N N 29.146 28.171 11.040 -8.089  -1.756 3.114  "HO2'" ARX 91 
ARX "H3'"  H3*  H 0 1 N N N 28.767 24.728 11.164 -6.096  -1.572 0.540  "H3'"  ARX 92 
ARX "HO3'" HO3* H 0 0 N N N 30.885 26.272 11.703 -5.092  -0.269 2.304  "HO3'" ARX 93 
ARX H8     H8   H 0 1 N N N 27.861 23.541 8.744  -9.173  -0.981 -2.222 H8     ARX 94 
ARX H2     H2   H 0 1 N N N 23.670 28.383 7.510  -13.556 -0.251 2.537  H2     ARX 95 
ARX HN6    HN6  H 0 1 N N N 22.538 23.823 6.645  -15.177 -2.011 -1.345 HN6    ARX 96 
ARX HN6A   HN6A H 0 0 N N N 23.184 23.189 8.005  -13.870 -2.102 -2.396 HN6A   ARX 97 
# 
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 
ARX C6    C5     DOUB Y N 1  
ARX C5    C4     SING Y N 2  
ARX C5    N7     SING N N 3  
ARX C75   O77    DOUB N N 4  
ARX C32   C75    SING N N 5  
ARX C75   N76    SING N N 6  
ARX N76   HN76   SING N N 7  
ARX N76   HN7A   SING N N 8  
ARX N31   C32    SING N N 9  
ARX C78   C32    SING N N 10 
ARX C32   H32    SING N N 11 
ARX C79   C78    SING N N 12 
ARX C78   H78    SING N N 13 
ARX C78   H78A   SING N N 14 
ARX C85   C79    SING N N 15 
ARX C79   H79    SING N N 16 
ARX C79   H79A   SING N N 17 
ARX N77   C85    SING N N 18 
ARX C85   H85    SING N N 19 
ARX C85   H85A   SING N N 20 
ARX C86   N77    SING N N 21 
ARX N77   HN77   SING N N 22 
ARX N94   C86    DOUB N N 23 
ARX C86   N93    SING N N 24 
ARX N94   HN94   SING N N 25 
ARX N93   HN93   SING N N 26 
ARX N93   HN9A   SING N N 27 
ARX C30   N31    SING N N 28 
ARX N31   HN31   SING N N 29 
ARX C29   C30    SING N N 30 
ARX C30   O35    DOUB N N 31 
ARX N27   C29    SING N N 32 
ARX C29   C37    SING N N 33 
ARX C29   H29    SING N N 34 
ARX C37   C38    SING N N 35 
ARX C37   H37    SING N N 36 
ARX C37   H37A   SING N N 37 
ARX C38   C39    SING N N 38 
ARX C38   H38    SING N N 39 
ARX C38   H38A   SING N N 40 
ARX C39   N40    SING N N 41 
ARX C39   H39    SING N N 42 
ARX C39   H39A   SING N N 43 
ARX N40   C41    SING N N 44 
ARX N40   HN40   SING N N 45 
ARX N42   C41    DOUB N N 46 
ARX C41   N43    SING N N 47 
ARX N42   HN42   SING N N 48 
ARX N43   HN43   SING N N 49 
ARX N43   HN4A   SING N N 50 
ARX C26   N27    SING N N 51 
ARX N27   HN27   SING N N 52 
ARX O28   C26    DOUB N N 53 
ARX C25   C26    SING N N 54 
ARX C24   C25    SING N N 55 
ARX C25   H25    SING N N 56 
ARX C25   H25A   SING N N 57 
ARX C24   C23    SING N N 58 
ARX C24   H24    SING N N 59 
ARX C24   H24A   SING N N 60 
ARX C23   C22    SING N N 61 
ARX C23   H23    SING N N 62 
ARX C23   H23A   SING N N 63 
ARX C22   C21    SING N N 64 
ARX C22   H22    SING N N 65 
ARX C22   H22A   SING N N 66 
ARX N20   C21    SING N N 67 
ARX C21   H21    SING N N 68 
ARX C21   H21A   SING N N 69 
ARX "C5'" N20    SING N N 70 
ARX N20   HN20   SING N N 71 
ARX "O5'" "C5'"  DOUB N N 72 
ARX "C5'" "C4'"  SING N N 73 
ARX "O4'" "C4'"  SING N N 74 
ARX "C4'" "C3'"  SING N N 75 
ARX "C4'" "H4'"  SING N N 76 
ARX "O4'" "C1'"  SING N N 77 
ARX N9    "C1'"  SING N N 78 
ARX "C1'" "C2'"  SING N N 79 
ARX "C1'" "H1'"  SING N N 80 
ARX "C2'" "O2'"  SING N N 81 
ARX "C2'" "C3'"  SING N N 82 
ARX "C2'" "H2'"  SING N N 83 
ARX "O2'" "HO2'" SING N N 84 
ARX "C3'" "O3'"  SING N N 85 
ARX "C3'" "H3'"  SING N N 86 
ARX "O3'" "HO3'" SING Y N 87 
ARX C4    N9     SING Y N 88 
ARX N9    C8     SING Y N 89 
ARX N3    C4     DOUB N N 90 
ARX N7    C8     DOUB Y N 91 
ARX C8    H8     SING Y N 92 
ARX C2    N3     SING N N 93 
ARX N1    C2     DOUB Y N 94 
ARX C2    H2     SING Y N 95 
ARX N1    C6     SING Y N 96 
ARX N6    C6     SING N N 97 
ARX N6    HN6    SING N N 98 
ARX N6    HN6A   SING N N 99 
# 
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 
ARX SMILES           ACDLabs              10.04 O=C(N)C(NC(=O)C(NC(=O)CCCCCNC(=O)C3OC(n2cnc1c(ncnc12)N)C(O)C3O)CCCNC(=[N@H])N)CCCNC(=[N@H])N 
ARX InChI            InChI                1.02b 
;InChI=1/C28H47N15O7/c29-21-17-23(39-12-38-21)43(13-40-17)26-19(46)18(45)20(50-26)25(49)35-9-3-1-2-8-16(44)41-15(7-5-11-37-28(33)34)24(48)42-14(22(30)47)6-4-10-36-27(31)32/h12-15,18-20,26,45-46H,1-11H2,(H2,30,47)(H,35,49)(H,41,44)(H,42,48)(H2,29,38,39)(H4,31,32,36)(H4,33,34,37)/t14-,15-,18+,19-,20+,26-/m1/s1/f/h31,33,35-37,41-42H,29-30,32,34H2/b31-27+,33-28+
;
ARX InChIKey         InChI                1.02b KFJBBCJEBVHMMY-KDSBPZMYDI 
ARX SMILES_CANONICAL CACTVS               3.341 NC(=N)NCCC[C@@H](NC(=O)[C@@H](CCCNC(N)=N)NC(=O)CCCCCNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23)C(N)=O 
ARX SMILES           CACTVS               3.341 NC(=N)NCCC[CH](NC(=O)[CH](CCCNC(N)=N)NC(=O)CCCCCNC(=O)[CH]1O[CH]([CH](O)[CH]1O)n2cnc3c(N)ncnc23)C(N)=O 
ARX SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(\N)/NCCC[C@H](C(=O)N)NC(=O)[C@@H](CCCN/C(=N/[H])/N)NC(=O)CCCCCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)n2cnc3c2ncnc3N)O)O 
ARX SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(N)NCCCC(C(=O)N)NC(=O)C(CCCNC(=N[H])N)NC(=O)CCCCCNC(=O)C1C(C(C(O1)n2cnc3c2ncnc3N)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 
ARX "SYSTEMATIC NAME" ACDLabs              10.04 
"(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-(6-{[(1R)-4-carbamimidamido-1-{[(1R)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}butyl]amino}-6-oxohexyl)-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name)" 
ARX "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S,3S,4R,5R)-N-[6-[[(2R)-1-[[(2R)-1-amino-5-carbamimidamido-1-oxo-pentan-2-yl]amino]-5-carbamimidamido-1-oxo-pentan-2-yl]amino]-6-oxo-hexyl]-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolane-2-carboxamide 
# 
