data_XN3
# 
_chem_comp.id                                    XN3 
_chem_comp.name                                  "N-[2(R)-HYDROXY-1(S)-INDANYL]-5-[(2(S)-TERTIARY BUTYLAMINOCARBONYL)-4(BENZO[1,3]DIOXOL-5-YLMETHYL)-PIPERAZINO]-4(S)-HYDROXY-2(R)-PHENYLMETHYLPENTANAMIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C38 H48 N4 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "ANALOGUE OF INDINAVIR DRUG" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-11-02 
_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                        656.811 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     XN3 
_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        1K6P 
_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 
XN3 N1   N1   N 0 1 N N N 2.987  -5.221  16.433 0.792  -0.232 4.823  N1   XN3 1  
XN3 C1   C1   C 0 1 N N N 4.424  -5.136  15.883 1.947  -0.633 4.009  C1   XN3 2  
XN3 C2   C2   C 0 1 N N S 5.274  -4.003  16.455 1.933  0.132  2.685  C2   XN3 3  
XN3 C3   C3   C 0 1 N N N 6.589  -4.107  15.780 3.159  -0.227 1.885  C3   XN3 4  
XN3 O1   O1   O 0 1 N N N 6.690  -3.717  14.587 3.040  -0.731 0.789  O1   XN3 5  
XN3 N2   N2   N 0 1 N N N 7.625  -4.613  16.505 4.386  0.011  2.389  N2   XN3 6  
XN3 C4   C4   C 0 1 N N N 9.044  -4.825  16.155 5.577  -0.337 1.611  C4   XN3 7  
XN3 C5   C5   C 0 1 N N N 9.776  -5.467  17.364 6.831  0.034  2.404  C5   XN3 8  
XN3 C6   C6   C 0 1 N N N 9.731  -3.618  15.929 5.565  0.429  0.287  C6   XN3 9  
XN3 C7   C7   C 0 1 N N N 9.271  -5.728  14.980 5.579  -1.841 1.329  C7   XN3 10 
XN3 N3   N3   N 0 1 N N N 4.408  -2.732  16.155 0.730  -0.223 1.923  N3   XN3 11 
XN3 C8   C8   C 0 1 N N N 2.977  -2.721  16.623 -0.423 0.178  2.736  C8   XN3 12 
XN3 C9   C9   C 0 1 N N N 2.304  -3.992  16.089 -0.410 -0.587 4.060  C9   XN3 13 
XN3 C10  C10  C 0 1 N N N 5.034  -1.478  16.685 0.721  0.630  0.728  C10  XN3 14 
XN3 C11  C11  C 0 1 N N S 5.031  -0.404  15.652 -0.342 0.129  -0.249 C11  XN3 15 
XN3 O2   O2   O 0 1 N N N 5.026  0.651   16.597 -1.639 0.320  0.319  O2   XN3 16 
XN3 C12  C12  C 0 1 N N N 6.260  -0.144  14.795 -0.240 0.911  -1.560 C12  XN3 17 
XN3 C13  C13  C 0 1 N N R 6.247  0.968   13.736 -1.181 0.294  -2.597 C13  XN3 18 
XN3 C14  C14  C 0 1 N N N 7.676  1.026   12.987 -2.632 0.546  -2.183 C14  XN3 19 
XN3 C15  C15  C 0 1 Y N N 7.708  2.134   11.912 -3.558 -0.093 -3.185 C15  XN3 20 
XN3 C16  C16  C 0 1 Y N N 7.564  3.576   12.269 -3.878 -1.433 -3.073 C16  XN3 21 
XN3 C17  C17  C 0 1 Y N N 7.586  4.581   11.223 -4.728 -2.020 -3.992 C17  XN3 22 
XN3 C18  C18  C 0 1 Y N N 7.753  4.151   9.811  -5.258 -1.266 -5.022 C18  XN3 23 
XN3 C19  C19  C 0 1 Y N N 7.895  2.718   9.474  -4.940 0.073  -5.134 C19  XN3 24 
XN3 C20  C20  C 0 1 Y N N 7.872  1.729   10.518 -4.093 0.661  -4.212 C20  XN3 25 
XN3 C21  C21  C 0 1 N N N 5.136  0.742   12.627 -0.925 0.921  -3.943 C21  XN3 26 
XN3 O3   O3   O 0 1 N N N 4.774  -0.409  12.158 -0.706 2.111  -4.026 O3   XN3 27 
XN3 N4   N4   N 0 1 N N N 4.646  1.895   12.231 -0.941 0.160  -5.055 N4   XN3 28 
XN3 C22  C22  C 0 1 N N S 3.633  2.075   11.211 -0.581 0.746  -6.349 C22  XN3 29 
XN3 C23  C23  C 0 1 N N R 3.599  3.499   10.677 -1.275 -0.019 -7.495 C23  XN3 30 
XN3 O4   O4   O 0 1 N N N 3.736  4.453   11.726 -1.540 -1.371 -7.115 O4   XN3 31 
XN3 C24  C24  C 0 1 N N N 2.302  3.578   9.921  -0.220 0.041  -8.620 C24  XN3 32 
XN3 C25  C25  C 0 1 Y N N 1.255  2.845   10.718 1.108  0.179  -7.910 C25  XN3 33 
XN3 C26  C26  C 0 1 Y N N -0.140 2.839   10.859 2.398  -0.032 -8.369 C26  XN3 34 
XN3 C27  C27  C 0 1 Y N N -0.724 1.905   11.805 3.476  0.160  -7.527 C27  XN3 35 
XN3 C28  C28  C 0 1 Y N N 0.109  0.984   12.599 3.268  0.565  -6.222 C28  XN3 36 
XN3 C29  C29  C 0 1 Y N N 1.518  0.980   12.465 1.983  0.777  -5.762 C29  XN3 37 
XN3 C30  C30  C 0 1 Y N N 2.167  1.848   11.576 0.901  0.586  -6.604 C30  XN3 38 
XN3 C31  C31  C 0 1 N N N 2.237  -6.357  15.862 0.802  -1.086 6.018  C31  XN3 39 
XN3 C32  C32  C 0 1 Y N N 2.785  -7.749  16.170 -0.363 -0.726 6.902  C32  XN3 40 
XN3 C33  C33  C 0 1 Y N N 2.627  -8.346  17.497 -1.578 -1.366 6.737  C33  XN3 41 
XN3 C34  C34  C 0 1 Y N N 3.824  -10.363 16.761 -2.510 -0.069 8.525  C34  XN3 42 
XN3 C35  C35  C 0 1 Y N N 4.019  -9.841  15.442 -1.286 0.575  8.691  C35  XN3 43 
XN3 C36  C36  C 0 1 Y N N 3.485  -8.508  15.132 -0.214 0.238  7.880  C36  XN3 44 
XN3 O5   O5   O 0 1 N N N 4.418  -11.636 16.810 -3.393 0.430  9.438  O5   XN3 45 
XN3 C38  C38  C 0 1 N N N 5.050  -12.091 15.549 -2.819 1.670  9.891  C38  XN3 46 
XN3 O6   O6   O 0 1 N N N 4.711  -10.844 14.773 -1.403 1.477  9.708  O6   XN3 47 
XN3 C37  C37  C 0 1 Y N N 3.134  -9.674  17.873 -2.650 -1.039 7.546  C37  XN3 48 
XN3 H11A 1H1  H 0 0 N N N 4.406  -5.077  14.770 1.896  -1.703 3.810  H11A XN3 49 
XN3 H12  2H1  H 0 1 N N N 4.945  -6.112  16.019 2.867  -0.408 4.549  H12  XN3 50 
XN3 H2   H2   H 0 1 N N N 5.511  -4.002  17.545 1.932  1.203  2.886  H2   XN3 51 
XN3 HN2  HN2  H 0 1 N N N 7.294  -4.867  17.436 4.480  0.414  3.266  HN2  XN3 52 
XN3 H51  1H5  H 0 1 N N N 9.281  -6.404  17.710 7.718  -0.225 1.826  H51  XN3 53 
XN3 H52  2H5  H 0 1 N N N 10.847 -5.627  17.100 6.830  1.105  2.605  H52  XN3 54 
XN3 H53  3H5  H 0 1 N N N 9.655  -4.870  18.298 6.840  -0.512 3.347  H53  XN3 55 
XN3 H61  1H6  H 0 1 N N N 9.632  -2.931  16.802 5.563  1.500  0.488  H61  XN3 56 
XN3 H62  2H6  H 0 1 N N N 10.802 -3.778  15.665 6.451  0.169  -0.291 H62  XN3 57 
XN3 H63  3H6  H 0 1 N N N 9.215  -3.002  15.156 4.671  0.164  -0.277 H63  XN3 58 
XN3 H71  1H7  H 0 1 N N N 8.705  -5.359  14.093 5.588  -2.387 2.272  H71  XN3 59 
XN3 H72  2H7  H 0 1 N N N 10.342 -5.888  14.716 4.686  -2.106 0.764  H72  XN3 60 
XN3 H73  3H7  H 0 1 N N N 8.762  -6.707  15.140 6.466  -2.101 0.751  H73  XN3 61 
XN3 H81  1H8  H 0 1 N N N 2.434  -1.790  16.337 -1.343 -0.046 2.197  H81  XN3 62 
XN3 H82  2H8  H 0 1 N N N 2.883  -2.612  17.729 -0.373 1.248  2.936  H82  XN3 63 
XN3 H91  1H9  H 0 1 N N N 1.239  -4.035  16.416 -0.409 -1.658 3.860  H91  XN3 64 
XN3 H92  2H9  H 0 1 N N N 2.162  -3.922  14.985 -1.296 -0.327 4.639  H92  XN3 65 
XN3 H101 1H10 H 0 0 N N N 6.059  -1.665  17.081 0.495  1.657  1.016  H101 XN3 66 
XN3 H102 2H10 H 0 0 N N N 4.547  -1.142  17.630 1.700  0.595  0.249  H102 XN3 67 
XN3 H11  H11  H 0 1 N N N 4.249  -0.593  14.880 -0.184 -0.931 -0.446 H11  XN3 68 
XN3 HO2  HO2  H 0 1 N N N 5.024  1.336   15.938 -1.738 1.268  0.477  HO2  XN3 69 
XN3 H121 1H12 H 0 0 N N N 6.548  -1.099  14.297 -0.522 1.949  -1.386 H121 XN3 70 
XN3 H122 2H12 H 0 0 N N N 7.129  0.027   15.472 0.784  0.870  -1.929 H122 XN3 71 
XN3 H13  H13  H 0 1 N N N 6.026  1.918   14.277 -1.001 -0.779 -2.657 H13  XN3 72 
XN3 H141 1H14 H 0 0 N N N 7.952  0.034   12.559 -2.809 0.116  -1.198 H141 XN3 73 
XN3 H142 2H14 H 0 0 N N N 8.513  1.140   13.715 -2.818 1.620  -2.150 H142 XN3 74 
XN3 H16  H16  H 0 1 N N N 7.440  3.902   13.315 -3.463 -2.021 -2.268 H16  XN3 75 
XN3 H17  H17  H 0 1 N N N 7.479  5.645   11.494 -4.977 -3.067 -3.905 H17  XN3 76 
XN3 H18  H18  H 0 1 N N N 7.772  4.903   9.005  -5.922 -1.725 -5.741 H18  XN3 77 
XN3 H19  H19  H 0 1 N N N 8.020  2.383   8.431  -5.354 0.662  -5.939 H19  XN3 78 
XN3 H20  H20  H 0 1 N N N 7.980  0.664   10.251 -3.844 1.709  -4.299 H20  XN3 79 
XN3 HN4  HN4  H 0 1 N N N 5.067  2.677   12.733 -1.191 -0.775 -4.999 HN4  XN3 80 
XN3 H22  H22  H 0 1 N N N 3.971  1.282   10.504 -0.859 1.800  -6.376 H22  XN3 81 
XN3 H23  H23  H 0 1 N N N 4.454  3.745   10.005 -2.193 0.483  -7.798 H23  XN3 82 
XN3 HO4  HO4  H 0 1 N N N 3.715  5.342   11.393 -1.907 -1.813 -7.893 HO4  XN3 83 
XN3 H241 1H24 H 0 0 N N N 2.389  3.203   8.875  -0.241 -0.876 -9.209 H241 XN3 84 
XN3 H242 2H24 H 0 0 N N N 2.006  4.626   9.680  -0.399 0.905  -9.260 H242 XN3 85 
XN3 H26  H26  H 0 1 N N N -0.748 3.534   10.256 2.561  -0.348 -9.389 H26  XN3 86 
XN3 H27  H27  H 0 1 N N N -1.821 1.895   11.923 4.480  -0.006 -7.888 H27  XN3 87 
XN3 H28  H28  H 0 1 N N N -0.336 0.275   13.317 4.110  0.715  -5.562 H28  XN3 88 
XN3 H29  H29  H 0 1 N N N 2.125  0.284   13.068 1.822  1.093  -4.742 H29  XN3 89 
XN3 H311 1H31 H 0 0 N N N 2.137  -6.227  14.759 0.721  -2.131 5.718  H311 XN3 90 
XN3 H312 2H31 H 0 0 N N N 1.167  -6.296  16.170 1.733  -0.936 6.565  H312 XN3 91 
XN3 H33  H33  H 0 1 N N N 2.092  -7.758  18.262 -1.689 -2.122 5.974  H33  XN3 92 
XN3 H36  H36  H 0 1 N N N 3.609  -8.079  14.124 0.736  0.733  8.011  H36  XN3 93 
XN3 H381 1H38 H 0 0 N N N 4.726  -13.071 15.128 -3.174 2.501  9.282  H381 XN3 94 
XN3 H382 2H38 H 0 0 N N N 6.119  -12.407 15.586 -3.050 1.837  10.943 H382 XN3 95 
XN3 H37  H37  H 0 1 N N N 3.010  -10.106 18.880 -3.598 -1.540 7.414  H37  XN3 96 
# 
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 
XN3 N1  C1   SING N N 1   
XN3 N1  C9   SING N N 2   
XN3 N1  C31  SING N N 3   
XN3 C1  C2   SING N N 4   
XN3 C1  H11A SING N N 5   
XN3 C1  H12  SING N N 6   
XN3 C2  C3   SING N N 7   
XN3 C2  N3   SING N N 8   
XN3 C2  H2   SING N N 9   
XN3 C3  O1   DOUB N N 10  
XN3 C3  N2   SING N N 11  
XN3 N2  C4   SING N N 12  
XN3 N2  HN2  SING N N 13  
XN3 C4  C5   SING N N 14  
XN3 C4  C6   SING N N 15  
XN3 C4  C7   SING N N 16  
XN3 C5  H51  SING N N 17  
XN3 C5  H52  SING N N 18  
XN3 C5  H53  SING N N 19  
XN3 C6  H61  SING N N 20  
XN3 C6  H62  SING N N 21  
XN3 C6  H63  SING N N 22  
XN3 C7  H71  SING N N 23  
XN3 C7  H72  SING N N 24  
XN3 C7  H73  SING N N 25  
XN3 N3  C8   SING N N 26  
XN3 N3  C10  SING N N 27  
XN3 C8  C9   SING N N 28  
XN3 C8  H81  SING N N 29  
XN3 C8  H82  SING N N 30  
XN3 C9  H91  SING N N 31  
XN3 C9  H92  SING N N 32  
XN3 C10 C11  SING N N 33  
XN3 C10 H101 SING N N 34  
XN3 C10 H102 SING N N 35  
XN3 C11 O2   SING N N 36  
XN3 C11 C12  SING N N 37  
XN3 C11 H11  SING N N 38  
XN3 O2  HO2  SING N N 39  
XN3 C12 C13  SING N N 40  
XN3 C12 H121 SING N N 41  
XN3 C12 H122 SING N N 42  
XN3 C13 C14  SING N N 43  
XN3 C13 C21  SING N N 44  
XN3 C13 H13  SING N N 45  
XN3 C14 C15  SING N N 46  
XN3 C14 H141 SING N N 47  
XN3 C14 H142 SING N N 48  
XN3 C15 C16  DOUB Y N 49  
XN3 C15 C20  SING Y N 50  
XN3 C16 C17  SING Y N 51  
XN3 C16 H16  SING N N 52  
XN3 C17 C18  DOUB Y N 53  
XN3 C17 H17  SING N N 54  
XN3 C18 C19  SING Y N 55  
XN3 C18 H18  SING N N 56  
XN3 C19 C20  DOUB Y N 57  
XN3 C19 H19  SING N N 58  
XN3 C20 H20  SING N N 59  
XN3 C21 O3   DOUB N N 60  
XN3 C21 N4   SING N N 61  
XN3 N4  C22  SING N N 62  
XN3 N4  HN4  SING N N 63  
XN3 C22 C23  SING N N 64  
XN3 C22 C30  SING N N 65  
XN3 C22 H22  SING N N 66  
XN3 C23 O4   SING N N 67  
XN3 C23 C24  SING N N 68  
XN3 C23 H23  SING N N 69  
XN3 O4  HO4  SING N N 70  
XN3 C24 C25  SING N N 71  
XN3 C24 H241 SING N N 72  
XN3 C24 H242 SING N N 73  
XN3 C25 C26  DOUB Y N 74  
XN3 C25 C30  SING Y N 75  
XN3 C26 C27  SING Y N 76  
XN3 C26 H26  SING N N 77  
XN3 C27 C28  DOUB Y N 78  
XN3 C27 H27  SING N N 79  
XN3 C28 C29  SING Y N 80  
XN3 C28 H28  SING N N 81  
XN3 C29 C30  DOUB Y N 82  
XN3 C29 H29  SING N N 83  
XN3 C31 C32  SING N N 84  
XN3 C31 H311 SING N N 85  
XN3 C31 H312 SING N N 86  
XN3 C32 C33  DOUB Y N 87  
XN3 C32 C36  SING Y N 88  
XN3 C33 C37  SING Y N 89  
XN3 C33 H33  SING N N 90  
XN3 C34 C35  SING Y N 91  
XN3 C34 O5   SING N N 92  
XN3 C34 C37  DOUB Y N 93  
XN3 C35 C36  DOUB Y N 94  
XN3 C35 O6   SING N N 95  
XN3 C36 H36  SING N N 96  
XN3 O5  C38  SING N N 97  
XN3 C38 O6   SING N N 98  
XN3 C38 H381 SING N N 99  
XN3 C38 H382 SING N N 100 
XN3 C37 H37  SING N N 101 
# 
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 
XN3 SMILES           ACDLabs              10.04 O=C(NC2c1ccccc1CC2O)C(Cc3ccccc3)CC(O)CN4C(C(=O)NC(C)(C)C)CN(CC4)Cc5ccc6OCOc6c5 
XN3 InChI            InChI                1.02b 
;InChI=1/C38H48N4O6/c1-38(2,3)40-37(46)31-23-41(21-26-13-14-33-34(18-26)48-24-47-33)15-16-42(31)22-29(43)19-28(17-25-9-5-4-6-10-25)36(45)39-35-30-12-8-7-11-27(30)20-32(35)44/h4-14,18,28-29,31-32,35,43-44H,15-17,19-24H2,1-3H3,(H,39,45)(H,40,46)/t28-,29+,31+,32-,35+/m1/s1/f/h39-40H
;
XN3 InChIKey         InChI                1.02b BJZTWVIYUGVEFV-QVHLZYLNDY 
XN3 SMILES_CANONICAL CACTVS               3.341 CC(C)(C)NC(=O)[C@@H]1CN(CCN1C[C@@H](O)C[C@@H](Cc2ccccc2)C(=O)N[C@@H]3[C@H](O)Cc4ccccc34)Cc5ccc6OCOc6c5 
XN3 SMILES           CACTVS               3.341 CC(C)(C)NC(=O)[CH]1CN(CCN1C[CH](O)C[CH](Cc2ccccc2)C(=O)N[CH]3[CH](O)Cc4ccccc34)Cc5ccc6OCOc6c5 
XN3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)(C)NC(=O)[C@@H]1C[N@@](CC[N@]1C[C@H](C[C@@H](Cc2ccccc2)C(=O)N[C@H]3c4ccccc4C[C@H]3O)O)Cc5ccc6c(c5)OCO6 
XN3 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)(C)NC(=O)C1CN(CCN1CC(CC(Cc2ccccc2)C(=O)NC3c4ccccc4CC3O)O)Cc5ccc6c(c5)OCO6 
# 
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 
XN3 "SYSTEMATIC NAME" ACDLabs              10.04 "(2S)-4-(1,3-benzodioxol-5-ylmethyl)-1-[(2S,4R)-4-benzyl-2-hydroxy-5-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}-5-oxopentyl]-N-tert-butylpiperazine-2-carboxamide (non-preferred name)" 
XN3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (1S,2S,4R)-4-(1,3-benzodioxol-5-ylmethyl)-N-tert-butyl-1-[(2S,4R)-2-hydroxy-5-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino]-5-oxo-4-(phenylmethyl)pentyl]piperazine-2-carboxamide          
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