data_XN2
# 
_chem_comp.id                                    XN2 
_chem_comp.name                                  N-[2-HYDROXY-1-INDANYL]-5-[(2-TERTIARYBUTYLAMINOCARBONYL)-4(BENZO[1,3]DIOXOL-5-YLMETHYL)-PIPERAZINO]-4-HYDROXY-2-(1-PHENYLETHYL)-PENTANAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C39 H50 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                     2001-11-05 
_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                        670.837 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     XN2 
_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        1K6V 
_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 
XN2 N1   N1   N 0 1 N N N 3.118  -5.284  16.285 -0.481 2.517  -4.309 N1   XN2 1  
XN2 C1   C1   C 0 1 N N N 4.586  -5.168  15.716 -0.964 1.139  -4.454 C1   XN2 2  
XN2 C2   C2   C 0 1 N N S 5.384  -4.013  16.309 -1.920 0.805  -3.308 C2   XN2 3  
XN2 C3   C3   C 0 1 N N N 6.711  -4.050  15.650 -2.469 -0.584 -3.501 C3   XN2 4  
XN2 O1   O1   O 0 1 N N N 6.784  -3.698  14.415 -2.276 -1.434 -2.658 O1   XN2 5  
XN2 N2   N2   N 0 1 N N N 7.799  -4.446  16.411 -3.173 -0.883 -4.611 N2   XN2 6  
XN2 C4   C4   C 0 1 N N N 9.245  -4.568  16.053 -3.707 -2.234 -4.798 C4   XN2 7  
XN2 C5   C5   C 0 1 N N N 10.049 -5.068  17.284 -4.460 -2.305 -6.128 C5   XN2 8  
XN2 C6   C6   C 0 1 N N N 9.837  -3.326  15.749 -2.554 -3.240 -4.810 C6   XN2 9  
XN2 C7   C7   C 0 1 N N N 9.530  -5.506  14.912 -4.663 -2.568 -3.652 C7   XN2 10 
XN2 N3   N3   N 0 1 N N N 4.472  -2.771  16.007 -1.201 0.873  -2.030 N3   XN2 11 
XN2 C8   C8   C 0 1 N N N 3.022  -2.764  16.440 -0.718 2.252  -1.885 C8   XN2 12 
XN2 C9   C9   C 0 1 N N N 2.406  -4.057  15.871 0.237  2.585  -3.031 C9   XN2 13 
XN2 C10  C10  C 0 1 N N N 5.092  -1.507  16.561 -2.199 0.662  -0.973 C10  XN2 14 
XN2 C11  C11  C 0 1 N N S 5.037  -0.433  15.553 -1.550 0.891  0.393  C11  XN2 15 
XN2 O2   O2   O 0 1 N N N 5.191  0.590   16.510 -1.259 2.281  0.555  O2   XN2 16 
XN2 C12  C12  C 0 1 N N N 6.197  -0.217  14.654 -2.510 0.439  1.495  C12  XN2 17 
XN2 C13  C13  C 0 1 N N S 6.150  0.869   13.593 -1.818 0.558  2.855  C13  XN2 18 
XN2 C14  C14  C 0 1 N N S 7.587  0.864   12.798 -2.831 0.289  3.968  C14  XN2 19 
XN2 C15  C15  C 0 1 Y N N 7.548  1.976   11.672 -2.196 0.571  5.305  C15  XN2 20 
XN2 C16  C16  C 0 1 Y N N 7.335  3.476   11.991 -2.092 -0.434 6.248  C16  XN2 21 
XN2 C17  C17  C 0 1 Y N N 7.297  4.460   10.893 -1.509 -0.174 7.474  C17  XN2 22 
XN2 C18  C18  C 0 1 Y N N 7.467  3.973   9.458  -1.029 1.090  7.758  C18  XN2 23 
XN2 C19  C19  C 0 1 Y N N 7.673  2.509   9.160  -1.132 2.095  6.815  C19  XN2 24 
XN2 C20  C20  C 0 1 Y N N 7.711  1.532   10.253 -1.711 1.835  5.587  C20  XN2 25 
XN2 C21  C21  C 0 1 N N N 4.997  0.611   12.505 -0.699 -0.448 2.939  C21  XN2 26 
XN2 O3   O3   O 0 1 N N N 4.651  -0.542  12.012 -0.478 -1.188 2.003  O3   XN2 27 
XN2 N4   N4   N 0 1 N N N 4.461  1.752   12.151 0.054  -0.526 4.053  N4   XN2 28 
XN2 C22  C22  C 0 1 N N S 3.419  1.890   11.155 1.141  -1.505 4.135  C22  XN2 29 
XN2 C23  C23  C 0 1 N N R 3.430  3.272   10.534 1.375  -1.924 5.602  C23  XN2 30 
XN2 O4   O4   O 0 1 N N N 3.710  4.288   11.495 0.974  -0.885 6.497  O4   XN2 31 
XN2 C24  C24  C 0 1 N N N 2.100  3.384   9.835  2.903  -2.134 5.646  C24  XN2 32 
XN2 C25  C25  C 0 1 Y N N 1.054  2.722   10.670 3.458  -1.241 4.557  C25  XN2 33 
XN2 C26  C26  C 0 1 Y N N -0.360 2.771   10.835 4.747  -0.782 4.342  C26  XN2 34 
XN2 C27  C27  C 0 1 Y N N -0.973 1.876   11.843 5.023  0.035  3.264  C27  XN2 35 
XN2 C28  C28  C 0 1 Y N N -0.150 0.933   12.679 4.010  0.396  2.395  C28  XN2 36 
XN2 C29  C29  C 0 1 Y N N 1.287  0.882   12.513 2.724  -0.060 2.608  C29  XN2 37 
XN2 C30  C30  C 0 1 Y N N 1.954  1.715   11.564 2.445  -0.881 3.686  C30  XN2 38 
XN2 C31  C31  C 0 1 N N N 2.408  -6.407  15.697 0.516  2.729  -5.367 C31  XN2 39 
XN2 C32  C32  C 0 1 Y N N 2.958  -7.777  16.044 1.482  1.572  -5.384 C32  XN2 40 
XN2 C33  C33  C 0 1 Y N N 2.752  -8.297  17.426 1.220  0.467  -6.172 C33  XN2 41 
XN2 C34  C34  C 0 1 Y N N 3.975  -10.400 16.841 3.254  -0.555 -5.421 C34  XN2 42 
XN2 C35  C35  C 0 1 Y N N 4.219  -9.965  15.465 3.518  0.557  -4.628 C35  XN2 43 
XN2 C36  C36  C 0 1 Y N N 3.702  -8.623  15.045 2.630  1.622  -4.617 C36  XN2 44 
XN2 O5   O5   O 0 1 N N N 4.542  -11.657 16.990 4.269  -1.454 -5.263 O5   XN2 45 
XN2 C38  C38  C 0 1 N N N 5.209  -12.201 15.787 4.949  -1.058 -4.058 C38  XN2 46 
XN2 O6   O6   O 0 1 N N N 4.922  -11.017 14.900 4.698  0.357  -3.973 O6   XN2 47 
XN2 C37  C37  C 0 1 Y N N 3.240  -9.621  17.906 2.103  -0.596 -6.192 C37  XN2 48 
XN2 C39  C39  C 0 1 N N N 8.810  0.899   13.231 -4.049 1.196  3.780  C39  XN2 49 
XN2 H11A 1H1  H 0 0 N N N 4.573  -5.106  14.603 -1.487 1.035  -5.405 H11A XN2 50 
XN2 H12  2H1  H 0 1 N N N 5.134  -6.131  15.843 -0.117 0.453  -4.431 H12  XN2 51 
XN2 H2   H2   H 0 1 N N N 5.607  -4.022  17.402 -2.741 1.522  -3.301 H2   XN2 52 
XN2 HN2  HN2  H 0 1 N N N 7.496  -4.678  17.357 -3.327 -0.203 -5.285 HN2  XN2 53 
XN2 H51  1H5  H 0 1 N N N 9.637  -6.018  17.697 -4.857 -3.311 -6.267 H51  XN2 54 
XN2 H52  2H5  H 0 1 N N N 11.128 -5.159  17.017 -5.281 -1.588 -6.119 H52  XN2 55 
XN2 H53  3H5  H 0 1 N N N 9.891  -4.422  18.179 -3.778 -2.067 -6.945 H53  XN2 56 
XN2 H61  1H6  H 0 1 N N N 9.691  -2.599  16.582 -1.873 -3.002 -5.627 H61  XN2 57 
XN2 H62  2H6  H 0 1 N N N 10.916 -3.417  15.482 -2.018 -3.190 -3.863 H62  XN2 58 
XN2 H63  3H6  H 0 1 N N N 9.270  -2.798  14.947 -2.951 -4.246 -4.950 H63  XN2 59 
XN2 H71  1H7  H 0 1 N N N 8.932  -5.219  14.016 -5.484 -1.851 -3.643 H71  XN2 60 
XN2 H72  2H7  H 0 1 N N N 10.609 -5.597  14.645 -5.060 -3.574 -3.791 H72  XN2 61 
XN2 H73  3H7  H 0 1 N N N 9.096  -6.512  15.119 -4.127 -2.518 -2.704 H73  XN2 62 
XN2 H81  1H8  H 0 1 N N N 2.473  -1.840  16.143 -1.566 2.937  -1.909 H81  XN2 63 
XN2 H82  2H8  H 0 1 N N N 2.886  -2.653  17.541 -0.195 2.355  -0.935 H82  XN2 64 
XN2 H91  1H9  H 0 1 N N N 1.323  -4.124  16.128 0.634  3.591  -2.891 H91  XN2 65 
XN2 H92  2H9  H 0 1 N N N 2.330  -4.001  14.760 1.058  1.869  -3.039 H92  XN2 66 
XN2 H101 1H10 H 0 0 N N N 6.129  -1.679  16.932 -2.577 -0.358 -1.029 H101 XN2 67 
XN2 H102 2H10 H 0 0 N N N 4.623  -1.199  17.525 -3.023 1.362  -1.106 H102 XN2 68 
XN2 H11  H11  H 0 1 N N N 4.179  -0.565  14.854 -0.626 0.316  0.457  H11  XN2 69 
XN2 HO2  HO2  H 0 1 N N N 5.156  1.282   15.860 -2.108 2.744  0.572  HO2  XN2 70 
XN2 H121 1H12 H 0 0 N N N 6.440  -1.184  14.156 -2.798 -0.597 1.324  H121 XN2 71 
XN2 H122 2H12 H 0 0 N N N 7.103  -0.055  15.283 -3.399 1.070  1.484  H122 XN2 72 
XN2 H13  H13  H 0 1 N N N 5.943  1.838   14.104 -1.411 1.563  2.969  H13  XN2 73 
XN2 H141 1H14 H 0 0 N N N 7.523  -0.238  12.638 -3.146 -0.753 3.929  H141 XN2 74 
XN2 H16  H16  H 0 1 N N N 7.208  3.851   13.021 -2.467 -1.422 6.026  H16  XN2 75 
XN2 H17  H17  H 0 1 N N N 7.146  5.525   11.137 -1.429 -0.960 8.211  H17  XN2 76 
XN2 H18  H18  H 0 1 N N N 7.441  4.692   8.622  -0.574 1.293  8.716  H18  XN2 77 
XN2 H19  H19  H 0 1 N N N 7.798  2.147   8.126  -0.757 3.084  7.036  H19  XN2 78 
XN2 H20  H20  H 0 1 N N N 7.862  0.467   10.009 -1.791 2.621  4.850  H20  XN2 79 
XN2 HN4  HN4  H 0 1 N N N 4.860  2.543   12.657 -0.123 0.065  4.801  HN4  XN2 80 
XN2 H22  H22  H 0 1 N N N 3.698  1.037   10.493 0.910  -2.378 3.524  H22  XN2 81 
XN2 H23  H23  H 0 1 N N N 4.254  3.421   9.798  0.849  -2.852 5.828  H23  XN2 82 
XN2 HO4  HO4  H 0 1 N N N 3.717  5.155   11.106 1.145  -1.207 7.393  HO4  XN2 83 
XN2 H241 1H24 H 0 0 N N N 2.131  2.981   8.796  3.298  -1.836 6.617  H241 XN2 84 
XN2 H242 2H24 H 0 0 N N N 1.839  4.439   9.586  3.148  -3.177 5.442  H242 XN2 85 
XN2 H26  H26  H 0 1 N N N -0.950 3.466   10.214 5.538  -1.064 5.020  H26  XN2 86 
XN2 H27  H27  H 0 1 N N N -2.068 1.913   11.974 6.029  0.391  3.100  H27  XN2 87 
XN2 H28  H28  H 0 1 N N N -0.609 0.266   13.428 4.224  1.036  1.552  H28  XN2 88 
XN2 H29  H29  H 0 1 N N N 1.889  0.190   13.126 1.933  0.222  1.929  H29  XN2 89 
XN2 H311 1H31 H 0 0 N N N 2.352  -6.287  14.590 0.013  2.797  -6.332 H311 XN2 90 
XN2 H312 2H31 H 0 0 N N N 1.325  -6.353  15.956 1.059  3.653  -5.173 H312 XN2 91 
XN2 H33  H33  H 0 1 N N N 2.203  -7.661  18.140 0.323  0.433  -6.773 H33  XN2 92 
XN2 H36  H36  H 0 1 N N N 3.867  -8.263  14.015 2.835  2.489  -4.007 H36  XN2 93 
XN2 H381 1H38 H 0 0 N N N 4.883  -13.205 15.427 4.529  -1.574 -3.194 H381 XN2 94 
XN2 H382 2H38 H 0 0 N N N 6.272  -12.522 15.889 6.018  -1.253 -4.139 H382 XN2 95 
XN2 H37  H37  H 0 1 N N N 3.076  -9.984  18.935 1.896  -1.458 -6.808 H37  XN2 96 
XN2 H391 1H39 H 0 0 N N N 8.880  0.044   13.943 -3.744 2.238  3.879  H391 XN2 97 
XN2 H392 2H39 H 0 0 N N N 9.786  0.896   12.691 -4.473 1.034  2.790  H392 XN2 98 
XN2 H393 3H39 H 0 0 N N N 8.852  1.804   13.880 -4.796 0.963  4.539  H393 XN2 99 
# 
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 
XN2 N1  C1   SING N N 1   
XN2 N1  C9   SING N N 2   
XN2 N1  C31  SING N N 3   
XN2 C1  C2   SING N N 4   
XN2 C1  H11A SING N N 5   
XN2 C1  H12  SING N N 6   
XN2 C2  C3   SING N N 7   
XN2 C2  N3   SING N N 8   
XN2 C2  H2   SING N N 9   
XN2 C3  O1   DOUB N N 10  
XN2 C3  N2   SING N N 11  
XN2 N2  C4   SING N N 12  
XN2 N2  HN2  SING N N 13  
XN2 C4  C5   SING N N 14  
XN2 C4  C6   SING N N 15  
XN2 C4  C7   SING N N 16  
XN2 C5  H51  SING N N 17  
XN2 C5  H52  SING N N 18  
XN2 C5  H53  SING N N 19  
XN2 C6  H61  SING N N 20  
XN2 C6  H62  SING N N 21  
XN2 C6  H63  SING N N 22  
XN2 C7  H71  SING N N 23  
XN2 C7  H72  SING N N 24  
XN2 C7  H73  SING N N 25  
XN2 N3  C8   SING N N 26  
XN2 N3  C10  SING N N 27  
XN2 C8  C9   SING N N 28  
XN2 C8  H81  SING N N 29  
XN2 C8  H82  SING N N 30  
XN2 C9  H91  SING N N 31  
XN2 C9  H92  SING N N 32  
XN2 C10 C11  SING N N 33  
XN2 C10 H101 SING N N 34  
XN2 C10 H102 SING N N 35  
XN2 C11 O2   SING N N 36  
XN2 C11 C12  SING N N 37  
XN2 C11 H11  SING N N 38  
XN2 O2  HO2  SING N N 39  
XN2 C12 C13  SING N N 40  
XN2 C12 H121 SING N N 41  
XN2 C12 H122 SING N N 42  
XN2 C13 C14  SING N N 43  
XN2 C13 C21  SING N N 44  
XN2 C13 H13  SING N N 45  
XN2 C14 C15  SING N N 46  
XN2 C14 C39  SING N N 47  
XN2 C14 H141 SING N N 48  
XN2 C15 C16  DOUB Y N 49  
XN2 C15 C20  SING Y N 50  
XN2 C16 C17  SING Y N 51  
XN2 C16 H16  SING N N 52  
XN2 C17 C18  DOUB Y N 53  
XN2 C17 H17  SING N N 54  
XN2 C18 C19  SING Y N 55  
XN2 C18 H18  SING N N 56  
XN2 C19 C20  DOUB Y N 57  
XN2 C19 H19  SING N N 58  
XN2 C20 H20  SING N N 59  
XN2 C21 O3   DOUB N N 60  
XN2 C21 N4   SING N N 61  
XN2 N4  C22  SING N N 62  
XN2 N4  HN4  SING N N 63  
XN2 C22 C23  SING N N 64  
XN2 C22 C30  SING N N 65  
XN2 C22 H22  SING N N 66  
XN2 C23 O4   SING N N 67  
XN2 C23 C24  SING N N 68  
XN2 C23 H23  SING N N 69  
XN2 O4  HO4  SING N N 70  
XN2 C24 C25  SING N N 71  
XN2 C24 H241 SING N N 72  
XN2 C24 H242 SING N N 73  
XN2 C25 C26  DOUB Y N 74  
XN2 C25 C30  SING Y N 75  
XN2 C26 C27  SING Y N 76  
XN2 C26 H26  SING N N 77  
XN2 C27 C28  DOUB Y N 78  
XN2 C27 H27  SING N N 79  
XN2 C28 C29  SING Y N 80  
XN2 C28 H28  SING N N 81  
XN2 C29 C30  DOUB Y N 82  
XN2 C29 H29  SING N N 83  
XN2 C31 C32  SING N N 84  
XN2 C31 H311 SING N N 85  
XN2 C31 H312 SING N N 86  
XN2 C32 C33  DOUB Y N 87  
XN2 C32 C36  SING Y N 88  
XN2 C33 C37  SING Y N 89  
XN2 C33 H33  SING N N 90  
XN2 C34 C35  SING Y N 91  
XN2 C34 O5   SING N N 92  
XN2 C34 C37  DOUB Y N 93  
XN2 C35 C36  DOUB Y N 94  
XN2 C35 O6   SING N N 95  
XN2 C36 H36  SING N N 96  
XN2 O5  C38  SING N N 97  
XN2 C38 O6   SING N N 98  
XN2 C38 H381 SING N N 99  
XN2 C38 H382 SING N N 100 
XN2 C37 H37  SING N N 101 
XN2 C39 H391 SING N N 102 
XN2 C39 H392 SING N N 103 
XN2 C39 H393 SING N N 104 
# 
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 
XN2 SMILES           ACDLabs              10.04 O=C(NC2c1ccccc1CC2O)C(C(c3ccccc3)C)CC(O)CN4C(C(=O)NC(C)(C)C)CN(CC4)Cc5ccc6OCOc6c5 
XN2 InChI            InChI                1.02b 
;InChI=1/C39H50N4O6/c1-25(27-10-6-5-7-11-27)31(37(46)40-36-30-13-9-8-12-28(30)19-33(36)45)20-29(44)22-43-17-16-42(23-32(43)38(47)41-39(2,3)4)21-26-14-15-34-35(18-26)49-24-48-34/h5-15,18,25,29,31-33,36,44-45H,16-17,19-24H2,1-4H3,(H,40,46)(H,41,47)/t25-,29+,31+,32+,33-,36+/m1/s1/f/h40-41H
;
XN2 InChIKey         InChI                1.02b MJIRDPUZGGHJMX-SMZPTXTMDN 
XN2 SMILES_CANONICAL CACTVS               3.341 C[C@@H]([C@H](C[C@H](O)CN1CCN(C[C@H]1C(=O)NC(C)(C)C)Cc2ccc3OCOc3c2)C(=O)N[C@@H]4[C@H](O)Cc5ccccc45)c6ccccc6 
XN2 SMILES           CACTVS               3.341 C[CH]([CH](C[CH](O)CN1CCN(C[CH]1C(=O)NC(C)(C)C)Cc2ccc3OCOc3c2)C(=O)N[CH]4[CH](O)Cc5ccccc45)c6ccccc6 
XN2 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@H](c1ccccc1)[C@H](C[C@@H](C[N@@]2CC[N@](C[C@H]2C(=O)NC(C)(C)C)Cc3ccc4c(c3)OCO4)O)C(=O)N[C@H]5c6ccccc6C[C@H]5O 
XN2 SMILES           "OpenEye OEToolkits" 1.5.0 CC(c1ccccc1)C(CC(CN2CCN(CC2C(=O)NC(C)(C)C)Cc3ccc4c(c3)OCO4)O)C(=O)NC5c6ccccc6CC5O 
# 
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 
XN2 "SYSTEMATIC NAME" ACDLabs              10.04 "(2S)-4-(1,3-benzodioxol-5-ylmethyl)-N-tert-butyl-1-[(2S,4S,5S)-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}-5-phenylhexyl]piperazine-2-carboxamide (non-preferred name)" 
XN2 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (1S,2S,4R)-4-(1,3-benzodioxol-5-ylmethyl)-N-tert-butyl-1-[(2S,4S,5S)-2-hydroxy-4-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl]-5-phenyl-hexyl]piperazine-2-carboxamide                 
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