data_LIO
# 
_chem_comp.id                                    LIO 
_chem_comp.name                                  "[1-PENTADECANOYL-2-DECANOYL-GLYCEROL-3-YL]PHOSPHONYL CHOLINE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C33 H67 N O8 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     1999-12-15 
_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                        636.861 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     LIO 
_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        1DMH 
_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 
LIO C1   C1   C 0 1 N N N 2.273  68.844 98.854  -3.323  2.288  -1.795 C1   LIO 1   
LIO C2   C2   C 0 1 N N R 1.993  70.068 99.438  -3.497  1.006  -2.612 C2   LIO 2   
LIO C3   C3   C 0 1 N N N 3.094  70.893 99.272  -2.152  0.600  -3.218 C3   LIO 3   
LIO C4   C4   C 0 1 N N N 4.150  65.214 97.380  -1.130  4.502  1.957  C4   LIO 4   
LIO C5   C5   C 0 1 N N N 3.915  63.685 97.448  -0.145  4.390  3.123  C5   LIO 5   
LIO C6   C6   C 0 1 N N N 5.368  63.218 95.507  1.477   5.460  1.716  C6   LIO 6   
LIO C7   C7   C 0 1 N N N 4.779  61.451 97.032  2.178   4.342  3.719  C7   LIO 7   
LIO C8   C8   C 0 1 N N N 6.301  63.150 97.737  1.394   3.066  1.845  C8   LIO 8   
LIO C11  C11  C 0 1 N N N 5.293  71.576 98.488  0.100   0.135  -2.461 C11  LIO 9   
LIO C12  C12  C 0 1 N N N 4.901  72.950 99.097  1.128   0.014  -1.365 C12  LIO 10  
LIO C13  C13  C 0 1 N N N 5.573  74.081 98.317  2.473   -0.392 -1.971 C13  LIO 11  
LIO C14  C14  C 0 1 N N N 5.206  75.443 98.899  3.516   -0.515 -0.858 C14  LIO 12  
LIO C15  C15  C 0 1 N N N 4.978  76.395 97.734  4.861   -0.921 -1.464 C15  LIO 13  
LIO C16  C16  C 0 1 N N N 5.422  77.806 98.077  5.905   -1.044 -0.352 C16  LIO 14  
LIO C17  C17  C 0 1 N N N 5.162  78.681 96.852  7.250   -1.450 -0.957 C17  LIO 15  
LIO C18  C18  C 0 1 N N N 5.284  80.160 97.207  8.293   -1.573 0.155  C18  LIO 16  
LIO C19  C19  C 0 1 N N N 3.945  80.847 96.948  9.639   -1.979 -0.450 C19  LIO 17  
LIO C20  C20  C 0 1 N N N 4.040  81.682 95.678  10.682  -2.102 0.662  C20  LIO 18  
LIO C21  C21  C 0 1 N N N 2.635  82.108 95.254  12.027  -2.508 0.057  C21  LIO 19  
LIO C22  C22  C 0 1 N N N 2.737  83.041 94.040  13.071  -2.631 1.169  C22  LIO 20  
LIO C23  C23  C 0 1 N N N 1.357  83.184 93.412  14.416  -3.037 0.564  C23  LIO 21  
LIO C24  C24  C 0 1 N N N 1.428  84.105 92.209  15.459  -3.160 1.676  C24  LIO 22  
LIO C25  C25  C 0 1 N N N 0.179  83.900 91.368  16.804  -3.567 1.070  C25  LIO 23  
LIO C31  C31  C 0 1 N N N 0.081  71.935 99.427  -5.299  -0.245 -1.590 C31  LIO 24  
LIO C32  C32  C 0 1 N N N 0.765  72.964 100.337 -5.800  -1.348 -0.693 C32  LIO 25  
LIO C33  C33  C 0 1 N N N 1.113  74.207 99.499  -7.330  -1.346 -0.688 C33  LIO 26  
LIO C34  C34  C 0 1 N N N 0.304  75.412 99.976  -7.839  -2.465 0.222  C34  LIO 27  
LIO C35  C35  C 0 1 N N N 1.209  76.636 100.020 -9.369  -2.463 0.227  C35  LIO 28  
LIO C36  C36  C 0 1 N N N 0.411  77.883 99.665  -9.877  -3.583 1.137  C36  LIO 29  
LIO C37  C37  C 0 1 N N N 0.991  79.077 100.424 -11.407 -3.581 1.142  C37  LIO 30  
LIO C38  C38  C 0 1 N N N 0.207  80.352 100.088 -11.916 -4.701 2.052  C38  LIO 31  
LIO C39  C39  C 0 1 N N N -0.912 80.567 101.120 -13.446 -4.698 2.058  C39  LIO 32  
LIO C40  C40  C 0 1 N N N -1.089 82.067 101.383 -13.954 -5.818 2.968  C40  LIO 33  
LIO N    N    N 1 1 N N N 5.088  62.889 96.929  1.226   4.315  2.601  N    LIO 34  
LIO O2   O2   O 0 1 N N N 0.668  70.634 99.024  -3.980  -0.056 -1.749 O2   LIO 35  
LIO O3   O3   O 0 1 N N N 4.309  70.484 98.594  -1.162  0.484  -2.162 O3   LIO 36  
LIO O11  O11  O 0 1 N N N 6.378  71.388 97.933  0.411   -0.081 -3.608 O11  LIO 37  
LIO O31  O31  O 0 1 N N N -1.037 72.218 98.987  -6.085  0.470  -2.165 O31  LIO 38  
LIO O1P  O1P  O 0 1 N N N 4.382  67.095 99.770  -1.651  4.640  -0.989 O1P  LIO 39  
LIO O2P  O2P  O 0 1 N N N 2.691  65.333 100.107 -3.487  3.847  0.551  O2P  LIO 40  
LIO O3P  O3P  O 0 1 N N N 1.931  67.596 99.507  -2.294  2.096  -0.821 O3P  LIO 41  
LIO O4P  O4P  O 0 1 N N N 3.141  66.175 97.833  -1.112  3.289  1.201  O4P  LIO 42  
LIO P    P    P 0 1 N N R 3.041  66.562 99.300  -2.165  3.476  -0.003 P    LIO 43  
LIO H11  1H1  H 0 1 N N N 1.814  68.836 97.837  -3.046  3.107  -2.459 H11  LIO 44  
LIO H12  2H1  H 0 1 N N N 3.362  68.819 98.616  -4.259  2.529  -1.292 H12  LIO 45  
LIO H21  1H2  H 0 1 N N N 1.841  69.948 100.536 -4.218  1.180  -3.412 H21  LIO 46  
LIO H31  1H3  H 0 1 N N N 2.736  71.824 98.773  -1.832  1.357  -3.934 H31  LIO 47  
LIO H32  2H3  H 0 1 N N N 3.388  71.257 100.283 -2.257  -0.359 -3.725 H32  LIO 48  
LIO H41  1H4  H 0 1 N N N 5.098  65.436 97.921  -0.840  5.334  1.315  H41  LIO 49  
LIO H42  2H4  H 0 1 N N N 4.415  65.470 96.328  -2.134  4.674  2.344  H42  LIO 50  
LIO H51  1H5  H 0 1 N N N 3.643  63.368 98.482  -0.242  5.266  3.765  H51  LIO 51  
LIO H52  2H5  H 0 1 N N N 2.975  63.401 96.919  -0.365  3.491  3.699  H52  LIO 52  
LIO H61  1H6  H 0 1 N N N 6.234  62.630 95.123  1.352   6.387  2.277  H61  LIO 53  
LIO H62  2H6  H 0 1 N N N 4.464  63.082 94.868  2.494   5.404  1.329  H62  LIO 54  
LIO H63  3H6  H 0 1 N N N 5.517  64.313 95.360  0.770   5.440  0.886  H63  LIO 55  
LIO H71  1H7  H 0 1 N N N 5.645  60.863 96.648  1.992   3.492  4.375  H71  LIO 56  
LIO H72  2H7  H 0 1 N N N 4.488  61.152 98.066  3.195   4.286  3.332  H72  LIO 57  
LIO H73  3H7  H 0 1 N N N 3.825  61.184 96.518  2.053   5.268  4.280  H73  LIO 58  
LIO H81  1H8  H 0 1 N N N 7.167  62.562 97.353  0.833   3.128  0.912  H81  LIO 59  
LIO H82  2H8  H 0 1 N N N 6.533  64.239 97.791  2.450   2.914  1.625  H82  LIO 60  
LIO H83  3H8  H 0 1 N N N 6.122  62.961 98.821  1.022   2.230  2.437  H83  LIO 61  
LIO H121 1H12 H 0 0 N N N 3.795  73.081 99.153  0.808   -0.743 -0.649 H121 LIO 62  
LIO H122 2H12 H 0 0 N N N 5.127  73.003 100.187 1.232   0.973  -0.858 H122 LIO 63  
LIO H131 1H13 H 0 0 N N N 6.678  73.942 98.262  2.792   0.365  -2.687 H131 LIO 64  
LIO H132 2H13 H 0 0 N N N 5.340  74.023 97.228  2.368   -1.351 -2.478 H132 LIO 65  
LIO H141 1H14 H 0 0 N N N 4.338  75.396 99.597  3.197   -1.272 -0.142 H141 LIO 66  
LIO H142 2H14 H 0 0 N N N 5.960  75.821 99.627  3.621   0.444  -0.351 H142 LIO 67  
LIO H151 1H15 H 0 0 N N N 5.469  76.026 96.803  5.181   -0.164 -2.180 H151 LIO 68  
LIO H152 2H15 H 0 0 N N N 3.917  76.372 97.389  4.757   -1.880 -1.971 H152 LIO 69  
LIO H161 1H16 H 0 0 N N N 4.940  78.200 99.002  5.585   -1.801 0.364  H161 LIO 70  
LIO H162 2H16 H 0 0 N N N 6.478  77.855 98.429  6.009   -0.085 0.156  H162 LIO 71  
LIO H171 1H17 H 0 0 N N N 5.825  78.405 95.999  7.570   -0.693 -1.673 H171 LIO 72  
LIO H172 2H17 H 0 0 N N N 4.178  78.449 96.380  7.145   -2.409 -1.465 H172 LIO 73  
LIO H181 1H18 H 0 0 N N N 5.647  80.317 98.249  7.974   -2.330 0.871  H181 LIO 74  
LIO H182 2H18 H 0 0 N N N 6.126  80.656 96.671  8.398   -0.614 0.663  H182 LIO 75  
LIO H191 1H19 H 0 0 N N N 3.099  80.121 96.913  9.958   -1.222 -1.166 H191 LIO 76  
LIO H192 2H19 H 0 0 N N N 3.603  81.448 97.822  9.534   -2.938 -0.958 H192 LIO 77  
LIO H201 1H20 H 0 0 N N N 4.730  82.550 95.792  10.362  -2.859 1.378  H201 LIO 78  
LIO H202 2H20 H 0 0 N N N 4.586  81.153 94.862  10.787  -1.143 1.170  H202 LIO 79  
LIO H211 1H21 H 0 0 N N N 1.967  81.235 95.063  12.347  -1.751 -0.659 H211 LIO 80  
LIO H212 2H21 H 0 0 N N N 2.059  82.565 96.092  11.923  -3.467 -0.451 H212 LIO 81  
LIO H221 1H22 H 0 0 N N N 3.191  84.026 94.297  12.751  -3.389 1.885  H221 LIO 82  
LIO H222 2H22 H 0 0 N N N 3.505  82.702 93.306  13.175  -1.673 1.677  H222 LIO 83  
LIO H231 1H23 H 0 0 N N N 0.909  82.195 93.155  14.735  -2.280 -0.152 H231 LIO 84  
LIO H232 2H23 H 0 0 N N N 0.593  83.520 94.151  14.311  -3.996 0.056  H232 LIO 85  
LIO H241 1H24 H 0 0 N N N 1.579  85.171 92.495  15.140  -3.918 2.392  H241 LIO 86  
LIO H242 2H24 H 0 0 N N N 2.365  83.969 91.621  15.564  -2.202 2.183  H242 LIO 87  
LIO H251 1H25 H 0 0 N N N 0.231  84.577 90.483  17.548  -3.654 1.863  H251 LIO 88  
LIO H252 2H25 H 0 0 N N N 0.027  82.833 91.081  16.700  -4.525 0.563  H252 LIO 89  
LIO H253 3H25 H 0 0 N N N -0.758 84.035 91.955  17.124  -2.809 0.354  H253 LIO 90  
LIO H321 1H32 H 0 0 N N N 0.153  73.212 101.235 -5.439  -2.308 -1.062 H321 LIO 91  
LIO H322 2H32 H 0 0 N N N 1.651  72.543 100.865 -5.433  -1.187 0.320  H322 LIO 92  
LIO H331 1H33 H 0 0 N N N 2.208  74.415 99.499  -7.691  -0.386 -0.319 H331 LIO 93  
LIO H332 2H33 H 0 0 N N N 0.980  74.022 98.407  -7.697  -1.506 -1.702 H332 LIO 94  
LIO H341 1H34 H 0 0 N N N -0.607 75.581 99.357  -7.478  -3.426 -0.147 H341 LIO 95  
LIO H342 2H34 H 0 0 N N N -0.201 75.223 100.952 -7.472  -2.305 1.236  H342 LIO 96  
LIO H351 1H35 H 0 0 N N N 1.729  76.737 101.001 -9.729  -1.503 0.596  H351 LIO 97  
LIO H352 2H35 H 0 0 N N N 2.108  76.515 99.371  -9.736  -2.624 -0.787 H352 LIO 98  
LIO H361 1H36 H 0 0 N N N 0.366  78.059 98.565  -9.517  -4.543 0.768  H361 LIO 99  
LIO H362 2H36 H 0 0 N N N -0.681 77.754 99.846  -9.510  -3.422 2.151  H362 LIO 100 
LIO H371 1H37 H 0 0 N N N 1.032  78.891 101.522 -11.768 -2.621 1.511  H371 LIO 101 
LIO H372 2H37 H 0 0 N N N 2.083  79.198 100.236 -11.774 -3.742 0.129  H372 LIO 102 
LIO H381 1H38 H 0 0 N N N 0.873  81.242 100.001 -11.555 -5.661 1.684  H381 LIO 103 
LIO H382 2H38 H 0 0 N N N -0.183 80.339 99.043  -11.549 -4.540 3.066  H382 LIO 104 
LIO H391 1H39 H 0 0 N N N -1.866 80.078 100.813 -13.807 -3.738 2.427  H391 LIO 105 
LIO H392 2H39 H 0 0 N N N -0.733 79.993 102.059 -13.813 -4.859 1.044  H392 LIO 106 
LIO H401 1H40 H 0 0 N N N -1.900 82.222 102.131 -13.594 -6.778 2.599  H401 LIO 107 
LIO H402 2H40 H 0 0 N N N -0.134 82.555 101.689 -13.587 -5.657 3.981  H402 LIO 108 
LIO H403 3H40 H 0 0 N N N -1.267 82.640 100.443 -15.044 -5.817 2.971  H403 LIO 109 
LIO HOP1 1HOP H 0 0 N N N 4.602  67.867 99.262  -0.789  4.359  -1.327 HOP1 LIO 110 
# 
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 
LIO C1  C2   SING N N 1   
LIO C1  O3P  SING N N 2   
LIO C1  H11  SING N N 3   
LIO C1  H12  SING N N 4   
LIO C2  C3   SING N N 5   
LIO C2  O2   SING N N 6   
LIO C2  H21  SING N N 7   
LIO C3  O3   SING N N 8   
LIO C3  H31  SING N N 9   
LIO C3  H32  SING N N 10  
LIO C4  C5   SING N N 11  
LIO C4  O4P  SING N N 12  
LIO C4  H41  SING N N 13  
LIO C4  H42  SING N N 14  
LIO C5  N    SING N N 15  
LIO C5  H51  SING N N 16  
LIO C5  H52  SING N N 17  
LIO C6  N    SING N N 18  
LIO C6  H61  SING N N 19  
LIO C6  H62  SING N N 20  
LIO C6  H63  SING N N 21  
LIO C7  N    SING N N 22  
LIO C7  H71  SING N N 23  
LIO C7  H72  SING N N 24  
LIO C7  H73  SING N N 25  
LIO C8  N    SING N N 26  
LIO C8  H81  SING N N 27  
LIO C8  H82  SING N N 28  
LIO C8  H83  SING N N 29  
LIO C11 C12  SING N N 30  
LIO C11 O3   SING N N 31  
LIO C11 O11  DOUB N N 32  
LIO C12 C13  SING N N 33  
LIO C12 H121 SING N N 34  
LIO C12 H122 SING N N 35  
LIO C13 C14  SING N N 36  
LIO C13 H131 SING N N 37  
LIO C13 H132 SING N N 38  
LIO C14 C15  SING N N 39  
LIO C14 H141 SING N N 40  
LIO C14 H142 SING N N 41  
LIO C15 C16  SING N N 42  
LIO C15 H151 SING N N 43  
LIO C15 H152 SING N N 44  
LIO C16 C17  SING N N 45  
LIO C16 H161 SING N N 46  
LIO C16 H162 SING N N 47  
LIO C17 C18  SING N N 48  
LIO C17 H171 SING N N 49  
LIO C17 H172 SING N N 50  
LIO C18 C19  SING N N 51  
LIO C18 H181 SING N N 52  
LIO C18 H182 SING N N 53  
LIO C19 C20  SING N N 54  
LIO C19 H191 SING N N 55  
LIO C19 H192 SING N N 56  
LIO C20 C21  SING N N 57  
LIO C20 H201 SING N N 58  
LIO C20 H202 SING N N 59  
LIO C21 C22  SING N N 60  
LIO C21 H211 SING N N 61  
LIO C21 H212 SING N N 62  
LIO C22 C23  SING N N 63  
LIO C22 H221 SING N N 64  
LIO C22 H222 SING N N 65  
LIO C23 C24  SING N N 66  
LIO C23 H231 SING N N 67  
LIO C23 H232 SING N N 68  
LIO C24 C25  SING N N 69  
LIO C24 H241 SING N N 70  
LIO C24 H242 SING N N 71  
LIO C25 H251 SING N N 72  
LIO C25 H252 SING N N 73  
LIO C25 H253 SING N N 74  
LIO C31 C32  SING N N 75  
LIO C31 O2   SING N N 76  
LIO C31 O31  DOUB N N 77  
LIO C32 C33  SING N N 78  
LIO C32 H321 SING N N 79  
LIO C32 H322 SING N N 80  
LIO C33 C34  SING N N 81  
LIO C33 H331 SING N N 82  
LIO C33 H332 SING N N 83  
LIO C34 C35  SING N N 84  
LIO C34 H341 SING N N 85  
LIO C34 H342 SING N N 86  
LIO C35 C36  SING N N 87  
LIO C35 H351 SING N N 88  
LIO C35 H352 SING N N 89  
LIO C36 C37  SING N N 90  
LIO C36 H361 SING N N 91  
LIO C36 H362 SING N N 92  
LIO C37 C38  SING N N 93  
LIO C37 H371 SING N N 94  
LIO C37 H372 SING N N 95  
LIO C38 C39  SING N N 96  
LIO C38 H381 SING N N 97  
LIO C38 H382 SING N N 98  
LIO C39 C40  SING N N 99  
LIO C39 H391 SING N N 100 
LIO C39 H392 SING N N 101 
LIO C40 H401 SING N N 102 
LIO C40 H402 SING N N 103 
LIO C40 H403 SING N N 104 
LIO O1P P    SING N N 105 
LIO O1P HOP1 SING N N 106 
LIO O2P P    DOUB N N 107 
LIO O3P P    SING N N 108 
LIO O4P P    SING N N 109 
# 
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 
LIO SMILES           ACDLabs              10.04 O=C(OC(COP(=O)(OCC[N+](C)(C)C)O)COC(=O)CCCCCCCCCCCCCC)CCCCCCCCC                                                                                                                                   
LIO InChI            InChI                1.02b InChI=1/C33H66NO8P/c1-6-8-10-12-14-15-16-17-18-20-21-23-25-32(35)39-29-31(30-41-43(37,38)40-28-27-34(3,4)5)42-33(36)26-24-22-19-13-11-9-7-2/h31H,6-30H2,1-5H3/p+1/t31-/m1/s1/fC33H67NO8P/h37H/q+1 
LIO InChIKey         InChI                1.02b YAOVLDDMIGILIT-WWKDCWTEDM                                                                                                                                                                         
LIO SMILES_CANONICAL CACTVS               3.341 CCCCCCCCCCCCCCC(=O)OC[C@H](CO[P@@](O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC                                                                                                                           
LIO SMILES           CACTVS               3.341 CCCCCCCCCCCCCCC(=O)OC[CH](CO[P](O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC                                                                                                                              
LIO SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCCCCCCCCCCCCCC(=O)OC[C@H](CO[P@](=O)(O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC                                                                                                                            
LIO SMILES           "OpenEye OEToolkits" 1.5.0 CCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC                                                                                                                                   
# 
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 
LIO "SYSTEMATIC NAME" ACDLabs              10.04 "(4R,7R)-7-(decanoyloxy)-4-hydroxy-N,N,N-trimethyl-10-oxo-3,5,9-trioxa-4-phosphatetracosan-1-aminium 4-oxide" 
LIO "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-[[(2R)-2-decanoyloxy-3-pentadecanoyloxy-propoxy]-hydroxy-phosphoryl]oxyethyl-trimethyl-azanium              
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