data_MK1
# 
_chem_comp.id                                    MK1 
_chem_comp.name                                  "N-[2(R)-HYDROXY-1(S)-INDANYL]-5-[(2(S)-TERTIARY BUTYLAMINOCARBONYL)-4(3-PYRIDYLMETHYL)PIPERAZINO]-4(S)-HYDROXY-2(R)-PHENYLMETHYLPENTANAMIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C36 H47 N5 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         INDINAVIR 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        613.789 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     MK1 
_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        1HSG 
_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 
MK1 N1   N1   N 0 1 N N N 9.280  23.763 3.004  0.011  0.044  5.540  N1   MK1 1  
MK1 C1   C1   C 0 1 N N N 9.498  23.983 4.459  1.228  -0.429 4.871  C1   MK1 2  
MK1 C2   C2   C 0 1 N N S 10.591 24.905 4.962  1.387  0.283  3.527  C2   MK1 3  
MK1 C3   C3   C 0 1 N N N 10.591 24.864 6.466  2.675  -0.151 2.878  C3   MK1 4  
MK1 O1   O1   O 0 1 N N N 10.937 23.849 7.057  2.654  -0.693 1.793  O1   MK1 5  
MK1 N2   N2   N 0 1 N N N 10.193 25.953 7.094  3.851  0.060  3.502  N2   MK1 6  
MK1 C4   C4   C 0 1 N N N 10.145 26.250 8.490  5.103  -0.362 2.871  C4   MK1 7  
MK1 C5   C5   C 0 1 N N N 9.379  27.577 8.641  6.279  -0.006 3.782  C5   MK1 8  
MK1 C6   C6   C 0 1 N N N 11.398 26.347 9.074  5.264  0.352  1.528  C6   MK1 9  
MK1 C7   C7   C 0 1 N N N 9.364  25.283 9.268  5.073  -1.875 2.643  C7   MK1 10 
MK1 N3   N3   N 0 1 N N N 11.819 24.282 4.355  0.259  -0.056 2.652  N3   MK1 11 
MK1 C8   C8   C 0 1 N N N 11.753 23.776 2.961  -0.957 0.418  3.321  C8   MK1 12 
MK1 C9   C9   C 0 1 N N N 10.440 23.182 2.493  -1.116 -0.294 4.664  C9   MK1 13 
MK1 C10  C10  C 0 1 N N N 13.083 24.963 4.552  0.413  0.750  1.434  C10  MK1 14 
MK1 C11  C11  C 0 1 N N S 14.203 24.064 5.078  -0.560 0.250  0.365  C11  MK1 15 
MK1 O2   O2   O 0 1 N N N 15.242 24.884 4.634  -1.901 0.511  0.783  O2   MK1 16 
MK1 C12  C12  C 0 1 N N N 14.440 23.761 6.569  -0.286 0.977  -0.953 C12  MK1 17 
MK1 C13  C13  C 0 1 N N R 15.573 22.821 7.005  -1.135 0.355  -2.063 C13  MK1 18 
MK1 C14  C14  C 0 1 N N N 15.644 22.664 8.534  -2.611 0.677  -1.818 C14  MK1 19 
MK1 C15  C15  C 0 1 Y N N 16.733 21.750 8.961  -3.450 0.033  -2.892 C15  MK1 20 
MK1 C16  C16  C 0 1 Y N N 18.058 21.916 8.553  -3.835 -1.288 -2.769 C16  MK1 21 
MK1 C17  C17  C 0 1 Y N N 19.037 21.016 8.947  -4.605 -1.878 -3.753 C17  MK1 22 
MK1 C18  C18  C 0 1 Y N N 18.673 19.939 9.758  -4.991 -1.146 -4.860 C18  MK1 23 
MK1 C19  C19  C 0 1 Y N N 17.347 19.773 10.176 -4.607 0.175  -4.983 C19  MK1 24 
MK1 C20  C20  C 0 1 Y N N 16.374 20.687 9.772  -3.841 0.767  -3.996 C20  MK1 25 
MK1 C21  C21  C 0 1 N N N 15.447 21.440 6.373  -0.712 0.920  -3.395 C21  MK1 26 
MK1 O3   O3   O 0 1 N N N 14.367 20.831 6.397  -0.436 2.097  -3.495 O3   MK1 27 
MK1 N4   N4   N 0 1 N N N 16.583 20.913 5.924  -0.640 0.117  -4.475 N4   MK1 28 
MK1 C22  C22  C 0 1 N N S 16.692 19.500 5.604  -0.121 0.638  -5.742 C22  MK1 29 
MK1 C23  C23  C 0 1 N N R 18.067 18.945 5.936  -0.719 -0.145 -6.929 C23  MK1 30 
MK1 O4   O4   O 0 1 N N N 19.061 19.938 5.729  -1.078 -1.470 -6.534 O4   MK1 31 
MK1 C24  C24  C 0 1 N N N 18.226 17.726 5.057  0.451  -0.167 -7.935 C24  MK1 32 
MK1 C25  C25  C 0 1 Y N N 17.476 17.904 3.760  1.702  -0.050 -7.090 C25  MK1 33 
MK1 C26  C26  C 0 1 Y N N 17.500 17.363 2.496  3.023  -0.327 -7.399 C26  MK1 34 
MK1 C27  C27  C 0 1 Y N N 16.613 17.872 1.541  4.012  -0.143 -6.453 C27  MK1 35 
MK1 C28  C28  C 0 1 Y N N 15.722 18.906 1.865  3.683  0.320  -5.193 C28  MK1 36 
MK1 C29  C29  C 0 1 Y N N 15.683 19.479 3.129  2.366  0.597  -4.882 C29  MK1 37 
MK1 C30  C30  C 0 1 Y N N 16.504 19.061 4.128  1.373  0.414  -5.829 C30  MK1 38 
MK1 C31  C31  C 0 1 N N N 8.033  23.100 2.604  -0.142 -0.762 6.758  C31  MK1 39 
MK1 C32  C32  C 0 1 Y N N 6.666  23.739 2.876  -1.380 -0.324 7.498  C32  MK1 40 
MK1 C33  C33  C 0 1 Y N N 6.158  24.808 2.124  -1.308 0.670  8.454  C33  MK1 41 
MK1 N5   N5   N 0 1 Y N N 4.911  25.430 2.300  -2.388 1.062  9.102  N5   MK1 42 
MK1 C34  C34  C 0 1 Y N N 4.207  24.839 3.348  -3.568 0.519  8.875  C34  MK1 43 
MK1 C35  C35  C 0 1 Y N N 4.654  23.774 4.136  -3.716 -0.485 7.937  C35  MK1 44 
MK1 C36  C36  C 0 1 Y N N 5.905  23.211 3.897  -2.604 -0.919 7.232  C36  MK1 45 
MK1 H11A 1H1  H 0 0 N N N 8.532  24.318 4.904  1.155  -1.504 4.704  H11A MK1 46 
MK1 H12  2H1  H 0 1 N N N 9.639  22.987 4.940  2.094  -0.217 5.499  H12  MK1 47 
MK1 H2   H2   H 0 1 N N N 10.493 25.982 4.690  1.409  1.361  3.689  H2   MK1 48 
MK1 HN2  HN2  H 0 1 N N N 9.884  26.651 6.417  3.867  0.494  4.370  HN2  MK1 49 
MK1 H51  1H5  H 0 1 N N N 9.341  27.808 9.731  7.211  -0.321 3.312  H51  MK1 50 
MK1 H52  2H5  H 0 1 N N N 9.811  28.404 8.031  6.300  1.071  3.944  H52  MK1 51 
MK1 H53  3H5  H 0 1 N N N 8.372  27.558 8.161  6.165  -0.515 4.739  H53  MK1 52 
MK1 H61  1H6  H 0 1 N N N 11.360 26.578 10.164 5.285  1.430  1.690  H61  MK1 53 
MK1 H62  2H6  H 0 1 N N N 11.994 25.424 8.886  6.195  0.037  1.058  H62  MK1 54 
MK1 H63  3H6  H 0 1 N N N 12.030 27.089 8.533  4.425  0.098  0.878  H63  MK1 55 
MK1 H71  1H7  H 0 1 N N N 9.326  25.514 10.358 4.959  -2.384 3.600  H71  MK1 56 
MK1 H72  2H7  H 0 1 N N N 8.335  25.180 8.850  4.235  -2.128 1.994  H72  MK1 57 
MK1 H73  3H7  H 0 1 N N N 9.737  24.246 9.097  6.005  -2.190 2.173  H73  MK1 58 
MK1 H81  1H8  H 0 1 N N N 12.061 24.586 2.259  -1.823 0.207  2.693  H81  MK1 59 
MK1 H82  2H8  H 0 1 N N N 12.571 23.035 2.798  -0.885 1.493  3.488  H82  MK1 60 
MK1 H91  1H9  H 0 1 N N N 10.430 22.085 2.693  -1.139 -1.372 4.502  H91  MK1 61 
MK1 H92  2H9  H 0 1 N N N 10.402 23.184 1.378  -2.048 0.020  5.134  H92  MK1 62 
MK1 H101 1H10 H 0 0 N N N 13.401 25.474 3.613  0.199  1.794  1.660  H101 MK1 63 
MK1 H102 2H10 H 0 0 N N N 12.949 25.849 5.215  1.435  0.660  1.065  H102 MK1 64 
MK1 H11  H11  H 0 1 N N N 14.024 23.013 4.749  -0.425 -0.821 0.223  H11  MK1 65 
MK1 HO2  HO2  H 0 1 N N N 15.937 24.325 4.960  -1.977 1.468  0.896  HO2  MK1 66 
MK1 H121 1H12 H 0 0 N N N 14.564 24.730 7.106  -0.542 2.031  -0.847 H121 MK1 67 
MK1 H122 2H12 H 0 0 N N N 13.485 23.382 7.003  0.769  0.883  -1.207 H122 MK1 68 
MK1 H13  H13  H 0 1 N N N 16.513 23.301 6.646  -0.995 -0.725 -2.066 H13  MK1 69 
MK1 H141 1H14 H 0 0 N N N 15.732 23.655 9.035  -2.909 0.292  -0.843 H141 MK1 70 
MK1 H142 2H14 H 0 0 N N N 14.661 22.340 8.950  -2.756 1.757  -1.842 H142 MK1 71 
MK1 H16  H16  H 0 1 N N N 18.334 22.769 7.911  -3.533 -1.860 -1.904 H16  MK1 72 
MK1 H17  H17  H 0 1 N N N 20.082 21.153 8.622  -4.904 -2.911 -3.657 H17  MK1 73 
MK1 H18  H18  H 0 1 N N N 19.440 19.211 10.071 -5.592 -1.608 -5.630 H18  MK1 74 
MK1 H19  H19  H 0 1 N N N 17.069 18.923 10.822 -4.909 0.747  -5.848 H19  MK1 75 
MK1 H20  H20  H 0 1 N N N 15.325 20.569 10.092 -3.541 1.800  -4.092 H20  MK1 76 
MK1 HN4  HN4  H 0 1 N N N 17.351 21.576 5.827  -0.932 -0.805 -4.414 HN4  MK1 77 
MK1 H22  H22  H 0 1 N N N 15.845 19.112 6.216  -0.350 1.700  -5.836 H22  MK1 78 
MK1 H23  H23  H 0 1 N N N 18.179 18.653 7.006  -1.578 0.379  -7.347 H23  MK1 79 
MK1 HO4  HO4  H 0 1 N N N 19.920 19.591 5.936  -1.377 -1.928 -7.331 HO4  MK1 80 
MK1 H241 1H24 H 0 0 N N N 19.299 17.478 4.883  0.456  -1.105 -8.490 H241 MK1 81 
MK1 H242 2H24 H 0 0 N N N 17.922 16.792 5.585  0.377  0.677  -8.620 H242 MK1 82 
MK1 H26  H26  H 0 1 N N N 18.205 16.549 2.256  3.281  -0.689 -8.384 H26  MK1 83 
MK1 H27  H27  H 0 1 N N N 16.616 17.453 0.520  5.041  -0.360 -6.697 H27  MK1 84 
MK1 H28  H28  H 0 1 N N N 15.025 19.282 1.096  4.454  0.464  -4.451 H28  MK1 85 
MK1 H29  H29  H 0 1 N N N 14.974 20.295 3.347  2.109  0.959  -3.898 H29  MK1 86 
MK1 H311 1H31 H 0 0 N N N 8.097  22.876 1.513  -0.233 -1.814 6.488  H311 MK1 87 
MK1 H312 2H31 H 0 0 N N N 8.029  22.077 3.049  0.730  -0.625 7.397  H312 MK1 88 
MK1 H33  H33  H 0 1 N N N 6.801  25.196 1.316  -0.359 1.138  8.667  H33  MK1 89 
MK1 H34  H34  H 0 1 N N N 3.208  25.250 3.573  -4.430 0.864  9.428  H34  MK1 90 
MK1 H35  H35  H 0 1 N N N 4.019  23.377 4.946  -4.685 -0.925 7.755  H35  MK1 91 
MK1 H36  H36  H 0 1 N N N 6.283  22.368 4.500  -2.689 -1.702 6.493  H36  MK1 92 
# 
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 
MK1 N1  C1   SING N N 1  
MK1 N1  C9   SING N N 2  
MK1 N1  C31  SING N N 3  
MK1 C1  C2   SING N N 4  
MK1 C1  H11A SING N N 5  
MK1 C1  H12  SING N N 6  
MK1 C2  C3   SING N N 7  
MK1 C2  N3   SING N N 8  
MK1 C2  H2   SING N N 9  
MK1 C3  O1   DOUB N N 10 
MK1 C3  N2   SING N N 11 
MK1 N2  C4   SING N N 12 
MK1 N2  HN2  SING N N 13 
MK1 C4  C5   SING N N 14 
MK1 C4  C6   SING N N 15 
MK1 C4  C7   SING N N 16 
MK1 C5  H51  SING N N 17 
MK1 C5  H52  SING N N 18 
MK1 C5  H53  SING N N 19 
MK1 C6  H61  SING N N 20 
MK1 C6  H62  SING N N 21 
MK1 C6  H63  SING N N 22 
MK1 C7  H71  SING N N 23 
MK1 C7  H72  SING N N 24 
MK1 C7  H73  SING N N 25 
MK1 N3  C8   SING N N 26 
MK1 N3  C10  SING N N 27 
MK1 C8  C9   SING N N 28 
MK1 C8  H81  SING N N 29 
MK1 C8  H82  SING N N 30 
MK1 C9  H91  SING N N 31 
MK1 C9  H92  SING N N 32 
MK1 C10 C11  SING N N 33 
MK1 C10 H101 SING N N 34 
MK1 C10 H102 SING N N 35 
MK1 C11 O2   SING N N 36 
MK1 C11 C12  SING N N 37 
MK1 C11 H11  SING N N 38 
MK1 O2  HO2  SING N N 39 
MK1 C12 C13  SING N N 40 
MK1 C12 H121 SING N N 41 
MK1 C12 H122 SING N N 42 
MK1 C13 C14  SING N N 43 
MK1 C13 C21  SING N N 44 
MK1 C13 H13  SING N N 45 
MK1 C14 C15  SING N N 46 
MK1 C14 H141 SING N N 47 
MK1 C14 H142 SING N N 48 
MK1 C15 C16  DOUB Y N 49 
MK1 C15 C20  SING Y N 50 
MK1 C16 C17  SING Y N 51 
MK1 C16 H16  SING N N 52 
MK1 C17 C18  DOUB Y N 53 
MK1 C17 H17  SING N N 54 
MK1 C18 C19  SING Y N 55 
MK1 C18 H18  SING N N 56 
MK1 C19 C20  DOUB Y N 57 
MK1 C19 H19  SING N N 58 
MK1 C20 H20  SING N N 59 
MK1 C21 O3   DOUB N N 60 
MK1 C21 N4   SING N N 61 
MK1 N4  C22  SING N N 62 
MK1 N4  HN4  SING N N 63 
MK1 C22 C23  SING N N 64 
MK1 C22 C30  SING N N 65 
MK1 C22 H22  SING N N 66 
MK1 C23 O4   SING N N 67 
MK1 C23 C24  SING N N 68 
MK1 C23 H23  SING N N 69 
MK1 O4  HO4  SING N N 70 
MK1 C24 C25  SING N N 71 
MK1 C24 H241 SING N N 72 
MK1 C24 H242 SING N N 73 
MK1 C25 C26  DOUB Y N 74 
MK1 C25 C30  SING Y N 75 
MK1 C26 C27  SING Y N 76 
MK1 C26 H26  SING N N 77 
MK1 C27 C28  DOUB Y N 78 
MK1 C27 H27  SING N N 79 
MK1 C28 C29  SING Y N 80 
MK1 C28 H28  SING N N 81 
MK1 C29 C30  DOUB Y N 82 
MK1 C29 H29  SING N N 83 
MK1 C31 C32  SING N N 84 
MK1 C31 H311 SING N N 85 
MK1 C31 H312 SING N N 86 
MK1 C32 C33  SING Y N 87 
MK1 C32 C36  DOUB Y N 88 
MK1 C33 N5   DOUB Y N 89 
MK1 C33 H33  SING N N 90 
MK1 N5  C34  SING Y N 91 
MK1 C34 C35  DOUB Y N 92 
MK1 C34 H34  SING N N 93 
MK1 C35 C36  SING Y N 94 
MK1 C35 H35  SING N N 95 
MK1 C36 H36  SING N N 96 
# 
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 
MK1 SMILES           ACDLabs              10.04 O=C(NC2c1ccccc1CC2O)C(Cc3ccccc3)CC(O)CN5C(C(=O)NC(C)(C)C)CN(Cc4cnccc4)CC5 
MK1 InChI            InChI                1.02b 
;InChI=1/C36H47N5O4/c1-36(2,3)39-35(45)31-24-40(22-26-12-9-15-37-21-26)16-17-41(31)23-29(42)19-28(18-25-10-5-4-6-11-25)34(44)38-33-30-14-8-7-13-27(30)20-32(33)43/h4-15,21,28-29,31-33,42-43H,16-20,22-24H2,1-3H3,(H,38,44)(H,39,45)/t28-,29+,31+,32-,33+/m1/s1/f/h38-39H
;
MK1 InChIKey         InChI                1.02b CBVCZFGXHXORBI-WCUGGTCDDP 
MK1 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)Cc5cccnc5 
MK1 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)Cc5cccnc5 
MK1 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)Cc5cccnc5 
MK1 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)(C)NC(=O)C1CN(CCN1CC(CC(Cc2ccccc2)C(=O)NC3c4ccccc4CC3O)O)Cc5cccnc5 
# 
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 
MK1 "SYSTEMATIC NAME" ACDLabs              10.04 "(2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-5-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}-5-oxopentyl]-N-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide (non-preferred name)" 
MK1 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (1S,2S,4R)-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]-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide          
# 
