data_AB1
# 
_chem_comp.id                                    AB1 
_chem_comp.name                                  N-{1-BENZYL-4-[2-(2,6-DIMETHYL-PHENOXY)-ACETYLAMINO]-3-HYDROXY-5-PHENYL-PENTYL}-3-METHYL-2-(2-OXO-TETRAHYDRO-PYRIMIDIN-1-YL)-BUTYRAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C37 H48 N4 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "ABT-378, LOPINAVIR" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-09-24 
_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                        628.801 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AB1 
_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        1MUI 
_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 
AB1 C1  C1  C 0 1 N N N -12.826 12.835 34.863 -8.080 1.420  -1.368 C1  AB1 1  
AB1 C2  C2  C 0 1 N N N -10.695 13.456 33.693 -6.591 -0.544 -1.711 C2  AB1 2  
AB1 N1  N1  N 0 1 N N N -11.312 14.795 33.369 -5.463 0.351  -1.450 N1  AB1 3  
AB1 C3  C3  C 0 1 N N N -12.602 15.111 33.773 -5.652 1.648  -1.166 C3  AB1 4  
AB1 N2  N2  N 0 1 N N N -13.303 14.178 34.478 -6.871 2.208  -1.125 N2  AB1 5  
AB1 C4  C4  C 0 1 Y N N -6.228  18.149 27.522 3.144  3.169  1.052  C4  AB1 6  
AB1 C5  C5  C 0 1 Y N N -5.533  18.892 26.537 4.081  2.994  0.052  C5  AB1 7  
AB1 C6  C6  C 0 1 Y N N -4.218  18.535 26.149 5.404  3.326  0.278  C6  AB1 8  
AB1 C7  C7  C 0 1 Y N N -3.583  17.429 26.745 5.789  3.834  1.504  C7  AB1 9  
AB1 C8  C8  C 0 1 Y N N -4.266  16.681 27.729 4.851  4.011  2.505  C8  AB1 10 
AB1 C9  C9  C 0 1 Y N N -5.579  17.037 28.116 3.528  3.682  2.277  C9  AB1 11 
AB1 O1  O1  O 0 1 N N N -13.116 16.186 33.516 -4.681 2.346  -0.947 O1  AB1 12 
AB1 C10 C10 C 0 1 N N S -10.526 15.812 32.587 -4.099 -0.182 -1.493 C10 AB1 13 
AB1 C11 C11 C 0 1 N N N -10.356 15.313 31.126 -3.491 -0.121 -0.116 C11 AB1 14 
AB1 N3  N3  N 0 1 N N N -11.218 15.924 30.255 -2.284 -0.673 0.114  N3  AB1 15 
AB1 C12 C12 C 0 1 N N S -11.283 15.652 28.802 -1.754 -0.736 1.478  C12 AB1 16 
AB1 C13 C13 C 0 1 N N N -9.141  16.141 33.272 -3.256 0.652  -2.460 C13 AB1 17 
AB1 C14 C14 C 0 1 N N N -8.309  17.186 32.504 -1.882 0.000  -2.632 C14 AB1 18 
AB1 C15 C15 C 0 1 N N N -9.349  16.648 34.718 -3.959 0.724  -3.817 C15 AB1 19 
AB1 O2  O2  O 0 1 N N N -9.523  14.456 30.826 -4.089 0.427  0.787  O2  AB1 20 
AB1 C16 C16 C 0 1 Y N N -12.704 11.139 29.135 -5.547 -3.147 1.273  C16 AB1 21 
AB1 C17 C17 C 0 1 Y N N -13.365 11.100 30.386 -6.197 -2.802 2.444  C17 AB1 22 
AB1 C18 C18 C 0 1 Y N N -13.773 12.306 31.002 -5.487 -2.241 3.489  C18 AB1 23 
AB1 C19 C19 C 0 1 Y N N -13.519 13.542 30.365 -4.127 -2.028 3.365  C19 AB1 24 
AB1 C20 C20 C 0 1 Y N N -12.855 13.590 29.109 -3.478 -2.368 2.193  C20 AB1 25 
AB1 C21 C21 C 0 1 Y N N -12.451 12.379 28.501 -4.188 -2.930 1.148  C21 AB1 26 
AB1 C22 C22 C 0 1 N N N -12.591 14.910 28.442 -1.996 -2.131 2.056  C22 AB1 27 
AB1 C23 C23 C 0 1 N N N -11.287 16.960 27.981 -0.251 -0.447 1.455  C23 AB1 28 
AB1 C24 C24 C 0 1 N N S -10.116 17.951 28.112 -0.019 1.014  1.065  C24 AB1 29 
AB1 C25 C25 C 0 1 N N S -8.712  17.443 27.695 1.469  1.346  1.197  C25 AB1 30 
AB1 N4  N4  N 0 1 N N N -8.753  17.097 26.255 2.244  0.474  0.311  N4  AB1 31 
AB1 C26 C26 C 0 1 N N N -8.266  15.927 25.732 3.536  0.208  0.589  C26 AB1 32 
AB1 C27 C27 C 0 1 N N N -8.399  15.807 24.201 4.334  -0.689 -0.322 C27 AB1 33 
AB1 O3  O3  O 0 1 N N N -8.721  17.070 23.590 5.665  -0.817 0.181  O3  AB1 34 
AB1 C28 C28 C 0 1 Y N N -8.297  17.183 22.252 6.333  -1.632 -0.677 C28 AB1 35 
AB1 O4  O4  O 0 1 N N N -10.433 19.034 27.271 -0.434 1.217  -0.287 O4  AB1 36 
AB1 C29 C29 C 0 1 N N N -7.637  18.548 27.916 1.702  2.807  0.806  C29 AB1 37 
AB1 O5  O5  O 0 1 N N N -7.742  15.021 26.389 4.056  0.690  1.573  O5  AB1 38 
AB1 C30 C30 C 0 1 Y N N -9.067  16.640 21.165 7.010  -1.094 -1.761 C30 AB1 39 
AB1 C31 C31 C 0 1 Y N N -8.587  16.788 19.836 7.688  -1.924 -2.632 C31 AB1 40 
AB1 C32 C32 C 0 1 Y N N -7.374  17.459 19.574 7.692  -3.291 -2.424 C32 AB1 41 
AB1 C33 C33 C 0 1 Y N N -6.614  17.997 20.632 7.018  -3.830 -1.344 C33 AB1 42 
AB1 C34 C34 C 0 1 Y N N -7.061  17.868 21.969 6.343  -3.003 -0.467 C34 AB1 43 
AB1 C35 C35 C 0 1 N N N -6.234  18.451 23.064 5.608  -3.591 0.710  C35 AB1 44 
AB1 C36 C36 C 0 1 N N N -10.374 15.915 21.383 7.007  0.396  -1.989 C36 AB1 45 
AB1 C37 C37 C 0 1 N N N -11.296 12.774 34.940 -7.744 0.263  -2.316 C37 AB1 46 
AB1 H2  H2  H 0 1 N N N -13.230 12.050 34.182 -8.843 2.053  -1.821 H2  AB1 47 
AB1 H3  H3  H 0 1 N N N -13.294 12.496 35.817 -8.450 1.021  -0.423 H3  AB1 48 
AB1 H4  H4  H 0 1 N N N -9.588  13.549 33.792 -6.285 -1.322 -2.411 H4  AB1 49 
AB1 H5  H5  H 0 1 N N N -10.749 12.776 32.811 -6.917 -1.002 -0.777 H5  AB1 50 
AB1 H8  H8  H 0 1 N N N -14.236 14.503 34.732 -6.952 3.154  -0.927 H8  AB1 51 
AB1 H30 H30 H 0 1 N N N -6.023  19.761 26.066 3.780  2.597  -0.906 H30 AB1 52 
AB1 H31 H31 H 0 1 N N N -3.686  19.120 25.380 6.136  3.188  -0.504 H31 AB1 53 
AB1 H32 H32 H 0 1 N N N -2.559  17.151 26.444 6.822  4.093  1.681  H32 AB1 54 
AB1 H33 H33 H 0 1 N N N -3.771  15.814 28.198 5.152  4.407  3.463  H33 AB1 55 
AB1 H34 H34 H 0 1 N N N -6.100  16.444 28.886 2.795  3.820  3.059  H34 AB1 56 
AB1 H9  H9  H 0 1 N N N -11.091 16.773 32.572 -4.124 -1.218 -1.833 H9  AB1 57 
AB1 H15 H15 H 0 1 N N N -11.832 16.604 30.703 -1.765 -1.030 -0.625 H15 AB1 58 
AB1 H16 H16 H 0 1 N N N -10.385 15.037 28.559 -2.257 0.007  2.097  H16 AB1 59 
AB1 H10 H10 H 0 1 N N N -8.574  15.181 33.268 -3.133 1.658  -2.060 H10 AB1 60 
AB1 H11 H11 H 0 1 N N N -8.899  18.118 32.340 -1.315 0.542  -3.388 H11 AB1 61 
AB1 H12 H12 H 0 1 N N N -7.331  17.418 32.988 -1.345 0.029  -1.684 H12 AB1 62 
AB1 H47 H47 H 0 1 N N N -8.161  16.872 31.445 -2.009 -1.036 -2.946 H47 AB1 63 
AB1 H13 H13 H 0 1 N N N -9.949  15.930 35.325 -4.896 1.270  -3.712 H13 AB1 64 
AB1 H14 H14 H 0 1 N N N -8.371  16.880 35.202 -3.317 1.239  -4.532 H14 AB1 65 
AB1 H48 H48 H 0 1 N N N -10.044 17.519 34.753 -4.164 -0.285 -4.175 H48 AB1 66 
AB1 H20 H20 H 0 1 N N N -12.385 10.200 28.653 -6.102 -3.585 0.457  H20 AB1 67 
AB1 H21 H21 H 0 1 N N N -13.561 10.133 30.879 -7.259 -2.971 2.541  H21 AB1 68 
AB1 H22 H22 H 0 1 N N N -14.288 12.283 31.977 -5.995 -1.971 4.403  H22 AB1 69 
AB1 H23 H23 H 0 1 N N N -13.842 14.477 30.852 -3.573 -1.590 4.182  H23 AB1 70 
AB1 H19 H19 H 0 1 N N N -11.935 12.402 27.526 -3.680 -3.199 0.234  H19 AB1 71 
AB1 H17 H17 H 0 1 N N N -12.646 14.779 27.336 -1.569 -2.880 1.389  H17 AB1 72 
AB1 H18 H18 H 0 1 N N N -13.458 15.589 28.617 -1.525 -2.206 3.036  H18 AB1 73 
AB1 H24 H24 H 0 1 N N N -12.237 17.506 28.190 0.169  -0.630 2.444  H24 AB1 74 
AB1 H25 H25 H 0 1 N N N -11.412 16.701 26.904 0.233  -1.099 0.728  H25 AB1 75 
AB1 H26 H26 H 0 1 N N N -10.024 18.182 29.199 -0.596 1.663  1.724  H26 AB1 76 
AB1 H27 H27 H 0 1 N N N -8.444  16.556 28.315 1.786  1.191  2.228  H27 AB1 77 
AB1 H35 H35 H 0 1 N N N -9.155  17.724 25.558 1.828  0.089  -0.476 H35 AB1 78 
AB1 H36 H36 H 0 1 N N N -9.137  15.020 23.919 3.866  -1.672 -0.365 H36 AB1 79 
AB1 H37 H37 H 0 1 N N N -7.484  15.359 23.748 4.364  -0.256 -1.322 H37 AB1 80 
AB1 H1  H1  H 0 1 N N N -9.710  19.646 27.352 0.096  0.623  -0.835 H1  AB1 81 
AB1 H28 H28 H 0 1 N N N -7.934  19.487 27.393 1.468  2.942  -0.250 H28 AB1 82 
AB1 H29 H29 H 0 1 N N N -7.658  18.902 28.973 1.058  3.451  1.406  H29 AB1 83 
AB1 H41 H41 H 0 1 N N N -9.166  16.375 18.993 8.216  -1.506 -3.477 H41 AB1 84 
AB1 H42 H42 H 0 1 N N N -7.018  17.564 18.535 8.223  -3.939 -3.106 H42 AB1 85 
AB1 H43 H43 H 0 1 N N N -5.668  18.520 20.413 7.022  -4.898 -1.183 H43 AB1 86 
AB1 H44 H44 H 0 1 N N N -6.020  17.643 23.802 6.280  -3.648 1.567  H44 AB1 87 
AB1 H45 H45 H 0 1 N N N -5.278  18.981 22.845 4.755  -2.959 0.958  H45 AB1 88 
AB1 H46 H46 H 0 1 N N N -6.881  19.138 23.657 5.257  -4.591 0.456  H46 AB1 89 
AB1 H38 H38 H 0 1 N N N -11.042 16.592 21.965 7.854  0.845  -1.470 H38 AB1 90 
AB1 H39 H39 H 0 1 N N N -10.971 15.494 20.541 7.085  0.601  -3.057 H39 AB1 91 
AB1 H40 H40 H 0 1 N N N -10.185 15.090 22.108 6.079  0.820  -1.605 H40 AB1 92 
AB1 H6  H6  H 0 1 N N N -10.921 11.733 35.074 -7.444 0.661  -3.285 H6  AB1 93 
AB1 H7  H7  H 0 1 N N N -10.903 13.207 35.889 -8.618 -0.378 -2.435 H7  AB1 94 
# 
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 
AB1 C1  N2  SING N N 1  
AB1 C1  C37 SING N N 2  
AB1 C1  H2  SING N N 3  
AB1 C1  H3  SING N N 4  
AB1 C2  N1  SING N N 5  
AB1 C2  C37 SING N N 6  
AB1 C2  H4  SING N N 7  
AB1 C2  H5  SING N N 8  
AB1 N1  C3  SING N N 9  
AB1 N1  C10 SING N N 10 
AB1 C3  N2  SING N N 11 
AB1 C3  O1  DOUB N N 12 
AB1 N2  H8  SING N N 13 
AB1 C4  C5  DOUB Y N 14 
AB1 C4  C9  SING Y N 15 
AB1 C4  C29 SING N N 16 
AB1 C5  C6  SING Y N 17 
AB1 C5  H30 SING N N 18 
AB1 C6  C7  DOUB Y N 19 
AB1 C6  H31 SING N N 20 
AB1 C7  C8  SING Y N 21 
AB1 C7  H32 SING N N 22 
AB1 C8  C9  DOUB Y N 23 
AB1 C8  H33 SING N N 24 
AB1 C9  H34 SING N N 25 
AB1 C10 C11 SING N N 26 
AB1 C10 C13 SING N N 27 
AB1 C10 H9  SING N N 28 
AB1 C11 N3  SING N N 29 
AB1 C11 O2  DOUB N N 30 
AB1 N3  C12 SING N N 31 
AB1 N3  H15 SING N N 32 
AB1 C12 C22 SING N N 33 
AB1 C12 C23 SING N N 34 
AB1 C12 H16 SING N N 35 
AB1 C13 C14 SING N N 36 
AB1 C13 C15 SING N N 37 
AB1 C13 H10 SING N N 38 
AB1 C14 H11 SING N N 39 
AB1 C14 H12 SING N N 40 
AB1 C14 H47 SING N N 41 
AB1 C15 H13 SING N N 42 
AB1 C15 H14 SING N N 43 
AB1 C15 H48 SING N N 44 
AB1 C16 C17 DOUB Y N 45 
AB1 C16 C21 SING Y N 46 
AB1 C16 H20 SING N N 47 
AB1 C17 C18 SING Y N 48 
AB1 C17 H21 SING N N 49 
AB1 C18 C19 DOUB Y N 50 
AB1 C18 H22 SING N N 51 
AB1 C19 C20 SING Y N 52 
AB1 C19 H23 SING N N 53 
AB1 C20 C21 DOUB Y N 54 
AB1 C20 C22 SING N N 55 
AB1 C21 H19 SING N N 56 
AB1 C22 H17 SING N N 57 
AB1 C22 H18 SING N N 58 
AB1 C23 C24 SING N N 59 
AB1 C23 H24 SING N N 60 
AB1 C23 H25 SING N N 61 
AB1 C24 C25 SING N N 62 
AB1 C24 O4  SING N N 63 
AB1 C24 H26 SING N N 64 
AB1 C25 N4  SING N N 65 
AB1 C25 C29 SING N N 66 
AB1 C25 H27 SING N N 67 
AB1 N4  C26 SING N N 68 
AB1 N4  H35 SING N N 69 
AB1 C26 C27 SING N N 70 
AB1 C26 O5  DOUB N N 71 
AB1 C27 O3  SING N N 72 
AB1 C27 H36 SING N N 73 
AB1 C27 H37 SING N N 74 
AB1 O3  C28 SING N N 75 
AB1 C28 C30 DOUB Y N 76 
AB1 C28 C34 SING Y N 77 
AB1 O4  H1  SING N N 78 
AB1 C29 H28 SING N N 79 
AB1 C29 H29 SING N N 80 
AB1 C30 C31 SING Y N 81 
AB1 C30 C36 SING N N 82 
AB1 C31 C32 DOUB Y N 83 
AB1 C31 H41 SING N N 84 
AB1 C32 C33 SING Y N 85 
AB1 C32 H42 SING N N 86 
AB1 C33 C34 DOUB Y N 87 
AB1 C33 H43 SING N N 88 
AB1 C34 C35 SING N N 89 
AB1 C35 H44 SING N N 90 
AB1 C35 H45 SING N N 91 
AB1 C35 H46 SING N N 92 
AB1 C36 H38 SING N N 93 
AB1 C36 H39 SING N N 94 
AB1 C36 H40 SING N N 95 
AB1 C37 H6  SING N N 96 
AB1 C37 H7  SING N N 97 
# 
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 
AB1 SMILES           ACDLabs              10.04 O=C(NC(Cc1ccccc1)C(O)CC(NC(=O)C(N2C(=O)NCCC2)C(C)C)Cc3ccccc3)COc4c(cccc4C)C 
AB1 InChI            InChI                1.02b 
;InChI=1/C37H48N4O5/c1-25(2)34(41-20-12-19-38-37(41)45)36(44)39-30(21-28-15-7-5-8-16-28)23-32(42)31(22-29-17-9-6-10-18-29)40-33(43)24-46-35-26(3)13-11-14-27(35)4/h5-11,13-18,25,30-32,34,42H,12,19-24H2,1-4H3,(H,38,45)(H,39,44)(H,40,43)/t30-,31-,32-,34-/m0/s1/f/h38-40H
;
AB1 InChIKey         InChI                1.02b KJHKTHWMRKYKJE-WDUOEAFFDT 
AB1 SMILES_CANONICAL CACTVS               3.341 CC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)COc3c(C)cccc3C)Cc4ccccc4 
AB1 SMILES           CACTVS               3.341 CC(C)[CH](N1CCCNC1=O)C(=O)N[CH](C[CH](O)[CH](Cc2ccccc2)NC(=O)COc3c(C)cccc3C)Cc4ccccc4 
AB1 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1cccc(c1OCC(=O)N[C@@H](Cc2ccccc2)[C@H](C[C@H](Cc3ccccc3)NC(=O)[C@H](C(C)C)N4CCCNC4=O)O)C 
AB1 SMILES           "OpenEye OEToolkits" 1.5.0 Cc1cccc(c1OCC(=O)NC(Cc2ccccc2)C(CC(Cc3ccccc3)NC(=O)C(C(C)C)N4CCCNC4=O)O)C 
# 
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 
AB1 "SYSTEMATIC NAME" ACDLabs              10.04 (2S)-N-[(1S,3S,4S)-1-benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-hydroxy-5-phenylpentyl]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanamide 
AB1 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S)-N-[(2S,4S,5S)-5-[2-(2,6-dimethylphenoxy)ethanoylamino]-4-hydroxy-1,6-diphenyl-hexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide         
# 
