data_4PR
# 
_chem_comp.id                                    4PR 
_chem_comp.name                                  (3S)-1-{[(3,5-DIMETHYLISOXAZOL-4-YL)AMINO]CARBONYL}-4,4-DIMETHYLPYRROLIDIN-3-YL{(1S)-1-[1-HYDROXY-2-OXO-2-{[(1R)-1-PHENYLETHYL]AMINO}ETHYL]PENTYL}CARBAMATE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C28 H41 N5 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-11-08 
_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                        543.655 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     4PR 
_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        2BDL 
_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 
4PR C1   C1   C 0 1 N N N 73.688 93.336  163.171 0.271   3.833  1.197  C1   4PR 1  
4PR C2   C2   C 0 1 N N N 74.814 94.247  162.765 -0.774  3.582  0.108  C2   4PR 2  
4PR C3   C3   C 0 1 N N N 75.497 94.763  164.006 -1.106  2.090  0.054  C3   4PR 3  
4PR C4   C4   C 0 1 N N N 76.967 94.440  163.922 -2.151  1.839  -1.035 C4   4PR 4  
4PR C5   C5   C 0 1 N N S 77.754 95.261  164.921 -2.483  0.347  -1.089 C5   4PR 5  
4PR N1   N1   N 0 1 N N N 77.860 96.596  164.388 -1.297  -0.403 -1.510 N1   4PR 6  
4PR C6   C6   C 0 1 N N N 77.386 97.691  165.067 -0.375  -0.773 -0.599 C6   4PR 7  
4PR O1   O1   O 0 1 N N N 76.781 97.685  166.128 -0.528  -0.485 0.572  O1   4PR 8  
4PR O2   O2   O 0 1 N N N 77.708 98.808  164.368 0.715   -1.462 -0.986 O2   4PR 9  
4PR C7   C7   C 0 1 N N S 77.231 100.013 164.950 1.708   -1.861 -0.004 C7   4PR 10 
4PR C8   C8   C 0 1 N N N 75.837 100.255 164.424 2.840   -0.816 0.083  C8   4PR 11 
4PR N2   N2   N 0 1 N N N 76.030 101.107 163.286 4.103   -1.552 0.234  N2   4PR 12 
4PR C9   C9   C 0 1 N N N 77.338 101.704 163.227 3.807   -2.996 0.271  C9   4PR 13 
4PR C10  C10  C 0 1 N N N 78.074 101.161 164.433 2.449   -3.144 -0.463 C10  4PR 14 
4PR C11  C11  C 0 1 N N N 78.203 102.249 165.476 1.712   -4.404 -0.004 C11  4PR 15 
4PR C12  C12  C 0 1 N N N 79.458 100.689 164.053 2.643   -3.148 -1.981 C12  4PR 16 
4PR C13  C13  C 0 1 N N N 74.990 101.414 162.437 5.329   -0.999 0.324  C13  4PR 17 
4PR O3   O3   O 0 1 N N N 73.835 101.058 162.640 6.309   -1.709 0.447  O3   4PR 18 
4PR N3   N3   N 0 1 N N N 75.387 102.156 161.350 5.469   0.341  0.278  N3   4PR 19 
4PR C14  C14  C 0 1 Y N N 74.704 102.047 160.156 6.734   0.924  0.483  C14  4PR 20 
4PR C15  C15  C 0 1 Y N N 74.645 100.952 159.260 7.707   1.265  -0.491 C15  4PR 21 
4PR C16  C16  C 0 1 N N N 75.300 99.642  159.368 7.596   1.079  -1.982 C16  4PR 22 
4PR N4   N4   N 0 1 Y N N 73.875 101.231 158.202 8.712   1.778  0.159  N4   4PR 23 
4PR O4   O4   O 0 1 Y N N 73.418 102.533 158.403 8.512   1.795  1.351  O4   4PR 24 
4PR C17  C17  C 0 1 Y N N 73.920 103.014 159.574 7.308   1.286  1.659  C17  4PR 25 
4PR C18  C18  C 0 1 N N N 73.543 104.385 159.952 6.714   1.143  3.036  C18  4PR 26 
4PR C19  C19  C 0 1 N N S 79.175 94.764  164.949 -3.616  0.112  -2.090 C19  4PR 27 
4PR O5   O5   O 0 1 N N N 80.029 95.187  163.900 -3.252  0.661  -3.358 O5   4PR 28 
4PR C20  C20  C 0 1 N N N 79.264 93.273  165.139 -4.871  0.783  -1.594 C20  4PR 29 
4PR O6   O6   O 0 1 N N N 78.812 92.764  166.154 -5.352  1.707  -2.216 O6   4PR 30 
4PR N5   N5   N 0 1 N N N 79.863 92.627  164.076 -5.461  0.355  -0.460 N5   4PR 31 
4PR C21  C21  C 0 1 N N R 80.008 91.184  164.045 -6.681  1.007  0.022  C21  4PR 32 
4PR C22  C22  C 0 1 N N N 80.894 90.762  162.896 -6.308  2.236  0.853  C22  4PR 33 
4PR C23  C23  C 0 1 Y N N 78.702 90.469  163.927 -7.462  0.041  0.876  C23  4PR 34 
4PR C24  C24  C 0 1 Y N N 78.501 89.298  164.627 -6.800  -0.800 1.751  C24  4PR 35 
4PR C25  C25  C 0 1 Y N N 77.304 88.624  164.530 -7.516  -1.682 2.538  C25  4PR 36 
4PR C26  C26  C 0 1 Y N N 76.297 89.120  163.733 -8.895  -1.730 2.443  C26  4PR 37 
4PR C27  C27  C 0 1 Y N N 76.493 90.287  163.032 -9.557  -0.892 1.564  C27  4PR 38 
4PR C28  C28  C 0 1 Y N N 77.691 90.959  163.127 -8.840  -0.007 0.781  C28  4PR 39 
4PR H11  1H1  H 0 1 N N N 73.750 92.399  162.598 0.508   4.896  1.236  H11  4PR 40 
4PR H12  2H1  H 0 1 N N N 72.726 93.829  162.967 -0.125  3.514  2.161  H12  4PR 41 
4PR H13  3H1  H 0 1 N N N 73.765 93.114  164.246 1.175   3.267  0.971  H13  4PR 42 
4PR H21A 1H2  H 0 0 N N N 74.418 95.090  162.180 -1.677  4.148  0.335  H21A 4PR 43 
4PR H22  2H2  H 0 1 N N N 75.536 93.691  162.149 -0.377  3.901  -0.856 H22  4PR 44 
4PR H31  1H3  H 0 1 N N N 75.061 94.288  164.897 -0.202  1.524  -0.172 H31  4PR 45 
4PR H32  2H3  H 0 1 N N N 75.360 95.852  164.079 -1.502  1.771  1.018  H32  4PR 46 
4PR H41  1H4  H 0 1 N N N 77.324 94.677  162.909 -3.055  2.405  -0.809 H41  4PR 47 
4PR H42  2H4  H 0 1 N N N 77.113 93.372  164.141 -1.754  2.158  -1.999 H42  4PR 48 
4PR H5   H5   H 0 1 N N N 77.269 95.209  165.907 -2.795  0.008  -0.101 H5   4PR 49 
4PR HN1  HN1  H 0 1 N N N 78.292 96.729  163.496 -1.175  -0.633 -2.444 HN1  4PR 50 
4PR H7   H7   H 0 1 N N N 77.262 99.943  166.047 1.245   -2.011 0.971  H7   4PR 51 
4PR H81  1H8  H 0 1 N N N 75.178 100.709 165.179 2.865   -0.220 -0.829 H81  4PR 52 
4PR H82  2H8  H 0 1 N N N 75.350 99.311  164.137 2.682   -0.169 0.946  H82  4PR 53 
4PR H91  1H9  H 0 1 N N N 77.288 102.803 163.237 4.584   -3.556 -0.250 H91  4PR 54 
4PR H92  2H9  H 0 1 N N N 77.854 101.430 162.295 3.718   -3.339 1.301  H92  4PR 55 
4PR H111 1H11 H 0 0 N N N 77.339 102.927 165.407 1.548   -4.357 1.073  H111 4PR 56 
4PR H112 2H11 H 0 0 N N N 79.129 102.816 165.301 0.752   -4.470 -0.515 H112 4PR 57 
4PR H113 3H11 H 0 0 N N N 78.234 101.796 166.478 2.312   -5.283 -0.242 H113 4PR 58 
4PR H121 1H12 H 0 0 N N N 79.660 99.721  164.535 3.264   -3.997 -2.266 H121 4PR 59 
4PR H122 2H12 H 0 0 N N N 80.202 101.428 164.387 1.673   -3.227 -2.471 H122 4PR 60 
4PR H123 3H12 H 0 0 N N N 79.520 100.574 162.961 3.130   -2.222 -2.287 H123 4PR 61 
4PR HN3  HN3  H 0 1 N N N 76.170 102.774 161.424 4.698   0.903  0.103  HN3  4PR 62 
4PR H161 1H16 H 0 0 N N N 74.659 98.958  159.945 8.087   0.150  -2.270 H161 4PR 63 
4PR H162 2H16 H 0 0 N N N 76.267 99.757  159.879 6.544   1.037  -2.266 H162 4PR 64 
4PR H163 3H16 H 0 0 N N N 75.464 99.229  158.362 8.076   1.916  -2.489 H163 4PR 65 
4PR H181 1H18 H 0 0 N N N 72.581 104.642 159.485 6.988   0.173  3.452  H181 4PR 66 
4PR H182 2H18 H 0 0 N N N 74.317 105.086 159.607 7.095   1.935  3.681  H182 4PR 67 
4PR H183 3H18 H 0 0 N N N 73.449 104.452 161.046 5.628   1.217  2.973  H183 4PR 68 
4PR H19  H19  H 0 1 N N N 79.572 95.273  165.840 -3.793  -0.958 -2.195 H19  4PR 69 
4PR HO5  HO5  H 0 1 N N N 79.526 95.282  163.100 -3.105  1.607  -3.222 HO5  4PR 70 
4PR HN5  HN5  H 0 1 N N N 80.206 93.168  163.308 -5.077  -0.384 0.037  HN5  4PR 71 
4PR H21  H21  H 0 1 N N N 80.464 90.906  165.007 -7.289  1.314  -0.828 H21  4PR 72 
4PR H221 1H22 H 0 0 N N N 81.366 89.797  163.133 -5.743  2.934  0.235  H221 4PR 73 
4PR H222 2H22 H 0 0 N N N 81.673 91.522  162.735 -7.216  2.721  1.212  H222 4PR 74 
4PR H223 3H22 H 0 0 N N N 80.288 90.659  161.984 -5.700  1.929  1.704  H223 4PR 75 
4PR H24  H24  H 0 1 N N N 79.287 88.907  165.255 -5.723  -0.762 1.825  H24  4PR 76 
4PR H25  H25  H 0 1 N N N 77.155 87.706  165.079 -6.999  -2.336 3.224  H25  4PR 77 
4PR H26  H26  H 0 1 N N N 75.356 88.595  163.658 -9.455  -2.421 3.055  H26  4PR 78 
4PR H27  H27  H 0 1 N N N 75.705 90.677  162.405 -10.633 -0.930 1.490  H27  4PR 79 
4PR H28  H28  H 0 1 N N N 77.840 91.874  162.573 -9.357  0.647  0.095  H28  4PR 80 
# 
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 
4PR C1  C2   SING N N 1  
4PR C1  H11  SING N N 2  
4PR C1  H12  SING N N 3  
4PR C1  H13  SING N N 4  
4PR C2  C3   SING N N 5  
4PR C2  H21A SING N N 6  
4PR C2  H22  SING N N 7  
4PR C3  C4   SING N N 8  
4PR C3  H31  SING N N 9  
4PR C3  H32  SING N N 10 
4PR C4  C5   SING N N 11 
4PR C4  H41  SING N N 12 
4PR C4  H42  SING N N 13 
4PR C5  N1   SING N N 14 
4PR C5  C19  SING N N 15 
4PR C5  H5   SING N N 16 
4PR N1  C6   SING N N 17 
4PR N1  HN1  SING N N 18 
4PR C6  O1   DOUB N N 19 
4PR C6  O2   SING N N 20 
4PR O2  C7   SING N N 21 
4PR C7  C8   SING N N 22 
4PR C7  C10  SING N N 23 
4PR C7  H7   SING N N 24 
4PR C8  N2   SING N N 25 
4PR C8  H81  SING N N 26 
4PR C8  H82  SING N N 27 
4PR N2  C9   SING N N 28 
4PR N2  C13  SING N N 29 
4PR C9  C10  SING N N 30 
4PR C9  H91  SING N N 31 
4PR C9  H92  SING N N 32 
4PR C10 C11  SING N N 33 
4PR C10 C12  SING N N 34 
4PR C11 H111 SING N N 35 
4PR C11 H112 SING N N 36 
4PR C11 H113 SING N N 37 
4PR C12 H121 SING N N 38 
4PR C12 H122 SING N N 39 
4PR C12 H123 SING N N 40 
4PR C13 O3   DOUB N N 41 
4PR C13 N3   SING N N 42 
4PR N3  C14  SING N N 43 
4PR N3  HN3  SING N N 44 
4PR C14 C15  SING Y N 45 
4PR C14 C17  DOUB Y N 46 
4PR C15 C16  SING N N 47 
4PR C15 N4   DOUB Y N 48 
4PR C16 H161 SING N N 49 
4PR C16 H162 SING N N 50 
4PR C16 H163 SING N N 51 
4PR N4  O4   SING Y N 52 
4PR O4  C17  SING Y N 53 
4PR C17 C18  SING N N 54 
4PR C18 H181 SING N N 55 
4PR C18 H182 SING N N 56 
4PR C18 H183 SING N N 57 
4PR C19 O5   SING N N 58 
4PR C19 C20  SING N N 59 
4PR C19 H19  SING N N 60 
4PR O5  HO5  SING N N 61 
4PR C20 O6   DOUB N N 62 
4PR C20 N5   SING N N 63 
4PR N5  C21  SING N N 64 
4PR N5  HN5  SING N N 65 
4PR C21 C22  SING N N 66 
4PR C21 C23  SING N N 67 
4PR C21 H21  SING N N 68 
4PR C22 H221 SING N N 69 
4PR C22 H222 SING N N 70 
4PR C22 H223 SING N N 71 
4PR C23 C24  SING Y N 72 
4PR C23 C28  DOUB Y N 73 
4PR C24 C25  DOUB Y N 74 
4PR C24 H24  SING N N 75 
4PR C25 C26  SING Y N 76 
4PR C25 H25  SING N N 77 
4PR C26 C27  DOUB Y N 78 
4PR C26 H26  SING N N 79 
4PR C27 C28  SING Y N 80 
4PR C27 H27  SING N N 81 
4PR C28 H28  SING N N 82 
# 
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 
4PR SMILES           ACDLabs              10.04 O=C(Nc1c(onc1C)C)N3CC(C)(C)C(OC(=O)NC(C(O)C(=O)NC(c2ccccc2)C)CCCC)C3 
4PR InChI            InChI                1.02b 
InChI=1/C28H41N5O6/c1-7-8-14-21(24(34)25(35)29-17(2)20-12-10-9-11-13-20)30-27(37)38-22-15-33(16-28(22,5)6)26(36)31-23-18(3)32-39-19(23)4/h9-13,17,21-22,24,34H,7-8,14-16H2,1-6H3,(H,29,35)(H,30,37)(H,31,36)/t17-,21+,22-,24+/m1/s1/f/h29-31H 
4PR InChIKey         InChI                1.02b VVZICJQTDYOKIN-ZMMHZLKFDA 
4PR SMILES_CANONICAL CACTVS               3.341 CCCC[C@H](NC(=O)O[C@@H]1CN(CC1(C)C)C(=O)Nc2c(C)onc2C)[C@H](O)C(=O)N[C@H](C)c3ccccc3 
4PR SMILES           CACTVS               3.341 CCCC[CH](NC(=O)O[CH]1CN(CC1(C)C)C(=O)Nc2c(C)onc2C)[CH](O)C(=O)N[CH](C)c3ccccc3 
4PR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCCC[C@@H]([C@@H](C(=O)N[C@H](C)c1ccccc1)O)NC(=O)O[C@@H]2CN(CC2(C)C)C(=O)Nc3c(noc3C)C 
4PR SMILES           "OpenEye OEToolkits" 1.5.0 CCCCC(C(C(=O)NC(C)c1ccccc1)O)NC(=O)OC2CN(CC2(C)C)C(=O)Nc3c(noc3C)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 
4PR "SYSTEMATIC NAME" ACDLabs              10.04 "(3S)-1-[(3,5-dimethylisoxazol-4-yl)carbamoyl]-4,4-dimethylpyrrolidin-3-yl {(1S)-1-[(1S)-1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl]pentyl}carbamate"   
4PR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(3S)-1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbamoyl]-4,4-dimethyl-pyrrolidin-3-yl] N-[(2S,3S)-2-hydroxy-1-oxo-1-[[(1R)-1-phenylethyl]amino]heptan-3-yl]carbamate" 
# 
