data_78A
# 
_chem_comp.id                                    78A 
_chem_comp.name                                  N-({(2S,3S)-3-[(BENZYLAMINO)CARBONYL]OXIRAN-2-YL}CARBONYL)-L-ISOLEUCYL-L-PROLINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H29 N3 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "CA078, N-(L-3-TRANS-BENZYLCARBAMOYLOXIRANE-2-CARBONYL)-L-ISOLEUCYL-L-PROLINE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-01-05 
_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                        431.482 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     78A 
_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        2DCD 
_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 
78A N3   N3   N 0 1 N N N 14.155 17.815 -5.902  3.812  -0.578 -0.694 N3   78A 1  
78A C10  C10  C 0 1 N N N 15.487 17.556 -5.313  5.141  0.037  -0.642 C10  78A 2  
78A C11  C11  C 0 1 Y N N 15.998 18.691 -4.427  5.030  1.421  -0.055 C11  78A 3  
78A C16  C16  C 0 1 Y N N 15.087 19.627 -3.859  4.820  2.508  -0.882 C16  78A 4  
78A C15  C15  C 0 1 Y N N 15.563 20.676 -3.039  4.714  3.777  -0.344 C15  78A 5  
78A C14  C14  C 0 1 Y N N 16.949 20.793 -2.784  4.829  3.959  1.022  C14  78A 6  
78A C13  C13  C 0 1 Y N N 17.866 19.870 -3.343  5.044  2.873  1.849  C13  78A 7  
78A C12  C12  C 0 1 Y N N 17.387 18.820 -4.163  5.146  1.604  1.311  C12  78A 8  
78A C2   C2   C 0 1 N N S 12.534 18.176 -7.709  2.299  -2.457 -1.240 C2   78A 9  
78A O1   O1   O 0 1 N N N 11.777 17.143 -7.061  2.169  -3.804 -0.774 O1   78A 10 
78A C3   C3   C 0 1 N N S 11.765 19.501 -7.534  1.620  -2.804 0.086  C3   78A 11 
78A C4   C4   C 0 1 N N N 10.341 19.474 -8.088  0.119  -2.687 0.158  C4   78A 12 
78A O4   O4   O 0 1 N N N 10.150 19.673 -9.290  -0.560 -3.681 0.306  O4   78A 13 
78A N1   N1   N 0 1 N N N 9.366  19.221 -7.213  -0.468 -1.478 0.058  N1   78A 14 
78A C5   C5   C 0 1 N N S 8.132  18.427 -7.543  -1.927 -1.365 0.127  C5   78A 15 
78A C6   C6   C 0 1 N N N 7.121  19.353 -8.337  -2.369 -0.115 -0.591 C6   78A 16 
78A O5   O5   O 0 1 N N N 7.073  20.553 -8.012  -1.546 0.609  -1.110 O5   78A 17 
78A C17  C17  C 0 1 N N S 7.474  17.836 -6.224  -2.364 -1.292 1.592  C17  78A 18 
78A C19  C19  C 0 1 N N N 7.251  18.889 -5.083  -1.725 -0.070 2.255  C19  78A 19 
78A C18  C18  C 0 1 N N N 8.317  16.668 -5.623  -1.916 -2.561 2.321  C18  78A 20 
78A C20  C20  C 0 1 N N N 5.845  18.895 -4.475  -2.258 0.073  3.682  C20  78A 21 
78A N2   N2   N 0 1 N N N 6.242  18.888 -9.300  -3.678 0.197  -0.656 N2   78A 22 
78A C7   C7   C 0 1 N N S 5.202  19.704 -9.967  -4.244 1.383  -1.317 C7   78A 23 
78A C8   C8   C 0 1 N N N 3.927  20.045 -9.117  -3.726 2.640  -0.667 C8   78A 24 
78A O6   O6   O 0 1 N N N 2.993  20.710 -9.546  -4.128 3.840  -1.114 O6   78A 25 
78A C23  C23  C 0 1 N N N 4.922  18.887 -11.238 -5.777 1.305  -1.161 C23  78A 26 
78A C22  C22  C 0 1 N N N 5.144  17.432 -10.827 -6.027 -0.205 -0.906 C22  78A 27 
78A C21  C21  C 0 1 N N N 6.272  17.489 -9.796  -4.779 -0.590 -0.072 C21  78A 28 
78A O7   O7   O 0 1 N N N 3.945  19.539 -7.856  -2.949 2.567  0.255  O7   78A 29 
78A C9   C9   C 0 1 N N N 13.968 18.273 -7.142  3.666  -1.824 -1.186 C9   78A 30 
78A O2   O2   O 0 1 N N N 14.871 18.751 -7.829  4.634  -2.437 -1.585 O2   78A 31 
78A HN3  HN3  H 0 1 N N N 13.348 17.637 -5.339  3.038  -0.088 -0.375 HN3  78A 32 
78A H101 1H10 H 0 0 N N N 16.196 17.453 -6.148  5.798  -0.570 -0.019 H101 78A 33 
78A H102 2H10 H 0 0 N N N 15.417 16.647 -4.697  5.551  0.102  -1.649 H102 78A 34 
78A H16  H16  H 0 1 N N N 14.029 19.535 -4.055  4.730  2.365  -1.949 H16  78A 35 
78A H15  H15  H 0 1 N N N 14.871 21.385 -2.609  4.545  4.625  -0.990 H15  78A 36 
78A H14  H14  H 0 1 N N N 17.312 21.594 -2.157  4.749  4.951  1.442  H14  78A 37 
78A H13  H13  H 0 1 N N N 18.923 19.966 -3.145  5.134  3.016  2.916  H13  78A 38 
78A H12  H12  H 0 1 N N N 18.082 18.113 -4.590  5.314  0.755  1.957  H12  78A 39 
78A H2   H2   H 0 1 N N N 12.646 17.944 -8.778  1.665  -2.143 -2.069 H2   78A 40 
78A H3   H3   H 0 1 N N N 12.009 20.562 -7.375  2.156  -2.576 1.007  H3   78A 41 
78A HN1  HN1  H 0 1 N N N 9.461  19.580 -6.284  0.075  -0.684 -0.061 HN1  78A 42 
78A H5   H5   H 0 1 N N N 8.401  17.570 -8.178  -2.382 -2.235 -0.345 H5   78A 43 
78A H17  H17  H 0 1 N N N 6.491  17.479 -6.565  -3.449 -1.208 1.644  H17  78A 44 
78A H191 1H19 H 0 0 N N N 7.396  19.879 -5.540  -1.972 0.824  1.683  H191 78A 45 
78A H192 2H19 H 0 0 N N N 7.963  18.663 -4.276  -0.642 -0.196 2.282  H192 78A 46 
78A H181 1H18 H 0 0 N N N 7.759  16.200 -4.799  -0.830 -2.645 2.269  H181 78A 47 
78A H182 2H18 H 0 0 N N N 9.271  17.062 -5.243  -2.227 -2.509 3.364  H182 78A 48 
78A H183 3H18 H 0 0 N N N 8.515  15.919 -6.404  -2.371 -3.431 1.849  H183 78A 49 
78A H201 1H20 H 0 0 N N N 5.300  17.998 -4.804  -1.803 0.944  4.154  H201 78A 50 
78A H202 2H20 H 0 0 N N N 5.306  19.795 -4.807  -3.340 0.199  3.654  H202 78A 51 
78A H203 3H20 H 0 0 N N N 5.920  18.896 -3.378  -2.011 -0.821 4.253  H203 78A 52 
78A H7   H7   H 0 1 N N N 5.548  20.730 -10.162 -3.978 1.375  -2.374 H7   78A 53 
78A HO6  HO6  H 0 1 N N N 2.330  20.797 -8.872  -3.795 4.647  -0.697 HO6  78A 54 
78A H231 1H23 H 0 0 N N N 5.576  19.184 -12.071 -6.277 1.630  -2.074 H231 78A 55 
78A H232 2H23 H 0 0 N N N 3.892  19.045 -11.590 -6.106 1.900  -0.309 H232 78A 56 
78A H221 1H22 H 0 0 N N N 5.399  16.793 -11.685 -6.057 -0.760 -1.843 H221 78A 57 
78A H222 2H22 H 0 0 N N N 4.231  17.000 -10.392 -6.942 -0.358 -0.333 H222 78A 58 
78A H211 1H21 H 0 0 N N N 6.138  16.755 -8.988  -4.575 -1.656 -0.166 H211 78A 59 
78A H212 2H21 H 0 0 N N N 7.243  17.249 -10.253 -4.925 -0.321 0.974  H212 78A 60 
# 
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 
78A N3  C10  SING N N 1  
78A N3  C9   SING N N 2  
78A N3  HN3  SING N N 3  
78A C10 C11  SING N N 4  
78A C10 H101 SING N N 5  
78A C10 H102 SING N N 6  
78A C11 C16  SING Y N 7  
78A C11 C12  DOUB Y N 8  
78A C16 C15  DOUB Y N 9  
78A C16 H16  SING N N 10 
78A C15 C14  SING Y N 11 
78A C15 H15  SING N N 12 
78A C14 C13  DOUB Y N 13 
78A C14 H14  SING N N 14 
78A C13 C12  SING Y N 15 
78A C13 H13  SING N N 16 
78A C12 H12  SING N N 17 
78A C2  O1   SING N N 18 
78A C2  C3   SING N N 19 
78A C2  C9   SING N N 20 
78A C2  H2   SING N N 21 
78A O1  C3   SING N N 22 
78A C3  C4   SING N N 23 
78A C3  H3   SING N N 24 
78A C4  O4   DOUB N N 25 
78A C4  N1   SING N N 26 
78A N1  C5   SING N N 27 
78A N1  HN1  SING N N 28 
78A C5  C6   SING N N 29 
78A C5  C17  SING N N 30 
78A C5  H5   SING N N 31 
78A C6  O5   DOUB N N 32 
78A C6  N2   SING N N 33 
78A C17 C19  SING N N 34 
78A C17 C18  SING N N 35 
78A C17 H17  SING N N 36 
78A C19 C20  SING N N 37 
78A C19 H191 SING N N 38 
78A C19 H192 SING N N 39 
78A C18 H181 SING N N 40 
78A C18 H182 SING N N 41 
78A C18 H183 SING N N 42 
78A C20 H201 SING N N 43 
78A C20 H202 SING N N 44 
78A C20 H203 SING N N 45 
78A N2  C7   SING N N 46 
78A N2  C21  SING N N 47 
78A C7  C8   SING N N 48 
78A C7  C23  SING N N 49 
78A C7  H7   SING N N 50 
78A C8  O6   SING N N 51 
78A C8  O7   DOUB N N 52 
78A O6  HO6  SING N N 53 
78A C23 C22  SING N N 54 
78A C23 H231 SING N N 55 
78A C23 H232 SING N N 56 
78A C22 C21  SING N N 57 
78A C22 H221 SING N N 58 
78A C22 H222 SING N N 59 
78A C21 H211 SING N N 60 
78A C21 H212 SING N N 61 
78A C9  O2   DOUB N N 62 
# 
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 
78A SMILES           ACDLabs              10.04 O=C(NC(C(=O)N1C(C(=O)O)CCC1)C(C)CC)C3OC3C(=O)NCc2ccccc2 
78A InChI            InChI                1.02b 
InChI=1/C22H29N3O6/c1-3-13(2)16(21(28)25-11-7-10-15(25)22(29)30)24-20(27)18-17(31-18)19(26)23-12-14-8-5-4-6-9-14/h4-6,8-9,13,15-18H,3,7,10-12H2,1-2H3,(H,23,26)(H,24,27)(H,29,30)/t13-,15-,16-,17-,18-/m0/s1/f/h23-24,29H 
78A InChIKey         InChI                1.02b MERYMLLGRCNRKE-JOUAYTKNDD 
78A SMILES_CANONICAL CACTVS               3.341 CC[C@H](C)[C@H](NC(=O)[C@H]1O[C@@H]1C(=O)NCc2ccccc2)C(=O)N3CCC[C@H]3C(O)=O 
78A SMILES           CACTVS               3.341 CC[CH](C)[CH](NC(=O)[CH]1O[CH]1C(=O)NCc2ccccc2)C(=O)N3CCC[CH]3C(O)=O 
78A SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O)NC(=O)[C@@H]2[C@H](O2)C(=O)NCc3ccccc3 
78A SMILES           "OpenEye OEToolkits" 1.5.0 CCC(C)C(C(=O)N1CCCC1C(=O)O)NC(=O)C2C(O2)C(=O)NCc3ccccc3 
# 
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 
78A "SYSTEMATIC NAME" ACDLabs              10.04 N-{[(2S,3S)-3-(benzylcarbamoyl)oxiran-2-yl]carbonyl}-L-isoleucyl-L-proline                                                        
78A "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-1-[(2S,3S)-3-methyl-2-[[(2S,3S)-3-(phenylmethylcarbamoyl)oxiran-2-yl]carbonylamino]pentanoyl]pyrrolidine-2-carboxylic acid" 
# 
