data_77B
# 
_chem_comp.id                                    77B 
_chem_comp.name                                  "BENZYL N-({(2S,3S)-3-[(BENZYLAMINO)CARBONYL]OXIRAN-2-YL}CARBONYL)-L-ISOLEUCYL-L-PROLINATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C29 H35 N3 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "CA077, N-(L-3-TRANS-BENZYLCARBAMOYLOXIRANE-2-CARBONYL)-L-ISOLEUCYL-L-PROLINE BENZYL ESTER" 
_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                        521.605 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     77B 
_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        2DCC 
_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 
77B C14  C14  C 0 1 Y N N 21.672 15.309 -1.324  -6.419 3.772  -1.820 C14  77B 1  
77B C13  C13  C 0 1 Y N N 21.655 16.534 -0.563  -7.731 3.576  -1.428 C13  77B 2  
77B C12  C12  C 0 1 Y N N 20.404 17.069 -0.076  -8.023 2.691  -0.407 C12  77B 3  
77B C11  C11  C 0 1 Y N N 19.169 16.382 -0.348  -7.003 2.002  0.222  C11  77B 4  
77B C10  C10  C 0 1 Y N N 19.180 15.156 -1.111  -5.692 2.196  -0.170 C10  77B 5  
77B C15  C15  C 0 1 Y N N 20.436 14.618 -1.600  -5.400 3.085  -1.187 C15  77B 6  
77B C20  C20  C 0 1 Y N N 6.567  17.150 -10.677 4.669  4.042  2.556  C20  77B 7  
77B C19  C19  C 0 1 Y N N 6.875  18.321 -9.886  5.216  3.240  1.571  C19  77B 8  
77B C18  C18  C 0 1 Y N N 7.680  18.206 -8.686  4.806  3.381  0.258  C18  77B 9  
77B C17  C17  C 0 1 N N N 8.012  19.455 -7.840  5.402  2.507  -0.815 C17  77B 10 
77B N3   N3   N 0 1 N N N 9.382  19.476 -7.256  4.601  1.288  -0.953 N3   77B 11 
77B C16  C16  C 0 1 N N N 10.530 19.617 -7.948  4.948  0.353  -1.859 C16  77B 12 
77B C2   C2   C 0 1 N N S 11.843 19.589 -7.134  4.124  -0.901 -2.001 C2   77B 13 
77B O1   O1   O 0 1 N N N 11.924 17.241 -6.931  4.818  -2.151 -2.066 O1   77B 14 
77B C3   C3   C 0 1 N N S 12.624 18.335 -7.545  4.132  -1.896 -0.839 C3   77B 15 
77B C4   C4   C 0 1 N N N 14.104 18.343 -7.113  2.868  -2.669 -0.567 C4   77B 16 
77B O4   O4   O 0 1 N N N 14.976 18.849 -7.822  2.844  -3.871 -0.733 O4   77B 17 
77B O2   O2   O 0 1 N N N 10.575 19.744 -9.175  5.922  0.521  -2.561 O2   77B 18 
77B C23  C23  C 0 1 Y N N 8.174  16.899 -8.287  3.853  4.327  -0.070 C23  77B 19 
77B C22  C22  C 0 1 Y N N 7.866  15.729 -9.081  3.303  5.126  0.915  C22  77B 20 
77B C21  C21  C 0 1 Y N N 7.065  15.859 -10.271 3.713  4.984  2.228  C21  77B 21 
77B N1   N1   N 0 1 N N N 14.330 17.750 -5.929  1.763  -2.026 -0.140 N1   77B 22 
77B C5   C5   C 0 1 N N S 15.563 17.608 -5.320  0.566  -2.789 0.223  C5   77B 23 
77B C6   C6   C 0 1 N N N 15.560 16.084 -4.831  -0.664 -1.998 -0.143 C6   77B 24 
77B O5   O5   O 0 1 N N N 14.628 15.782 -4.079  -0.554 -0.863 -0.557 O5   77B 25 
77B C24  C24  C 0 1 N N S 15.913 18.581 -4.086  0.570  -3.056 1.730  C24  77B 26 
77B C26  C26  C 0 1 N N N 15.906 20.089 -4.535  0.778  -1.740 2.481  C26  77B 27 
77B C25  C25  C 0 1 N N N 17.346 18.289 -3.499  1.704  -4.024 2.073  C25  77B 28 
77B C27  C27  C 0 1 N N N 16.205 21.135 -3.467  -0.457 -0.854 2.310  C27  77B 29 
77B N2   N2   N 0 1 N N N 16.505 15.090 -5.191  -1.885 -2.552 -0.010 N2   77B 30 
77B C7   C7   C 0 1 N N S 16.490 13.623 -4.730  -3.151 -1.952 -0.457 C7   77B 31 
77B C8   C8   C 0 1 N N N 16.681 13.490 -3.376  -3.395 -0.650 0.261  C8   77B 32 
77B O7   O7   O 0 1 N N N 17.560 14.429 -2.825  -4.346 0.190  -0.176 O7   77B 33 
77B C9   C9   C 0 1 N N N 17.878 14.433 -1.402  -4.581 1.445  0.516  C9   77B 34 
77B O6   O6   O 0 1 N N N 16.090 12.589 -2.756  -2.734 -0.362 1.231  O6   77B 35 
77B C30  C30  C 0 1 N N N 17.494 12.994 -5.736  -4.276 -2.955 -0.123 C30  77B 36 
77B C29  C29  C 0 1 N N N 18.424 14.097 -6.251  -3.519 -4.305 -0.011 C29  77B 37 
77B C28  C28  C 0 1 N N N 17.652 15.402 -6.103  -2.174 -3.856 0.613  C28  77B 38 
77B H14  H14  H 0 1 N N N 22.608 14.910 -1.686  -6.191 4.463  -2.618 H14  77B 39 
77B H13  H13  H 0 1 N N N 22.579 17.053 -0.357  -8.527 4.115  -1.921 H13  77B 40 
77B H12  H12  H 0 1 N N N 20.396 17.987 0.493   -9.047 2.538  -0.102 H12  77B 41 
77B H11  H11  H 0 1 N N N 18.235 16.783 0.018   -7.231 1.310  1.020  H11  77B 42 
77B H15  H15  H 0 1 N N N 20.445 13.701 -2.170  -4.375 3.238  -1.493 H15  77B 43 
77B H20  H20  H 0 1 N N N 5.966  17.242 -11.569 4.989  3.931  3.581  H20  77B 44 
77B H19  H19  H 0 1 N N N 6.503  19.288 -10.191 5.963  2.504  1.827  H19  77B 45 
77B H171 1H17 H 0 0 N N N 7.313  19.449 -6.991  6.423  2.242  -0.542 H171 77B 46 
77B H172 2H17 H 0 0 N N N 7.914  20.335 -8.492  5.407  3.047  -1.762 H172 77B 47 
77B HN3  HN3  H 0 1 N N N 9.457  19.377 -6.264  3.821  1.154  -0.391 HN3  77B 48 
77B H2   H2   H 0 1 N N N 12.015 20.600 -6.735  3.204  -0.800 -2.577 H2   77B 49 
77B H3   H3   H 0 1 N N N 12.665 18.266 -8.642  4.733  -1.649 0.037  H3   77B 50 
77B H23  H23  H 0 1 N N N 8.774  16.800 -7.394  3.533  4.438  -1.096 H23  77B 51 
77B H22  H22  H 0 1 N N N 8.236  14.760 -8.782  2.556  5.862  0.659  H22  77B 52 
77B H21  H21  H 0 1 N N N 6.836  14.985 -10.862 3.285  5.610  2.998  H21  77B 53 
77B HN1  HN1  H 0 1 N N N 13.537 17.379 -5.446  1.760  -1.058 -0.074 HN1  77B 54 
77B H5   H5   H 0 1 N N N 16.340 17.890 -6.046  0.562  -3.737 -0.314 H5   77B 55 
77B H24  H24  H 0 1 N N N 15.142 18.392 -3.324  -0.383 -3.495 2.023  H24  77B 56 
77B H261 1H26 H 0 0 N N N 14.873 20.290 -4.854  1.652  -1.227 2.079  H261 77B 57 
77B H262 2H26 H 0 0 N N N 16.676 20.196 -5.314  0.934  -1.947 3.540  H262 77B 58 
77B H251 1H25 H 0 0 N N N 17.329 17.338 -2.946  1.640  -4.300 3.125  H251 77B 59 
77B H252 2H25 H 0 0 N N N 17.637 19.104 -2.820  1.617  -4.919 1.456  H252 77B 60 
77B H253 3H25 H 0 0 N N N 18.073 18.221 -4.322  2.663  -3.543 1.881  H253 77B 61 
77B H271 1H27 H 0 0 N N N 15.396 21.880 -3.447  -1.355 -1.471 2.347  H271 77B 62 
77B H272 2H27 H 0 0 N N N 17.158 21.634 -3.699  -0.490 -0.117 3.113  H272 77B 63 
77B H273 3H27 H 0 0 N N N 16.277 20.646 -2.484  -0.407 -0.343 1.349  H273 77B 64 
77B H7   H7   H 0 1 N N N 15.535 13.079 -4.776  -3.115 -1.781 -1.533 H7   77B 65 
77B H91  1H9  H 0 1 N N N 17.070 14.961 -0.874  -4.863 1.242  1.550  H91  77B 66 
77B H92  2H9  H 0 1 N N N 17.971 13.392 -1.060  -3.671 2.045  0.499  H92  77B 67 
77B H301 1H30 H 0 0 N N N 16.949 12.539 -6.576  -5.014 -2.991 -0.924 H301 77B 68 
77B H302 2H30 H 0 0 N N N 18.085 12.214 -5.234  -4.747 -2.697 0.826  H302 77B 69 
77B H291 1H29 H 0 0 N N N 18.715 13.920 -7.297  -3.365 -4.749 -0.994 H291 77B 70 
77B H292 2H29 H 0 0 N N N 19.353 14.127 -5.662  -4.045 -4.994 0.649  H292 77B 71 
77B H281 1H28 H 0 0 N N N 18.286 16.204 -5.697  -1.388 -4.573 0.375  H281 77B 72 
77B H282 2H28 H 0 0 N N N 17.289 15.754 -7.080  -2.274 -3.747 1.693  H282 77B 73 
# 
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 
77B C14 C13  SING Y N 1  
77B C14 C15  DOUB Y N 2  
77B C14 H14  SING N N 3  
77B C13 C12  DOUB Y N 4  
77B C13 H13  SING N N 5  
77B C12 C11  SING Y N 6  
77B C12 H12  SING N N 7  
77B C11 C10  DOUB Y N 8  
77B C11 H11  SING N N 9  
77B C10 C15  SING Y N 10 
77B C10 C9   SING N N 11 
77B C15 H15  SING N N 12 
77B C20 C19  SING Y N 13 
77B C20 C21  DOUB Y N 14 
77B C20 H20  SING N N 15 
77B C19 C18  DOUB Y N 16 
77B C19 H19  SING N N 17 
77B C18 C17  SING N N 18 
77B C18 C23  SING Y N 19 
77B C17 N3   SING N N 20 
77B C17 H171 SING N N 21 
77B C17 H172 SING N N 22 
77B N3  C16  SING N N 23 
77B N3  HN3  SING N N 24 
77B C16 C2   SING N N 25 
77B C16 O2   DOUB N N 26 
77B C2  O1   SING N N 27 
77B C2  C3   SING N N 28 
77B C2  H2   SING N N 29 
77B O1  C3   SING N N 30 
77B C3  C4   SING N N 31 
77B C3  H3   SING N N 32 
77B C4  O4   DOUB N N 33 
77B C4  N1   SING N N 34 
77B C23 C22  DOUB Y N 35 
77B C23 H23  SING N N 36 
77B C22 C21  SING Y N 37 
77B C22 H22  SING N N 38 
77B C21 H21  SING N N 39 
77B N1  C5   SING N N 40 
77B N1  HN1  SING N N 41 
77B C5  C6   SING N N 42 
77B C5  C24  SING N N 43 
77B C5  H5   SING N N 44 
77B C6  O5   DOUB N N 45 
77B C6  N2   SING N N 46 
77B C24 C26  SING N N 47 
77B C24 C25  SING N N 48 
77B C24 H24  SING N N 49 
77B C26 C27  SING N N 50 
77B C26 H261 SING N N 51 
77B C26 H262 SING N N 52 
77B C25 H251 SING N N 53 
77B C25 H252 SING N N 54 
77B C25 H253 SING N N 55 
77B C27 H271 SING N N 56 
77B C27 H272 SING N N 57 
77B C27 H273 SING N N 58 
77B N2  C7   SING N N 59 
77B N2  C28  SING N N 60 
77B C7  C8   SING N N 61 
77B C7  C30  SING N N 62 
77B C7  H7   SING N N 63 
77B C8  O7   SING N N 64 
77B C8  O6   DOUB N N 65 
77B O7  C9   SING N N 66 
77B C9  H91  SING N N 67 
77B C9  H92  SING N N 68 
77B C30 C29  SING N N 69 
77B C30 H301 SING N N 70 
77B C30 H302 SING N N 71 
77B C29 C28  SING N N 72 
77B C29 H291 SING N N 73 
77B C29 H292 SING N N 74 
77B C28 H281 SING N N 75 
77B C28 H282 SING N N 76 
# 
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 
77B SMILES           ACDLabs              10.04 O=C(NC(C(=O)N2C(C(=O)OCc1ccccc1)CCC2)C(C)CC)C4OC4C(=O)NCc3ccccc3 
77B InChI            InChI                1.02b 
InChI=1/C29H35N3O6/c1-3-19(2)23(31-27(34)25-24(38-25)26(33)30-17-20-11-6-4-7-12-20)28(35)32-16-10-15-22(32)29(36)37-18-21-13-8-5-9-14-21/h4-9,11-14,19,22-25H,3,10,15-18H2,1-2H3,(H,30,33)(H,31,34)/t19-,22-,23-,24-,25-/m0/s1/f/h30-31H 
77B InChIKey         InChI                1.02b NFVQITLYIOBLMG-GCBGBUGSDJ 
77B 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)OCc4ccccc4 
77B SMILES           CACTVS               3.341 CC[CH](C)[CH](NC(=O)[CH]1O[CH]1C(=O)NCc2ccccc2)C(=O)N3CCC[CH]3C(=O)OCc4ccccc4 
77B SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)OCc2ccccc2)NC(=O)[C@@H]3[C@H](O3)C(=O)NCc4ccccc4 
77B SMILES           "OpenEye OEToolkits" 1.5.0 CCC(C)C(C(=O)N1CCCC1C(=O)OCc2ccccc2)NC(=O)C3C(O3)C(=O)NCc4ccccc4 
# 
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 
77B "SYSTEMATIC NAME" ACDLabs              10.04 "benzyl N-{[(2S,3S)-3-(benzylcarbamoyl)oxiran-2-yl]carbonyl}-L-isoleucyl-L-prolinate"                                                      
77B "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "phenylmethyl (2S)-1-[(2S,3S)-3-methyl-2-[[(2S,3S)-3-(phenylmethylcarbamoyl)oxiran-2-yl]carbonylamino]pentanoyl]pyrrolidine-2-carboxylate" 
# 
