data_186
# 
_chem_comp.id                                    186 
_chem_comp.name                                  "[1-(1-METHYL-4,5-DIOXO-PENT-2-ENYLCARBAMOYL)-2-PHENYL-ETHYL]-CARBAMIC ACID BENZYL ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H24 N2 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-08-18 
_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                        408.447 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     186 
_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        ? 
_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 
186 O34  O34  O 0 1 N N N 0.503  13.373 5.698  1.798  0.743  -1.209 O34  186 1  
186 C18  C18  C 0 1 N N N 1.016  12.328 5.374  1.898  -0.064 -0.306 C18  186 2  
186 O26  O26  O 0 1 N N N 0.985  12.012 3.965  3.054  -0.730 -0.123 O26  186 3  
186 C27  C27  C 0 1 N N N 0.597  13.147 3.119  4.181  -0.484 -1.005 C27  186 4  
186 C28  C28  C 0 1 Y N N 0.699  12.926 1.624  5.343  -1.349 -0.589 C28  186 5  
186 C33  C33  C 0 1 Y N N -0.344 12.300 0.917  5.493  -2.612 -1.129 C33  186 6  
186 C32  C32  C 0 1 Y N N -0.184 12.051 -0.445 6.558  -3.405 -0.748 C32  186 7  
186 C31  C31  C 0 1 Y N N 1.003  12.446 -1.085 7.475  -2.935 0.174  C31  186 8  
186 C30  C30  C 0 1 Y N N 2.048  13.073 -0.415 7.326  -1.671 0.714  C30  186 9  
186 C29  C29  C 0 1 Y N N 1.862  13.307 0.950  6.262  -0.876 0.329  C29  186 10 
186 N17  N17  N 0 1 N N N 1.474  11.649 6.400  0.852  -0.293 0.513  N17  186 11 
186 C13  C13  C 0 1 N N R 2.209  10.466 6.436  -0.405 0.432  0.314  C13  186 12 
186 C16  C16  C 0 1 N N N 1.672  9.544  7.528  -0.333 1.785  1.025  C16  186 13 
186 C20  C20  C 0 1 Y N N 0.507  8.729  6.974  0.726  2.638  0.374  C20  186 14 
186 C25  C25  C 0 1 Y N N 0.739  7.607  6.202  0.393  3.469  -0.679 C25  186 15 
186 C24  C24  C 0 1 Y N N -0.344 6.885  5.712  1.364  4.252  -1.275 C24  186 16 
186 C23  C23  C 0 1 Y N N -1.656 7.274  5.978  2.667  4.203  -0.819 C23  186 17 
186 C22  C22  C 0 1 Y N N -1.904 8.401  6.749  3.000  3.372  0.235  C22  186 18 
186 C21  C21  C 0 1 Y N N -0.812 9.118  7.245  2.029  2.593  0.834  C21  186 19 
186 C12  C12  C 0 1 N N N 3.513  11.084 6.813  -1.544 -0.374 0.883  C12  186 20 
186 O19  O19  O 0 1 N N N 4.364  11.199 5.955  -1.327 -1.448 1.404  O19  186 21 
186 N11  N11  N 0 1 N N N 3.712  11.547 8.023  -2.805 0.098  0.813  N11  186 22 
186 C8   C8   C 0 1 N N S 5.058  12.118 8.310  -3.912 -0.685 1.367  C8   186 23 
186 C14  C14  C 0 1 N N N 4.993  13.655 8.474  -4.043 -0.397 2.863  C14  186 24 
186 C7   C7   C 0 1 N N N 5.723  11.469 9.540  -5.193 -0.307 0.668  C7   186 25 
186 C6   C6   C 0 1 N N N 5.845  12.338 10.534 -5.889 -1.233 0.000  C6   186 26 
186 C5   C5   C 0 1 N N N 6.387  12.244 11.880 -7.134 -0.865 -0.679 C5   186 27 
186 O10  O10  O 0 1 N N N 7.481  11.779 12.112 -7.535 0.281  -0.635 O10  186 28 
186 C4   C4   C 0 1 N N N 5.559  12.827 12.947 -7.909 -1.896 -1.423 C4   186 29 
186 O9   O9   O 0 1 N N N 5.455  12.218 13.991 -8.936 -1.593 -1.983 O9   186 30 
186 H271 1H27 H 0 0 N N N 1.181  14.052 3.409  3.899  -0.723 -2.030 H271 186 31 
186 H272 2H27 H 0 0 N N N -0.434 13.481 3.383  4.469  0.566  -0.942 H272 186 32 
186 H33  H33  H 0 1 N N N -1.278 12.007 1.426  4.777  -2.979 -1.850 H33  186 33 
186 H32  H32  H 0 1 N N N -0.987 11.548 -1.009 6.675  -4.393 -1.170 H32  186 34 
186 H31  H31  H 0 1 N N N 1.120  12.255 -2.165 8.307  -3.555 0.473  H31  186 35 
186 H30  H30  H 0 1 N N N 2.973  13.368 -0.937 8.041  -1.304 1.435  H30  186 36 
186 H29  H29  H 0 1 N N N 2.663  13.811 1.517  6.146  0.111  0.751  H29  186 37 
186 H17  H17  H 0 1 N N N 1.227  12.098 7.282  0.932  -0.936 1.234  H17  186 38 
186 H13  H13  H 0 1 N N N 2.214  9.827  5.523  -0.569 0.590  -0.752 H13  186 39 
186 H161 1H16 H 0 0 N N N 1.395  10.102 8.453  -1.298 2.285  0.952  H161 186 40 
186 H162 2H16 H 0 0 N N N 2.469  8.898  7.965  -0.081 1.631  2.074  H162 186 41 
186 H25  H25  H 0 1 N N N 1.773  7.293  5.980  -0.626 3.507  -1.035 H25  186 42 
186 H24  H24  H 0 1 N N N -0.159 5.986  5.100  1.103  4.901  -2.098 H24  186 43 
186 H23  H23  H 0 1 N N N -2.500 6.688  5.577  3.426  4.814  -1.285 H23  186 44 
186 H22  H22  H 0 1 N N N -2.939 8.718  6.961  4.019  3.334  0.591  H22  186 45 
186 H21  H21  H 0 1 N N N -0.995 10.012 7.865  2.289  1.944  1.657  H21  186 46 
186 H11  H11  H 0 1 N N N 2.920  11.472 8.661  -2.979 0.957  0.397  H11  186 47 
186 H8   H8   H 0 1 N N N 5.696  11.883 7.427  -3.717 -1.747 1.217  H8   186 48 
186 H141 1H14 H 0 0 N N N 4.248  13.953 9.249  -4.239 0.665  3.013  H141 186 49 
186 H142 2H14 H 0 0 N N N 6.000  14.082 8.689  -4.867 -0.980 3.275  H142 186 50 
186 H143 3H14 H 0 0 N N N 4.522  14.142 7.588  -3.117 -0.671 3.369  H143 186 51 
186 H7   H7   H 0 1 N N N 6.091  10.441 9.700  -5.549 0.712  0.708  H7   186 52 
186 H6   H6   H 0 1 N N N 5.427  13.297 10.184 -5.533 -2.252 -0.039 H6   186 53 
186 H4   H4   H 0 1 N N N 4.987  13.770 12.965 -7.553 -2.915 -1.462 H4   186 54 
# 
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 
186 O34 C18  DOUB N N 1  
186 C18 O26  SING N N 2  
186 C18 N17  SING N N 3  
186 O26 C27  SING N N 4  
186 C27 C28  SING N N 5  
186 C27 H271 SING N N 6  
186 C27 H272 SING N N 7  
186 C28 C33  DOUB Y N 8  
186 C28 C29  SING Y N 9  
186 C33 C32  SING Y N 10 
186 C33 H33  SING N N 11 
186 C32 C31  DOUB Y N 12 
186 C32 H32  SING N N 13 
186 C31 C30  SING Y N 14 
186 C31 H31  SING N N 15 
186 C30 C29  DOUB Y N 16 
186 C30 H30  SING N N 17 
186 C29 H29  SING N N 18 
186 N17 C13  SING N N 19 
186 N17 H17  SING N N 20 
186 C13 C16  SING N N 21 
186 C13 C12  SING N N 22 
186 C13 H13  SING N N 23 
186 C16 C20  SING N N 24 
186 C16 H161 SING N N 25 
186 C16 H162 SING N N 26 
186 C20 C25  DOUB Y N 27 
186 C20 C21  SING Y N 28 
186 C25 C24  SING Y N 29 
186 C25 H25  SING N N 30 
186 C24 C23  DOUB Y N 31 
186 C24 H24  SING N N 32 
186 C23 C22  SING Y N 33 
186 C23 H23  SING N N 34 
186 C22 C21  DOUB Y N 35 
186 C22 H22  SING N N 36 
186 C21 H21  SING N N 37 
186 C12 O19  DOUB N N 38 
186 C12 N11  SING N N 39 
186 N11 C8   SING N N 40 
186 N11 H11  SING N N 41 
186 C8  C14  SING N N 42 
186 C8  C7   SING N N 43 
186 C8  H8   SING N N 44 
186 C14 H141 SING N N 45 
186 C14 H142 SING N N 46 
186 C14 H143 SING N N 47 
186 C7  C6   DOUB N E 48 
186 C7  H7   SING N N 49 
186 C6  C5   SING N N 50 
186 C6  H6   SING N N 51 
186 C5  O10  DOUB N N 52 
186 C5  C4   SING N N 53 
186 C4  O9   DOUB N N 54 
186 C4  H4   SING N N 55 
# 
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 
186 SMILES           ACDLabs              10.04 O=CC(=O)\C=C\C(NC(=O)C(NC(=O)OCc1ccccc1)Cc2ccccc2)C                                                                                                                                        
186 InChI            InChI                1.02b InChI=1/C23H24N2O5/c1-17(12-13-20(27)15-26)24-22(28)21(14-18-8-4-2-5-9-18)25-23(29)30-16-19-10-6-3-7-11-19/h2-13,15,17,21H,14,16H2,1H3,(H,24,28)(H,25,29)/b13-12+/t17-,21+/m0/s1/f/h24-25H 
186 InChIKey         InChI                1.02b NOXVWFAAXREWMI-OPLAELLTDD                                                                                                                                                                  
186 SMILES_CANONICAL CACTVS               3.341 C[C@H](NC(=O)[C@@H](Cc1ccccc1)NC(=O)OCc2ccccc2)\C=C\C(=O)C=O                                                                                                                               
186 SMILES           CACTVS               3.341 C[CH](NC(=O)[CH](Cc1ccccc1)NC(=O)OCc2ccccc2)C=CC(=O)C=O                                                                                                                                    
186 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@@H](\C=C\C(=O)C=O)NC(=O)[C@@H](Cc1ccccc1)NC(=O)OCc2ccccc2                                                                                                                              
186 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C=CC(=O)C=O)NC(=O)C(Cc1ccccc1)NC(=O)OCc2ccccc2                                                                                                                                          
# 
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 
186 "SYSTEMATIC NAME" ACDLabs              10.04 Nalpha-[(benzyloxy)carbonyl]-N-[(1S,2E)-1-methyl-4,5-dioxopent-2-en-1-yl]-D-phenylalaninamide        
186 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "phenylmethyl N-[(2R)-1-[[(E,2S)-5,6-dioxohex-3-en-2-yl]amino]-1-oxo-3-phenyl-propan-2-yl]carbamate" 
# 
