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 2011-06-04 _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 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" 186 InChI InChI 1.03 "InChI=1S/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" 186 InChIKey InChI 1.03 NOXVWFAAXREWMI-GURWAVDKSA-N # 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" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 186 "Create component" 2004-08-18 RCSB 186 "Modify descriptor" 2011-06-04 RCSB #