data_5E8 # _chem_comp.id 5E8 _chem_comp.name "ethyl (2Z,4S)-4-{[(2S)-2-methyl-3-phenylpropanoyl]amino}-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H28 N2 O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2015-09-16 _chem_comp.pdbx_modified_date 2016-03-25 _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 372.458 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 5E8 _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 5DP4 _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 5E8 O1 O1 O 0 1 N N N 29.994 3.981 21.677 -2.750 0.997 1.779 O1 5E8 1 5E8 O2 O2 O 0 1 N N N 24.984 6.386 28.094 -3.066 -3.375 -0.355 O2 5E8 2 5E8 C3 C1 C 0 1 N N N 23.367 2.101 26.228 3.201 0.139 0.840 C3 5E8 3 5E8 C5 C2 C 0 1 Y N N 21.966 0.748 27.882 5.255 -1.186 0.302 C5 5E8 4 5E8 C7 C3 C 0 1 Y N N 20.353 -0.906 27.169 7.381 -0.126 -0.003 C7 5E8 5 5E8 C8 C4 C 0 1 Y N N 20.692 -0.621 25.834 6.800 1.106 0.234 C8 5E8 6 5E8 C12 C5 C 0 1 N N S 28.749 3.460 23.706 -3.246 1.943 -0.394 C12 5E8 7 5E8 C9 C6 C 0 1 Y N N 21.675 0.349 25.515 5.449 1.191 0.516 C9 5E8 8 5E8 C13 C7 C 0 1 N N N 29.952 3.572 22.814 -3.342 1.818 1.111 C13 5E8 9 5E8 C14 C8 C 0 1 N N N 25.745 5.859 24.329 -2.130 -0.290 -2.045 C14 5E8 10 5E8 C15 C9 C 0 1 N N N 24.914 6.059 25.591 -2.735 -1.454 -1.824 C15 5E8 11 5E8 C16 C10 C 0 1 N N N 25.713 6.491 26.824 -2.359 -2.268 -0.660 C16 5E8 12 5E8 C17 C11 C 0 1 N N N 25.566 2.764 25.596 0.949 0.290 -0.188 C17 5E8 13 5E8 C18 C12 C 0 1 N N N 25.605 6.418 29.388 -2.637 -4.131 0.809 C18 5E8 14 5E8 O3 O3 O 0 1 N N N 26.879 6.943 26.804 -1.411 -1.944 0.028 O3 5E8 15 5E8 C19 C13 C 0 1 N N N 26.812 5.480 29.476 -3.552 -5.343 0.995 C19 5E8 16 5E8 C10 C14 C 0 1 N N S 26.696 4.656 24.526 -1.368 0.386 -0.935 C10 5E8 17 5E8 C11 C15 C 0 1 N N N 27.711 4.532 23.405 -1.788 1.855 -0.849 C11 5E8 18 5E8 C26 C16 C 0 1 N N N 29.372 3.581 25.080 -3.823 3.345 -0.696 C26 5E8 19 5E8 C25 C17 C 0 1 N N N 30.740 2.941 24.910 -4.741 3.577 0.526 C25 5E8 20 5E8 N1 N1 N 0 1 N N N 30.971 3.155 23.489 -4.181 2.748 1.599 N1 5E8 21 5E8 N N2 N 0 1 N N N 25.816 3.475 24.466 0.069 0.304 -1.208 N 5E8 22 5E8 O4 O4 O 0 1 N N N 26.051 3.040 26.682 0.550 0.253 0.957 O4 5E8 23 5E8 C2 C18 C 0 1 N N S 24.600 1.619 25.477 2.430 0.319 -0.469 C2 5E8 24 5E8 C1 C19 C 0 1 N N N 25.260 0.371 26.009 2.802 1.663 -1.100 C1 5E8 25 5E8 C4 C20 C 0 1 Y N N 22.321 1.039 26.539 4.676 0.045 0.544 C4 5E8 26 5E8 C6 C21 C 0 1 Y N N 20.992 -0.215 28.205 6.608 -1.272 0.031 C6 5E8 27 5E8 H1 H1 H 0 1 N N N 23.701 2.534 27.182 3.015 0.992 1.492 H1 5E8 28 5E8 H2 H2 H 0 1 N N N 22.885 2.881 25.620 2.871 -0.775 1.333 H2 5E8 29 5E8 H3 H3 H 0 1 N N N 22.459 1.282 28.681 4.652 -2.082 0.328 H3 5E8 30 5E8 H4 H4 H 0 1 N N N 19.605 -1.652 27.393 8.438 -0.193 -0.214 H4 5E8 31 5E8 H5 H5 H 0 1 N N N 20.193 -1.152 25.036 7.403 2.001 0.207 H5 5E8 32 5E8 H6 H6 H 0 1 N N N 28.293 2.465 23.593 -3.843 1.171 -0.880 H6 5E8 33 5E8 H7 H7 H 0 1 N N N 21.922 0.552 24.484 4.996 2.153 0.701 H7 5E8 34 5E8 H8 H8 H 0 1 N N N 25.680 6.463 23.436 -2.184 0.170 -3.021 H8 5E8 35 5E8 H10 H10 H 0 1 N N N 23.845 5.908 25.614 -3.503 -1.801 -2.500 H10 5E8 36 5E8 H12 H12 H 0 1 N N N 25.939 7.445 29.595 -1.611 -4.469 0.665 H12 5E8 37 5E8 H13 H13 H 0 1 N N N 24.865 6.114 30.143 -2.690 -3.497 1.694 H13 5E8 38 5E8 H14 H14 H 0 1 N N N 27.251 5.540 30.483 -3.230 -5.910 1.868 H14 5E8 39 5E8 H15 H15 H 0 1 N N N 26.489 4.447 29.278 -4.578 -5.005 1.139 H15 5E8 40 5E8 H16 H16 H 0 1 N N N 27.563 5.778 28.730 -3.500 -5.977 0.110 H16 5E8 41 5E8 H17 H17 H 0 1 N N N 27.202 4.727 25.500 -1.587 -0.110 0.011 H17 5E8 42 5E8 H18 H18 H 0 1 N N N 28.222 5.498 23.277 -1.684 2.320 -1.829 H18 5E8 43 5E8 H19 H19 H 0 1 N N N 27.186 4.269 22.475 -1.151 2.374 -0.132 H19 5E8 44 5E8 H20 H20 H 0 1 N N N 29.466 4.636 25.377 -3.031 4.093 -0.736 H20 5E8 45 5E8 H21 H21 H 0 1 N N N 28.776 3.041 25.830 -4.399 3.339 -1.621 H21 5E8 46 5E8 H22 H22 H 0 1 N N N 30.719 1.870 25.159 -4.726 4.628 0.814 H22 5E8 47 5E8 H23 H23 H 0 1 N N N 31.501 3.445 25.524 -5.759 3.264 0.297 H23 5E8 48 5E8 H24 H24 H 0 1 N N N 31.861 2.990 23.063 -4.389 2.857 2.540 H24 5E8 49 5E8 H25 H25 H 0 1 N N N 25.405 3.199 23.597 0.387 0.261 -2.124 H25 5E8 50 5E8 H26 H26 H 0 1 N N N 24.341 1.469 24.418 2.685 -0.488 -1.156 H26 5E8 51 5E8 H27 H27 H 0 1 N N N 24.563 -0.476 25.928 3.853 1.649 -1.390 H27 5E8 52 5E8 H28 H28 H 0 1 N N N 26.166 0.157 25.423 2.184 1.834 -1.981 H28 5E8 53 5E8 H29 H29 H 0 1 N N N 25.532 0.522 27.064 2.635 2.462 -0.377 H29 5E8 54 5E8 H30 H30 H 0 1 N N N 20.742 -0.418 29.236 7.062 -2.235 -0.154 H30 5E8 55 # 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 5E8 O1 C13 DOUB N N 1 5E8 C13 N1 SING N N 2 5E8 C13 C12 SING N N 3 5E8 C11 C12 SING N N 4 5E8 C11 C10 SING N N 5 5E8 N1 C25 SING N N 6 5E8 C12 C26 SING N N 7 5E8 C14 C10 SING N N 8 5E8 C14 C15 DOUB N Z 9 5E8 N C10 SING N N 10 5E8 N C17 SING N N 11 5E8 C25 C26 SING N N 12 5E8 C2 C17 SING N N 13 5E8 C2 C1 SING N N 14 5E8 C2 C3 SING N N 15 5E8 C9 C8 DOUB Y N 16 5E8 C9 C4 SING Y N 17 5E8 C15 C16 SING N N 18 5E8 C17 O4 DOUB N N 19 5E8 C8 C7 SING Y N 20 5E8 C3 C4 SING N N 21 5E8 C4 C5 DOUB Y N 22 5E8 O3 C16 DOUB N N 23 5E8 C16 O2 SING N N 24 5E8 C7 C6 DOUB Y N 25 5E8 C5 C6 SING Y N 26 5E8 O2 C18 SING N N 27 5E8 C18 C19 SING N N 28 5E8 C3 H1 SING N N 29 5E8 C3 H2 SING N N 30 5E8 C5 H3 SING N N 31 5E8 C7 H4 SING N N 32 5E8 C8 H5 SING N N 33 5E8 C12 H6 SING N N 34 5E8 C9 H7 SING N N 35 5E8 C14 H8 SING N N 36 5E8 C15 H10 SING N N 37 5E8 C18 H12 SING N N 38 5E8 C18 H13 SING N N 39 5E8 C19 H14 SING N N 40 5E8 C19 H15 SING N N 41 5E8 C19 H16 SING N N 42 5E8 C10 H17 SING N N 43 5E8 C11 H18 SING N N 44 5E8 C11 H19 SING N N 45 5E8 C26 H20 SING N N 46 5E8 C26 H21 SING N N 47 5E8 C25 H22 SING N N 48 5E8 C25 H23 SING N N 49 5E8 N1 H24 SING N N 50 5E8 N H25 SING N N 51 5E8 C2 H26 SING N N 52 5E8 C1 H27 SING N N 53 5E8 C1 H28 SING N N 54 5E8 C1 H29 SING N N 55 5E8 C6 H30 SING N N 56 # 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 5E8 SMILES ACDLabs 12.01 "O=C1C(CCN1)CC(\C=C/C(OCC)=O)NC(=O)C(Cc2ccccc2)C" 5E8 InChI InChI 1.03 "InChI=1S/C21H28N2O4/c1-3-27-19(24)10-9-18(14-17-11-12-22-21(17)26)23-20(25)15(2)13-16-7-5-4-6-8-16/h4-10,15,17-18H,3,11-14H2,1-2H3,(H,22,26)(H,23,25)/t15-,17-,18+/m0/s1" 5E8 InChIKey InChI 1.03 XDPDGHIMOBFVDD-RYQLBKOJSA-N 5E8 SMILES_CANONICAL CACTVS 3.385 "CCOC(=O)\C=C/[C@H](C[C@@H]1CCNC1=O)NC(=O)[C@@H](C)Cc2ccccc2" 5E8 SMILES CACTVS 3.385 "CCOC(=O)C=C[CH](C[CH]1CCNC1=O)NC(=O)[CH](C)Cc2ccccc2" 5E8 SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "CCOC(=O)C=C[C@H](C[C@@H]1CCNC1=O)NC(=O)[C@@H](C)Cc2ccccc2" 5E8 SMILES "OpenEye OEToolkits" 1.9.2 "CCOC(=O)C=CC(CC1CCNC1=O)NC(=O)C(C)Cc2ccccc2" # 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 5E8 "SYSTEMATIC NAME" ACDLabs 12.01 "ethyl (2Z,4S)-4-{[(2S)-2-methyl-3-phenylpropanoyl]amino}-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate" 5E8 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "ethyl (4S)-4-[[(2S)-2-methyl-3-phenyl-propanoyl]amino]-5-[(3S)-2-oxidanylidenepyrrolidin-3-yl]pent-2-enoate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 5E8 "Create component" 2015-09-16 RCSB 5E8 "Initial release" 2016-03-30 RCSB #