data_EEA # _chem_comp.id EEA _chem_comp.name "N-{3-[3-(3'-chlorobiphenyl-4-yl)isoxazol-5-yl]propanoyl}-L-alpha-glutamyl-L-alpha-glutamyl-amide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C28 H29 Cl N4 O8" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2010-03-18 _chem_comp.pdbx_modified_date 2012-09-13 _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 585.005 _chem_comp.one_letter_code ? _chem_comp.three_letter_code EEA _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 3LIL _chem_comp.pdbx_subcomponent_list "0YD GLU GLU NH2" _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 EEA C1 C1 C 0 1 N N N 7.927 24.886 3.526 -0.692 -0.952 0.475 C1 0YD 1 EEA CL1 CL1 CL 0 0 N N N -2.787 22.718 11.168 11.327 2.847 -0.771 CL1 0YD 2 EEA C2 C2 C 0 1 N N N 8.035 23.592 4.316 0.142 -1.236 1.726 C2 0YD 3 EEA O2 O2 O 0 1 N N N 9.840 25.792 4.568 -2.367 -0.440 2.056 O2 0YD 4 EEA C3 C3 C 0 1 Y N N 6.806 23.124 5.108 1.526 -1.672 1.320 C3 0YD 5 EEA C4 C4 C 0 1 Y N N 5.392 23.650 5.067 2.598 -0.873 1.122 C4 0YD 6 EEA C5 C5 C 0 1 Y N N 4.662 22.801 5.938 3.636 -1.776 0.758 C5 0YD 7 EEA C6 C6 C 0 1 Y N N 3.186 22.815 6.275 5.041 -1.433 0.426 C6 0YD 8 EEA C7 C7 C 0 1 Y N N 2.779 22.003 7.472 5.943 -2.440 0.087 C7 0YD 9 EEA C8 C8 C 0 1 Y N N 1.415 21.968 7.825 7.248 -2.122 -0.221 C8 0YD 10 EEA C9 C9 C 0 1 Y N N 0.476 22.670 7.016 7.666 -0.792 -0.192 C9 0YD 11 EEA C10 C10 C 0 1 Y N N 0.879 23.447 5.854 6.764 0.216 0.147 C10 0YD 12 EEA C11 C11 C 0 1 Y N N 2.273 23.498 5.467 5.458 -0.102 0.450 C11 0YD 13 EEA C12 C12 C 0 1 N N N 8.725 25.995 4.206 -2.076 -0.516 0.882 C12 0YD 14 EEA N12 N12 N 0 1 Y N N 5.510 21.828 6.505 3.101 -2.971 0.774 N12 0YD 15 EEA O12 O12 O 0 1 Y N N 6.852 22.069 5.961 1.934 -2.928 1.089 O12 0YD 16 EEA C18 C18 C 0 1 Y N N -0.985 22.705 7.461 9.071 -0.449 -0.523 C18 0YD 17 EEA C19 C19 C 0 1 Y N N -1.242 22.697 8.927 9.491 0.879 -0.496 C19 0YD 18 EEA C20 C20 C 0 1 Y N N -2.523 22.802 9.400 10.801 1.193 -0.804 C20 0YD 19 EEA C21 C21 C 0 1 Y N N -3.595 22.994 8.487 11.694 0.190 -1.140 C21 0YD 20 EEA C22 C22 C 0 1 Y N N -3.330 23.088 7.073 11.281 -1.130 -1.168 C22 0YD 21 EEA C23 C23 C 0 1 Y N N -1.994 22.974 6.582 9.976 -1.454 -0.857 C23 0YD 22 EEA N2 N2 N 0 1 N N N 7.960 27.125 4.717 -2.990 -0.211 -0.060 N GLU 23 EEA C13 C13 C 0 1 N N S 8.664 28.157 5.479 -4.336 0.213 0.335 CA GLU 24 EEA C14 C14 C 0 1 N N N 7.920 28.358 6.798 -5.305 -0.092 -0.778 C GLU 25 EEA O1 O1 O 0 1 N N N 6.738 28.194 6.854 -4.911 -0.612 -1.800 O GLU 26 EEA C15 C15 C 0 1 N N N 8.607 29.508 4.761 -4.335 1.717 0.613 CB GLU 27 EEA C16 C16 C 0 1 N N N 9.593 29.829 3.649 -3.446 2.012 1.823 CG GLU 28 EEA C17 C17 C 0 1 N N N 9.281 31.224 3.148 -3.446 3.494 2.098 CD GLU 29 EEA O4 O4 O 0 1 N N N 8.524 31.374 2.135 -4.091 4.238 1.397 OE1 GLU 30 EEA O4E O4E O 0 1 N N N 9.723 32.259 3.902 -2.730 3.987 3.120 OE2 GLU 31 EEA N1 N1 N 0 1 N N N 8.582 29.128 7.828 -6.610 0.213 -0.637 N GLU 32 EEA C24 C24 C 0 1 N N S 7.744 29.487 8.950 -7.553 -0.083 -1.718 CA GLU 33 EEA C28 C28 C 0 1 N N N 6.875 30.696 8.598 -7.545 1.047 -2.715 C GLU 34 EEA O9 O9 O 0 1 N N N 7.079 31.333 7.613 -6.823 2.006 -2.539 O GLU 35 EEA C25 C25 C 0 1 N N N 8.571 29.620 10.239 -8.960 -0.242 -1.139 CB GLU 36 EEA C26 C26 C 0 1 N N N 8.929 31.023 10.730 -8.999 -1.466 -0.222 CG GLU 37 EEA C27 C27 C 0 1 N N N 10.324 31.254 11.331 -10.385 -1.623 0.349 CD GLU 38 EEA O8 O8 O 0 1 N N N 11.141 32.268 10.801 -11.253 -0.837 0.052 OE1 GLU 39 EEA O8E O8E O 0 1 N N N 10.595 30.747 12.376 -10.655 -2.637 1.186 OE2 GLU 40 EEA N9 N9 N 0 1 N N N 5.664 30.948 9.346 -8.340 0.993 -3.802 N NH2 41 EEA H1 H1 H 0 1 N N N 6.870 25.186 3.465 -0.217 -0.161 -0.106 H1 0YD 42 EEA H2 H2 H 0 1 N N N 8.322 24.725 2.512 -0.759 -1.856 -0.130 H2 0YD 43 EEA H4 H4 H 0 1 N N N 8.287 22.794 3.602 0.209 -0.332 2.331 H4 0YD 44 EEA H5 H5 H 0 1 N N N 8.859 23.716 5.034 -0.333 -2.028 2.307 H5 0YD 45 EEA H7 H7 H 0 1 N N N 5.018 24.489 4.499 2.655 0.201 1.218 H7 0YD 46 EEA H8 H8 H 0 1 N N N 3.514 21.460 8.048 5.619 -3.470 0.065 H8 0YD 47 EEA H9 H9 H 0 1 N N N 1.087 21.418 8.695 7.947 -2.902 -0.483 H9 0YD 48 EEA H12 H12 H 0 1 N N N 0.139 23.985 5.281 7.087 1.246 0.169 H12 0YD 49 EEA H13 H13 H 0 1 N N N 2.594 24.041 4.590 4.759 0.678 0.712 H13 0YD 50 EEA H19 H19 H 0 1 N N N -0.417 22.608 9.619 8.794 1.662 -0.234 H19 0YD 51 EEA H20 H20 H 0 1 N N N -4.608 23.070 8.853 12.717 0.439 -1.380 H20 0YD 52 EEA H21 H21 H 0 1 N N N -4.145 23.245 6.382 11.982 -1.908 -1.431 H21 0YD 53 EEA H22 H22 H 0 1 N N N -1.785 23.099 5.530 9.655 -2.486 -0.879 H22 0YD 54 EEA H6 H6 H 0 1 N N N 6.976 27.194 4.551 -2.757 -0.271 -1.000 H GLU 55 EEA H14 H14 H 0 1 N N N 9.709 27.870 5.669 -4.635 -0.323 1.235 HA GLU 56 EEA H15 H15 H 0 1 N N N 8.738 30.281 5.532 -3.951 2.248 -0.258 HB2 GLU 57 EEA H16 H16 H 0 1 N N N 7.601 29.592 4.325 -5.353 2.049 0.821 HB3 GLU 58 EEA H17 H17 H 0 1 N N N 9.484 29.103 2.830 -3.831 1.481 2.694 HG2 GLU 59 EEA H18 H18 H 0 1 N N N 10.621 29.791 4.037 -2.429 1.681 1.616 HG3 GLU 60 EEA H28 H28 H 0 1 N N N 9.381 33.074 3.553 -2.761 4.944 3.257 HE2 GLU 61 EEA H3 H3 H 0 1 N N N 9.545 29.392 7.769 -6.926 0.629 0.181 H GLU 62 EEA H23 H23 H 0 1 N N N 7.051 28.650 9.118 -7.258 -1.007 -2.215 HA GLU 63 EEA H24 H24 H 0 1 N N N 8.002 29.129 11.043 -9.221 0.649 -0.567 HB2 GLU 64 EEA H25 H25 H 0 1 N N N 9.516 29.081 10.076 -9.675 -0.374 -1.951 HB3 GLU 65 EEA H26 H26 H 0 1 N N N 8.828 31.703 9.872 -8.738 -2.357 -0.794 HG2 GLU 66 EEA H27 H27 H 0 1 N N N 8.194 31.295 11.502 -8.284 -1.334 0.590 HG3 GLU 67 EEA H29 H29 H 0 1 N N N 11.389 31.138 12.722 -11.558 -2.696 1.526 HE2 GLU 68 EEA H10 H10 H 0 1 N N N 5.019 31.645 9.033 -8.918 0.226 -3.942 HN1 NH2 69 EEA H11 H11 H 0 1 N N N 5.471 30.425 10.176 -8.335 1.720 -4.444 HN2 NH2 70 # 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 EEA O4 C17 DOUB N N 1 EEA C17 C16 SING N N 2 EEA C17 O4E SING N N 3 EEA C1 C12 SING N N 4 EEA C1 C2 SING N N 5 EEA C16 C15 SING N N 6 EEA C12 O2 DOUB N N 7 EEA C12 N2 SING N N 8 EEA C2 C3 SING N N 9 EEA N2 C13 SING N N 10 EEA C15 C13 SING N N 11 EEA C4 C3 DOUB Y N 12 EEA C4 C5 SING Y N 13 EEA C3 O12 SING Y N 14 EEA C11 C10 DOUB Y N 15 EEA C11 C6 SING Y N 16 EEA C13 C14 SING N N 17 EEA C10 C9 SING Y N 18 EEA C5 C6 SING N N 19 EEA C5 N12 DOUB Y N 20 EEA O12 N12 SING Y N 21 EEA C6 C7 DOUB Y N 22 EEA C23 C22 DOUB Y N 23 EEA C23 C18 SING Y N 24 EEA C14 O1 DOUB N N 25 EEA C14 N1 SING N N 26 EEA C9 C18 SING N N 27 EEA C9 C8 DOUB Y N 28 EEA C22 C21 SING Y N 29 EEA C18 C19 DOUB Y N 30 EEA C7 C8 SING Y N 31 EEA O9 C28 DOUB N N 32 EEA N1 C24 SING N N 33 EEA C21 C20 DOUB Y N 34 EEA C28 C24 SING N N 35 EEA C28 N9 SING N N 36 EEA C19 C20 SING Y N 37 EEA C24 C25 SING N N 38 EEA C20 CL1 SING N N 39 EEA C25 C26 SING N N 40 EEA C26 C27 SING N N 41 EEA O8 C27 DOUB N N 42 EEA C27 O8E SING N N 43 EEA C1 H1 SING N N 44 EEA C1 H2 SING N N 45 EEA N1 H3 SING N N 46 EEA C2 H4 SING N N 47 EEA C2 H5 SING N N 48 EEA N2 H6 SING N N 49 EEA C4 H7 SING N N 50 EEA C7 H8 SING N N 51 EEA C8 H9 SING N N 52 EEA N9 H10 SING N N 53 EEA N9 H11 SING N N 54 EEA C10 H12 SING N N 55 EEA C11 H13 SING N N 56 EEA C13 H14 SING N N 57 EEA C15 H15 SING N N 58 EEA C15 H16 SING N N 59 EEA C16 H17 SING N N 60 EEA C16 H18 SING N N 61 EEA C19 H19 SING N N 62 EEA C21 H20 SING N N 63 EEA C22 H21 SING N N 64 EEA C23 H22 SING N N 65 EEA C24 H23 SING N N 66 EEA C25 H24 SING N N 67 EEA C25 H25 SING N N 68 EEA C26 H26 SING N N 69 EEA C26 H27 SING N N 70 EEA O4E H28 SING N N 71 EEA O8E H29 SING N N 72 # 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 EEA SMILES ACDLabs 12.01 "O=C(O)CCC(C(=O)N)NC(=O)C(NC(=O)CCc3onc(c2ccc(c1cccc(Cl)c1)cc2)c3)CCC(=O)O" EEA InChI InChI 1.03 "InChI=1S/C28H29ClN4O8/c29-19-3-1-2-18(14-19)16-4-6-17(7-5-16)23-15-20(41-33-23)8-11-24(34)31-22(10-13-26(37)38)28(40)32-21(27(30)39)9-12-25(35)36/h1-7,14-15,21-22H,8-13H2,(H2,30,39)(H,31,34)(H,32,40)(H,35,36)(H,37,38)/t21-,22-/m0/s1" EEA InChIKey InChI 1.03 KOVQMCGGWATESY-VXKWHMMOSA-N EEA SMILES_CANONICAL CACTVS 3.370 "NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CCc1onc(c1)c2ccc(cc2)c3cccc(Cl)c3" EEA SMILES CACTVS 3.370 "NC(=O)[CH](CCC(O)=O)NC(=O)[CH](CCC(O)=O)NC(=O)CCc1onc(c1)c2ccc(cc2)c3cccc(Cl)c3" EEA SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1cc(cc(c1)Cl)c2ccc(cc2)c3cc(on3)CCC(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N" EEA SMILES "OpenEye OEToolkits" 1.7.6 "c1cc(cc(c1)Cl)c2ccc(cc2)c3cc(on3)CCC(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)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 EEA "SYSTEMATIC NAME" ACDLabs 12.01 "N-{3-[3-(3'-chlorobiphenyl-4-yl)-1,2-oxazol-5-yl]propanoyl}-L-alpha-glutamyl-L-alpha-glutamine" EEA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(4S)-5-azanyl-4-[[(2S)-2-[3-[3-[4-(3-chlorophenyl)phenyl]-1,2-oxazol-5-yl]propanoylamino]-5-oxidanyl-5-oxidanylidene-pentanoyl]amino]-5-oxidanylidene-pentanoic acid" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site EEA "Create component" 2010-03-18 RCSB EEA "Modify aromatic_flag" 2011-06-04 RCSB EEA "Modify descriptor" 2011-06-04 RCSB EEA "Modify subcomponent list" 2012-09-13 RCSB #