data_REW # _chem_comp.id REW _chem_comp.name "(2S,3S)-1-(4-METHOXYPHENYL)-3-(3-(2-(5-METHYL-2-PHENYLOXAZOL-4-YL)ETHOXY)BENZYL)-4-OXOAZETIDINE-2-CARBOXYLIC ACID" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C30 H28 N2 O6" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ;4-[2-(3-{[(2S,3S)-2-carboxy-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl]methyl}phenoxy)ethyl]-5-methyl-2-phenyl-1,3-oxazol-3 -ium ; _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2007-10-30 _chem_comp.pdbx_modified_date 2020-06-17 _chem_comp.pdbx_ambiguous_flag ? _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 512.553 _chem_comp.one_letter_code ? _chem_comp.three_letter_code REW _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 2REW _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 REW C13 C13 C 0 1 N N N -24.058 18.113 4.286 4.581 -1.564 -0.945 C13 REW 1 REW C18 C18 C 0 1 Y N N -29.261 19.807 3.060 0.232 0.001 2.221 C18 REW 2 REW C17 C17 C 0 1 Y N N -27.922 19.497 3.286 1.325 -0.369 1.462 C17 REW 3 REW C16 C16 C 0 1 Y N N -27.580 18.163 3.538 1.146 -1.128 0.315 C16 REW 4 REW C19 C19 C 0 1 Y N N -30.233 18.798 3.088 -1.039 -0.384 1.839 C19 REW 5 REW C20 C20 C 0 1 Y N N -29.884 17.471 3.341 -1.220 -1.140 0.696 C20 REW 6 REW C21 C21 C 0 1 Y N N -28.549 17.165 3.561 -0.131 -1.513 -0.067 C21 REW 7 REW C22 C22 C 0 1 N N N -30.923 16.373 3.416 -2.608 -1.559 0.282 C22 REW 8 REW C23 C23 C 0 1 N N S -30.926 15.883 4.874 -3.210 -0.494 -0.636 C23 REW 9 REW C24 C24 C 0 1 N N S -32.184 16.001 5.758 -4.587 -0.878 -1.187 C24 REW 10 REW C11 C11 C 0 1 Y N N -21.500 15.941 10.814 10.802 2.156 0.313 C11 REW 11 REW C12 C12 C 0 1 Y N N -22.052 15.855 9.537 9.892 1.124 0.410 C12 REW 12 REW C33 C33 C 0 1 Y N N -32.417 12.266 6.696 -6.517 1.913 0.593 C33 REW 13 REW O38 O38 O 0 1 N N N -34.084 15.619 4.413 -5.902 -2.256 0.199 O38 REW 14 REW C36 C36 C 0 1 N N N -33.426 16.446 5.085 -5.096 -2.210 -0.700 C36 REW 15 REW O37 O37 O 0 1 N N N -33.739 17.632 5.273 -4.653 -3.345 -1.264 O37 REW 16 REW N25 N25 N 0 1 N N N -32.075 14.544 5.925 -5.050 0.268 -0.395 N25 REW 17 REW C28 C28 C 0 1 Y N N -32.761 13.627 6.701 -6.332 0.804 -0.223 C28 REW 18 REW C32 C32 C 0 1 Y N N -33.100 11.315 7.475 -7.781 2.441 0.763 C32 REW 19 REW C31 C31 C 0 1 Y N N -34.162 11.720 8.291 -8.867 1.865 0.120 C31 REW 20 REW O34 O34 O 0 1 N N N -34.831 10.774 9.055 -10.112 2.385 0.288 O34 REW 21 REW C35 C35 C 0 1 N N N -35.911 11.123 9.923 -11.183 1.741 -0.404 C35 REW 22 REW C30 C30 C 0 1 Y N N -34.527 13.079 8.303 -8.683 0.758 -0.695 C30 REW 23 REW C29 C29 C 0 1 Y N N -33.829 14.007 7.519 -7.419 0.228 -0.866 C29 REW 24 REW C26 C26 C 0 1 N N N -31.057 14.410 5.098 -3.857 0.644 0.116 C26 REW 25 REW O27 O27 O 0 1 N N N -30.442 13.461 4.656 -3.472 1.520 0.861 O27 REW 26 REW O15 O15 O 0 1 N N N -26.282 17.800 3.752 2.220 -1.493 -0.434 O15 REW 27 REW C14 C14 C 0 1 N N N -25.422 18.742 4.362 3.504 -1.061 0.019 C14 REW 28 REW C3 C3 C 0 1 Y N N -23.721 17.342 5.540 5.935 -1.108 -0.467 C3 REW 29 REW N4 N4 N 0 1 Y N N -23.333 17.888 6.706 6.544 0.042 -0.797 N4 REW 30 REW C5 C5 C 0 1 Y N N -23.127 16.870 7.565 7.706 0.091 -0.190 C5 REW 31 REW O6 O6 O 0 1 Y N N -23.343 15.693 6.902 7.855 -1.030 0.538 O6 REW 32 REW C2 C2 C 0 1 Y N N -23.696 15.969 5.745 6.747 -1.778 0.370 C2 REW 33 REW C1 C1 C 0 1 N N N -24.001 14.752 4.919 6.470 -3.119 1.001 C1 REW 34 REW C7 C7 C 0 1 Y N N -22.613 16.992 8.941 8.686 1.193 -0.289 C7 REW 35 REW C10 C10 C 0 1 Y N N -21.476 17.175 11.464 10.522 3.258 -0.475 C10 REW 36 REW C9 C9 C 0 1 Y N N -21.990 18.324 10.848 9.331 3.330 -1.175 C9 REW 37 REW C8 C8 C 0 1 Y N N -22.554 18.232 9.573 8.410 2.307 -1.083 C8 REW 38 REW H131 1H13 H 0 0 N N N -24.037 17.421 3.431 4.556 -2.653 -0.981 H131 REW 39 REW H132 2H13 H 0 0 N N N -23.317 18.918 4.170 4.393 -1.163 -1.941 H132 REW 40 REW H18 H18 H 0 1 N N N -29.551 20.828 2.863 0.372 0.588 3.117 H18 REW 41 REW H17 H17 H 0 1 N N N -27.165 20.268 3.267 2.318 -0.068 1.761 H17 REW 42 REW H19 H19 H 0 1 N N N -31.268 19.051 2.911 -1.892 -0.093 2.434 H19 REW 43 REW H21 H21 H 0 1 N N N -28.259 16.142 3.752 -0.273 -2.104 -0.960 H21 REW 44 REW H221 1H22 H 0 0 N N N -31.914 16.759 3.136 -2.557 -2.510 -0.249 H221 REW 45 REW H222 2H22 H 0 0 N N N -30.689 15.554 2.720 -3.233 -1.671 1.168 H222 REW 46 REW H23 H23 H 0 1 N N N -30.025 16.473 5.099 -2.513 -0.161 -1.404 H23 REW 47 REW H24 H24 H 0 1 N N N -32.231 16.707 6.600 -4.688 -0.745 -2.264 H24 REW 48 REW H11 H11 H 0 1 N N N -21.096 15.062 11.295 11.733 2.106 0.858 H11 REW 49 REW H12 H12 H 0 1 N N N -22.047 14.913 9.008 10.112 0.264 1.026 H12 REW 50 REW H33 H33 H 0 1 N N N -31.599 11.938 6.072 -5.673 2.359 1.097 H33 REW 51 REW HO37 HO37 H 0 0 N N N -34.557 17.818 4.828 -5.009 -4.175 -0.917 HO37 REW 52 REW H32 H32 H 0 1 N N N -32.806 10.276 7.444 -7.925 3.304 1.397 H32 REW 53 REW H351 1H35 H 0 0 N N N -35.539 11.213 10.954 -11.254 0.703 -0.079 H351 REW 54 REW H352 2H35 H 0 0 N N N -36.342 12.084 9.604 -12.119 2.255 -0.183 H352 REW 55 REW H353 3H35 H 0 0 N N N -36.684 10.341 9.879 -10.995 1.775 -1.477 H353 REW 56 REW H30 H30 H 0 1 N N N -35.350 13.409 8.920 -9.528 0.309 -1.196 H30 REW 57 REW H29 H29 H 0 1 N N N -34.124 15.045 7.547 -7.276 -0.634 -1.501 H29 REW 58 REW H141 1H14 H 0 0 N N N -25.446 19.704 3.829 3.692 -1.462 1.015 H141 REW 59 REW H142 2H14 H 0 0 N N N -25.719 18.967 5.397 3.529 0.028 0.054 H142 REW 60 REW H11A 1H1 H 0 0 N N N -24.076 15.037 3.859 6.845 -3.910 0.351 H11A REW 61 REW H12A 2H1 H 0 0 N N N -23.196 14.013 5.044 6.971 -3.175 1.968 H12A REW 62 REW H13 3H1 H 0 1 N N N -24.955 14.315 5.249 5.396 -3.240 1.140 H13 REW 63 REW H10 H10 H 0 1 N N N -21.055 17.246 12.456 11.236 4.065 -0.544 H10 REW 64 REW H9 H9 H 0 1 N N N -21.950 19.276 11.356 9.118 4.193 -1.789 H9 REW 65 REW H8 H8 H 0 1 N N N -22.940 19.113 9.082 7.478 2.366 -1.627 H8 REW 66 # # 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 REW C18 C19 DOUB Y N 1 REW C18 C17 SING Y N 2 REW C19 C20 SING Y N 3 REW C17 C16 DOUB Y N 4 REW C20 C22 SING N N 5 REW C20 C21 DOUB Y N 6 REW C22 C23 SING N N 7 REW C16 C21 SING Y N 8 REW C16 O15 SING N N 9 REW O15 C14 SING N N 10 REW C13 C14 SING N N 11 REW C13 C3 SING N N 12 REW O38 C36 DOUB N N 13 REW O27 C26 DOUB N N 14 REW C23 C26 SING N N 15 REW C23 C24 SING N N 16 REW C1 C2 SING N N 17 REW C36 O37 SING N N 18 REW C36 C24 SING N N 19 REW C26 N25 SING N N 20 REW C3 C2 DOUB Y N 21 REW C3 N4 SING Y N 22 REW C2 O6 SING Y N 23 REW C24 N25 SING N N 24 REW N25 C28 SING N N 25 REW C33 C28 DOUB Y N 26 REW C33 C32 SING Y N 27 REW C28 C29 SING Y N 28 REW N4 C5 DOUB Y N 29 REW O6 C5 SING Y N 30 REW C32 C31 DOUB Y N 31 REW C29 C30 DOUB Y N 32 REW C5 C7 SING Y N 33 REW C31 C30 SING Y N 34 REW C31 O34 SING N N 35 REW C7 C12 DOUB Y N 36 REW C7 C8 SING Y N 37 REW O34 C35 SING N N 38 REW C12 C11 SING Y N 39 REW C8 C9 DOUB Y N 40 REW C11 C10 DOUB Y N 41 REW C9 C10 SING Y N 42 REW C13 H131 SING N N 43 REW C13 H132 SING N N 44 REW C18 H18 SING N N 45 REW C17 H17 SING N N 46 REW C19 H19 SING N N 47 REW C21 H21 SING N N 48 REW C22 H221 SING N N 49 REW C22 H222 SING N N 50 REW C23 H23 SING N N 51 REW C24 H24 SING N N 52 REW C11 H11 SING N N 53 REW C12 H12 SING N N 54 REW C33 H33 SING N N 55 REW O37 HO37 SING N N 56 REW C32 H32 SING N N 57 REW C35 H351 SING N N 58 REW C35 H352 SING N N 59 REW C35 H353 SING N N 60 REW C30 H30 SING N N 61 REW C29 H29 SING N N 62 REW C14 H141 SING N N 63 REW C14 H142 SING N N 64 REW C1 H11A SING N N 65 REW C1 H12A SING N N 66 REW C1 H13 SING N N 67 REW C10 H10 SING N N 68 REW C9 H9 SING N N 69 REW C8 H8 SING N N 70 # # 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 REW SMILES ACDLabs 10.04 "O=C(O)C2N(c1ccc(OC)cc1)C(=O)C2Cc5cc(OCCc3nc(oc3C)c4ccccc4)ccc5" REW SMILES_CANONICAL CACTVS 3.341 "COc1ccc(cc1)N2[C@@H]([C@H](Cc3cccc(OCCc4nc(oc4C)c5ccccc5)c3)C2=O)C(O)=O" REW SMILES CACTVS 3.341 "COc1ccc(cc1)N2[CH]([CH](Cc3cccc(OCCc4nc(oc4C)c5ccccc5)c3)C2=O)C(O)=O" REW SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "Cc1c(nc(o1)c2ccccc2)CCOc3cccc(c3)C[C@H]4[C@H](N(C4=O)c5ccc(cc5)OC)C(=O)O" REW SMILES "OpenEye OEToolkits" 1.5.0 "Cc1c(nc(o1)c2ccccc2)CCOc3cccc(c3)CC4C(N(C4=O)c5ccc(cc5)OC)C(=O)O" REW InChI InChI 1.03 "InChI=1S/C30H28N2O6/c1-19-26(31-28(38-19)21-8-4-3-5-9-21)15-16-37-24-10-6-7-20(17-24)18-25-27(30(34)35)32(29(25)33)22-11-13-23(36-2)14-12-22/h3-14,17,25,27H,15-16,18H2,1-2H3,(H,34,35)/t25-,27-/m0/s1" REW InChIKey InChI 1.03 DKIUFVFEAUCDLY-BDYUSTAISA-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 REW "SYSTEMATIC NAME" ACDLabs 10.04 "(2S,3S)-1-(4-methoxyphenyl)-3-{3-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]benzyl}-4-oxoazetidine-2-carboxylic acid" REW "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S,3S)-1-(4-methoxyphenyl)-3-[[3-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-4-oxo-azetidine-2-carboxylic 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 REW "Create component" 2007-10-30 RCSB REW "Modify aromatic_flag" 2011-06-04 RCSB REW "Modify descriptor" 2011-06-04 RCSB REW "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id REW _pdbx_chem_comp_synonyms.name "4-[2-(3-{[(2S,3S)-2-carboxy-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl]methyl}phenoxy)ethyl]-5-methyl-2-phenyl-1,3-oxazol-3-ium" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##