data_AU9
# 
_chem_comp.id                                    AU9 
_chem_comp.name                                  "(2~{S})-2-[[3-[[5-[(2-methyl-3-phenyl-phenoxy)methyl]-1,3,4-oxadiazol-2-yl]sulfanylmethyl]phenyl]methylamino]-3-oxidanyl-propanoic acid" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H27 N3 O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2023-05-17 
_chem_comp.pdbx_modified_date                    2023-10-20 
_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                        505.585 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AU9 
_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        8JBA 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBC 
# 
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 
AU9 C10 C1  C 0 1 N N N 24.256 5.462  -0.159 -3.107  1.793  0.097  C10 AU9 1  
AU9 N12 N1  N 0 1 Y N N 24.021 4.599  -2.569 -1.130  1.091  -1.272 N12 AU9 2  
AU9 C17 C2  C 0 1 N N N 20.377 1.386  -2.998 2.542   -0.893 -0.582 C17 AU9 3  
AU9 C20 C3  C 0 1 Y N N 24.118 4.089  8.151  -10.955 -0.864 -1.076 C20 AU9 4  
AU9 C21 C4  C 0 1 Y N N 24.942 2.984  8.302  -10.970 -2.033 -0.337 C21 AU9 5  
AU9 C22 C5  C 0 1 Y N N 25.729 2.556  7.246  -9.948  -2.306 0.554  C22 AU9 6  
AU9 C24 C6  C 0 1 Y N N 18.185 1.628  -4.243 3.864   -2.990 -0.236 C24 AU9 7  
AU9 C26 C7  C 0 1 Y N N 16.447 -0.017 -4.079 6.132   -2.924 0.531  C26 AU9 8  
AU9 C28 C8  C 0 1 Y N N 18.502 -0.315 -2.864 4.918   -0.886 0.206  C28 AU9 9  
AU9 C01 C9  C 0 1 Y N N 24.801 5.138  4.546  -7.766  0.725  0.124  C01 AU9 10 
AU9 C02 C10 C 0 1 Y N N 25.249 6.451  4.551  -8.032  2.052  0.458  C02 AU9 11 
AU9 C03 C11 C 0 1 Y N N 25.218 7.216  3.393  -6.992  2.947  0.609  C03 AU9 12 
AU9 C04 C12 C 0 1 Y N N 24.729 6.667  2.221  -5.686  2.531  0.431  C04 AU9 13 
AU9 C05 C13 C 0 1 Y N N 24.278 5.356  2.211  -5.413  1.212  0.098  C05 AU9 14 
AU9 C06 C14 C 0 1 Y N N 24.309 4.583  3.368  -6.450  0.305  -0.050 C06 AU9 15 
AU9 C07 C15 C 0 1 N N N 23.810 3.145  3.315  -6.155  -1.128 -0.411 C07 AU9 16 
AU9 C08 C16 C 0 1 Y N N 24.864 4.341  5.881  -8.882  -0.239 -0.040 C08 AU9 17 
AU9 C11 C17 C 0 1 Y N N 23.524 4.826  -1.357 -1.757  1.166  -0.135 C11 AU9 18 
AU9 C14 C18 C 0 1 Y N N 21.951 3.902  -2.513 0.128   0.161  0.158  C14 AU9 19 
AU9 C18 C19 C 0 1 Y N N 18.974 0.880  -3.382 3.810   -1.609 -0.193 C18 AU9 20 
AU9 C19 C20 C 0 1 Y N N 24.083 4.770  6.939  -9.917  0.034  -0.932 C19 AU9 21 
AU9 C23 C21 C 0 1 Y N N 25.697 3.239  6.035  -8.908  -1.413 0.711  C23 AU9 22 
AU9 C25 C22 C 0 1 Y N N 16.917 1.181  -4.593 5.025   -3.647 0.126  C25 AU9 23 
AU9 C27 C23 C 0 1 Y N N 17.234 -0.762 -3.215 6.077   -1.544 0.573  C27 AU9 24 
AU9 C29 C24 C 0 1 N N N 16.705 -2.093 -2.641 7.281   -0.755 1.021  C29 AU9 25 
AU9 C31 C25 C 0 1 N N S 16.761 -4.053 -4.001 9.307   0.328  0.256  C31 AU9 26 
AU9 C32 C26 C 0 1 N N N 16.798 -5.500 -3.508 8.958   1.793  0.318  C32 AU9 27 
AU9 C35 C27 C 0 1 N N N 17.365 -3.967 -5.402 10.424  0.112  -0.768 C35 AU9 28 
AU9 N13 N2  N 0 1 Y N N 23.010 4.011  -3.309 -0.004  0.492  -1.105 N13 AU9 29 
AU9 N30 N3  N 0 1 N N N 17.530 -3.210 -3.094 8.121   -0.442 -0.143 N30 AU9 30 
AU9 O09 O1  O 0 1 N N N 23.784 4.799  1.001  -4.127  0.807  -0.077 O09 AU9 31 
AU9 O15 O2  O 0 1 Y N N 22.264 4.402  -1.319 -0.980  0.581  0.798  O15 AU9 32 
AU9 O33 O3  O 0 1 N N N 17.843 -6.191 -3.652 7.837   2.158  0.056  O33 AU9 33 
AU9 O34 O4  O 0 1 N N N 15.774 -5.999 -2.955 9.893   2.691  0.663  O34 AU9 34 
AU9 O36 O5  O 0 1 N N N 16.427 -3.350 -6.252 10.026  0.657  -2.028 O36 AU9 35 
AU9 S16 S1  S 0 1 N N N 20.317 3.206  -2.944 1.498   -0.677 0.881  S16 AU9 36 
AU9 H1  H1  H 0 1 N N N 25.342 5.323  -0.260 -3.154  2.189  1.112  H1  AU9 37 
AU9 H2  H2  H 0 1 N N N 24.028 6.537  -0.102 -3.260  2.603  -0.616 H2  AU9 38 
AU9 H3  H3  H 0 1 N N N 20.660 0.991  -2.011 2.790   0.083  -0.999 H3  AU9 39 
AU9 H4  H4  H 0 1 N N N 21.111 1.058  -3.748 2.007   -1.481 -1.327 H4  AU9 40 
AU9 H5  H5  H 0 1 N N N 23.503 4.421  8.975  -11.756 -0.655 -1.771 H5  AU9 41 
AU9 H6  H6  H 0 1 N N N 24.970 2.457  9.244  -11.782 -2.735 -0.456 H6  AU9 42 
AU9 H7  H7  H 0 1 N N N 26.367 1.693  7.363  -9.965  -3.221 1.129  H7  AU9 43 
AU9 H8  H8  H 0 1 N N N 18.557 2.560  -4.642 2.999   -3.555 -0.548 H8  AU9 44 
AU9 H9  H9  H 0 1 N N N 15.464 -0.371 -4.353 7.037   -3.438 0.818  H9  AU9 45 
AU9 H10 H10 H 0 1 N N N 19.116 -0.896 -2.191 4.876   0.193  0.238  H10 AU9 46 
AU9 H11 H11 H 0 1 N N N 25.626 6.883  5.466  -9.052  2.380  0.598  H11 AU9 47 
AU9 H12 H12 H 0 1 N N N 25.574 8.235  3.407  -7.200  3.974  0.868  H12 AU9 48 
AU9 H13 H13 H 0 1 N N N 24.699 7.257  1.317  -4.876  3.235  0.550  H13 AU9 49 
AU9 H14 H14 H 0 1 N N N 24.645 2.476  3.058  -6.112  -1.730 0.496  H14 AU9 50 
AU9 H15 H15 H 0 1 N N N 23.402 2.862  4.297  -6.943  -1.508 -1.062 H15 AU9 51 
AU9 H16 H16 H 0 1 N N N 23.023 3.058  2.552  -5.198  -1.182 -0.930 H16 AU9 52 
AU9 H17 H17 H 0 1 N N N 23.446 5.634  6.824  -9.902  0.942  -1.516 H17 AU9 53 
AU9 H18 H18 H 0 1 N N N 26.319 2.913  5.215  -8.108  -1.630 1.403  H18 AU9 54 
AU9 H19 H19 H 0 1 N N N 16.301 1.764  -5.262 5.068   -4.726 0.093  H19 AU9 55 
AU9 H20 H20 H 0 1 N N N 16.729 -2.048 -1.542 6.954   0.171  1.493  H20 AU9 56 
AU9 H21 H21 H 0 1 N N N 15.670 -2.247 -2.980 7.856   -1.344 1.735  H21 AU9 57 
AU9 H22 H22 H 0 1 N N N 15.716 -3.712 -4.038 9.644   -0.007 1.237  H22 AU9 58 
AU9 H23 H23 H 0 1 N N N 17.593 -4.978 -5.771 11.331  0.611  -0.427 H23 AU9 59 
AU9 H24 H24 H 0 1 N N N 18.289 -3.371 -5.373 10.615  -0.955 -0.877 H24 AU9 60 
AU9 H25 H25 H 0 1 N N N 17.821 -3.750 -2.304 7.593   0.049  -0.849 H25 AU9 61 
AU9 H27 H27 H 0 1 N N N 15.954 -6.898 -2.707 9.622   3.619  0.689  H27 AU9 62 
AU9 H28 H28 H 0 1 N N N 16.787 -3.288 -7.129 10.687  0.555  -2.726 H28 AU9 63 
# 
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 
AU9 O36 C35 SING N N 1  
AU9 C35 C31 SING N N 2  
AU9 C25 C24 DOUB Y N 3  
AU9 C25 C26 SING Y N 4  
AU9 C24 C18 SING Y N 5  
AU9 C26 C27 DOUB Y N 6  
AU9 C31 C32 SING N N 7  
AU9 C31 N30 SING N N 8  
AU9 O33 C32 DOUB N N 9  
AU9 C32 O34 SING N N 10 
AU9 C18 C17 SING N N 11 
AU9 C18 C28 DOUB Y N 12 
AU9 N13 N12 SING Y N 13 
AU9 N13 C14 DOUB Y N 14 
AU9 C27 C28 SING Y N 15 
AU9 C27 C29 SING N N 16 
AU9 N30 C29 SING N N 17 
AU9 C17 S16 SING N N 18 
AU9 S16 C14 SING N N 19 
AU9 N12 C11 DOUB Y N 20 
AU9 C14 O15 SING Y N 21 
AU9 C11 O15 SING Y N 22 
AU9 C11 C10 SING N N 23 
AU9 C10 O09 SING N N 24 
AU9 O09 C05 SING N N 25 
AU9 C05 C04 DOUB Y N 26 
AU9 C05 C06 SING Y N 27 
AU9 C04 C03 SING Y N 28 
AU9 C07 C06 SING N N 29 
AU9 C06 C01 DOUB Y N 30 
AU9 C03 C02 DOUB Y N 31 
AU9 C01 C02 SING Y N 32 
AU9 C01 C08 SING N N 33 
AU9 C08 C23 DOUB Y N 34 
AU9 C08 C19 SING Y N 35 
AU9 C23 C22 SING Y N 36 
AU9 C19 C20 DOUB Y N 37 
AU9 C22 C21 DOUB Y N 38 
AU9 C20 C21 SING Y N 39 
AU9 C10 H1  SING N N 40 
AU9 C10 H2  SING N N 41 
AU9 C17 H3  SING N N 42 
AU9 C17 H4  SING N N 43 
AU9 C20 H5  SING N N 44 
AU9 C21 H6  SING N N 45 
AU9 C22 H7  SING N N 46 
AU9 C24 H8  SING N N 47 
AU9 C26 H9  SING N N 48 
AU9 C28 H10 SING N N 49 
AU9 C02 H11 SING N N 50 
AU9 C03 H12 SING N N 51 
AU9 C04 H13 SING N N 52 
AU9 C07 H14 SING N N 53 
AU9 C07 H15 SING N N 54 
AU9 C07 H16 SING N N 55 
AU9 C19 H17 SING N N 56 
AU9 C23 H18 SING N N 57 
AU9 C25 H19 SING N N 58 
AU9 C29 H20 SING N N 59 
AU9 C29 H21 SING N N 60 
AU9 C31 H22 SING N N 61 
AU9 C35 H23 SING N N 62 
AU9 C35 H24 SING N N 63 
AU9 N30 H25 SING N N 64 
AU9 O34 H27 SING N N 65 
AU9 O36 H28 SING N N 66 
# 
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 
AU9 InChI            InChI                1.06  "InChI=1S/C27H27N3O5S/c1-18-22(21-9-3-2-4-10-21)11-6-12-24(18)34-16-25-29-30-27(35-25)36-17-20-8-5-7-19(13-20)14-28-23(15-31)26(32)33/h2-13,23,28,31H,14-17H2,1H3,(H,32,33)/t23-/m0/s1" 
AU9 InChIKey         InChI                1.06  AAJMOHIHVOUUDE-QHCPKHFHSA-N                                                                                                                                                             
AU9 SMILES_CANONICAL CACTVS               3.385 "Cc1c(OCc2oc(SCc3cccc(CN[C@@H](CO)C(O)=O)c3)nn2)cccc1c4ccccc4"                                                                                                                          
AU9 SMILES           CACTVS               3.385 "Cc1c(OCc2oc(SCc3cccc(CN[CH](CO)C(O)=O)c3)nn2)cccc1c4ccccc4"                                                                                                                            
AU9 SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "Cc1c(cccc1OCc2nnc(o2)SCc3cccc(c3)CN[C@@H](CO)C(=O)O)c4ccccc4"                                                                                                                          
AU9 SMILES           "OpenEye OEToolkits" 2.0.7 "Cc1c(cccc1OCc2nnc(o2)SCc3cccc(c3)CNC(CO)C(=O)O)c4ccccc4"                                                                                                                               
# 
_pdbx_chem_comp_identifier.comp_id           AU9 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   2.0.7 
_pdbx_chem_comp_identifier.identifier        "(2~{S})-2-[[3-[[5-[(2-methyl-3-phenyl-phenoxy)methyl]-1,3,4-oxadiazol-2-yl]sulfanylmethyl]phenyl]methylamino]-3-oxidanyl-propanoic 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 
AU9 "Create component" 2023-05-17 PDBC 
AU9 "Initial release"  2023-10-25 RCSB 
# 
