data_YAU # _chem_comp.id YAU _chem_comp.name "N-{2-chloro-5-[(3S,4R)-1-[(3R)-4-(4-chlorophenyl)-3-hydroxybutanoyl]-4-(hydroxymethyl)pyrrolidin-3-yl]phenyl}-2-(4-fluorophenyl)acetamide" _chem_comp.type non-polymer _chem_comp.pdbx_type HETAIN _chem_comp.formula "C29 H29 Cl2 F N2 O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2014-04-14 _chem_comp.pdbx_modified_date 2014-09-26 _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 559.456 _chem_comp.one_letter_code ? _chem_comp.three_letter_code YAU _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 4CYQ _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # 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 YAU CL1 CL1 CL 0 0 N N N 6.111 48.888 60.042 -11.452 -1.114 1.607 CL1 YAU 1 YAU C26 C26 C 0 1 Y N N 5.360 47.374 59.413 -9.951 -0.906 0.760 C26 YAU 2 YAU C25 C25 C 0 1 Y N N 4.587 46.623 60.300 -9.566 0.351 0.331 C25 YAU 3 YAU C24 C24 C 0 1 Y N N 3.949 45.499 59.860 -8.371 0.516 -0.344 C24 YAU 4 YAU C27 C27 C 0 1 Y N N 5.452 46.995 58.065 -9.136 -1.998 0.518 C27 YAU 5 YAU C28 C28 C 0 1 Y N N 4.828 45.812 57.629 -7.942 -1.833 -0.156 C28 YAU 6 YAU C23 C23 C 0 1 Y N N 4.096 45.072 58.524 -7.560 -0.576 -0.590 C23 YAU 7 YAU C22 C22 C 0 1 N N N 3.338 43.805 58.137 -6.258 -0.397 -1.325 C22 YAU 8 YAU C21 C21 C 0 1 N N R 2.331 44.053 57.015 -5.139 -0.115 -0.320 C21 YAU 9 YAU O3 O3 O 0 1 N N N 1.854 42.751 56.616 -4.948 -1.261 0.513 O3 YAU 10 YAU C20 C20 C 0 1 N N N 1.156 44.951 57.408 -3.842 0.190 -1.072 C20 YAU 11 YAU C19 C19 C 0 1 N N N 1.515 46.406 57.183 -2.772 0.587 -0.088 C19 YAU 12 YAU O2 O2 O 0 1 N N N 1.818 46.769 56.035 -3.022 0.622 1.098 O2 YAU 13 YAU N N N 0 1 N N N 1.420 47.298 58.172 -1.537 0.903 -0.526 N YAU 14 YAU C2 C2 C 0 1 N N N 0.959 46.978 59.542 -1.100 0.903 -1.930 C2 YAU 15 YAU C3 C3 C 0 1 N N N 1.655 48.728 57.983 -0.403 1.312 0.322 C3 YAU 16 YAU C4 C4 C 0 1 N N S 1.008 49.369 59.203 0.858 0.960 -0.505 C4 YAU 17 YAU C1 C1 C 0 1 N N R 1.150 48.282 60.272 0.390 1.303 -1.946 C1 YAU 18 YAU C C C 0 1 N N N 0.128 48.439 61.443 1.161 0.479 -2.979 C YAU 19 YAU O O O 0 1 N N N -1.186 48.381 60.901 0.710 0.819 -4.292 O YAU 20 YAU C5 C5 C 0 1 Y N N 1.720 50.643 59.596 2.028 1.819 -0.099 C5 YAU 21 YAU C18 C18 C 0 1 Y N N 2.945 50.697 60.243 3.188 1.231 0.366 C18 YAU 22 YAU C9 C9 C 0 1 Y N N 3.495 51.989 60.593 4.265 2.023 0.739 C9 YAU 23 YAU C8 C8 C 0 1 Y N N 2.829 53.124 60.258 4.172 3.407 0.644 C8 YAU 24 YAU CL CL CL 0 0 N N N 3.687 54.629 60.796 5.516 4.402 1.110 CL YAU 25 YAU C7 C7 C 0 1 Y N N 1.607 53.121 59.587 3.009 3.989 0.178 C7 YAU 26 YAU C6 C6 C 0 1 Y N N 1.017 51.852 59.300 1.940 3.196 -0.198 C6 YAU 27 YAU N1 N1 N 0 1 N N N 4.692 52.121 61.265 5.442 1.429 1.211 N1 YAU 28 YAU C10 C10 C 0 1 N N N 4.737 52.275 62.634 5.748 0.165 0.858 C10 YAU 29 YAU O1 O1 O 0 1 N N N 3.757 52.122 63.381 5.057 -0.423 0.053 O1 YAU 30 YAU C11 C11 C 0 1 N N N 6.063 52.661 63.314 6.947 -0.517 1.463 C11 YAU 31 YAU C12 C12 C 0 1 Y N N 6.499 51.455 64.111 7.067 -1.912 0.905 C12 YAU 32 YAU C17 C17 C 0 1 Y N N 7.357 50.495 63.581 7.806 -2.136 -0.241 C17 YAU 33 YAU C16 C16 C 0 1 Y N N 7.684 49.384 64.376 7.916 -3.415 -0.754 C16 YAU 34 YAU C15 C15 C 0 1 Y N N 7.134 49.346 65.678 7.285 -4.471 -0.119 C15 YAU 35 YAU F F F 0 1 N N N 7.393 48.355 66.509 7.392 -5.722 -0.619 F YAU 36 YAU C14 C14 C 0 1 Y N N 6.271 50.296 66.209 6.545 -4.245 1.029 C14 YAU 37 YAU C13 C13 C 0 1 Y N N 5.981 51.365 65.400 6.441 -2.967 1.543 C13 YAU 38 YAU H25 H25 H 0 1 N N N 4.494 46.930 61.331 -10.200 1.205 0.523 H25 YAU 39 YAU H27 H27 H 0 1 N N N 6.000 47.609 57.365 -9.434 -2.980 0.857 H27 YAU 40 YAU H24 H24 H 0 1 N N N 3.328 44.934 60.539 -8.071 1.497 -0.679 H24 YAU 41 YAU H28 H28 H 0 1 N N N 4.924 45.490 56.603 -7.305 -2.685 -0.345 H28 YAU 42 YAU H221 H221 H 0 0 N N N 4.062 43.048 57.802 -6.026 -1.305 -1.882 H221 YAU 43 YAU H222 H222 H 0 0 N N N 2.799 43.431 59.020 -6.343 0.441 -2.017 H222 YAU 44 YAU H21 H21 H 0 1 N N N 2.860 44.524 56.173 -5.412 0.741 0.297 H21 YAU 45 YAU H3 H3 H 0 1 N N N 1.220 42.847 55.915 -4.703 -2.062 0.030 H3 YAU 46 YAU H201 H201 H 0 0 N N N 0.280 44.693 56.795 -3.522 -0.696 -1.619 H201 YAU 47 YAU H202 H202 H 0 0 N N N 0.918 44.795 58.471 -4.012 1.008 -1.773 H202 YAU 48 YAU H21C H21C H 0 0 N N N -0.098 46.674 59.543 -1.221 -0.093 -2.356 H21C YAU 49 YAU H22C H22C H 0 0 N N N 1.570 46.180 59.989 -1.684 1.626 -2.500 H22C YAU 50 YAU H31C H31C H 0 0 N N N 2.733 48.947 57.951 -0.442 2.384 0.517 H31C YAU 51 YAU H32C H32C H 0 0 N N N 1.181 49.084 57.056 -0.410 0.755 1.259 H32C YAU 52 YAU H1 H1 H 0 1 N N N 2.168 48.320 60.688 0.501 2.370 -2.141 H1 YAU 53 YAU H4 H4 H 0 1 N N N -0.056 49.570 59.007 1.103 -0.098 -0.413 H4 YAU 54 YAU HC1 HC1 H 0 1 N N N 0.267 47.625 62.169 2.226 0.695 -2.894 HC1 YAU 55 YAU HC2 HC2 H 0 1 N N N 0.281 49.407 61.943 0.990 -0.582 -2.799 HC2 YAU 56 YAU H H H 0 1 N N N -1.822 48.475 61.600 1.156 0.333 -4.999 H YAU 57 YAU H18 H18 H 0 1 N N N 3.480 49.790 60.482 3.257 0.156 0.439 H18 YAU 58 YAU H6 H6 H 0 1 N N N 0.033 51.806 58.856 1.033 3.653 -0.566 H6 YAU 59 YAU HA HA H 0 1 N N N 5.547 52.105 60.747 6.037 1.928 1.793 HA YAU 60 YAU H7 H7 H 0 1 N N N 1.125 54.042 59.295 2.935 5.064 0.105 H7 YAU 61 YAU H111 H111 H 0 0 N N N 6.821 52.911 62.557 7.847 0.049 1.222 H111 YAU 62 YAU H112 H112 H 0 0 N N N 5.912 53.523 63.980 6.829 -0.567 2.545 H112 YAU 63 YAU H17 H17 H 0 1 N N N 7.760 50.602 62.585 8.298 -1.312 -0.736 H17 YAU 64 YAU H13 H13 H 0 1 N N N 5.339 52.151 65.770 5.867 -2.791 2.441 H13 YAU 65 YAU H16 H16 H 0 1 N N N 8.325 48.596 64.010 8.493 -3.590 -1.650 H16 YAU 66 YAU H14 H14 H 0 1 N N N 5.853 50.199 67.200 6.052 -5.068 1.525 H14 YAU 67 # 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 YAU CL1 C26 SING N N 1 YAU C26 C25 SING Y N 2 YAU C26 C27 DOUB Y N 3 YAU C25 C24 DOUB Y N 4 YAU C24 C23 SING Y N 5 YAU C27 C28 SING Y N 6 YAU C28 C23 DOUB Y N 7 YAU C23 C22 SING N N 8 YAU C22 C21 SING N N 9 YAU C21 O3 SING N N 10 YAU C21 C20 SING N N 11 YAU C20 C19 SING N N 12 YAU C19 O2 DOUB N N 13 YAU C19 N SING N N 14 YAU N C2 SING N N 15 YAU N C3 SING N N 16 YAU C2 C1 SING N N 17 YAU C3 C4 SING N N 18 YAU C4 C1 SING N N 19 YAU C4 C5 SING N N 20 YAU C1 C SING N N 21 YAU C O SING N N 22 YAU C5 C18 SING Y N 23 YAU C5 C6 DOUB Y N 24 YAU C18 C9 DOUB Y N 25 YAU C9 C8 SING Y N 26 YAU C9 N1 SING N N 27 YAU C8 CL SING N N 28 YAU C8 C7 DOUB Y N 29 YAU C7 C6 SING Y N 30 YAU N1 C10 SING N N 31 YAU C10 O1 DOUB N N 32 YAU C10 C11 SING N N 33 YAU C11 C12 SING N N 34 YAU C12 C17 SING Y N 35 YAU C12 C13 DOUB Y N 36 YAU C17 C16 DOUB Y N 37 YAU C16 C15 SING Y N 38 YAU C15 F SING N N 39 YAU C15 C14 DOUB Y N 40 YAU C14 C13 SING Y N 41 YAU C25 H25 SING N N 42 YAU C27 H27 SING N N 43 YAU C24 H24 SING N N 44 YAU C28 H28 SING N N 45 YAU C22 H221 SING N N 46 YAU C22 H222 SING N N 47 YAU C21 H21 SING N N 48 YAU O3 H3 SING N N 49 YAU C20 H201 SING N N 50 YAU C20 H202 SING N N 51 YAU C2 H21C SING N N 52 YAU C2 H22C SING N N 53 YAU C3 H31C SING N N 54 YAU C3 H32C SING N N 55 YAU C1 H1 SING N N 56 YAU C4 H4 SING N N 57 YAU C HC1 SING N N 58 YAU C HC2 SING N N 59 YAU O H SING N N 60 YAU C18 H18 SING N N 61 YAU C6 H6 SING N N 62 YAU N1 HA SING N N 63 YAU C7 H7 SING N N 64 YAU C11 H111 SING N N 65 YAU C11 H112 SING N N 66 YAU C17 H17 SING N N 67 YAU C13 H13 SING N N 68 YAU C16 H16 SING N N 69 YAU C14 H14 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 YAU SMILES ACDLabs 12.01 "O=C(N3CC(c2ccc(Cl)c(NC(=O)Cc1ccc(F)cc1)c2)C(CO)C3)CC(O)Cc4ccc(Cl)cc4" YAU InChI InChI 1.03 "InChI=1S/C29H29Cl2FN2O4/c30-22-6-1-18(2-7-22)11-24(36)14-29(38)34-15-21(17-35)25(16-34)20-5-10-26(31)27(13-20)33-28(37)12-19-3-8-23(32)9-4-19/h1-10,13,21,24-25,35-36H,11-12,14-17H2,(H,33,37)/t21-,24-,25-/m1/s1" YAU InChIKey InChI 1.03 LMARVLAZWJAMGJ-NQHRYMMQSA-N YAU SMILES_CANONICAL CACTVS 3.385 "OC[C@H]1CN(C[C@@H]1c2ccc(Cl)c(NC(=O)Cc3ccc(F)cc3)c2)C(=O)C[C@H](O)Cc4ccc(Cl)cc4" YAU SMILES CACTVS 3.385 "OC[CH]1CN(C[CH]1c2ccc(Cl)c(NC(=O)Cc3ccc(F)cc3)c2)C(=O)C[CH](O)Cc4ccc(Cl)cc4" YAU SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1cc(ccc1C[C@H](CC(=O)N2C[C@@H]([C@H](C2)c3ccc(c(c3)NC(=O)Cc4ccc(cc4)F)Cl)CO)O)Cl" YAU SMILES "OpenEye OEToolkits" 1.7.6 "c1cc(ccc1CC(CC(=O)N2CC(C(C2)c3ccc(c(c3)NC(=O)Cc4ccc(cc4)F)Cl)CO)O)Cl" # 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 YAU "SYSTEMATIC NAME" ACDLabs 12.01 "N-{2-chloro-5-[(3S,4R)-1-[(3R)-4-(4-chlorophenyl)-3-hydroxybutanoyl]-4-(hydroxymethyl)pyrrolidin-3-yl]phenyl}-2-(4-fluorophenyl)acetamide" YAU "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "N-[2-chloranyl-5-[(3S,4R)-1-[(3R)-4-(4-chlorophenyl)-3-oxidanyl-butanoyl]-4-(hydroxymethyl)pyrrolidin-3-yl]phenyl]-2-(4-fluorophenyl)ethanamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site YAU "Create component" 2014-04-14 EBI YAU "Initial release" 2014-10-01 RCSB #