data_5AM # _chem_comp.id 5AM _chem_comp.name "BENZYL {(1S)-5-AMINO-1-[(S)-HYDROXY(5-{[4-(4-PHENYLBUTANOYL)PIPERAZIN-1-YL]METHYL}-1,2,4-OXADIAZOL-3-YL)METHYL]PENTYL}CARBAMATE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C31 H42 N6 O5" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2006-03-30 _chem_comp.pdbx_modified_date 2011-06-04 _chem_comp.pdbx_ambiguous_flag ? _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 578.702 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 5AM _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details ? _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 2GDD _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 5AM C1 C1 C 0 1 N N N 17.551 81.555 100.670 -6.837 1.631 -1.428 C1 5AM 1 5AM C3 C3 C 0 1 N N N 18.217 79.579 102.132 -5.143 0.271 -0.353 C3 5AM 2 5AM C7 C7 C 0 1 Y N N 16.764 76.878 103.642 -1.729 -2.832 1.179 C7 5AM 3 5AM C8 C8 C 0 1 Y N N 16.386 80.999 99.924 -8.341 1.715 -1.486 C8 5AM 4 5AM C9 C9 C 0 1 Y N N 15.019 81.385 100.286 -9.035 1.012 -2.453 C9 5AM 5 5AM C10 C10 C 0 1 Y N N 13.885 80.844 99.556 -10.414 1.085 -2.504 C10 5AM 6 5AM C11 C11 C 0 1 Y N N 14.107 79.912 98.458 -11.099 1.870 -1.594 C11 5AM 7 5AM C12 C12 C 0 1 Y N N 15.444 79.524 98.094 -10.404 2.577 -0.631 C12 5AM 8 5AM C13 C13 C 0 1 Y N N 16.581 80.061 98.817 -9.025 2.500 -0.577 C13 5AM 9 5AM C15 C15 C 0 1 N N N 20.120 78.341 105.075 -2.831 -0.144 1.803 C15 5AM 10 5AM C16 C16 C 0 1 N N N 21.464 78.781 104.424 -2.881 1.321 1.362 C16 5AM 11 5AM C22 C22 C 0 1 Y N N 15.023 77.137 102.346 0.211 -3.579 0.785 C22 5AM 12 5AM N23 N23 N 0 1 Y N N 15.825 77.823 103.241 -1.005 -3.542 0.296 N23 5AM 13 5AM N26 N26 N 0 1 N N N 12.514 77.420 102.098 2.108 -3.307 -0.709 N26 5AM 14 5AM C27 C27 C 0 1 N N N 11.536 78.159 101.185 2.426 -2.132 0.110 C27 5AM 15 5AM N29 N29 N 0 1 N N N 9.772 76.526 101.860 4.329 -1.711 -1.353 N29 5AM 16 5AM C30 C30 C 0 1 N N N 10.756 75.707 102.677 4.157 -3.011 -2.021 C30 5AM 17 5AM C31 C31 C 0 1 N N N 12.198 75.926 102.108 3.379 -3.939 -1.082 C31 5AM 18 5AM C32 C32 C 0 1 N N N 8.583 75.950 101.239 5.535 -1.114 -1.293 C32 5AM 19 5AM C33 C33 C 0 1 N N N 7.750 74.862 101.771 5.684 0.217 -0.602 C33 5AM 20 5AM C35 C35 C 0 1 N N N 6.703 75.399 102.771 7.143 0.671 -0.677 C35 5AM 21 5AM O2 O2 O 0 1 N N N 17.777 80.819 101.891 -6.447 0.537 -0.557 O2 5AM 22 5AM N4 N4 N 0 1 N N N 18.523 79.301 103.513 -4.781 -0.745 0.456 N4 5AM 23 5AM C5 C5 C 0 1 N N S 19.026 78.021 104.017 -3.362 -1.034 0.678 C5 5AM 24 5AM O14 O14 O 0 1 N N N 18.368 78.696 101.287 -4.293 0.947 -0.897 O14 5AM 25 5AM C17 C17 C 0 1 N N N 22.705 78.561 105.312 -2.349 2.211 2.487 C17 5AM 26 5AM C18 C18 C 0 1 N N N 23.988 79.087 104.642 -2.400 3.675 2.046 C18 5AM 27 5AM N19 N19 N 0 1 N N N 25.093 79.042 105.593 -1.890 4.530 3.126 N19 5AM 28 5AM N20 N20 N 0 1 Y N N 16.489 75.722 103.002 -0.934 -2.486 2.146 N20 5AM 29 5AM O21 O21 O 0 1 Y N N 15.448 75.867 102.223 0.186 -2.905 1.939 O21 5AM 30 5AM O24 O24 O 0 1 N N N 18.356 75.833 105.049 -3.831 -2.736 2.328 O24 5AM 31 5AM C25 C25 C 0 1 N N N 13.888 77.738 101.631 1.407 -4.256 0.167 C25 5AM 32 5AM C28 C28 C 0 1 N N N 10.087 78.006 101.763 3.141 -1.085 -0.750 C28 5AM 33 5AM O34 O34 O 0 1 N N N 8.160 76.380 100.146 6.501 -1.647 -1.796 O34 5AM 34 5AM C36 C36 C 0 1 N N N 6.303 74.314 103.774 7.294 2.022 0.025 C36 5AM 35 5AM C37 C37 C 0 1 Y N N 5.196 74.703 104.674 8.731 2.468 -0.049 C37 5AM 36 5AM C38 C38 C 0 1 Y N N 5.397 75.690 105.703 9.616 2.117 0.953 C38 5AM 37 5AM C39 C39 C 0 1 Y N N 3.901 74.090 104.537 9.163 3.235 -1.115 C39 5AM 38 5AM C40 C40 C 0 1 Y N N 4.331 76.055 106.575 10.936 2.522 0.883 C40 5AM 39 5AM C41 C41 C 0 1 Y N N 2.832 74.454 105.412 10.482 3.644 -1.183 C41 5AM 40 5AM C42 C42 C 0 1 Y N N 3.051 75.436 106.433 11.368 3.288 -0.183 C42 5AM 41 5AM C6 C6 C 0 1 N N S 17.864 77.120 104.588 -3.196 -2.504 1.069 C6 5AM 42 5AM H11A 1H1 H 0 0 N N N 17.339 82.604 100.924 -6.436 2.567 -1.037 H11A 5AM 43 5AM H12A 2H1 H 0 0 N N N 18.448 81.485 100.038 -6.444 1.457 -2.429 H12A 5AM 44 5AM H9 H9 H 0 1 N N N 14.854 82.075 101.100 -8.500 0.399 -3.163 H9 5AM 45 5AM H10 H10 H 0 1 N N N 12.880 81.132 99.827 -10.957 0.532 -3.256 H10 5AM 46 5AM H11 H11 H 0 1 N N N 13.264 79.511 97.915 -12.176 1.929 -1.635 H11 5AM 47 5AM H12 H12 H 0 1 N N N 15.601 78.831 97.280 -10.939 3.190 0.080 H12 5AM 48 5AM H13 H13 H 0 1 N N N 17.581 79.766 98.536 -8.482 3.053 0.175 H13 5AM 49 5AM H151 1H15 H 0 0 N N N 20.309 77.424 105.652 -1.801 -0.420 2.029 H151 5AM 50 5AM H152 2H15 H 0 0 N N N 19.758 79.159 105.715 -3.446 -0.276 2.693 H152 5AM 51 5AM H161 1H16 H 0 0 N N N 21.390 79.864 104.247 -3.911 1.597 1.136 H161 5AM 52 5AM H162 2H16 H 0 0 N N N 21.600 78.195 103.503 -2.266 1.453 0.472 H162 5AM 53 5AM H271 1H27 H 0 0 N N N 11.579 77.734 100.171 1.504 -1.707 0.508 H271 5AM 54 5AM H272 2H27 H 0 0 N N N 11.806 79.224 101.139 3.074 -2.429 0.934 H272 5AM 55 5AM H301 1H30 H 0 0 N N N 10.491 74.641 102.617 5.133 -3.443 -2.239 H301 5AM 56 5AM H302 2H30 H 0 0 N N N 10.721 76.029 103.728 3.600 -2.876 -2.948 H302 5AM 57 5AM H311 1H31 H 0 0 N N N 12.928 75.399 102.740 3.969 -4.125 -0.185 H311 5AM 58 5AM H312 2H31 H 0 0 N N N 12.253 75.531 101.083 3.180 -4.883 -1.588 H312 5AM 59 5AM H331 1H33 H 0 0 N N N 8.401 74.148 102.297 5.049 0.955 -1.094 H331 5AM 60 5AM H332 2H33 H 0 0 N N N 7.227 74.372 100.936 5.386 0.120 0.442 H332 5AM 61 5AM H351 1H35 H 0 0 N N N 5.808 75.711 102.212 7.778 -0.067 -0.186 H351 5AM 62 5AM H352 2H35 H 0 0 N N N 7.133 76.252 103.317 7.440 0.768 -1.721 H352 5AM 63 5AM HN4 HN4 H 0 1 N N N 18.381 80.036 104.176 -5.460 -1.285 0.890 HN4 5AM 64 5AM H5 H5 H 0 1 N N N 19.466 77.427 103.202 -2.803 -0.836 -0.237 H5 5AM 65 5AM H171 1H17 H 0 0 N N N 22.822 77.480 105.476 -1.320 1.935 2.713 H171 5AM 66 5AM H172 2H17 H 0 0 N N N 22.558 79.096 106.262 -2.965 2.078 3.377 H172 5AM 67 5AM H181 1H18 H 0 0 N N N 23.830 80.126 104.316 -3.430 3.951 1.820 H181 5AM 68 5AM H182 2H18 H 0 0 N N N 24.229 78.459 103.772 -1.785 3.808 1.156 H182 5AM 69 5AM H191 1H19 H 0 0 N N N 25.057 79.848 106.184 -1.941 5.481 2.792 H191 5AM 70 5AM H192 2H19 H 0 0 N N N 25.961 79.032 105.096 -2.545 4.454 3.889 H192 5AM 71 5AM HO24 HO24 H 0 0 N N N 18.463 75.250 104.307 -3.397 -2.159 2.971 HO24 5AM 72 5AM H251 1H25 H 0 0 N N N 13.942 77.312 100.618 2.083 -4.590 0.955 H251 5AM 73 5AM H252 2H25 H 0 0 N N N 14.005 78.829 101.715 1.077 -5.114 -0.417 H252 5AM 74 5AM H281 1H28 H 0 0 N N N 9.361 78.507 101.106 3.445 -0.244 -0.127 H281 5AM 75 5AM H282 2H28 H 0 0 N N N 10.030 78.467 102.760 2.471 -0.737 -1.537 H282 5AM 76 5AM H361 1H36 H 0 0 N N N 7.181 74.126 104.409 6.659 2.759 -0.467 H361 5AM 77 5AM H362 2H36 H 0 0 N N N 5.983 73.428 103.206 6.997 1.925 1.069 H362 5AM 78 5AM H38 H38 H 0 1 N N N 6.364 76.158 105.815 9.279 1.519 1.787 H38 5AM 79 5AM H39 H39 H 0 1 N N N 3.736 73.350 103.768 8.471 3.513 -1.896 H39 5AM 80 5AM H40 H40 H 0 1 N N N 4.490 76.798 107.342 11.629 2.244 1.664 H40 5AM 81 5AM H41 H41 H 0 1 N N N 1.862 73.991 105.305 10.820 4.242 -2.016 H41 5AM 82 5AM H42 H42 H 0 1 N N N 2.245 75.709 107.098 12.399 3.607 -0.236 H42 5AM 83 5AM H6 H6 H 0 1 N N N 17.464 77.706 105.429 -3.654 -3.136 0.309 H6 5AM 84 # 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 5AM C1 C8 SING N N 1 5AM C1 O2 SING N N 2 5AM C1 H11A SING N N 3 5AM C1 H12A SING N N 4 5AM C3 O2 SING N N 5 5AM C3 N4 SING N N 6 5AM C3 O14 DOUB N N 7 5AM C7 N23 SING Y N 8 5AM C7 N20 DOUB Y N 9 5AM C7 C6 SING N N 10 5AM C8 C9 SING Y N 11 5AM C8 C13 DOUB Y N 12 5AM C9 C10 DOUB Y N 13 5AM C9 H9 SING N N 14 5AM C10 C11 SING Y N 15 5AM C10 H10 SING N N 16 5AM C11 C12 DOUB Y N 17 5AM C11 H11 SING N N 18 5AM C12 C13 SING Y N 19 5AM C12 H12 SING N N 20 5AM C13 H13 SING N N 21 5AM C15 C16 SING N N 22 5AM C15 C5 SING N N 23 5AM C15 H151 SING N N 24 5AM C15 H152 SING N N 25 5AM C16 C17 SING N N 26 5AM C16 H161 SING N N 27 5AM C16 H162 SING N N 28 5AM C22 N23 DOUB Y N 29 5AM C22 O21 SING Y N 30 5AM C22 C25 SING N N 31 5AM N26 C27 SING N N 32 5AM N26 C31 SING N N 33 5AM N26 C25 SING N N 34 5AM C27 C28 SING N N 35 5AM C27 H271 SING N N 36 5AM C27 H272 SING N N 37 5AM N29 C30 SING N N 38 5AM N29 C32 SING N N 39 5AM N29 C28 SING N N 40 5AM C30 C31 SING N N 41 5AM C30 H301 SING N N 42 5AM C30 H302 SING N N 43 5AM C31 H311 SING N N 44 5AM C31 H312 SING N N 45 5AM C32 C33 SING N N 46 5AM C32 O34 DOUB N N 47 5AM C33 C35 SING N N 48 5AM C33 H331 SING N N 49 5AM C33 H332 SING N N 50 5AM C35 C36 SING N N 51 5AM C35 H351 SING N N 52 5AM C35 H352 SING N N 53 5AM N4 C5 SING N N 54 5AM N4 HN4 SING N N 55 5AM C5 C6 SING N N 56 5AM C5 H5 SING N N 57 5AM C17 C18 SING N N 58 5AM C17 H171 SING N N 59 5AM C17 H172 SING N N 60 5AM C18 N19 SING N N 61 5AM C18 H181 SING N N 62 5AM C18 H182 SING N N 63 5AM N19 H191 SING N N 64 5AM N19 H192 SING N N 65 5AM N20 O21 SING Y N 66 5AM O24 C6 SING N N 67 5AM O24 HO24 SING N N 68 5AM C25 H251 SING N N 69 5AM C25 H252 SING N N 70 5AM C28 H281 SING N N 71 5AM C28 H282 SING N N 72 5AM C36 C37 SING N N 73 5AM C36 H361 SING N N 74 5AM C36 H362 SING N N 75 5AM C37 C38 SING Y N 76 5AM C37 C39 DOUB Y N 77 5AM C38 C40 DOUB Y N 78 5AM C38 H38 SING N N 79 5AM C39 C41 SING Y N 80 5AM C39 H39 SING N N 81 5AM C40 C42 SING Y N 82 5AM C40 H40 SING N N 83 5AM C41 C42 DOUB Y N 84 5AM C41 H41 SING N N 85 5AM C42 H42 SING N N 86 5AM C6 H6 SING N N 87 # 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 5AM SMILES ACDLabs 10.04 "O=C(N3CCN(Cc1nc(no1)C(O)C(NC(=O)OCc2ccccc2)CCCCN)CC3)CCCc4ccccc4" 5AM SMILES_CANONICAL CACTVS 3.341 "NCCCC[C@H](NC(=O)OCc1ccccc1)[C@H](O)c2noc(CN3CCN(CC3)C(=O)CCCc4ccccc4)n2" 5AM SMILES CACTVS 3.341 "NCCCC[CH](NC(=O)OCc1ccccc1)[CH](O)c2noc(CN3CCN(CC3)C(=O)CCCc4ccccc4)n2" 5AM SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1ccc(cc1)CCCC(=O)N2CCN(CC2)Cc3nc(no3)[C@H]([C@H](CCCCN)NC(=O)OCc4ccccc4)O" 5AM SMILES "OpenEye OEToolkits" 1.5.0 "c1ccc(cc1)CCCC(=O)N2CCN(CC2)Cc3nc(no3)C(C(CCCCN)NC(=O)OCc4ccccc4)O" 5AM InChI InChI 1.03 "InChI=1S/C31H42N6O5/c32-17-8-7-15-26(33-31(40)41-23-25-12-5-2-6-13-25)29(39)30-34-27(42-35-30)22-36-18-20-37(21-19-36)28(38)16-9-14-24-10-3-1-4-11-24/h1-6,10-13,26,29,39H,7-9,14-23,32H2,(H,33,40)/t26-,29-/m0/s1" 5AM InChIKey InChI 1.03 LRPAFCFDXNPFAF-WNJJXGMVSA-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 5AM "SYSTEMATIC NAME" ACDLabs 10.04 "benzyl {(1S)-5-amino-1-[(S)-hydroxy(5-{[4-(4-phenylbutanoyl)piperazin-1-yl]methyl}-1,2,4-oxadiazol-3-yl)methyl]pentyl}carbamate" 5AM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "phenylmethyl N-[(1S,2S)-6-amino-1-hydroxy-1-[5-[[4-(4-phenylbutanoyl)piperazin-1-yl]methyl]-1,2,4-oxadiazol-3-yl]hexan-2-yl]carbamate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 5AM "Create component" 2006-03-30 RCSB 5AM "Modify descriptor" 2011-06-04 RCSB #