data_383 # _chem_comp.id 383 _chem_comp.name "[2-AMINO-3-(4-HYDROXY-PHENYL)-PROPIONYLAMINO]- (2,4,5,8-TETRAHYDROXY-7-OXA-2-AZA-BICYCLO[3.2.1]OCT-3-YL)- ACETIC ACID" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C17 H23 N3 O9" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms SB-219383 _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2001-07-05 _chem_comp.pdbx_modified_date 2021-03-01 _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 413.379 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 383 _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 1JII _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 383 C8 C8 C 0 1 Y N N -8.237 11.144 83.743 0.586 0.569 -5.354 C8 383 1 383 C7 C7 C 0 1 Y N N -7.569 10.048 84.273 -0.083 0.448 -6.555 C7 383 2 383 C12 C12 C 0 1 Y N N -8.163 9.320 85.310 -1.105 -0.480 -6.688 C12 383 3 383 C11 C11 C 0 1 Y N N -9.502 9.529 85.668 -1.451 -1.286 -5.613 C11 383 4 383 C10 C10 C 0 1 Y N N -10.183 10.623 85.141 -0.774 -1.165 -4.415 C10 383 5 383 C9 C9 C 0 1 Y N N -9.563 11.475 84.180 0.239 -0.234 -4.283 C9 383 6 383 C14 C14 C 0 1 N N N -10.300 12.770 83.634 0.972 -0.100 -2.973 C14 383 7 383 C15 C15 C 0 1 N N S -11.871 12.770 83.597 0.264 0.934 -2.097 C15 383 8 383 C17 C17 C 0 1 N N N -12.557 14.171 83.860 0.997 1.068 -0.787 C17 383 9 383 N19 N19 N 0 1 N N N -11.874 14.988 84.551 0.660 0.285 0.256 N19 383 10 383 C20 C20 C 0 1 N N S -11.983 16.414 84.541 1.372 0.415 1.530 C20 383 11 383 C21 C21 C 0 1 N N N -10.851 16.958 83.699 2.558 -0.514 1.540 C21 383 12 383 O23 O23 O 0 1 N N N -10.050 15.950 83.175 2.607 -1.549 0.686 O23 383 13 383 O18 O18 O 0 1 N N N -13.653 14.456 83.413 1.890 1.880 -0.672 O18 383 14 383 N16 N16 N 0 1 N N N -12.344 12.214 82.322 0.250 2.231 -2.785 N16 383 15 383 O22 O22 O 0 1 N N N -10.675 18.184 83.507 3.465 -0.328 2.316 O22 383 16 383 C6 C6 C 0 1 N N S -12.106 16.891 85.965 0.431 0.053 2.680 C6 383 17 383 N5 N5 N 0 1 N N N -12.694 15.836 86.835 -0.108 -1.289 2.456 N5 383 18 383 C4 C4 C 0 1 N N S -13.114 16.326 88.154 -1.000 -1.600 3.588 C4 383 19 383 C3 C3 C 0 1 N N R -14.189 17.378 87.984 -2.266 -0.695 3.411 C3 383 20 383 C2 C2 C 0 1 N N R -13.308 18.488 87.420 -1.658 0.659 3.883 C2 383 21 383 C1 C1 C 0 1 N N S -13.065 18.074 85.924 -0.694 1.088 2.754 C1 383 22 383 O28 O28 O 0 1 N N N -11.768 14.786 87.038 1.029 -2.203 2.555 O28 383 23 383 O29 O29 O 0 1 N N N -13.910 19.758 87.577 -2.628 1.650 4.229 O29 383 24 383 C30 C30 C 0 1 N N N -11.955 18.394 88.152 -0.757 0.210 5.062 C30 383 25 383 O31 O31 O 0 1 N N N -11.973 17.054 88.670 -0.394 -1.153 4.813 O31 383 26 383 O32 O32 O 0 1 N N N -15.236 17.024 87.084 -2.685 -0.645 2.045 O32 383 27 383 O64 O64 O 0 1 N N N -12.548 19.136 85.141 -0.148 2.376 3.047 O64 383 28 383 O13 O13 O 0 1 N N N -7.436 8.432 85.969 -1.766 -0.601 -7.870 O13 383 29 383 H8 H8 H 0 1 N N N -7.717 11.747 82.979 1.382 1.292 -5.250 H8 383 30 383 H7 H7 H 0 1 N N N -6.581 9.759 83.876 0.187 1.077 -7.391 H7 383 31 383 H11 H11 H 0 1 N N N -10.015 8.838 86.358 -2.246 -2.009 -5.714 H11 383 32 383 H10 H10 H 0 1 N N N -11.213 10.814 85.484 -1.042 -1.792 -3.578 H10 383 33 383 H141 1H14 H 0 0 N N N -9.949 13.658 84.209 1.996 0.221 -3.161 H141 383 34 383 H142 2H14 H 0 0 N N N -9.911 13.008 82.616 0.982 -1.063 -2.463 H142 383 35 383 H15 H15 H 0 1 N N N -12.179 12.128 84.454 -0.759 0.611 -1.909 H15 383 36 383 H19 H19 H 0 1 N N N -11.212 14.479 85.136 -0.054 -0.364 0.164 H19 383 37 383 H20 H20 H 0 1 N N N -12.903 16.811 84.051 1.715 1.442 1.651 H20 383 38 383 H23 H23 H 0 1 N N N -9.338 16.291 82.646 3.368 -2.145 0.692 H23 383 39 383 H161 1H16 H 0 0 N N N -13.363 12.214 82.298 1.214 2.489 -2.937 H161 383 40 383 H162 2H16 H 0 0 N N N -11.957 11.287 82.142 -0.154 2.073 -3.695 H162 383 41 383 H6 H6 H 0 1 N N N -11.104 17.155 86.376 0.989 0.063 3.617 H6 383 42 383 H4 H4 H 0 1 N N N -13.468 15.483 88.792 -1.259 -2.658 3.624 H4 383 43 383 H3 H3 H 0 1 N N N -14.766 17.602 88.911 -3.079 -1.016 4.062 H3 383 44 383 H1 H1 H 0 1 N N N -14.029 17.802 85.434 -1.229 1.121 1.805 H1 383 45 383 H28 H28 H 0 1 N N N -12.143 14.112 87.593 1.509 -1.966 3.360 H28 383 46 383 H29 H29 H 0 1 N N N -13.361 20.449 87.225 -3.169 1.275 4.937 H29 383 47 383 H301 1H30 H 0 0 N N N -11.065 18.642 87.526 0.136 0.831 5.106 H301 383 48 383 H302 2H30 H 0 0 N N N -11.778 19.188 88.914 -1.308 0.283 6.000 H302 383 49 383 H32 H32 H 0 1 N N N -15.910 17.684 86.977 -2.913 -1.550 1.790 H32 383 50 383 H64 H64 H 0 1 N N N -13.146 19.873 85.115 0.384 2.634 2.282 H64 383 51 383 H13 H13 H 0 1 N N N -7.839 7.937 86.673 -1.288 -1.261 -8.391 H13 383 52 # # 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 383 C8 C7 DOUB Y N 1 383 C8 C9 SING Y N 2 383 C8 H8 SING N N 3 383 C7 C12 SING Y N 4 383 C7 H7 SING N N 5 383 C12 C11 DOUB Y N 6 383 C12 O13 SING N N 7 383 C11 C10 SING Y N 8 383 C11 H11 SING N N 9 383 C10 C9 DOUB Y N 10 383 C10 H10 SING N N 11 383 C9 C14 SING N N 12 383 C14 C15 SING N N 13 383 C14 H141 SING N N 14 383 C14 H142 SING N N 15 383 C15 C17 SING N N 16 383 C15 N16 SING N N 17 383 C15 H15 SING N N 18 383 C17 N19 SING N N 19 383 C17 O18 DOUB N N 20 383 N19 C20 SING N N 21 383 N19 H19 SING N N 22 383 C20 C21 SING N N 23 383 C20 C6 SING N N 24 383 C20 H20 SING N N 25 383 C21 O23 SING N N 26 383 C21 O22 DOUB N N 27 383 O23 H23 SING N N 28 383 N16 H161 SING N N 29 383 N16 H162 SING N N 30 383 C6 N5 SING N N 31 383 C6 C1 SING N N 32 383 C6 H6 SING N N 33 383 N5 C4 SING N N 34 383 N5 O28 SING N N 35 383 C4 C3 SING N N 36 383 C4 O31 SING N N 37 383 C4 H4 SING N N 38 383 C3 C2 SING N N 39 383 C3 O32 SING N N 40 383 C3 H3 SING N N 41 383 C2 C1 SING N N 42 383 C2 O29 SING N N 43 383 C2 C30 SING N N 44 383 C1 O64 SING N N 45 383 C1 H1 SING N N 46 383 O28 H28 SING N N 47 383 O29 H29 SING N N 48 383 C30 O31 SING N N 49 383 C30 H301 SING N N 50 383 C30 H302 SING N N 51 383 O32 H32 SING N N 52 383 O64 H64 SING N N 53 383 O13 H13 SING N N 54 # # 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 383 SMILES ACDLabs 10.04 "O=C(O)C(NC(=O)C(N)Cc1ccc(O)cc1)C3N(O)C2OCC(O)(C2O)C3O" 383 SMILES_CANONICAL CACTVS 3.341 "N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H]([C@H]2[C@H](O)[C@]3(O)CO[C@@H]([C@@H]3O)N2O)C(O)=O" 383 SMILES CACTVS 3.341 "N[CH](Cc1ccc(O)cc1)C(=O)N[CH]([CH]2[CH](O)[C]3(O)CO[CH]([CH]3O)N2O)C(O)=O" 383 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc(ccc1C[C@@H](C(=O)N[C@@H]([C@H]2[C@@H]([C@@]3(CO[C@@H]([C@@H]3O)[N@@]2O)O)O)C(=O)O)N)O" 383 SMILES "OpenEye OEToolkits" 1.5.0 "c1cc(ccc1CC(C(=O)NC(C2C(C3(COC(C3O)N2O)O)O)C(=O)O)N)O" 383 InChI InChI 1.03 "InChI=1S/C17H23N3O9/c18-9(5-7-1-3-8(21)4-2-7)14(24)19-10(16(25)26)11-12(22)17(27)6-29-15(13(17)23)20(11)28/h1-4,9-13,15,21-23,27-28H,5-6,18H2,(H,19,24)(H,25,26)/t9-,10-,11-,12-,13-,15-,17+/m0/s1" 383 InChIKey InChI 1.03 JOBDOAKLPNMGKV-OEUXZGCXSA-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 383 "SYSTEMATIC NAME" ACDLabs 10.04 "(2S)-[(1S,3S,4S,5R,8R)-2,4,5,8-tetrahydroxy-7-oxa-2-azabicyclo[3.2.1]oct-3-yl](L-tyrosylamino)ethanoic acid" 383 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-2-[(1S,2R,3S,4S,5R,8R)-2,4,5,8-tetrahydroxy-7-oxa-2-azabicyclo[3.2.1]octan-3-yl]ethanoic 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 383 "Create component" 2001-07-05 RCSB 383 "Modify descriptor" 2011-06-04 RCSB 383 "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 383 _pdbx_chem_comp_synonyms.name SB-219383 _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##