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                    2008-10-14 
_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 InChI            InChI                1.02b InChI=1/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/f/h19,25H 
383 InChIKey         InChI                1.02b JOBDOAKLPNMGKV-BMEILYKFDE                                                                                                                                                                                   
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                                                                                                                                                       
# 
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" 
# 
