data_5ZA
# 
_chem_comp.id                                    5ZA 
_chem_comp.name                                  "(5Z)-2-[(1S,2R)-1-AMINO-2-HYDROXYPROPYL]-5-[(4-AMINO-1H-INDOL-3-YL)METHYLENE]-3-(2-HYDROXYETHYL)-3,5-DIHYDRO-4H-IMIDAZOL-4-ONE" 
_chem_comp.type                                  "L-PEPTIDE LINKING" 
_chem_comp.pdbx_type                             ATOMP 
_chem_comp.formula                               "C17 H19 N5 O4" 
_chem_comp.mon_nstd_parent_comp_id               "THR, TRP, GLY" 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-04-22 
_chem_comp.pdbx_modified_date                    2009-01-07 
_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                        357.364 
_chem_comp.one_letter_code                       TWG 
_chem_comp.three_letter_code                     5ZA 
_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        1OXF 
_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 
5ZA C25  C25  C 0 1 N N N 0.112  56.967 -1.548 -4.172 3.252  -0.130 C25  5ZA 1  
5ZA C23  C23  C 0 1 N N R 0.937  57.004 -0.260 -3.307 2.020  -0.403 C23  5ZA 2  
5ZA O24  O24  O 0 1 N N N 1.924  57.790 -0.622 -2.186 2.392  -1.207 O24  5ZA 3  
5ZA C22  C22  C 0 1 N N R 0.127  57.453 0.893  -2.813 1.439  0.924  C22  5ZA 4  
5ZA N26  N26  N 0 1 N N N -0.873 58.508 0.396  -2.119 2.484  1.687  N26  5ZA 5  
5ZA C14  C14  C 0 1 N N N 0.748  58.191 2.064  -1.864 0.301  0.651  C14  5ZA 6  
5ZA N13  N13  N 0 1 N N N 1.910  58.725 2.041  -0.596 0.443  0.422  N13  5ZA 7  
5ZA C12  C12  C 0 1 N N N 2.231  59.268 3.219  -0.033 -0.785 0.217  C12  5ZA 8  
5ZA C11  C11  C 0 1 N N N 3.388  59.973 3.593  1.295  -1.059 -0.057 C11  5ZA 9  
5ZA C7   C7   C 0 1 Y N N 4.479  60.314 2.784  2.230  -0.003 -0.149 C7   5ZA 10 
5ZA C8   C8   C 0 1 Y N N 4.626  60.011 1.426  1.951  1.342  -0.298 C8   5ZA 11 
5ZA N9   N9   N 0 1 Y N N 5.776  60.514 0.952  3.110  2.040  -0.348 N9   5ZA 12 
5ZA C6   C6   C 0 1 Y N N 6.403  61.143 1.937  4.194  1.192  -0.235 C6   5ZA 13 
5ZA C5   C5   C 0 1 Y N N 7.644  61.825 1.869  5.569  1.407  -0.230 C5   5ZA 14 
5ZA C4   C4   C 0 1 Y N N 8.158  62.441 3.021  6.435  0.343  -0.099 C4   5ZA 15 
5ZA C3   C3   C 0 1 Y N N 7.423  62.364 4.212  5.953  -0.950 0.028  C3   5ZA 16 
5ZA C2   C2   C 0 1 Y N N 6.163  61.667 4.258  4.588  -1.188 0.024  C2   5ZA 17 
5ZA N10  N10  N 0 1 N N N 5.486  61.670 5.592  4.101  -2.490 0.152  N10  5ZA 18 
5ZA C1   C1   C 0 1 Y N N 5.633  61.050 3.134  3.702  -0.114 -0.101 C1   5ZA 19 
5ZA C16  C16  C 0 1 N N N 1.107  59.008 4.063  -1.128 -1.754 0.347  C16  5ZA 20 
5ZA O17  O17  O 0 1 N N N 0.969  59.339 5.279  -1.060 -2.966 0.237  O17  5ZA 21 
5ZA N15  N15  N 0 1 N N N 0.176  58.350 3.284  -2.227 -1.016 0.619  N15  5ZA 22 
5ZA C18  C18  C 0 1 N N N -1.198 57.909 3.688  -3.578 -1.539 0.840  C18  5ZA 23 
5ZA C19  C19  C 0 1 N N N -1.272 56.573 4.289  -4.310 -1.611 -0.475 C19  5ZA 24 
5ZA O21  O21  O 0 1 N N N -2.286 56.371 5.074  -3.760 -1.261 -1.493 O21  5ZA 25 
5ZA H251 H251 H 0 0 N N N -0.959 56.958 -1.298 -4.524 3.666  -1.075 H251 5ZA 26 
5ZA H252 H252 H 0 0 N N N 0.339  57.856 -2.155 -5.027 2.968  0.483  H252 5ZA 27 
5ZA H253 H253 H 0 0 N N N 0.363  56.060 -2.118 -3.580 4.001  0.397  H253 5ZA 28 
5ZA H23  H23  H 0 1 N N N 1.306  56.037 0.112  -3.899 1.271  -0.930 H23  5ZA 29 
5ZA H24  H24  H 0 1 N N N 1.854  57.980 -1.550 -2.425 2.769  -2.065 H24  5ZA 30 
5ZA H22  H22  H 0 1 N N N -0.217 56.477 1.265  -3.664 1.073  1.499  H22  5ZA 31 
5ZA H261 H261 H 0 0 N N N -1.090 59.139 1.141  -1.326 2.840  1.174  H261 5ZA 32 
5ZA H262 H262 H 0 0 N Y N -0.470 59.017 -0.365 -2.751 3.230  1.938  H262 5ZA 33 
5ZA H11  H11  H 0 1 N N N 3.442  60.288 4.624  1.618  -2.080 -0.200 H11  5ZA 34 
5ZA H8   H8   H 0 1 N N N 3.913  59.450 0.840  0.961  1.769  -0.364 H8   5ZA 35 
5ZA HN9  HN9  H 0 1 N N N 6.106  60.429 0.012  3.171  3.003  -0.449 HN9  5ZA 36 
5ZA H5   H5   H 0 1 N N N 8.190  61.870 0.938  5.958  2.410  -0.328 H5   5ZA 37 
5ZA H4   H4   H 0 1 N N N 9.102  62.964 2.990  7.501  0.518  -0.095 H4   5ZA 38 
5ZA H3   H3   H 0 1 N N N 7.806  62.833 5.106  6.643  -1.775 0.128  H3   5ZA 39 
5ZA H101 H101 H 0 0 N N N 6.176  61.671 6.316  4.706  -3.214 0.375  H101 5ZA 40 
5ZA H102 H102 H 0 0 N N N 4.916  62.487 5.674  3.157  -2.670 0.019  H102 5ZA 41 
5ZA H181 H181 H 0 0 N N N -1.574 58.629 4.430  -3.515 -2.536 1.276  H181 5ZA 42 
5ZA H182 H182 H 0 0 N N N -1.793 57.866 2.764  -4.117 -0.879 1.520  H182 5ZA 43 
5ZA OXT  OXT  O 0 1 N Y N -0.086 55.835 3.986  -5.573 -2.063 -0.517 OXT  5ZA 44 
5ZA HXT  HXT  H 0 1 N Y N -0.077 55.029 4.489  -6.001 -2.091 -1.383 HXT  5ZA 45 
# 
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 
5ZA C25 C23  SING N N 1  
5ZA C25 H251 SING N N 2  
5ZA C25 H252 SING N N 3  
5ZA C25 H253 SING N N 4  
5ZA C23 O24  SING N N 5  
5ZA C23 C22  SING N N 6  
5ZA C23 H23  SING N N 7  
5ZA O24 H24  SING N N 8  
5ZA C22 N26  SING N N 9  
5ZA C22 C14  SING N N 10 
5ZA C22 H22  SING N N 11 
5ZA N26 H261 SING N N 12 
5ZA N26 H262 SING N N 13 
5ZA C14 N13  DOUB N N 14 
5ZA C14 N15  SING N N 15 
5ZA N13 C12  SING N N 16 
5ZA C12 C11  DOUB N Z 17 
5ZA C12 C16  SING N N 18 
5ZA C11 C7   SING N N 19 
5ZA C11 H11  SING N N 20 
5ZA C7  C8   DOUB Y N 21 
5ZA C7  C1   SING Y N 22 
5ZA C8  N9   SING Y N 23 
5ZA C8  H8   SING N N 24 
5ZA N9  C6   SING Y N 25 
5ZA N9  HN9  SING N N 26 
5ZA C6  C5   DOUB Y N 27 
5ZA C6  C1   SING Y N 28 
5ZA C5  C4   SING Y N 29 
5ZA C5  H5   SING N N 30 
5ZA C4  C3   DOUB Y N 31 
5ZA C4  H4   SING N N 32 
5ZA C3  C2   SING Y N 33 
5ZA C3  H3   SING N N 34 
5ZA C2  N10  SING N N 35 
5ZA C2  C1   DOUB Y N 36 
5ZA N10 H101 SING N N 37 
5ZA N10 H102 SING N N 38 
5ZA C16 O17  DOUB N N 39 
5ZA C16 N15  SING N N 40 
5ZA N15 C18  SING N N 41 
5ZA C18 C19  SING N N 42 
5ZA C18 H181 SING N N 43 
5ZA C18 H182 SING N N 44 
5ZA C19 O21  DOUB N N 45 
5ZA C19 OXT  SING N N 46 
5ZA OXT HXT  SING N N 47 
# 
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 
5ZA SMILES           ACDLabs              10.04 "O=C1N(C(=N/C1=C\c3c2c(cccc2nc3)N)C(N)C(O)C)CC(=O)O"                                                                                                                    
5ZA InChI            InChI                1.02b "InChI=1/C17H19N5O4/c1-8(23)15(19)16-21-12(17(26)22(16)7-13(24)25)5-9-6-20-11-4-2-3-10(18)14(9)11/h2-6,8,15,20,23H,7,18-19H2,1H3,(H,24,25)/b12-5-/t8-,15+/m1/s1/f/h24H" 
5ZA InChIKey         InChI                1.02b JUWJATLABHTRDF-TXFIFOBFDW                                                                                                                                               
5ZA SMILES_CANONICAL CACTVS               3.341 "C[C@@H](O)[C@H](N)C1=N\C(=C/c2c[nH]c3cccc(N)c23)C(=O)N1CC(O)=O"                                                                                                        
5ZA SMILES           CACTVS               3.341 "C[CH](O)[CH](N)C1=NC(=Cc2c[nH]c3cccc(N)c23)C(=O)N1CC(O)=O"                                                                                                             
5ZA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@H]([C@@H](C1=N/C(=C\c2c[nH]c3c2c(ccc3)N)/C(=O)N1CC(=O)O)N)O"                                                                                                       
5ZA SMILES           "OpenEye OEToolkits" 1.5.0 "CC(C(C1=NC(=Cc2c[nH]c3c2c(ccc3)N)C(=O)N1CC(=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 
5ZA "SYSTEMATIC NAME" ACDLabs              10.04 "{(4Z)-2-[(1R,2R)-1-amino-2-hydroxypropyl]-4-[(4-amino-1H-indol-3-yl)methylidene]-5-oxo-4,5-dihydro-1H-imidazol-1-yl}acetic acid" 
5ZA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[(4Z)-2-[(1R,2R)-1-amino-2-hydroxy-propyl]-4-[(4-amino-1H-indol-3-yl)methylidene]-5-oxo-imidazol-1-yl]ethanoic acid"           
# 
