data_27U
# 
_chem_comp.id                                    27U 
_chem_comp.name                                  N-(4-carbamimidoylbenzyl)-1-(3-phenylpropanoyl)-L-prolinamide 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H26 N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-02-11 
_chem_comp.pdbx_modified_date                    2009-01-09 
_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                        378.467 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     27U 
_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        2ZHQ 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
27U C1   C1   C 0 1 N N N 18.177 -15.307 24.834 4.675  1.025  -0.542 C1   27U 1  
27U C2   C2   C 0 1 N N N 17.864 -15.354 23.324 4.010  -0.305 -0.180 C2   27U 2  
27U C3   C3   C 0 1 N N N 17.778 -13.976 22.711 2.546  -0.246 -0.533 C3   27U 3  
27U O1   O1   O 0 1 N N N 16.879 -13.243 23.084 2.081  0.760  -1.026 O1   27U 4  
27U N1   N1   N 0 1 N N N 18.670 -13.522 21.799 1.754  -1.312 -0.302 N1   27U 5  
27U C4   C4   C 0 1 N N N 19.936 -14.203 21.535 2.186  -2.592 0.289  C4   27U 6  
27U C5   C5   C 0 1 N N N 20.741 -13.017 20.944 1.153  -3.630 -0.214 C5   27U 7  
27U C6   C6   C 0 1 N N N 19.644 -12.219 20.188 -0.159 -2.801 -0.189 C6   27U 8  
27U C7   C7   C 0 1 N N S 18.505 -12.181 21.243 0.315  -1.389 -0.591 C7   27U 9  
27U C8   C8   C 0 1 N N N 17.159 -12.095 20.547 -0.426 -0.349 0.211  C8   27U 10 
27U N2   N2   N 0 1 N N N 16.397 -10.992 20.696 -1.764 -0.241 0.100  N2   27U 11 
27U C9   C9   C 0 1 N N N 15.109 -10.913 19.979 -2.484 0.770  0.880  C9   27U 12 
27U C10  C10  C 0 1 Y N N 13.991 -10.887 21.034 -3.957 0.683  0.577  C10  27U 13 
27U C11  C11  C 0 1 Y N N 13.405 -12.077 21.474 -4.769 -0.145 1.332  C11  27U 14 
27U C12  C12  C 0 1 Y N N 12.389 -12.047 22.431 -6.119 -0.229 1.058  C12  27U 15 
27U C13  C13  C 0 1 Y N N 11.939 -10.838 22.969 -6.665 0.523  0.019  C13  27U 16 
27U C14  C14  C 0 1 Y N N 12.524 -9.646  22.528 -5.842 1.356  -0.739 C14  27U 17 
27U C15  C15  C 0 1 Y N N 13.543 -9.682  21.567 -4.494 1.436  -0.452 C15  27U 18 
27U C16  C16  C 0 1 N N N 10.837 -10.798 24.012 -8.113 0.437  -0.280 C16  27U 19 
27U N3   N3   N 0 1 N N N 10.548 -9.649  24.558 -8.879 -0.342 0.428  N3   27U 20 
27U N4   N4   N 0 1 N N N 10.195 -11.885 24.355 -8.649 1.181  -1.308 N4   27U 21 
27U O2   O2   O 0 1 N N N 16.738 -13.124 20.033 0.184  0.389  0.956  O2   27U 22 
27U C17  C17  C 0 1 Y N N 19.585 -14.742 25.078 6.139  0.966  -0.188 C17  27U 23 
27U C18  C18  C 0 1 Y N N 20.716 -15.404 24.584 7.057  0.519  -1.119 C18  27U 24 
27U C19  C19  C 0 1 Y N N 21.993 -14.835 24.666 8.400  0.465  -0.795 C19  27U 25 
27U C20  C20  C 0 1 Y N N 22.155 -13.583 25.251 8.825  0.860  0.460  C20  27U 26 
27U C21  C21  C 0 1 Y N N 21.031 -12.914 25.748 7.906  1.309  1.391  C21  27U 27 
27U C22  C22  C 0 1 Y N N 19.756 -13.481 25.665 6.564  1.366  1.065  C22  27U 28 
27U H1   H1   H 0 1 N N N 17.439 -14.663 25.334 4.567  1.206  -1.611 H1   27U 29 
27U H1A  H1A  H 0 1 N N N 18.130 -16.329 25.238 4.199  1.832  0.014  H1A  27U 30 
27U H2   H2   H 0 1 N N N 18.666 -15.912 22.818 4.486  -1.112 -0.736 H2   27U 31 
27U H2A  H2A  H 0 1 N N N 16.886 -15.841 23.197 4.119  -0.486 0.889  H2A  27U 32 
27U H4   H4   H 0 1 N N N 20.395 -14.624 22.442 3.186  -2.852 -0.059 H4   27U 33 
27U H4A  H4A  H 0 1 N N N 19.863 -15.087 20.885 2.166  -2.533 1.378  H4A  27U 34 
27U H5   H5   H 0 1 N N N 21.221 -12.414 21.729 1.389  -3.957 -1.227 H5   27U 35 
27U H5A  H5A  H 0 1 N N N 21.576 -13.331 20.301 1.091  -4.480 0.465  H5A  27U 36 
27U H6   H6   H 0 1 N N N 19.983 -11.211 19.906 -0.875 -3.191 -0.913 H6   27U 37 
27U H6A  H6A  H 0 1 N N N 19.348 -12.669 19.229 -0.589 -2.790 0.812  H6A  27U 38 
27U H7   H7   H 0 1 N N N 18.543 -11.345 21.957 0.141  -1.231 -1.656 H7   27U 39 
27U HN2  HN2  H 0 1 N N N 16.699 -10.240 21.282 -2.252 -0.831 -0.495 HN2  27U 40 
27U H9   H9   H 0 1 N N N 15.072 -10.000 19.367 -2.321 0.592  1.943  H9   27U 41 
27U H9A  H9A  H 0 1 N N N 14.987 -11.777 19.309 -2.116 1.762  0.617  H9A  27U 42 
27U H11  H11  H 0 1 N N N 13.739 -13.022 21.073 -4.345 -0.727 2.137  H11  27U 43 
27U H12  H12  H 0 1 N N N 11.943 -12.974 22.761 -6.751 -0.876 1.648  H12  27U 44 
27U H14  H14  H 0 1 N N N 12.191 -8.700  22.928 -6.259 1.941  -1.546 H14  27U 45 
27U H15  H15  H 0 1 N N N 13.989 -8.757  21.233 -3.857 2.083  -1.036 H15  27U 46 
27U HN3  HN3  H 0 1 N N N 9.809  -9.791  25.217 -9.827 -0.398 0.233  HN3  27U 47 
27U HN4  HN4  H 0 1 N N N 10.565 -12.648 23.826 -8.079 1.762  -1.836 HN4  27U 48 
27U HN4A HN4A H 0 0 N N N 9.460  -11.943 25.031 -9.598 1.125  -1.504 HN4A 27U 49 
27U H18  H18  H 0 1 N N N 20.601 -16.377 24.129 6.726  0.210  -2.100 H18  27U 50 
27U H19  H19  H 0 1 N N N 22.849 -15.366 24.277 9.118  0.115  -1.522 H19  27U 51 
27U H20  H20  H 0 1 N N N 23.135 -13.134 25.321 9.873  0.817  0.714  H20  27U 52 
27U H21  H21  H 0 1 N N N 21.151 -11.942 26.204 8.238  1.617  2.371  H21  27U 53 
27U H22  H22  H 0 1 N N N 18.902 -12.947 26.054 5.847  1.720  1.791  H22  27U 54 
# 
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 
27U C1  C2   SING N N 1  
27U C1  C17  SING N N 2  
27U C2  C3   SING N N 3  
27U C3  O1   DOUB N N 4  
27U C3  N1   SING N N 5  
27U N1  C4   SING N N 6  
27U N1  C7   SING N N 7  
27U C4  C5   SING N N 8  
27U C5  C6   SING N N 9  
27U C6  C7   SING N N 10 
27U C7  C8   SING N N 11 
27U C8  N2   SING N N 12 
27U C8  O2   DOUB N N 13 
27U N2  C9   SING N N 14 
27U C9  C10  SING N N 15 
27U C10 C11  DOUB N N 16 
27U C10 C15  SING N N 17 
27U C11 C12  SING N N 18 
27U C12 C13  DOUB N N 19 
27U C13 C14  SING N N 20 
27U C13 C16  SING N N 21 
27U C14 C15  DOUB N N 22 
27U C16 N3   DOUB N N 23 
27U C16 N4   SING N N 24 
27U C17 C18  DOUB N N 25 
27U C17 C22  SING N N 26 
27U C18 C19  SING N N 27 
27U C19 C20  DOUB N N 28 
27U C20 C21  SING N N 29 
27U C21 C22  DOUB Y N 30 
27U C1  H1   SING Y N 31 
27U C1  H1A  SING Y N 32 
27U C2  H2   SING N N 33 
27U C2  H2A  SING Y N 34 
27U C4  H4   SING N N 35 
27U C4  H4A  SING Y N 36 
27U C5  H5   SING N N 37 
27U C5  H5A  SING Y N 38 
27U C6  H6   SING N N 39 
27U C6  H6A  SING N N 40 
27U C7  H7   SING N N 41 
27U N2  HN2  SING N N 42 
27U C9  H9   SING N N 43 
27U C9  H9A  SING N N 44 
27U C11 H11  SING N N 45 
27U C12 H12  SING Y N 46 
27U C14 H14  SING Y N 47 
27U C15 H15  SING Y N 48 
27U N3  HN3  SING N N 49 
27U N4  HN4  SING Y N 50 
27U N4  HN4A SING N N 51 
27U C18 H18  SING Y N 52 
27U C19 H19  SING N N 53 
27U C20 H20  SING Y N 54 
27U C21 H21  SING N N 55 
27U C22 H22  SING N N 56 
# 
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 
27U SMILES           ACDLabs              10.04 O=C(NCc1ccc(C(=[N@H])N)cc1)C3N(C(=O)CCc2ccccc2)CCC3                                                                                                                                                 
27U InChI            InChI                1.02b InChI=1/C22H26N4O2/c23-21(24)18-11-8-17(9-12-18)15-25-22(28)19-7-4-14-26(19)20(27)13-10-16-5-2-1-3-6-16/h1-3,5-6,8-9,11-12,19H,4,7,10,13-15H2,(H3,23,24)(H,25,28)/t19-/m0/s1/f/h23,25H,24H2/b23-21- 
27U InChIKey         InChI                1.02b RNZKCCPFUWHBFY-VRIPPLBLDZ                                                                                                                                                                           
27U SMILES_CANONICAL CACTVS               3.341 NC(=N)c1ccc(CNC(=O)[C@@H]2CCCN2C(=O)CCc3ccccc3)cc1                                                                                                                                                  
27U SMILES           CACTVS               3.341 NC(=N)c1ccc(CNC(=O)[CH]2CCCN2C(=O)CCc3ccccc3)cc1                                                                                                                                                    
27U SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(/c1ccc(cc1)CNC(=O)[C@@H]2CCCN2C(=O)CCc3ccccc3)\N                                                                                                                                            
27U SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(c1ccc(cc1)CNC(=O)C2CCCN2C(=O)CCc3ccccc3)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 
27U "SYSTEMATIC NAME" ACDLabs              10.04 N-(4-carbamimidoylbenzyl)-1-(3-phenylpropanoyl)-L-prolinamide                         
27U "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S)-N-[(4-carbamimidoylphenyl)methyl]-1-(3-phenylpropanoyl)pyrrolidine-2-carboxamide 
# 
