data_13U
# 
_chem_comp.id                                    13U 
_chem_comp.name                                  N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H35 N5 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         (2S)-N-[(4-carbamimidoylphenyl)methyl]-1-[2-(cyclooctylamino)ethanoyl]pyrrolidine-2-carboxamide 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-02-06 
_chem_comp.pdbx_modified_date                    2009-02-06 
_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                        413.556 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     13U 
_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        2ZHE 
_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 
13U O22  O22  O 0 1 N N N 16.540 -12.774 19.728 0.530  0.896  1.576  O22  13U 1  
13U C7   C7   C 0 1 N N N 17.016 -11.788 20.278 1.099  1.228  0.557  C7   13U 2  
13U N23  N23  N 0 1 N N N 16.246 -10.742 20.324 2.357  0.807  0.320  N23  13U 3  
13U C24  C24  C 0 1 N N N 14.912 -10.695 19.867 3.037  -0.052 1.292  C24  13U 4  
13U C25  C25  C 0 1 Y N N 13.891 -10.637 20.943 4.421  -0.379 0.792  C25  13U 5  
13U C26  C26  C 0 1 Y N N 13.506 -11.763 21.647 5.484  0.443  1.120  C26  13U 6  
13U C27  C27  C 0 1 Y N N 12.557 -11.700 22.646 6.753  0.150  0.665  C27  13U 7  
13U C28  C28  C 0 1 Y N N 11.955 -10.499 22.978 6.963  -0.978 -0.127 C28  13U 8  
13U C21  C21  C 0 1 N N N 10.916 -10.403 24.065 8.323  -1.299 -0.619 C21  13U 9  
13U N46  N46  N 0 1 N N N 10.143 -11.442 24.330 9.325  -0.527 -0.311 N46  13U 10 
13U N47  N47  N 0 1 N N N 10.771 -9.280  24.759 8.527  -2.414 -1.401 N47  13U 11 
13U C29  C29  C 0 1 Y N N 12.342 -9.373  22.271 5.888  -1.803 -0.455 C29  13U 12 
13U C30  C30  C 0 1 Y N N 13.290 -9.427  21.270 4.624  -1.503 0.011  C30  13U 13 
13U C1   C1   C 0 1 N N S 18.395 -11.869 20.860 0.397  2.107  -0.445 C1   13U 14 
13U C2   C2   C 0 1 N N N 19.396 -11.421 19.814 0.584  3.600  -0.078 C2   13U 15 
13U C3   C3   C 0 1 N N N 20.542 -12.396 19.701 -0.647 4.247  -0.766 C3   13U 16 
13U C4   C4   C 0 1 N N N 20.108 -13.572 20.546 -1.741 3.171  -0.600 C4   13U 17 
13U N1   N1   N 0 1 N N N 18.888 -13.128 21.294 -1.060 1.885  -0.391 N1   13U 18 
13U C14  C14  C 0 1 N N N 18.243 -13.928 22.166 -1.667 0.699  -0.185 C14  13U 19 
13U O32  O32  O 0 1 N N N 17.188 -13.420 22.538 -1.004 -0.287 0.057  O32  13U 20 
13U C5   C5   C 0 1 N N N 18.954 -15.244 22.511 -3.169 0.599  -0.255 C5   13U 21 
13U N21  N21  N 0 1 N N N 18.694 -15.931 23.746 -3.580 -0.787 0.004  N21  13U 22 
13U C49  C49  C 0 1 N N N 19.328 -15.780 25.040 -5.041 -0.923 -0.057 C49  13U 23 
13U C48  C48  C 0 1 N N N 18.965 -14.465 25.718 -5.477 -2.123 0.786  C48  13U 24 
13U C47  C47  C 0 1 N N N 19.990 -13.666 26.518 -6.554 -1.684 1.780  C47  13U 25 
13U C46  C46  C 0 1 N N N 21.085 -12.678 26.131 -7.885 -1.512 1.046  C46  13U 26 
13U C45  C45  C 0 1 N N N 22.025 -13.028 24.981 -7.862 -0.207 0.248  C45  13U 27 
13U C44  C44  C 0 1 N N N 22.646 -14.413 25.084 -7.882 -0.523 -1.249 C44  13U 28 
13U C43  C43  C 0 1 N N N 22.010 -15.644 24.454 -6.908 -1.666 -1.541 C43  13U 29 
13U C42  C42  C 0 1 N N N 20.744 -16.325 24.945 -5.474 -1.135 -1.509 C42  13U 30 
13U HN23 HN23 H 0 0 N N N 16.629 -9.905  20.714 2.812  1.072  -0.495 HN23 13U 31 
13U H24  H24  H 0 1 N N N 14.800 -9.792  19.249 3.109  0.466  2.248  H24  13U 32 
13U H24A H24A H 0 0 N N N 14.735 -11.631 19.316 2.471  -0.975 1.421  H24A 13U 33 
13U H26  H26  H 0 1 N N N 13.959 -12.714 21.409 5.320  1.316  1.734  H26  13U 34 
13U H27  H27  H 0 1 N N N 12.280 -12.599 23.176 7.582  0.793  0.922  H27  13U 35 
13U HN46 HN46 H 0 0 N N N 9.522  -11.194 25.073 10.216 -0.737 -0.633 HN46 13U 36 
13U HN47 HN47 H 0 0 N N N 11.434 -8.611  24.422 7.780  -2.989 -1.631 HN47 13U 37 
13U HN4A HN4A H 0 0 N N N 10.110 -9.129  25.494 9.418  -2.624 -1.723 HN4A 13U 38 
13U H29  H29  H 0 1 N N N 11.888 -8.423  22.511 6.044  -2.678 -1.069 H29  13U 39 
13U H30  H30  H 0 1 N N N 13.566 -8.528  20.740 3.791  -2.143 -0.239 H30  13U 40 
13U H1   H1   H 0 1 N N N 18.293 -11.244 21.759 0.774  1.913  -1.449 H1   13U 41 
13U H2   H2   H 0 1 N N N 18.888 -11.354 18.841 0.549  3.744  1.002  H2   13U 42 
13U H2A  H2A  H 0 1 N N N 19.799 -10.442 20.113 1.513  3.991  -0.493 H2A  13U 43 
13U H3   H3   H 0 1 N N N 20.711 -12.695 18.656 -0.932 5.169  -0.259 H3   13U 44 
13U H3A  H3A  H 0 1 N N N 21.496 -11.965 20.039 -0.446 4.433  -1.821 H3A  13U 45 
13U H4   H4   H 0 1 N N N 19.876 -14.439 19.910 -2.363 3.406  0.264  H4   13U 46 
13U H4A  H4A  H 0 1 N N N 20.907 -13.882 21.236 -2.354 3.124  -1.499 H4A  13U 47 
13U H5   H5   H 0 1 N N N 18.678 -15.950 21.714 -3.612 1.256  0.493  H5   13U 48 
13U H5A  H5A  H 0 1 N N N 20.005 -14.936 22.617 -3.507 0.899  -1.247 H5A  13U 49 
13U HN21 HN21 H 0 0 N N N 17.737 -15.710 23.933 -3.130 -1.423 -0.638 HN21 13U 50 
13U H49  H49  H 0 1 N N N 18.925 -16.412 25.845 -5.506 -0.018 0.332  H49  13U 51 
13U H48  H48  H 0 1 N N N 18.635 -13.797 24.909 -5.879 -2.898 0.134  H48  13U 52 
13U H48A H48A H 0 0 N N N 18.247 -14.780 26.490 -4.618 -2.516 1.330  H48A 13U 53 
13U H47  H47  H 0 1 N N N 19.349 -13.056 27.171 -6.662 -2.441 2.556  H47  13U 54 
13U H47A H47A H 0 0 N N N 20.657 -14.510 26.747 -6.264 -0.737 2.235  H47A 13U 55 
13U H46  H46  H 0 1 N N N 20.576 -11.747 25.843 -8.036 -2.351 0.366  H46  13U 56 
13U H46A H46A H 0 0 N N N 21.740 -12.643 27.014 -8.698 -1.480 1.771  H46A 13U 57 
13U H45  H45  H 0 1 N N N 21.447 -12.984 24.046 -8.736 0.391  0.504  H45  13U 58 
13U H45A H45A H 0 0 N N N 22.852 -12.304 25.013 -6.957 0.351  0.489  H45A 13U 59 
13U H44  H44  H 0 1 N N N 23.636 -14.324 24.613 -8.889 -0.819 -1.544 H44  13U 60 
13U H44A H44A H 0 0 N N N 22.559 -14.629 26.159 -7.584 0.362  -1.811 H44A 13U 61 
13U H43  H43  H 0 1 N N N 21.776 -15.337 23.424 -7.024 -2.444 -0.787 H43  13U 62 
13U H43A H43A H 0 0 N N N 22.762 -16.410 24.693 -7.120 -2.081 -2.527 H43A 13U 63 
13U H42  H42  H 0 1 N N N 20.985 -16.585 25.986 -5.425 -0.186 -2.044 H42  13U 64 
13U H42A H42A H 0 0 N N N 20.596 -17.022 24.107 -4.808 -1.855 -1.985 H42A 13U 65 
# 
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 
13U O22 C7   DOUB N N 1  
13U C7  N23  SING N N 2  
13U C7  C1   SING N N 3  
13U N23 C24  SING N N 4  
13U C24 C25  SING N N 5  
13U C25 C26  DOUB N N 6  
13U C25 C30  SING N N 7  
13U C26 C27  SING N N 8  
13U C27 C28  DOUB Y N 9  
13U C28 C21  SING Y N 10 
13U C28 C29  SING Y N 11 
13U C21 N46  DOUB N N 12 
13U C21 N47  SING Y N 13 
13U C29 C30  DOUB N N 14 
13U C1  C2   SING N N 15 
13U C1  N1   SING Y N 16 
13U C2  C3   SING N N 17 
13U C3  C4   SING N N 18 
13U C4  N1   SING N N 19 
13U N1  C14  SING N N 20 
13U C14 O32  DOUB N N 21 
13U C14 C5   SING Y N 22 
13U C5  N21  SING N N 23 
13U N21 C49  SING N N 24 
13U C49 C48  SING N N 25 
13U C49 C42  SING N N 26 
13U C48 C47  SING N N 27 
13U C47 C46  SING N N 28 
13U C46 C45  SING N N 29 
13U C45 C44  SING N N 30 
13U C44 C43  SING N N 31 
13U C43 C42  SING N N 32 
13U N23 HN23 SING N N 33 
13U C24 H24  SING N N 34 
13U C24 H24A SING N N 35 
13U C26 H26  SING N N 36 
13U C27 H27  SING N N 37 
13U N46 HN46 SING N N 38 
13U N47 HN47 SING N N 39 
13U N47 HN4A SING N N 40 
13U C29 H29  SING N N 41 
13U C30 H30  SING N N 42 
13U C1  H1   SING N N 43 
13U C2  H2   SING N N 44 
13U C2  H2A  SING N N 45 
13U C3  H3   SING N N 46 
13U C3  H3A  SING N N 47 
13U C4  H4   SING N N 48 
13U C4  H4A  SING N N 49 
13U C5  H5   SING N N 50 
13U C5  H5A  SING N N 51 
13U N21 HN21 SING N N 52 
13U C49 H49  SING N N 53 
13U C48 H48  SING N N 54 
13U C48 H48A SING N N 55 
13U C47 H47  SING N N 56 
13U C47 H47A SING N N 57 
13U C46 H46  SING N N 58 
13U C46 H46A SING N N 59 
13U C45 H45  SING N N 60 
13U C45 H45A SING N N 61 
13U C44 H44  SING N N 62 
13U C44 H44A SING N N 63 
13U C43 H43  SING N N 64 
13U C43 H43A SING N N 65 
13U C42 H42  SING N N 66 
13U C42 H42A SING N N 67 
# 
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 
13U SMILES           ACDLabs              10.04 O=C(NCc1ccc(C(=[N@H])N)cc1)C3N(C(=O)CNC2CCCCCCC2)CCC3                                                                                                                                            
13U InChI            InChI                1.02b InChI=1/C23H35N5O2/c24-22(25)18-12-10-17(11-13-18)15-27-23(30)20-9-6-14-28(20)21(29)16-26-19-7-4-2-1-3-5-8-19/h10-13,19-20,26H,1-9,14-16H2,(H3,24,25)(H,27,30)/t20-/m0/s1/f/h24,27H,25H2/b24-22- 
13U InChIKey         InChI                1.02b MMLOIDMSBRJZAE-YNVLCIMJDA                                                                                                                                                                        
13U SMILES_CANONICAL CACTVS               3.341 NC(=N)c1ccc(CNC(=O)[C@@H]2CCCN2C(=O)CNC3CCCCCCC3)cc1                                                                                                                                             
13U SMILES           CACTVS               3.341 NC(=N)c1ccc(CNC(=O)[CH]2CCCN2C(=O)CNC3CCCCCCC3)cc1                                                                                                                                               
13U SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(/c1ccc(cc1)CNC(=O)[C@@H]2CCCN2C(=O)CNC3CCCCCCC3)\N                                                                                                                                       
13U SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(c1ccc(cc1)CNC(=O)C2CCCN2C(=O)CNC3CCCCCCC3)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 
13U "SYSTEMATIC NAME" ACDLabs              10.04 N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide                                      
13U "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S)-N-[(4-carbamimidoylphenyl)methyl]-1-[2-(cyclooctylamino)ethanoyl]pyrrolidine-2-carboxamide 
# 
