data_37U
# 
_chem_comp.id                                    37U 
_chem_comp.name                                  D-phenylalanyl-N-(3-fluorobenzyl)-L-prolinamide 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H24 F N3 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         (2S)-1-((2R)-2-amino-3-phenyl-propanoyl)-N-((3-fluorophenyl)methyl)pyrrolidine-2-carboxamide 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-11-30 
_chem_comp.pdbx_modified_date                    2008-10-24 
_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                        369.433 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     37U 
_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        2ZDV 
_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 
37U C1   C1   C 0 1 Y N N 12.632 -11.615 21.577 5.666  0.948  1.113  C1   37U 1  
37U C2   C2   C 0 1 Y N N 13.519 -10.539 21.424 4.972  -0.165 0.675  C2   37U 2  
37U C3   C3   C 0 1 N N N 14.543 -10.576 20.292 3.543  -0.379 1.106  C3   37U 3  
37U N9   N9   N 0 1 N N N 15.861 -10.756 20.896 2.643  0.259  0.142  N9   37U 4  
37U C4   C4   C 0 1 N N N 16.559 -11.878 20.638 1.309  0.197  0.324  C4   37U 5  
37U O26  O26  O 0 1 N N N 16.090 -12.840 20.041 0.854  -0.387 1.285  O26  37U 6  
37U C5   C5   C 0 1 N N S 17.994 -11.964 21.114 0.382  0.853  -0.667 C5   37U 7  
37U N15  N15  N 0 1 N N N 18.287 -13.270 21.711 -1.015 0.649  -0.255 N15  37U 8  
37U C6   C6   C 0 1 N N N 17.489 -13.817 22.664 -1.631 -0.543 -0.129 C6   37U 9  
37U O27  O27  O 0 1 N N N 16.514 -13.172 23.099 -1.025 -1.566 -0.364 O27  37U 10 
37U C7   C7   C 0 1 N N R 17.656 -15.178 23.298 -3.074 -0.603 0.303  C7   37U 11 
37U N25  N25  N 0 1 N N N 16.404 -15.978 23.139 -3.373 -1.945 0.821  N25  37U 12 
37U C8   C8   C 0 1 N N N 18.106 -15.086 24.776 -3.978 -0.305 -0.895 C8   37U 13 
37U C9   C9   C 0 1 Y N N 19.539 -14.519 24.841 -5.413 -0.245 -0.438 C9   37U 14 
37U C10  C10  C 0 1 Y N N 20.609 -15.132 24.184 -5.956 0.957  -0.023 C10  37U 15 
37U C11  C11  C 0 1 Y N N 21.897 -14.579 24.271 -7.272 1.013  0.396  C11  37U 16 
37U C12  C12  C 0 1 Y N N 22.132 -13.424 25.006 -8.045 -0.133 0.400  C12  37U 17 
37U C13  C13  C 0 1 Y N N 21.066 -12.795 25.674 -7.502 -1.335 -0.016 C13  37U 18 
37U C14  C14  C 0 1 Y N N 19.785 -13.353 25.581 -6.187 -1.390 -0.439 C14  37U 19 
37U C15  C15  C 0 1 N N N 19.249 -14.093 20.968 -1.630 1.965  -0.003 C15  37U 20 
37U C16  C16  C 0 1 N N N 20.065 -12.959 20.319 -0.794 2.962  -0.844 C16  37U 21 
37U C17  C17  C 0 1 N N N 18.979 -11.945 19.914 0.635  2.375  -0.694 C17  37U 22 
37U C18  C18  C 0 1 Y N N 13.428 -9.470  22.315 5.587  -1.081 -0.157 C18  37U 23 
37U C19  C19  C 0 1 Y N N 12.486 -9.455  23.339 6.899  -0.884 -0.552 C19  37U 24 
37U F7   F7   F 0 1 N N N 12.403 -8.420  24.197 7.502  -1.779 -1.366 F7   37U 25 
37U C20  C20  C 0 1 Y N N 11.611 -10.534 23.480 7.594  0.231  -0.113 C20  37U 26 
37U C21  C21  C 0 1 Y N N 11.687 -11.614 22.595 6.977  1.145  0.719  C21  37U 27 
37U H1   H1   H 0 1 N N N 12.684 -12.452 20.897 5.183  1.666  1.759  H1   37U 28 
37U H3   H3   H 0 1 N N N 14.323 -11.410 19.609 3.333  -1.447 1.148  H3   37U 29 
37U H3A  H3A  H 0 1 N N N 14.509 -9.643  19.710 3.391  0.061  2.092  H3A  37U 30 
37U HN9  HN9  H 0 1 N N N 16.241 -10.052 21.496 3.006  0.726  -0.626 HN9  37U 31 
37U H5   H5   H 0 1 N N N 18.110 -11.121 21.811 0.541  0.430  -1.659 H5   37U 32 
37U H7   H7   H 0 1 N N N 18.466 -15.702 22.770 -3.250 0.136  1.084  H7   37U 33 
37U HN25 HN25 H 0 0 N N N 16.006 -16.157 24.039 -3.217 -2.648 0.115  HN25 37U 34 
37U HN2A HN2A H 0 0 N N N 15.751 -15.467 22.581 -2.835 -2.140 1.652  HN2A 37U 35 
37U H8   H8   H 0 1 N N N 17.423 -14.422 25.327 -3.696 0.651  -1.334 H8   37U 36 
37U H8A  H8A  H 0 1 N N N 18.087 -16.088 25.229 -3.867 -1.094 -1.639 H8A  37U 37 
37U H10  H10  H 0 1 N N N 20.445 -16.031 23.609 -5.352 1.852  -0.026 H10  37U 38 
37U H11  H11  H 0 1 N N N 22.717 -15.059 23.759 -7.696 1.951  0.721  H11  37U 39 
37U H12  H12  H 0 1 N N N 23.128 -13.011 25.064 -9.073 -0.090 0.728  H12  37U 40 
37U H13  H13  H 0 1 N N N 21.233 -11.896 26.249 -8.106 -2.230 -0.012 H13  37U 41 
37U H14  H14  H 0 1 N N N 18.964 -12.873 26.093 -5.764 -2.328 -0.767 H14  37U 42 
37U H15  H15  H 0 1 N N N 19.852 -14.748 21.614 -2.669 1.968  -0.332 H15  37U 43 
37U H15A H15A H 0 0 N N N 18.810 -14.821 20.270 -1.566 2.217  1.056  H15A 37U 44 
37U H16  H16  H 0 1 N N N 20.788 -12.522 21.024 -1.111 2.954  -1.887 H16  37U 45 
37U H16A H16A H 0 0 N N N 20.678 -13.298 19.471 -0.849 3.967  -0.428 H16A 37U 46 
37U H17  H17  H 0 1 N N N 18.480 -12.241 18.979 1.092  2.707  0.238  H17  37U 47 
37U H17A H17A H 0 0 N N N 19.387 -10.943 19.715 1.255  2.648  -1.547 H17A 37U 48 
37U H18  H18  H 0 1 N N N 14.104 -8.635  22.208 5.045  -1.950 -0.498 H18  37U 49 
37U H20  H20  H 0 1 N N N 10.876 -10.534 24.272 8.618  0.385  -0.420 H20  37U 50 
37U H21  H21  H 0 1 N N N 11.010 -12.448 22.703 7.518  2.015  1.061  H21  37U 51 
# 
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 
37U C1  C2   DOUB Y N 1  
37U C1  C21  SING Y N 2  
37U C2  C3   SING N N 3  
37U C2  C18  SING N N 4  
37U C3  N9   SING Y N 5  
37U N9  C4   SING N N 6  
37U C4  O26  DOUB N N 7  
37U C4  C5   SING N N 8  
37U C5  N15  SING N N 9  
37U C5  C17  SING N N 10 
37U N15 C6   SING N N 11 
37U N15 C15  SING N N 12 
37U C6  O27  DOUB N N 13 
37U C6  C7   SING N N 14 
37U C7  N25  SING N N 15 
37U C7  C8   SING N N 16 
37U C8  C9   SING N N 17 
37U C9  C10  DOUB N N 18 
37U C9  C14  SING N N 19 
37U C10 C11  SING N N 20 
37U C11 C12  DOUB N N 21 
37U C12 C13  SING N N 22 
37U C13 C14  DOUB N N 23 
37U C15 C16  SING N N 24 
37U C16 C17  SING N N 25 
37U C18 C19  DOUB N N 26 
37U C19 F7   SING N N 27 
37U C19 C20  SING Y N 28 
37U C20 C21  DOUB Y N 29 
37U C1  H1   SING Y N 30 
37U C3  H3   SING N N 31 
37U C3  H3A  SING Y N 32 
37U N9  HN9  SING N N 33 
37U C5  H5   SING Y N 34 
37U C7  H7   SING N N 35 
37U N25 HN25 SING Y N 36 
37U N25 HN2A SING N N 37 
37U C8  H8   SING N N 38 
37U C8  H8A  SING N N 39 
37U C10 H10  SING N N 40 
37U C11 H11  SING N N 41 
37U C12 H12  SING N N 42 
37U C13 H13  SING N N 43 
37U C14 H14  SING N N 44 
37U C15 H15  SING N N 45 
37U C15 H15A SING N N 46 
37U C16 H16  SING Y N 47 
37U C16 H16A SING N N 48 
37U C17 H17  SING N N 49 
37U C17 H17A SING Y N 50 
37U C18 H18  SING Y N 51 
37U C20 H20  SING N N 52 
37U C21 H21  SING N N 53 
# 
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 
37U SMILES           ACDLabs              10.04 O=C(NCc1cccc(F)c1)C3N(C(=O)C(N)Cc2ccccc2)CCC3                                                                                                                               
37U InChI            InChI                1.02b InChI=1/C21H24FN3O2/c22-17-9-4-8-16(12-17)14-24-20(26)19-10-5-11-25(19)21(27)18(23)13-15-6-2-1-3-7-15/h1-4,6-9,12,18-19H,5,10-11,13-14,23H2,(H,24,26)/t18-,19+/m1/s1/f/h24H 
37U InChIKey         InChI                1.02b JGZSVYZIJHGHMA-ZWSLWZHXDA                                                                                                                                                   
37U SMILES_CANONICAL CACTVS               3.341 N[C@H](Cc1ccccc1)C(=O)N2CCC[C@H]2C(=O)NCc3cccc(F)c3                                                                                                                         
37U SMILES           CACTVS               3.341 N[CH](Cc1ccccc1)C(=O)N2CCC[CH]2C(=O)NCc3cccc(F)c3                                                                                                                           
37U SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)C[C@H](C(=O)N2CCC[C@H]2C(=O)NCc3cccc(c3)F)N                                                                                                                       
37U SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CC(C(=O)N2CCCC2C(=O)NCc3cccc(c3)F)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 
37U "SYSTEMATIC NAME" ACDLabs              10.04 D-phenylalanyl-N-(3-fluorobenzyl)-L-prolinamide                                              
37U "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S)-1-[(2R)-2-amino-3-phenyl-propanoyl]-N-[(3-fluorophenyl)methyl]pyrrolidine-2-carboxamide 
# 
