data_DX9
# 
_chem_comp.id                                    DX9 
_chem_comp.name                                  "(2S)-3-(7-carbamimidoylnaphthalen-2-yl)-2-[4-({(3R)-1-[(1Z)-ethanimidoyl]pyrrolidin-3-yl}oxy)phenyl]propanoic acid" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C26 H28 N4 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         DX9056A 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        444.526 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DX9 
_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        1MTW 
_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 
DX9 C12  C12  C 0 1 Y N N 29.129 11.425 15.963 3.533  0.899  0.039  C12  DX9 1  
DX9 C13  C13  C 0 1 Y N N 28.811 10.645 17.078 2.585  1.515  0.797  C13  DX9 2  
DX9 C11  C11  C 0 1 Y N N 28.335 11.237 18.270 1.916  0.827  1.807  C11  DX9 3  
DX9 C10  C10  C 0 1 Y N N 28.174 12.638 18.336 2.190  -0.481 2.065  C10  DX9 4  
DX9 C7   C7   C 0 1 Y N N 28.489 13.420 17.212 3.161  -1.153 1.304  C7   DX9 5  
DX9 C6   C6   C 0 1 Y N N 28.342 14.807 17.232 3.467  -2.504 1.546  C6   DX9 6  
DX9 C5   C5   C 0 1 Y N N 28.670 15.554 16.085 4.410  -3.131 0.798  C5   DX9 7  
DX9 C4   C4   C 0 1 Y N N 29.159 14.925 14.911 5.092  -2.448 -0.224 C4   DX9 8  
DX9 C9   C9   C 0 1 Y N N 29.293 13.543 14.890 4.814  -1.118 -0.487 C9   DX9 9  
DX9 C8   C8   C 0 1 Y N N 28.974 12.803 16.021 3.843  -0.452 0.276  C8   DX9 10 
DX9 C2   C2   C 0 1 N N N 29.501 15.731 13.691 6.116  -3.156 -1.024 C2   DX9 11 
DX9 N2   N2   N 0 1 N N N 28.996 17.090 13.614 6.752  -2.528 -1.972 N2   DX9 12 
DX9 N1   N1   N 0 1 N N N 30.177 15.178 12.765 6.398  -4.481 -0.766 N1   DX9 13 
DX9 C14  C14  C 0 1 N N N 29.013 9.148  16.934 2.255  2.963  0.540  C14  DX9 14 
DX9 C22  C22  C 0 1 N N N 28.014 6.879  17.452 1.027  4.511  -0.959 C22  DX9 15 
DX9 O23  O23  O 0 1 N N N 27.619 6.227  18.415 1.517  5.378  -0.276 O23  DX9 16 
DX9 O24  O24  O 0 1 N N N 28.621 6.262  16.588 0.280  4.837  -2.025 O24  DX9 17 
DX9 C15  C15  C 0 1 N N S 27.754 8.336  17.338 1.256  3.061  -0.614 C15  DX9 18 
DX9 N28  N28  N 0 1 N N N 21.936 7.101  11.980 -5.980 -1.843 -0.155 N28  DX9 19 
DX9 C27  C27  C 0 1 N N N 21.928 6.989  13.431 -5.680 -0.460 0.256  C27  DX9 20 
DX9 C26  C26  C 0 1 N N R 21.982 8.481  13.833 -4.150 -0.313 0.068  C26  DX9 21 
DX9 C30  C30  C 0 1 N N N 21.026 9.099  12.797 -3.647 -1.716 0.500  C30  DX9 22 
DX9 C29  C29  C 0 1 N N N 21.512 8.419  11.489 -4.763 -2.654 -0.006 C29  DX9 23 
DX9 C31  C31  C 0 1 N N N 22.283 6.093  11.205 -7.194 -2.299 -0.598 C31  DX9 24 
DX9 N32  N32  N 0 1 N N N 22.253 6.189  9.930  -8.198 -1.488 -0.681 N32  DX9 25 
DX9 C33  C33  C 0 1 N N N 22.735 4.755  11.805 -7.359 -3.746 -0.987 C33  DX9 26 
DX9 C21  C21  C 0 1 Y N N 25.033 8.272  17.089 -0.551 1.356  -0.915 C21  DX9 27 
DX9 C20  C20  C 0 1 Y N N 24.006 8.444  16.260 -1.748 0.776  -0.540 C20  DX9 28 
DX9 C17  C17  C 0 1 Y N N 26.697 8.847  15.093 -0.744 2.928  0.884  C17  DX9 29 
DX9 C18  C18  C 0 1 Y N N 25.595 9.009  14.262 -1.941 2.351  1.263  C18  DX9 30 
DX9 C19  C19  C 0 1 Y N N 24.292 8.825  14.784 -2.446 1.273  0.551  C19  DX9 31 
DX9 O25  O25  O 0 1 N N N 23.316 9.037  13.805 -3.624 0.705  0.922  O25  DX9 32 
DX9 C16  C16  C 0 1 Y N N 26.488 8.497  16.449 -0.050 2.431  -0.204 C16  DX9 33 
DX9 H12  H12  H 0 1 N N N 29.494 10.958 15.060 4.041  1.443  -0.744 H12  DX9 34 
DX9 H11  H11  H 0 1 N N N 28.096 10.622 19.125 1.168  1.340  2.394  H11  DX9 35 
DX9 H10  H10  H 0 1 N N N 27.813 13.104 19.241 1.663  -1.001 2.852  H10  DX9 36 
DX9 H6   H6   H 0 1 N N N 27.980 15.303 18.120 2.952  -3.042 2.328  H6   DX9 37 
DX9 H5   H5   H 0 1 N N N 28.547 16.627 16.099 4.640  -4.169 0.990  H5   DX9 38 
DX9 H9   H9   H 0 1 N N N 29.644 13.046 13.998 5.341  -0.597 -1.273 H9   DX9 39 
DX9 H227 2H27 H 0 0 N N N 21.028 6.483  13.810 -6.210 0.249  -0.380 H227 DX9 40 
DX9 HN21 1HN2 H 0 0 N N N 29.319 17.467 12.746 7.423  -2.992 -2.496 HN21 DX9 41 
DX9 HN12 2HN1 H 0 0 N N N 30.373 14.246 13.070 5.925  -4.948 -0.060 HN12 DX9 42 
DX9 HN11 1HN1 H 0 0 N N N 30.457 15.594 11.900 7.069  -4.945 -1.290 HN11 DX9 43 
DX9 H141 1H14 H 0 0 N N N 29.247 8.928  15.882 1.818  3.401  1.437  H141 DX9 44 
DX9 H142 2H14 H 0 0 N N N 29.832 8.854  17.607 3.166  3.502  0.279  H142 DX9 45 
DX9 HO4  HO4  H 0 1 N N N 28.678 5.346  16.833 0.162  5.780  -2.206 HO4  DX9 46 
DX9 H15  H15  H 0 1 N N N 27.531 8.794  18.313 1.653  2.539  -1.485 H15  DX9 47 
DX9 H127 1H27 H 0 0 N N N 22.745 6.378  13.843 -5.952 -0.308 1.301  H127 DX9 48 
DX9 H130 1H30 H 0 0 N N N 19.972 8.875  13.017 -2.698 -1.951 0.017  H130 DX9 49 
DX9 H129 1H29 H 0 0 N N N 22.338 8.971  11.016 -4.935 -3.451 0.718  H129 DX9 50 
DX9 H229 2H29 H 0 0 N N N 20.746 8.374  10.701 -4.481 -3.080 -0.969 H229 DX9 51 
DX9 HN31 1HN3 H 0 0 N N N 22.544 5.342  9.485  -9.058 -1.811 -0.995 HN31 DX9 52 
DX9 H230 2H30 H 0 0 N N N 21.052 10.198 12.765 -3.555 -1.776 1.584  H230 DX9 53 
DX9 H331 1H33 H 0 0 N N N 22.843 4.011  11.002 -6.413 -4.269 -0.851 H331 DX9 54 
DX9 H332 2H33 H 0 0 N N N 23.701 4.889  12.313 -8.123 -4.206 -0.360 H332 DX9 55 
DX9 H333 3H33 H 0 0 N N N 21.984 4.406  12.530 -7.662 -3.808 -2.033 H333 DX9 56 
DX9 H21  H21  H 0 1 N N N 24.896 7.999  18.125 -0.005 0.967  -1.761 H21  DX9 57 
DX9 H20  H20  H 0 1 N N N 22.991 8.320  16.609 -2.139 -0.063 -1.096 H20  DX9 58 
DX9 H17  H17  H 0 1 N N N 27.697 8.986  14.710 -0.350 3.767  1.438  H17  DX9 59 
DX9 H18  H18  H 0 1 N N N 25.732 9.274  13.224 -2.483 2.740  2.113  H18  DX9 60 
DX9 H26  H26  H 0 1 N N N 21.690 8.677  14.875 -3.902 -0.113 -0.975 H26  DX9 61 
# 
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 
DX9 C12 C13  DOUB Y N 1  
DX9 C12 C8   SING Y N 2  
DX9 C12 H12  SING N N 3  
DX9 C13 C11  SING Y N 4  
DX9 C13 C14  SING N N 5  
DX9 C11 C10  DOUB Y N 6  
DX9 C11 H11  SING N N 7  
DX9 C10 C7   SING Y N 8  
DX9 C10 H10  SING N N 9  
DX9 C7  C6   DOUB Y N 10 
DX9 C7  C8   SING Y N 11 
DX9 C6  C5   SING Y N 12 
DX9 C6  H6   SING N N 13 
DX9 C5  C4   DOUB Y N 14 
DX9 C5  H5   SING N N 15 
DX9 C4  C9   SING Y N 16 
DX9 C4  C2   SING N N 17 
DX9 C9  C8   DOUB Y N 18 
DX9 C9  H9   SING N N 19 
DX9 C2  N2   DOUB N N 20 
DX9 C2  N1   SING N N 21 
DX9 C27 H227 SING N N 22 
DX9 N2  HN21 SING N N 23 
DX9 N1  HN12 SING N N 24 
DX9 N1  HN11 SING N N 25 
DX9 C14 C15  SING N N 26 
DX9 C14 H141 SING N N 27 
DX9 C14 H142 SING N N 28 
DX9 C22 O23  DOUB N N 29 
DX9 C22 O24  SING N N 30 
DX9 C22 C15  SING N N 31 
DX9 O24 HO4  SING N N 32 
DX9 C15 C16  SING N N 33 
DX9 C15 H15  SING N N 34 
DX9 N28 C27  SING N N 35 
DX9 N28 C29  SING N N 36 
DX9 N28 C31  SING N N 37 
DX9 C27 C26  SING N N 38 
DX9 C27 H127 SING N N 39 
DX9 C26 C30  SING N N 40 
DX9 C26 O25  SING N N 41 
DX9 C30 C29  SING N N 42 
DX9 C30 H130 SING N N 43 
DX9 C29 H129 SING N N 44 
DX9 C31 N32  DOUB N N 45 
DX9 C31 C33  SING N N 46 
DX9 C29 H229 SING N N 47 
DX9 N32 HN31 SING N N 48 
DX9 C30 H230 SING N N 49 
DX9 C33 H331 SING N N 50 
DX9 C33 H332 SING N N 51 
DX9 C33 H333 SING N N 52 
DX9 C21 C20  DOUB N N 53 
DX9 C21 C16  SING Y N 54 
DX9 C21 H21  SING Y N 55 
DX9 C20 C19  SING N N 56 
DX9 C20 H20  SING Y N 57 
DX9 C17 C18  SING N N 58 
DX9 C17 C16  DOUB Y N 59 
DX9 C17 H17  SING Y N 60 
DX9 C18 C19  DOUB N N 61 
DX9 C18 H18  SING Y N 62 
DX9 C19 O25  SING N N 63 
DX9 C26 H26  SING N N 64 
# 
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 
DX9 SMILES           ACDLabs              10.04 O=C(O)C(c2ccc(OC1CCN(C(=[N@H])C)C1)cc2)Cc4cc3cc(C(=[N@H])N)ccc3cc4 
DX9 InChI            InChI                1.02b 
InChI=1/C26H28N4O3/c1-16(27)30-11-10-23(15-30)33-22-8-6-19(7-9-22)24(26(31)32)13-17-2-3-18-4-5-20(25(28)29)14-21(18)12-17/h2-9,12,14,23-24,27H,10-11,13,15H2,1H3,(H3,28,29)(H,31,32)/b27-16+/t23-,24-/m0/s1/f/h28,31H,29H2/b27-16+,28-25- 
DX9 InChIKey         InChI                1.02b AGRCGQSFFMCBRE-ZETSHHEQDX 
DX9 SMILES_CANONICAL CACTVS               3.341 CC(=N)N1CC[C@@H](C1)Oc2ccc(cc2)[C@H](Cc3ccc4ccc(cc4c3)C(N)=N)C(O)=O 
DX9 SMILES           CACTVS               3.341 CC(=N)N1CC[CH](C1)Oc2ccc(cc2)[CH](Cc3ccc4ccc(cc4c3)C(N)=N)C(O)=O 
DX9 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(\C)/N1CC[C@@H](C1)Oc2ccc(cc2)[C@H](Cc3ccc4ccc(cc4c3)/C(=N/[H])/N)C(=O)O 
DX9 SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(C)N1CCC(C1)Oc2ccc(cc2)C(Cc3ccc4ccc(cc4c3)C(=N[H])N)C(=O)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 
DX9 "SYSTEMATIC NAME" ACDLabs              10.04 "(2S)-3-(7-carbamimidoylnaphthalen-2-yl)-2-[4-({(3S)-1-[(1E)-ethanimidoyl]pyrrolidin-3-yl}oxy)phenyl]propanoic acid" 
DX9 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-3-(7-carbamimidoylnaphthalen-2-yl)-2-[4-[(3S)-1-ethanimidoylpyrrolidin-3-yl]oxyphenyl]propanoic acid"          
# 
