data_14A
# 
_chem_comp.id                                    14A 
_chem_comp.name                                  N-ALLYL-5-AMIDINOAMINOOXY-PROPYLOXY-3-CHLORO-N-CYCLOPENTYLBENZAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H27 Cl N4 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-02-02 
_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                        394.896 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     14A 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1T4V 
_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 
14A N1   N1   N  0 1 N N N 10.221 -12.942 24.494 -1.790 0.335  9.042  N1   14A 1  
14A C2   C2   C  0 1 N N N 11.038 -11.963 24.139 -0.512 0.212  8.819  C2   14A 2  
14A N3   N3   N  0 1 N N N 10.899 -10.742 24.642 0.369  0.180  9.874  N3   14A 3  
14A N4   N4   N  0 1 N N N 11.950 -12.180 23.223 -0.045 0.114  7.530  N4   14A 4  
14A O5   O5   O  0 1 N N N 12.932 -11.315 22.941 -0.952 0.146  6.444  O5   14A 5  
14A C6   C6   C  0 1 N N N 12.875 -10.733 21.619 -0.174 0.025  5.251  C6   14A 6  
14A C7   C7   C  0 1 N N N 13.439 -11.716 20.568 -1.100 0.054  4.033  C7   14A 7  
14A C8   C8   C  0 1 N N N 14.937 -11.908 20.676 -0.266 -0.075 2.757  C8   14A 8  
14A O9   O9   O  0 1 N N N 15.153 -12.945 21.627 -1.131 -0.049 1.619  O9   14A 9  
14A C10  C10  C  0 1 Y N N 16.431 -13.482 21.642 -0.338 -0.167 0.521  C10  14A 10 
14A C11  C11  C  0 1 Y N N 17.466 -12.973 20.841 1.036  -0.282 0.667  C11  14A 11 
14A C12  C12  C  0 1 Y N N 18.750 -13.569 20.911 1.848  -0.404 -0.446 C12  14A 12 
14A C13  C13  C  0 1 Y N N 18.968 -14.625 21.740 1.293  -0.411 -1.711 C13  14A 13 
14A C14  C14  C  0 1 Y N N 17.968 -15.109 22.525 -0.088 -0.295 -1.867 C14  14A 14 
14A C15  C15  C  0 1 Y N N 16.701 -14.566 22.486 -0.905 -0.178 -0.742 C15  14A 15 
14A CL16 CL16 CL 0 0 N N N 20.038 -12.982 19.978 3.567  -0.548 -0.253 CL16 14A 16 
14A C17  C17  C  0 1 N N N 18.257 -16.270 23.398 -0.685 -0.302 -3.219 C17  14A 17 
14A O18  O18  O  0 1 N N N 17.459 -17.203 23.297 -1.690 -0.951 -3.437 O18  14A 18 
14A N19  N19  N  0 1 N N N 19.256 -16.348 24.308 -0.115 0.409  -4.211 N19  14A 19 
14A C20  C20  C  0 1 N N N 19.299 -17.503 25.269 1.110  1.169  -3.956 C20  14A 20 
14A C21  C21  C  0 1 N N N 18.034 -17.851 26.068 2.277  0.473  -4.609 C21  14A 21 
14A C22  C22  C  0 1 N N N 18.023 -18.320 27.302 2.991  1.098  -5.512 C22  14A 22 
14A C23  C23  C  0 1 N N N 19.783 -15.007 24.668 -0.722 0.424  -5.545 C23  14A 23 
14A C24  C24  C  0 1 N N N 21.305 -15.149 24.549 -2.021 1.257  -5.525 C24  14A 24 
14A C25  C25  C  0 1 N N N 21.979 -14.542 25.718 -2.975 0.495  -6.478 C25  14A 25 
14A C26  C26  C  0 1 N N N 20.915 -14.431 26.797 -2.648 -0.987 -6.175 C26  14A 26 
14A C27  C27  C  0 1 N N N 19.623 -14.914 26.187 -1.121 -1.002 -5.958 C27  14A 27 
14A HN1  HN1  H  0 1 N N N 9.253  -12.774 24.220 -2.412 0.357  8.298  HN1  14A 28 
14A HN31 1HN3 H  0 0 N N N 10.914 -10.814 25.659 0.039  0.249  10.784 HN31 14A 29 
14A HN32 2HN3 H  0 0 N N N 11.529 -9.988  24.368 1.320  0.085  9.709  HN32 14A 30 
14A HN4  HN4  H  0 1 N N N 11.461 -12.378 22.350 0.906  0.022  7.364  HN4  14A 31 
14A H61  1H6  H  0 1 N N N 13.389 -9.744  21.579 0.373  -0.916 5.269  H61  14A 32 
14A H62  2H6  H  0 1 N N N 11.845 -10.395 21.359 0.530  0.854  5.192  H62  14A 33 
14A H71  1H7  H  0 1 N N N 13.152 -11.403 19.537 -1.648 0.996  4.015  H71  14A 34 
14A H72  2H7  H  0 1 N N N 12.909 -12.696 20.616 -1.804 -0.775 4.093  H72  14A 35 
14A H81  1H8  H  0 1 N N N 15.484 -10.967 20.920 0.281  -1.017 2.775  H81  14A 36 
14A H82  2H8  H  0 1 N N N 15.426 -12.104 19.694 0.438  0.753  2.697  H82  14A 37 
14A H11  H11  H  0 1 N N N 17.274 -12.120 20.169 1.475  -0.277 1.654  H11  14A 38 
14A H13  H13  H  0 1 N N N 19.966 -15.094 21.776 1.929  -0.505 -2.579 H13  14A 39 
14A H15  H15  H  0 1 N N N 15.910 -14.995 23.124 -1.975 -0.089 -0.856 H15  14A 40 
14A H201 1H20 H  0 0 N N N 20.143 -17.347 25.981 1.281  1.234  -2.882 H201 14A 41 
14A H202 2H20 H  0 0 N N N 19.641 -18.413 24.723 1.009  2.173  -4.370 H202 14A 42 
14A H21  H21  H  0 1 N N N 16.996 -17.751 25.708 2.525  -0.540 -4.332 H21  14A 43 
14A H221 1H22 H  0 0 N N N 17.115 -18.570 27.876 3.827  0.599  -5.979 H221 14A 44 
14A H222 2H22 H  0 0 N N N 19.061 -18.420 27.662 2.744  2.112  -5.789 H222 14A 45 
14A H23  H23  H  0 1 N N N 19.315 -14.186 24.077 -0.022 0.841  -6.269 H23  14A 46 
14A H241 1H24 H  0 0 N N N 21.686 -14.730 23.589 -2.436 1.292  -4.517 H241 14A 47 
14A H242 2H24 H  0 0 N N N 21.611 -16.211 24.401 -1.834 2.264  -5.897 H242 14A 48 
14A H251 1H25 H  0 0 N N N 22.485 -13.575 25.489 -2.754 0.735  -7.518 H251 14A 49 
14A H252 2H25 H  0 0 N N N 22.890 -15.095 26.045 -4.015 0.718  -6.242 H252 14A 50 
14A H261 1H26 H  0 0 N N N 20.839 -13.409 27.235 -2.920 -1.618 -7.021 H261 14A 51 
14A H262 2H26 H  0 0 N N N 21.185 -14.967 27.737 -3.165 -1.315 -5.273 H262 14A 52 
14A H271 1H27 H  0 0 N N N 19.278 -15.875 26.635 -0.615 -1.278 -6.883 H271 14A 53 
14A H272 2H27 H  0 0 N N N 18.754 -14.281 26.482 -0.863 -1.706 -5.167 H272 14A 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 
14A N1  C2   DOUB N N 1  
14A N1  HN1  SING N N 2  
14A C2  N3   SING N N 3  
14A C2  N4   SING N N 4  
14A N3  HN31 SING N N 5  
14A N3  HN32 SING N N 6  
14A N4  O5   SING N N 7  
14A N4  HN4  SING N N 8  
14A O5  C6   SING N N 9  
14A C6  C7   SING N N 10 
14A C6  H61  SING N N 11 
14A C6  H62  SING N N 12 
14A C7  C8   SING N N 13 
14A C7  H71  SING N N 14 
14A C7  H72  SING N N 15 
14A C8  O9   SING N N 16 
14A C8  H81  SING N N 17 
14A C8  H82  SING N N 18 
14A O9  C10  SING N N 19 
14A C10 C11  DOUB Y N 20 
14A C10 C15  SING Y N 21 
14A C11 C12  SING Y N 22 
14A C11 H11  SING N N 23 
14A C12 C13  DOUB Y N 24 
14A C12 CL16 SING N N 25 
14A C13 C14  SING Y N 26 
14A C13 H13  SING N N 27 
14A C14 C15  DOUB Y N 28 
14A C14 C17  SING N N 29 
14A C15 H15  SING N N 30 
14A C17 O18  DOUB N N 31 
14A C17 N19  SING N N 32 
14A N19 C20  SING N N 33 
14A N19 C23  SING N N 34 
14A C20 C21  SING N N 35 
14A C20 H201 SING N N 36 
14A C20 H202 SING N N 37 
14A C21 C22  DOUB N N 38 
14A C21 H21  SING N N 39 
14A C22 H221 SING N N 40 
14A C22 H222 SING N N 41 
14A C23 C24  SING N N 42 
14A C23 C27  SING N N 43 
14A C23 H23  SING N N 44 
14A C24 C25  SING N N 45 
14A C24 H241 SING N N 46 
14A C24 H242 SING N N 47 
14A C25 C26  SING N N 48 
14A C25 H251 SING N N 49 
14A C25 H252 SING N N 50 
14A C26 C27  SING N N 51 
14A C26 H261 SING N N 52 
14A C26 H262 SING N N 53 
14A C27 H271 SING N N 54 
14A C27 H272 SING N N 55 
# 
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 
14A SMILES           ACDLabs              10.04 O=C(N(C\C=C)C1CCCC1)c2cc(OCCCONC(=[N@H])N)cc(Cl)c2                                                                                                     
14A InChI            InChI                1.02b InChI=1/C19H27ClN4O3/c1-2-8-24(16-6-3-4-7-16)18(25)14-11-15(20)13-17(12-14)26-9-5-10-27-23-19(21)22/h2,11-13,16H,1,3-10H2,(H4,21,22,23)/f/h21,23H,22H2 
14A InChIKey         InChI                1.02b XWIUMAPBZWNFNV-FPTGWPNKCO                                                                                                                              
14A SMILES_CANONICAL CACTVS               3.341 NC(=N)NOCCCOc1cc(Cl)cc(c1)C(=O)N(CC=C)C2CCCC2                                                                                                          
14A SMILES           CACTVS               3.341 NC(=N)NOCCCOc1cc(Cl)cc(c1)C(=O)N(CC=C)C2CCCC2                                                                                                          
14A SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C=CCN(C1CCCC1)C(=O)c2cc(cc(c2)Cl)OCCCONC(=N)N                                                                                                          
14A SMILES           "OpenEye OEToolkits" 1.5.0 C=CCN(C1CCCC1)C(=O)c2cc(cc(c2)Cl)OCCCONC(=N)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 
14A "SYSTEMATIC NAME" ACDLabs              10.04 3-[3-(carbamimidamidooxy)propoxy]-5-chloro-N-cyclopentyl-N-prop-2-en-1-ylbenzamide 
14A "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 3-(3-carbamimidamidooxypropoxy)-5-chloro-N-cyclopentyl-N-prop-2-enyl-benzamide     
# 
