data_497
# 
_chem_comp.id                                    497 
_chem_comp.name                                  6-[AMINO(IMINO)METHYL]-N-[(4R)-4-ETHYL-1,2,3,4-TETRAHYDROISOQUINOLIN-6-YL]-2-NAPHTHAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H24 N4 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         6-[N-(4-ETHYL-1,2,3,4-TETRAHYDRO-6-ISOQUINOLINYL)CARBAMYL]-2-NAPHTHALENECARBOXAMIDINE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-04-09 
_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                        372.463 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     497 
_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        1OWD 
_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 
497 C47  C47  C 0 1 N N N 29.961 10.510 33.511 3.234  1.093  6.539  C47  497 1  
497 C45  C45  C 0 1 N N N 28.519 10.844 33.159 2.200  0.965  5.419  C45  497 2  
497 C39  C39  C 0 1 N N R 28.361 10.962 31.653 1.167  -0.098 5.797  C39  497 3  
497 C38  C38  C 0 1 N N N 28.824 9.820  30.737 0.466  0.309  7.094  C38  497 4  
497 N37  N37  N 0 1 N N N 29.218 10.403 29.448 -0.649 -0.615 7.338  N37  497 5  
497 C36  C36  C 0 1 N N N 28.246 11.259 28.748 -1.708 -0.252 6.394  C36  497 6  
497 C26  C26  C 0 1 Y N N 27.331 12.062 29.656 -1.200 -0.297 4.977  C26  497 7  
497 C27  C27  C 0 1 Y N N 27.254 11.797 31.055 0.148  -0.224 4.693  C27  497 8  
497 C28  C28  C 0 1 Y N N 26.189 12.340 31.804 0.584  -0.267 3.380  C28  497 9  
497 C22  C22  C 0 1 Y N N 25.352 13.314 31.213 -0.332 -0.383 2.345  C22  497 10 
497 N21  N21  N 0 1 N N N 24.276 13.891 31.834 0.108  -0.426 1.018  N21  497 11 
497 C20  C20  C 0 1 N N N 24.375 14.638 32.938 -0.645 0.114  0.040  C20  497 12 
497 O23  O23  O 0 1 N N N 25.329 14.467 33.660 -1.657 0.726  0.321  O23  497 13 
497 C11  C11  C 0 1 Y N N 23.322 15.659 33.228 -0.240 -0.035 -1.372 C11  497 14 
497 C12  C12  C 0 1 Y N N 23.651 16.719 34.118 0.931  -0.744 -1.690 C12  497 15 
497 C13  C13  C 0 1 Y N N 22.705 17.695 34.479 1.324  -0.895 -2.981 C13  497 16 
497 C4   C4   C 0 1 Y N N 21.401 17.664 33.927 0.554  -0.340 -4.021 C4   497 17 
497 C5   C5   C 0 1 Y N N 20.495 18.721 34.149 0.943  -0.485 -5.361 C5   497 18 
497 C6   C6   C 0 1 Y N N 19.205 18.723 33.572 0.165  0.071  -6.361 C6   497 19 
497 C1   C1   C 0 1 Y N N 18.877 17.714 32.636 -1.005 0.779  -6.044 C1   497 20 
497 C2   C2   C 0 1 Y N N 19.793 16.679 32.373 -1.398 0.931  -4.753 C2   497 21 
497 C3   C3   C 0 1 Y N N 21.059 16.636 33.003 -0.630 0.376  -3.713 C3   497 22 
497 C10  C10  C 0 1 Y N N 22.014 15.632 32.669 -1.022 0.517  -2.373 C10  497 23 
497 C17  C17  C 0 1 N N N 18.211 19.735 33.989 0.571  -0.078 -7.777 C17  497 24 
497 N18  N18  N 0 1 N N N 18.588 20.929 34.408 -0.198 0.473  -8.777 N18  497 25 
497 N19  N19  N 0 1 N N N 16.924 19.496 33.978 1.657  -0.733 -8.077 N19  497 26 
497 C24  C24  C 0 1 Y N N 25.606 13.723 29.897 -1.689 -0.457 2.632  C24  497 27 
497 C25  C25  C 0 1 Y N N 26.544 13.083 29.089 -2.117 -0.414 3.943  C25  497 28 
497 H471 1H47 H 0 0 N N N 30.077 10.423 34.616 3.969  1.851  6.269  H471 497 29 
497 H472 2H47 H 0 0 N N N 30.318 9.595  32.981 2.735  1.384  7.463  H472 497 30 
497 H473 3H47 H 0 0 N N N 30.677 11.243 33.073 3.735  0.136  6.682  H473 497 31 
497 H451 1H45 H 0 0 N N N 27.802 10.110 33.596 1.699  1.922  5.275  H451 497 32 
497 H452 2H45 H 0 0 N N N 28.161 11.758 33.688 2.699  0.674  4.494  H452 497 33 
497 H39  H39  H 0 1 N N N 29.223 11.668 31.655 1.668  -1.056 5.940  H39  497 34 
497 H381 1H38 H 0 0 N N N 29.630 9.200  31.194 1.172  0.257  7.923  H381 497 35 
497 H382 2H38 H 0 0 N N N 28.059 9.015  30.630 0.085  1.325  6.999  H382 497 36 
497 H37  H37  H 0 1 N N N 29.516 9.655  28.821 -1.000 -0.409 8.261  H37  497 37 
497 H361 1H36 H 0 0 N N N 28.771 11.935 28.034 -2.538 -0.951 6.499  H361 497 38 
497 H362 2H36 H 0 0 N N N 27.643 10.652 28.032 -2.059 0.754  6.617  H362 497 39 
497 H28  H28  H 0 1 N N N 26.012 12.006 32.840 1.640  -0.210 3.161  H28  497 40 
497 H21  H21  H 0 1 N N N 23.340 13.755 31.449 0.956  -0.844 0.802  H21  497 41 
497 H12  H12  H 0 1 N N N 24.667 16.786 34.539 1.527  -1.173 -0.898 H12  497 42 
497 H13  H13  H 0 1 N N N 22.985 18.485 35.195 2.227  -1.442 -3.210 H13  497 43 
497 H5   H5   H 0 1 N N N 20.802 19.565 34.788 1.843  -1.028 -5.611 H5   497 44 
497 H1   H1   H 0 1 N N N 17.907 17.734 32.111 -1.601 1.207  -6.837 H1   497 45 
497 H2   H2   H 0 1 N N N 19.513 15.886 31.659 -2.301 1.478  -4.524 H2   497 46 
497 H10  H10  H 0 1 N N N 21.737 14.824 31.969 -1.923 1.056  -2.124 H10  497 47 
497 H181 1H18 H 0 0 N N N 17.902 21.627 34.695 0.067  0.375  -9.705 H181 497 48 
497 H182 2H18 H 0 0 N N N 19.179 21.344 33.688 -1.006 0.961  -8.554 H182 497 49 
497 H19  H19  H 0 1 N N N 16.261 20.271 33.986 1.923  -0.831 -9.005 H19  497 50 
497 H24  H24  H 0 1 N N N 25.047 14.579 29.482 -2.407 -0.548 1.831  H24  497 51 
497 H25  H25  H 0 1 N N N 26.660 13.375 28.032 -3.172 -0.472 4.165  H25  497 52 
# 
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 
497 C47 C45  SING N N 1  
497 C47 H471 SING N N 2  
497 C47 H472 SING N N 3  
497 C47 H473 SING N N 4  
497 C45 C39  SING N N 5  
497 C45 H451 SING N N 6  
497 C45 H452 SING N N 7  
497 C39 C38  SING N N 8  
497 C39 C27  SING N N 9  
497 C39 H39  SING N N 10 
497 C38 N37  SING N N 11 
497 C38 H381 SING N N 12 
497 C38 H382 SING N N 13 
497 N37 C36  SING N N 14 
497 N37 H37  SING N N 15 
497 C36 C26  SING N N 16 
497 C36 H361 SING N N 17 
497 C36 H362 SING N N 18 
497 C26 C27  DOUB Y N 19 
497 C26 C25  SING Y N 20 
497 C27 C28  SING Y N 21 
497 C28 C22  DOUB Y N 22 
497 C28 H28  SING N N 23 
497 C22 N21  SING N N 24 
497 C22 C24  SING Y N 25 
497 N21 C20  SING N N 26 
497 N21 H21  SING N N 27 
497 C20 O23  DOUB N N 28 
497 C20 C11  SING N N 29 
497 C11 C12  DOUB Y N 30 
497 C11 C10  SING Y N 31 
497 C12 C13  SING Y N 32 
497 C12 H12  SING N N 33 
497 C13 C4   DOUB Y N 34 
497 C13 H13  SING N N 35 
497 C4  C5   SING Y N 36 
497 C4  C3   SING Y N 37 
497 C5  C6   DOUB Y N 38 
497 C5  H5   SING N N 39 
497 C6  C1   SING Y N 40 
497 C6  C17  SING N N 41 
497 C1  C2   DOUB Y N 42 
497 C1  H1   SING N N 43 
497 C2  C3   SING Y N 44 
497 C2  H2   SING N N 45 
497 C3  C10  DOUB Y N 46 
497 C10 H10  SING N N 47 
497 C17 N18  SING N N 48 
497 C17 N19  DOUB N N 49 
497 N18 H181 SING N N 50 
497 N18 H182 SING N N 51 
497 N19 H19  SING N N 52 
497 C24 C25  DOUB Y N 53 
497 C24 H24  SING N N 54 
497 C25 H25  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 
497 SMILES           ACDLabs              10.04 O=C(c2cc1ccc(C(=[N@H])N)cc1cc2)Nc3ccc4c(c3)C(CNC4)CC                                                                                                                                       
497 InChI            InChI                1.02b InChI=1/C23H24N4O/c1-2-14-12-26-13-19-7-8-20(11-21(14)19)27-23(28)18-6-4-15-9-17(22(24)25)5-3-16(15)10-18/h3-11,14,26H,2,12-13H2,1H3,(H3,24,25)(H,27,28)/t14-/m0/s1/f/h24,27H,25H2/b24-22- 
497 InChIKey         InChI                1.02b LVNMYQLXKMSQTG-QTYDVEBWDY                                                                                                                                                                  
497 SMILES_CANONICAL CACTVS               3.341 CC[C@H]1CNCc2ccc(NC(=O)c3ccc4cc(ccc4c3)C(N)=N)cc12                                                                                                                                         
497 SMILES           CACTVS               3.341 CC[CH]1CNCc2ccc(NC(=O)c3ccc4cc(ccc4c3)C(N)=N)cc12                                                                                                                                          
497 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@H]1CNCc2c1cc(cc2)NC(=O)c3ccc4cc(ccc4c3)C(=N)N                                                                                                                                         
497 SMILES           "OpenEye OEToolkits" 1.5.0 CCC1CNCc2c1cc(cc2)NC(=O)c3ccc4cc(ccc4c3)C(=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 
497 "SYSTEMATIC NAME" ACDLabs              10.04 6-carbamimidoyl-N-[(4R)-4-ethyl-1,2,3,4-tetrahydroisoquinolin-6-yl]naphthalene-2-carboxamide 
497 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 6-carbamimidoyl-N-[(4R)-4-ethyl-1,2,3,4-tetrahydroisoquinolin-6-yl]naphthalene-2-carboxamide 
# 
