data_421
# 
_chem_comp.id                                    421 
_chem_comp.name                                  "6-CARBAMIMIDOYL-4-(3-HYDROXY-2-METHYL-BENZOYLAMINO)-NAPHTHALENE-2-CARBOXYLIC ACID METHYL ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H19 N3 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "METHYL 6-[AMINO(IMINO)METHYL]-4-[(3-HYDROXY-2-METHYLBENZOYL)AMINO]-2-NAPHTHOATE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-06-02 
_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                        377.393 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     421 
_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        1ZSK 
_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 
421 C1   C1   C 0 1 Y N N 9.732  72.799 82.614 3.013  -0.071 -0.037 C1   421 1  
421 C2   C2   C 0 1 Y N N 11.110 72.349 82.861 4.154  -0.887 -0.159 C2   421 2  
421 C3   C3   C 0 1 Y N N 11.954 72.090 81.798 4.020  -2.238 -0.198 C3   421 3  
421 C4   C4   C 0 1 Y N N 11.526 72.253 80.358 2.753  -2.839 -0.117 C4   421 4  
421 C5   C5   C 0 1 Y N N 10.222 72.683 80.052 1.613  -2.062 0.004  C5   421 5  
421 C6   C6   C 0 1 Y N N 9.247  72.987 81.131 1.729  -0.667 0.045  C6   421 6  
421 C7   C7   C 0 1 Y N N 7.856  73.463 80.869 0.584  0.153  0.168  C7   421 7  
421 C8   C8   C 0 1 Y N N 7.022  73.700 82.016 0.721  1.511  0.206  C8   421 8  
421 C9   C9   C 0 1 Y N N 7.496  73.509 83.426 1.990  2.107  0.125  C9   421 9  
421 C10  C10  C 0 1 Y N N 8.790  73.078 83.706 3.129  1.327  -0.001 C10  421 10 
421 C11  C11  C 0 1 N N N 12.472 71.952 79.261 2.636  -4.314 -0.160 C11  421 11 
421 N12  N12  N 0 1 N N N 13.861 71.974 79.464 3.767  -5.092 -0.280 N12  421 12 
421 N13  N13  N 0 1 N N N 12.027 71.660 78.077 1.463  -4.876 -0.085 N13  421 13 
421 N14  N14  N 0 1 N N N 7.480  73.628 79.457 -0.683 -0.424 0.249  N14  421 14 
421 C15  C15  C 0 1 N N N 6.339  73.225 78.835 -1.776 0.305  -0.052 C15  421 15 
421 C16  C16  C 0 1 Y N N 5.420  72.139 79.430 -3.124 -0.271 0.139  C16  421 16 
421 O17  O17  O 0 1 N N N 6.041  73.771 77.754 -1.653 1.436  -0.481 O17  421 17 
421 C18  C18  C 0 1 Y N N 5.868  70.703 79.492 -3.275 -1.506 0.772  C18  421 18 
421 C19  C19  C 0 1 Y N N 4.982  69.685 80.065 -4.535 -2.040 0.949  C19  421 19 
421 C20  C20  C 0 1 Y N N 3.679  70.057 80.549 -5.650 -1.356 0.501  C20  421 20 
421 C21  C21  C 0 1 Y N N 3.200  71.437 80.515 -5.510 -0.127 -0.130 C21  421 21 
421 C22  C22  C 0 1 Y N N 4.049  72.512 79.944 -4.251 0.421  -0.307 C22  421 22 
421 C23  C23  C 0 1 N N N 3.490  74.024 79.925 -4.096 1.755  -0.991 C23  421 23 
421 O24  O24  O 0 1 N N N 1.940  71.697 81.000 -6.609 0.541  -0.568 O24  421 24 
421 C25  C25  C 0 1 N N N 6.532  73.798 84.496 2.112  3.578  0.168  C25  421 25 
421 O26  O26  O 0 1 N N N 5.382  74.155 84.288 1.117  4.267  0.273  O26  421 26 
421 O27  O27  O 0 1 N N N 7.114  73.619 85.710 3.326  4.156  0.091  O27  421 27 
421 C28  C28  C 0 1 N N N 6.292  73.242 86.827 3.446  5.603  0.133  C28  421 28 
421 H2   H2   H 0 1 N N N 11.463 72.221 83.874 5.134  -0.439 -0.222 H2   421 29 
421 H3   H3   H 0 1 N N N 12.961 71.758 82.005 4.900  -2.858 -0.291 H3   421 30 
421 H5   H5   H 0 1 N N N 9.926  72.794 79.019 0.641  -2.529 0.066  H5   421 31 
421 H8   H8   H 0 1 N N N 6.007  74.031 81.855 -0.157 2.134  0.299  H8   421 32 
421 H10  H10  H 0 1 N N N 9.103  72.948 84.732 4.101  1.793  -0.067 H10  421 33 
421 H121 1H12 H 0 0 N N N 14.326 72.184 80.324 4.640  -4.673 -0.336 H121 421 34 
421 H122 2H12 H 0 0 N N N 14.304 71.743 78.598 3.690  -6.058 -0.309 H122 421 35 
421 H13  H13  H 0 1 N N N 11.028 71.689 78.106 1.386  -5.843 -0.114 H13  421 36 
421 H14  H14  H 0 1 N N N 8.149  74.097 78.880 -0.778 -1.350 0.523  H14  421 37 
421 H18  H18  H 0 1 N N N 6.841  70.423 79.115 -2.406 -2.043 1.123  H18  421 38 
421 H19  H19  H 0 1 N N N 5.307  68.657 80.124 -4.650 -2.995 1.439  H19  421 39 
421 H20  H20  H 0 1 N N N 3.033  69.290 80.951 -6.634 -1.779 0.642  H20  421 40 
421 H231 1H23 H 0 0 N N N 2.520  74.050 79.406 -4.007 2.540  -0.241 H231 421 41 
421 H232 2H23 H 0 0 N N N 4.205  74.673 79.398 -3.202 1.743  -1.614 H232 421 42 
421 H233 3H23 H 0 0 N N N 3.363  74.381 80.957 -4.970 1.946  -1.615 H233 421 43 
421 H24  H24  H 0 1 N N N 1.971  71.757 81.948 -6.902 1.106  0.160  H24  421 44 
421 H281 1H28 H 0 0 N N N 5.805  72.279 86.615 4.497  5.883  0.058  H281 421 45 
421 H282 2H28 H 0 0 N N N 5.525  74.013 86.994 2.894  6.038  -0.700 H282 421 46 
421 H283 3H28 H 0 0 N N N 6.917  73.146 87.727 3.037  5.974  1.073  H283 421 47 
# 
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 
421 C1  C2   DOUB Y N 1  
421 C1  C6   SING Y N 2  
421 C1  C10  SING Y N 3  
421 C2  C3   SING Y N 4  
421 C2  H2   SING N N 5  
421 C3  C4   DOUB Y N 6  
421 C3  H3   SING N N 7  
421 C4  C5   SING Y N 8  
421 C4  C11  SING N N 9  
421 C5  C6   DOUB Y N 10 
421 C5  H5   SING N N 11 
421 C6  C7   SING Y N 12 
421 C7  C8   DOUB Y N 13 
421 C7  N14  SING N N 14 
421 C8  C9   SING Y N 15 
421 C8  H8   SING N N 16 
421 C9  C10  DOUB Y N 17 
421 C9  C25  SING N N 18 
421 C10 H10  SING N N 19 
421 C11 N12  SING N N 20 
421 C11 N13  DOUB N E 21 
421 N12 H121 SING N N 22 
421 N12 H122 SING N N 23 
421 N13 H13  SING N N 24 
421 N14 C15  SING N N 25 
421 N14 H14  SING N N 26 
421 C15 C16  SING N N 27 
421 C15 O17  DOUB N N 28 
421 C16 C18  DOUB Y N 29 
421 C16 C22  SING Y N 30 
421 C18 C19  SING Y N 31 
421 C18 H18  SING N N 32 
421 C19 C20  DOUB Y N 33 
421 C19 H19  SING N N 34 
421 C20 C21  SING Y N 35 
421 C20 H20  SING N N 36 
421 C21 C22  DOUB Y N 37 
421 C21 O24  SING N N 38 
421 C22 C23  SING N N 39 
421 C23 H231 SING N N 40 
421 C23 H232 SING N N 41 
421 C23 H233 SING N N 42 
421 O24 H24  SING N N 43 
421 C25 O26  DOUB N N 44 
421 C25 O27  SING N N 45 
421 O27 C28  SING N N 46 
421 C28 H281 SING N N 47 
421 C28 H282 SING N N 48 
421 C28 H283 SING N N 49 
# 
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 
421 SMILES           ACDLabs              10.04 O=C(OC)c2cc1c(cc(C(=[N@H])N)cc1)c(c2)NC(=O)c3cccc(O)c3C                                                                                                            
421 InChI            InChI                1.02b InChI=1/C21H19N3O4/c1-11-15(4-3-5-18(11)25)20(26)24-17-10-14(21(27)28-2)8-12-6-7-13(19(22)23)9-16(12)17/h3-10,25H,1-2H3,(H3,22,23)(H,24,26)/f/h22,24H,23H2/b22-19+ 
421 InChIKey         InChI                1.02b OUBRALHIKGRAMA-GHCQOQGJDB                                                                                                                                          
421 SMILES_CANONICAL CACTVS               3.341 COC(=O)c1cc(NC(=O)c2cccc(O)c2C)c3cc(ccc3c1)C(N)=N                                                                                                                  
421 SMILES           CACTVS               3.341 COC(=O)c1cc(NC(=O)c2cccc(O)c2C)c3cc(ccc3c1)C(N)=N                                                                                                                  
421 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(\c1ccc2cc(cc(c2c1)NC(=O)c3cccc(c3C)O)C(=O)OC)/N                                                                                                            
421 SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(c1ccc2cc(cc(c2c1)NC(=O)c3cccc(c3C)O)C(=O)OC)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 
421 "SYSTEMATIC NAME" ACDLabs              10.04 "methyl 6-carbamimidoyl-4-{[(3-hydroxy-2-methylphenyl)carbonyl]amino}naphthalene-2-carboxylate" 
421 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "methyl 6-carbamimidoyl-4-[(3-hydroxy-2-methyl-phenyl)carbonylamino]naphthalene-2-carboxylate"  
# 
