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                   2021-03-01
_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  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"  
421  InChI             InChI                 1.03   "InChI=1S/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)"  
421  InChIKey          InChI                 1.03   OUBRALHIKGRAMA-UHFFFAOYSA-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"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
421  "Create component"   2005-06-02  RCSB  
421  "Modify descriptor"  2011-06-04  RCSB  
421  "Modify synonyms"    2021-03-01  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     421
_pdbx_chem_comp_synonyms.name        "METHYL 6-[AMINO(IMINO)METHYL]-4-[(3-HYDROXY-2-METHYLBENZOYL)AMINO]-2-NAPHTHOATE"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
