data_9KU
#

_chem_comp.id                                   9KU
_chem_comp.name                                 "5-hydroxy-2-[(2S)-1-{[(naphthalen-1-yl)oxy]acetyl}pyrrolidin-2-yl]-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C21 H19 N3 O6"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        SRI-29789
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2017-07-11
_chem_comp.pdbx_modified_date                   2020-06-17
_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                       409.392
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    9KU
_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       5WCS
_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
9KU  C1   C1   C  0  1  N  N  N  65.065  80.498   3.064  -5.015   0.708  -0.535  C1   9KU   1  
9KU  C10  C2   C  0  1  Y  N  N  71.838  81.471   6.759   3.725  -1.507   1.071  C10  9KU   2  
9KU  C11  C3   C  0  1  Y  N  N  72.634  81.995   7.790   5.014  -1.558   1.594  C11  9KU   3  
9KU  C12  C4   C  0  1  Y  N  N  72.914  81.266   8.903   5.975  -0.686   1.181  C12  9KU   4  
9KU  C13  C5   C  0  1  Y  N  N  72.409  79.953   9.056   5.666   0.284   0.211  C13  9KU   5  
9KU  C14  C6   C  0  1  Y  N  N  71.601  79.410   8.023   4.355   0.339  -0.325  C14  9KU   6  
9KU  C15  C7   C  0  1  Y  N  N  71.090  78.098   8.164   4.046   1.307  -1.293  C15  9KU   7  
9KU  C16  C8   C  0  1  Y  N  N  71.374  77.365   9.283   5.008   2.179  -1.704  C16  9KU   8  
9KU  C17  C9   C  0  1  Y  N  N  72.173  77.902  10.304   6.297   2.125  -1.179  C17  9KU   9  
9KU  C18  C10  C  0  1  Y  N  N  72.677  79.159  10.196   6.632   1.200  -0.239  C18  9KU  10  
9KU  C19  C11  C  0  1  N  N  N  69.542  82.373   2.779  -1.137  -3.215   0.772  C19  9KU  11  
9KU  C2   C12  C  0  1  N  N  N  64.029  80.876   3.913  -4.201   1.735   0.129  C2   9KU  12  
9KU  C20  C13  C  0  1  N  N  N  68.551  83.151   1.946  -2.279  -4.170   0.344  C20  9KU  13  
9KU  C21  C14  C  0  1  N  N  N  67.902  84.044   2.992  -3.362  -3.167  -0.134  C21  9KU  14  
9KU  C3   C15  C  0  1  N  N  N  64.205  81.915   4.777  -2.888   1.416   0.438  C3   9KU  15  
9KU  C4   C16  C  0  1  N  N  N  63.093  82.345   5.713  -2.018   2.408   1.107  C4   9KU  16  
9KU  C5   C17  C  0  1  N  N  N  66.360  82.264   4.039  -3.143  -0.702  -0.465  C5   9KU  17  
9KU  C6   C18  C  0  1  N  N  S  67.640  83.063   4.148  -2.528  -2.041  -0.781  C6   9KU  18  
9KU  C7   C19  C  0  1  N  N  N  69.140  81.327   5.027  -0.141  -1.316  -0.534  C7   9KU  19  
9KU  C8   C20  C  0  1  N  N  N  70.227  80.318   4.762   1.197  -1.508   0.132  C8   9KU  20  
9KU  C9   C21  C  0  1  Y  N  N  71.327  80.205   6.872   3.386  -0.580   0.127  C9   9KU  21  
9KU  N1   N1   N  0  1  N  N  N  65.352  82.605   4.843  -2.411   0.198   0.123  N1   9KU  22  
9KU  N2   N2   N  0  1  N  N  N  68.818  82.183   4.044  -1.175  -2.117  -0.211  N2   9KU  23  
9KU  N3   N3   N  0  1  N  N  N  66.232  81.224   3.156  -4.436  -0.482  -0.805  N3   9KU  24  
9KU  O1   O1   O  0  1  N  N  N  64.983  79.564   2.252  -6.179   0.922  -0.829  O1   9KU  25  
9KU  O2   O2   O  0  1  N  N  N  62.895  80.167   3.820  -4.717   2.953   0.430  O2   9KU  26  
9KU  O3   O3   O  0  1  N  N  N  63.338  83.280   6.496  -0.742   2.092   1.404  O3   9KU  27  
9KU  O4   O4   O  0  1  N  N  N  62.013  81.734   5.631  -2.453   3.506   1.389  O4   9KU  28  
9KU  O5   O5   O  0  1  N  N  N  70.550  79.589   5.939   2.124  -0.544  -0.374  O5   9KU  29  
9KU  O6   O6   O  0  1  N  N  N  68.568  81.380   6.112  -0.287  -0.441  -1.361  O6   9KU  30  
9KU  H1   H1   H  0  1  N  N  N  71.629  82.064   5.880   2.984  -2.214   1.414  H1   9KU  31  
9KU  H2   H2   H  0  1  N  N  N  73.031  82.995   7.697   5.257  -2.300   2.340  H2   9KU  32  
9KU  H3   H3   H  0  1  N  N  N  73.530  81.694   9.680   6.970  -0.738   1.597  H3   9KU  33  
9KU  H4   H4   H  0  1  N  N  N  70.474  77.674   7.385   3.051   1.360  -1.709  H4   9KU  34  
9KU  H5   H5   H  0  1  N  N  N  70.980  76.364   9.382   4.768   2.924  -2.449  H5   9KU  35  
9KU  H6   H6   H  0  1  N  N  N  72.389  77.312  11.182   7.042   2.828  -1.523  H6   9KU  36  
9KU  H7   H7   H  0  1  N  N  N  73.290  79.557  10.991   7.635   1.170   0.160  H7   9KU  37  
9KU  H8   H8   H  0  1  N  N  N  69.783  81.407   2.310  -1.320  -2.831   1.776  H8   9KU  38  
9KU  H9   H9   H  0  1  N  N  N  70.468  82.947   2.934  -0.176  -3.728   0.731  H9   9KU  39  
9KU  H10  H10  H  0  1  N  N  N  69.058  83.745   1.171  -1.961  -4.819  -0.472  H10  9KU  40  
9KU  H11  H11  H  0  1  N  N  N  67.814  82.485   1.474  -2.636  -4.756   1.191  H11  9KU  41  
9KU  H12  H12  H  0  1  N  N  N  68.581  84.852   3.302  -4.020  -3.631  -0.869  H12  9KU  42  
9KU  H13  H13  H  0  1  N  N  N  66.963  84.478   2.618  -3.934  -2.786   0.712  H13  9KU  43  
9KU  H14  H14  H  0  1  N  N  N  67.656  83.610   5.102  -2.487  -2.184  -1.861  H14  9KU  44  
9KU  H15  H15  H  0  1  N  N  N  69.884  79.616   3.988   1.089  -1.377   1.209  H15  9KU  45  
9KU  H16  H16  H  0  1  N  N  N  71.126  80.844   4.408   1.567  -2.511  -0.077  H16  9KU  46  
9KU  H17  H17  H  0  1  N  N  N  67.003  80.987   2.565  -4.947  -1.181  -1.243  H17  9KU  47  
9KU  H18  H18  H  0  1  N  N  N  62.254  80.512   4.431  -5.641   3.064   0.169  H18  9KU  48  
9KU  H19  H19  H  0  1  N  N  N  62.570  83.459   7.026  -0.212   2.772   1.842  H19  9KU  49  
#   #
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
9KU  C20  C19  SING  N  N   1  
9KU  C20  C21  SING  N  N   2  
9KU  O1   C1   DOUB  N  N   3  
9KU  C19  N2   SING  N  N   4  
9KU  C21  C6   SING  N  N   5  
9KU  C1   N3   SING  N  N   6  
9KU  C1   C2   SING  N  N   7  
9KU  N3   C5   SING  N  N   8  
9KU  O2   C2   SING  N  N   9  
9KU  C2   C3   DOUB  N  N  10  
9KU  C5   C6   SING  N  N  11  
9KU  C5   N1   DOUB  N  N  12  
9KU  N2   C6   SING  N  N  13  
9KU  N2   C7   SING  N  N  14  
9KU  C8   C7   SING  N  N  15  
9KU  C8   O5   SING  N  N  16  
9KU  C3   N1   SING  N  N  17  
9KU  C3   C4   SING  N  N  18  
9KU  C7   O6   DOUB  N  N  19  
9KU  O4   C4   DOUB  N  N  20  
9KU  C4   O3   SING  N  N  21  
9KU  O5   C9   SING  N  N  22  
9KU  C10  C9   DOUB  Y  N  23  
9KU  C10  C11  SING  Y  N  24  
9KU  C9   C14  SING  Y  N  25  
9KU  C11  C12  DOUB  Y  N  26  
9KU  C14  C15  DOUB  Y  N  27  
9KU  C14  C13  SING  Y  N  28  
9KU  C15  C16  SING  Y  N  29  
9KU  C12  C13  SING  Y  N  30  
9KU  C13  C18  DOUB  Y  N  31  
9KU  C16  C17  DOUB  Y  N  32  
9KU  C18  C17  SING  Y  N  33  
9KU  C10  H1   SING  N  N  34  
9KU  C11  H2   SING  N  N  35  
9KU  C12  H3   SING  N  N  36  
9KU  C15  H4   SING  N  N  37  
9KU  C16  H5   SING  N  N  38  
9KU  C17  H6   SING  N  N  39  
9KU  C18  H7   SING  N  N  40  
9KU  C19  H8   SING  N  N  41  
9KU  C19  H9   SING  N  N  42  
9KU  C20  H10  SING  N  N  43  
9KU  C20  H11  SING  N  N  44  
9KU  C21  H12  SING  N  N  45  
9KU  C21  H13  SING  N  N  46  
9KU  C6   H14  SING  N  N  47  
9KU  C8   H15  SING  N  N  48  
9KU  C8   H16  SING  N  N  49  
9KU  N3   H17  SING  N  N  50  
9KU  O2   H18  SING  N  N  51  
9KU  O3   H19  SING  N  N  52  
#   #
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
9KU  SMILES            ACDLabs               12.01  "C4(NC(C1CCCN1C(=O)COc3cccc2ccccc23)=NC(=C4O)C(O)=O)=O"  
9KU  InChI             InChI                 1.03   "InChI=1S/C21H19N3O6/c25-16(11-30-15-9-3-6-12-5-1-2-7-13(12)15)24-10-4-8-14(24)19-22-17(21(28)29)18(26)20(27)23-19/h1-3,5-7,9,14,26H,4,8,10-11H2,(H,28,29)(H,22,23,27)/t14-/m0/s1"  
9KU  InChIKey          InChI                 1.03   SALSCRPWDRUSQC-AWEZNQCLSA-N  
9KU  SMILES_CANONICAL  CACTVS                3.385  "OC(=O)C1=C(O)C(=O)NC(=N1)[C@@H]2CCCN2C(=O)COc3cccc4ccccc34"  
9KU  SMILES            CACTVS                3.385  "OC(=O)C1=C(O)C(=O)NC(=N1)[CH]2CCCN2C(=O)COc3cccc4ccccc34"  
9KU  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.6  "c1ccc2c(c1)cccc2OCC(=O)N3CCC[C@H]3C4=NC(=C(C(=O)N4)O)C(=O)O"  
9KU  SMILES            "OpenEye OEToolkits"  2.0.6  "c1ccc2c(c1)cccc2OCC(=O)N3CCCC3C4=NC(=C(C(=O)N4)O)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
9KU  "SYSTEMATIC NAME"  ACDLabs               12.01  "5-hydroxy-2-[(2S)-1-{[(naphthalen-1-yl)oxy]acetyl}pyrrolidin-2-yl]-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid"  
9KU  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  2.0.6  "2-[(2~{S})-1-(2-naphthalen-1-yloxyethanoyl)pyrrolidin-2-yl]-5-oxidanyl-6-oxidanylidene-1~{H}-pyrimidine-4-carboxylic acid"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
9KU  "Create component"  2017-07-11  RCSB  
9KU  "Initial release"   2018-01-03  RCSB  
9KU  "Modify synonyms"   2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     9KU
_pdbx_chem_comp_synonyms.name        SRI-29789
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
