data_BRE
#

_chem_comp.id                                   BRE
_chem_comp.name                                 "2-BIPHENYL-4-YL-6-FLUORO-3-METHYL-QUINOLINE-4-CARBOXYLIC ACID"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C23 H16 F N O2"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "BREQUINAR ANALOG"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    1999-10-01
_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                       357.377
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    BRE
_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       1D3G
_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
BRE  C1    C1    C  0  1  N  N  N  50.033  43.306  -5.250   2.354   0.240  -0.513  C1    BRE   1  
BRE  C2    C2    C  0  1  Y  N  N  49.712  42.458  -4.037   1.071   0.114  -1.293  C2    BRE   2  
BRE  C3    C3    C  0  1  Y  N  N  50.234  42.754  -2.792  -0.155  -0.007  -0.622  C3    BRE   3  
BRE  C4    C4    C  0  1  Y  N  N  48.851  41.372  -4.163   1.091   0.124  -2.681  C4    BRE   4  
BRE  N1    N1    N  0  1  Y  N  N  49.967  41.949  -1.727  -1.299  -0.120  -1.264  N1    BRE   5  
BRE  C5    C5    C  0  1  N  N  N  48.299  41.031  -5.521   2.357   0.257  -3.430  C5    BRE   6  
BRE  C23   C23   C  0  1  Y  N  N  51.170  43.872  -2.483  -0.163  -0.010   0.859  C23   BRE   7  
BRE  C6    C6    C  0  1  Y  N  N  48.524  40.594  -3.052  -0.192  -0.007  -3.372  C6    BRE   8  
BRE  C7    C7    C  0  1  Y  N  N  49.113  40.919  -1.836  -1.373  -0.126  -2.596  C7    BRE   9  
BRE  C8    C8    C  0  1  Y  N  N  52.283  44.062  -3.309  -1.168   0.664   1.552  C8    BRE  10  
BRE  C9    C9    C  0  1  Y  N  N  50.984  44.641  -1.357   0.830  -0.693   1.560  C9    BRE  11  
BRE  O1    O1    O  0  1  N  N  N  47.171  41.232  -5.868   2.769   1.358  -3.736  O1    BRE  12  
BRE  O2    O2    O  0  1  N  N  N  49.169  40.460  -6.379   3.055  -0.842  -3.774  O2    BRE  13  
BRE  C10   C10   C  0  1  Y  N  N  47.599  39.556  -3.078  -0.272  -0.013  -4.767  C10   BRE  14  
BRE  C11   C11   C  0  1  Y  N  N  48.781  40.210  -0.686  -2.611  -0.247  -3.253  C11   BRE  15  
BRE  C12   C12   C  0  1  Y  N  N  53.165  45.055  -2.944  -1.175   0.661   2.929  C12   BRE  16  
BRE  C13   C13   C  0  1  Y  N  N  51.886  45.630  -1.000   0.825  -0.691   2.938  C13   BRE  17  
BRE  C14   C14   C  0  1  Y  N  N  47.269  38.855  -1.932  -1.491  -0.133  -5.372  C14   BRE  18  
BRE  C15   C15   C  0  1  Y  N  N  47.872  39.167  -0.723  -2.656  -0.249  -4.613  C15   BRE  19  
BRE  C16   C16   C  0  1  Y  N  N  52.996  45.860  -1.829  -0.178  -0.016   3.631  C16   BRE  20  
BRE  F1    F1    F  0  1  N  N  N  46.397  37.974  -1.962  -1.570  -0.139  -6.721  F1    BRE  21  
BRE  C17   C17   C  0  1  Y  N  N  54.072  46.885  -1.423  -0.187  -0.019   5.114  C17   BRE  22  
BRE  C18   C18   C  0  1  Y  N  N  54.651  46.771  -0.148   0.145  -1.178   5.813  C18   BRE  23  
BRE  C19   C19   C  0  1  Y  N  N  54.616  47.788  -2.329  -0.521   1.138   5.814  C19   BRE  24  
BRE  C20   C20   C  0  1  Y  N  N  55.678  47.613   0.247   0.136  -1.175   7.193  C20   BRE  25  
BRE  C21   C21   C  0  1  Y  N  N  56.186  48.532  -0.653  -0.202  -0.025   7.882  C21   BRE  26  
BRE  C22   C22   C  0  1  Y  N  N  55.639  48.629  -1.915  -0.533   1.128   7.194  C22   BRE  27  
BRE  H11   1H1   H  0  1  N  N  N  49.611  43.067  -6.254   2.155   0.736   0.437  H11   BRE  28  
BRE  H12   2H1   H  0  1  N  N  N  49.770  44.362  -5.009   2.765  -0.751  -0.326  H12   BRE  29  
BRE  H13   3H1   H  0  1  N  N  N  51.142  43.360  -5.346   3.071   0.829  -1.085  H13   BRE  30  
BRE  H81   1H8   H  0  1  N  N  N  52.458  43.453  -4.211  -1.939   1.190   1.009  H81   BRE  31  
BRE  H91   1H9   H  0  1  N  N  N  50.095  44.461  -0.728   1.608  -1.216   1.024  H91   BRE  32  
BRE  HO2   HO2   H  0  1  N  N  N  48.820  40.244  -7.236   3.884  -0.754  -4.264  HO2   BRE  33  
BRE  H101  1H10  H  0  0  N  N  N  47.115  39.282  -4.030   0.623   0.076  -5.364  H101  BRE  34  
BRE  H111  1H11  H  0  0  N  N  N  49.248  40.480   0.275  -3.522  -0.339  -2.681  H111  BRE  35  
BRE  H121  1H12  H  0  0  N  N  N  54.053  45.213  -3.578  -1.953   1.184   3.466  H121  BRE  36  
BRE  H131  1H13  H  0  0  N  N  N  51.724  46.218  -0.080   1.597  -1.216   3.481  H131  BRE  37  
BRE  H151  1H15  H  0  0  N  N  N  47.633  38.597   0.190  -3.609  -0.343  -5.113  H151  BRE  38  
BRE  H181  1H18  H  0  0  N  N  N  54.291  46.003   0.558   0.410  -2.077   5.276  H181  BRE  39  
BRE  H191  1H19  H  0  0  N  N  N  54.240  47.836  -3.364  -0.780   2.039   5.277  H191  BRE  40  
BRE  H201  1H20  H  0  0  N  N  N  56.087  47.552   1.269   0.393  -2.073   7.736  H201  BRE  41  
BRE  H211  1H21  H  0  0  N  N  N  57.025  49.186  -0.364  -0.208  -0.027   8.962  H211  BRE  42  
BRE  H221  1H22  H  0  0  N  N  N  56.027  49.394  -2.607  -0.796   2.023   7.737  H221  BRE  43  
#   #
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
BRE  C1   C2    SING  N  N   1  
BRE  C1   H11   SING  N  N   2  
BRE  C1   H12   SING  N  N   3  
BRE  C1   H13   SING  N  N   4  
BRE  C2   C3    SING  Y  N   5  
BRE  C2   C4    DOUB  Y  N   6  
BRE  C3   N1    DOUB  Y  N   7  
BRE  C3   C23   SING  Y  N   8  
BRE  C4   C5    SING  N  N   9  
BRE  C4   C6    SING  Y  N  10  
BRE  N1   C7    SING  Y  N  11  
BRE  C5   O1    DOUB  N  N  12  
BRE  C5   O2    SING  N  N  13  
BRE  C23  C8    DOUB  Y  N  14  
BRE  C23  C9    SING  Y  N  15  
BRE  C6   C7    DOUB  Y  N  16  
BRE  C6   C10   SING  Y  N  17  
BRE  C7   C11   SING  Y  N  18  
BRE  C8   C12   SING  Y  N  19  
BRE  C8   H81   SING  N  N  20  
BRE  C9   C13   DOUB  Y  N  21  
BRE  C9   H91   SING  N  N  22  
BRE  O2   HO2   SING  N  N  23  
BRE  C10  C14   DOUB  Y  N  24  
BRE  C10  H101  SING  N  N  25  
BRE  C11  C15   DOUB  Y  N  26  
BRE  C11  H111  SING  N  N  27  
BRE  C12  C16   DOUB  Y  N  28  
BRE  C12  H121  SING  N  N  29  
BRE  C13  C16   SING  Y  N  30  
BRE  C13  H131  SING  N  N  31  
BRE  C14  C15   SING  Y  N  32  
BRE  C14  F1    SING  N  N  33  
BRE  C15  H151  SING  N  N  34  
BRE  C16  C17   SING  Y  N  35  
BRE  C17  C18   DOUB  Y  N  36  
BRE  C17  C19   SING  Y  N  37  
BRE  C18  C20   SING  Y  N  38  
BRE  C18  H181  SING  N  N  39  
BRE  C19  C22   DOUB  Y  N  40  
BRE  C19  H191  SING  N  N  41  
BRE  C20  C21   DOUB  Y  N  42  
BRE  C20  H201  SING  N  N  43  
BRE  C21  C22   SING  Y  N  44  
BRE  C21  H211  SING  N  N  45  
BRE  C22  H221  SING  N  N  46  
#   #
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
BRE  SMILES            ACDLabs               10.04  "Fc1ccc2nc(c(c(c2c1)C(=O)O)C)c4ccc(c3ccccc3)cc4"  
BRE  SMILES_CANONICAL  CACTVS                3.341  "Cc1c(nc2ccc(F)cc2c1C(O)=O)c3ccc(cc3)c4ccccc4"  
BRE  SMILES            CACTVS                3.341  "Cc1c(nc2ccc(F)cc2c1C(O)=O)c3ccc(cc3)c4ccccc4"  
BRE  SMILES_CANONICAL  "OpenEye OEToolkits"  1.5.0  "Cc1c(c2cc(ccc2nc1c3ccc(cc3)c4ccccc4)F)C(=O)O"  
BRE  SMILES            "OpenEye OEToolkits"  1.5.0  "Cc1c(c2cc(ccc2nc1c3ccc(cc3)c4ccccc4)F)C(=O)O"  
BRE  InChI             InChI                 1.03   "InChI=1S/C23H16FNO2/c1-14-21(23(26)27)19-13-18(24)11-12-20(19)25-22(14)17-9-7-16(8-10-17)15-5-3-2-4-6-15/h2-13H,1H3,(H,26,27)"  
BRE  InChIKey          InChI                 1.03   WYKKHJQZENLZID-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
BRE  "SYSTEMATIC NAME"  ACDLabs               10.04  "2-biphenyl-4-yl-6-fluoro-3-methylquinoline-4-carboxylic acid"  
BRE  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.5.0  "6-fluoro-3-methyl-2-(4-phenylphenyl)quinoline-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
BRE  "Create component"      1999-10-01  RCSB  
BRE  "Modify aromatic_flag"  2011-06-04  RCSB  
BRE  "Modify descriptor"     2011-06-04  RCSB  
BRE  "Modify synonyms"       2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     BRE
_pdbx_chem_comp_synonyms.name        "BREQUINAR ANALOG"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
