data_BOU
#

_chem_comp.id                                   BOU
_chem_comp.name                                 
;(2R,4S)-2-[(1R)-1-{[(2'-carboxybiphenyl-2-yl)carbonyl]amino}-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic
acid
;

_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C22 H22 N2 O6 S"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "CBAP, open form; benzoyl-6-amino penicilloic acid, open form"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2011-06-13
_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                       442.485
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    BOU
_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       3Q7Z
_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
BOU  S1    S1    S  0  1  N  N  N  -3.684   -9.937  32.180  -3.130   0.858  -0.985  S1    BOU   1  
BOU  C1    C1    C  0  1  N  N  N  -5.430   -9.701  31.916  -4.883   0.417  -0.658  C1    BOU   2  
BOU  C2    C2    C  0  1  N  N  S  -5.423   -8.356  31.199  -4.781  -0.910   0.118  C2    BOU   3  
BOU  N1    N1    N  0  1  N  N  N  -4.139   -8.412  30.425  -3.402  -1.393   0.241  N1    BOU   4  
BOU  C3    C3    C  0  1  N  N  R  -2.829   -8.796  31.002  -2.444  -0.255   0.311  C3    BOU   5  
BOU  C4    C4    C  0  1  N  N  R  -2.531   -7.430  31.550  -1.025  -0.705  -0.043  C4    BOU   6  
BOU  C5    C5    C  0  1  N  N  N  -2.981   -6.341  30.705  -1.010  -1.262  -1.443  C5    BOU   7  
BOU  O1    O1    O  0  1  N  N  N  -3.527   -5.019  30.705  -0.311  -0.755  -2.287  O1    BOU   8  
BOU  C6    C6    C  0  1  N  N  N  -6.071  -10.859  31.121  -5.559   1.493   0.195  C6    BOU   9  
BOU  C7    C7    C  0  1  N  N  N  -6.150   -9.593  33.260  -5.642   0.217  -1.971  C7    BOU  10  
BOU  C8    C8    C  0  1  N  N  N  -6.701   -8.001  30.452  -5.348  -0.711   1.499  C8    BOU  11  
BOU  O2    O2    O  0  1  N  N  N  -7.673   -7.425  31.026  -6.677  -0.732   1.689  O2    BOU  12  
BOU  O3    O3    O  0  1  N  N  N  -6.774   -8.290  29.235  -4.608  -0.532   2.437  O3    BOU  13  
BOU  N2    N2    N  0  1  N  N  N  -2.279   -6.937  32.862  -0.115   0.440   0.037  N2    BOU  14  
BOU  C9    C9    C  0  1  N  N  N  -1.782   -7.673  33.840   1.198   0.242   0.269  C9    BOU  15  
BOU  O4    O4    O  0  1  N  N  N  -1.582   -8.809  33.659   1.627  -0.887   0.411  O4    BOU  16  
BOU  C10   C10   C  0  1  Y  N  N  -1.431   -7.170  35.205   2.116   1.396   0.350  C10   BOU  17  
BOU  C11   C11   C  0  1  Y  N  N  -1.209   -5.797  35.287   1.629   2.692   0.187  C11   BOU  18  
BOU  C12   C12   C  0  1  Y  N  N  -0.854   -5.247  36.508   2.491   3.768   0.263  C12   BOU  19  
BOU  C13   C13   C  0  1  Y  N  N  -0.734   -6.063  37.621   3.841   3.569   0.500  C13   BOU  20  
BOU  C14   C14   C  0  1  Y  N  N  -0.968   -7.428  37.562   4.341   2.292   0.664  C14   BOU  21  
BOU  C15   C15   C  0  1  Y  N  N  -1.323   -8.021  36.336   3.487   1.195   0.597  C15   BOU  22  
BOU  C16   C16   C  0  1  Y  N  N  -1.573   -9.520  36.317   4.017  -0.175   0.778  C16   BOU  23  
BOU  C17   C17   C  0  1  Y  N  N  -2.802   -9.971  35.772   4.547  -0.564   2.006  C17   BOU  24  
BOU  C18   C18   C  0  1  Y  N  N  -3.108  -11.324  35.664   5.041  -1.843   2.170  C18   BOU  25  
BOU  C19   C19   C  0  1  Y  N  N  -2.201  -12.255  36.168   5.015  -2.746   1.121  C19   BOU  26  
BOU  C20   C20   C  0  1  Y  N  N  -0.993  -11.847  36.733   4.494  -2.379  -0.103  C20   BOU  27  
BOU  C21   C21   C  0  1  Y  N  N  -0.665  -10.495  36.818   3.984  -1.094  -0.287  C21   BOU  28  
BOU  C22   C22   C  0  1  N  N  N   0.677  -10.216  37.445   3.420  -0.699  -1.592  C22   BOU  29  
BOU  O5    O5    O  0  1  N  N  N   0.904  -10.698  38.575   3.391  -1.582  -2.609  O5    BOU  30  
BOU  O6    O6    O  0  1  N  N  N   1.539   -9.523  36.852   2.982   0.424  -1.749  O6    BOU  31  
BOU  H3    H3    H  0  1  N  N  N  -5.438   -7.489  31.876  -5.373  -1.666  -0.399  H3    BOU  32  
BOU  HN4   HN4   H  0  1  N  N  N  -4.306   -9.083  29.703  -3.302  -2.000   1.041  HN4   BOU  33  
BOU  H5    H5    H  0  1  N  N  N  -1.936   -9.226  30.525  -2.470   0.221   1.292  H5    BOU  34  
BOU  H6    H6    H  0  1  N  N  N  -1.576   -7.970  31.626  -0.703  -1.475   0.658  H6    BOU  35  
BOU  HO8   HO8   H  0  1  N  N  N  -2.855   -6.647  29.677  -1.624  -2.115  -1.692  HO8   BOU  36  
BOU  H9    H9    H  0  1  N  N  N  -7.145  -10.662  30.987  -5.550   2.441  -0.342  H9    BOU  37  
BOU  H9A   H9A   H  0  1  N  N  N  -5.588  -10.939  30.136  -6.589   1.200   0.400  H9A   BOU  38  
BOU  H9B   H9B   H  0  1  N  N  N  -5.937  -11.801  31.673  -5.019   1.603   1.136  H9B   BOU  39  
BOU  H10   H10   H  0  1  N  N  N  -7.227   -9.448  33.089  -5.161  -0.569  -2.553  H10   BOU  40  
BOU  H10A  H10A  H  0  0  N  N  N  -5.992  -10.517  33.836  -6.672  -0.068  -1.755  H10A  BOU  41  
BOU  H10B  H10B  H  0  0  N  N  N  -5.749   -8.737  33.823  -5.635   1.147  -2.540  H10B  BOU  42  
BOU  HO12  HO12  H  0  0  N  N  N  -8.373   -7.284  30.399  -6.994  -0.600   2.592  HO12  BOU  43  
BOU  HN14  HN14  H  0  0  N  N  N  -2.490   -5.979  33.054  -0.457   1.340  -0.076  HN14  BOU  44  
BOU  H18   H18   H  0  1  N  N  N  -1.312   -5.171  34.413   0.578   2.855   0.001  H18   BOU  45  
BOU  H19   H19   H  0  1  N  N  N  -0.671   -4.186  36.592   2.111   4.770   0.137  H19   BOU  46  
BOU  H20   H20   H  0  1  N  N  N  -0.449   -5.622  38.565   4.506   4.417   0.558  H20   BOU  47  
BOU  H21   H21   H  0  1  N  N  N  -0.878   -8.033  38.452   5.395   2.145   0.849  H21   BOU  48  
BOU  H24   H24   H  0  1  N  N  N  -3.522   -9.242  35.430   4.572   0.135   2.829  H24   BOU  49  
BOU  H25   H25   H  0  1  N  N  N  -4.028  -11.646  35.200   5.452  -2.141   3.124  H25   BOU  50  
BOU  H26   H26   H  0  1  N  N  N  -2.437  -13.308  36.120   5.405  -3.743   1.261  H26   BOU  51  
BOU  H27   H27   H  0  1  N  N  N  -0.303  -12.588  37.109   4.477  -3.089  -0.917  H27   BOU  52  
BOU  HO30  HO30  H  0  0  N  N  N   1.777  -10.451  38.855   3.011  -1.277  -3.444  HO30  BOU  53  
#   #
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
BOU  C1   S1    SING  N  N   1  
BOU  C1   C7    SING  N  N   2  
BOU  C2   C1    SING  N  N   3  
BOU  N1   C2    SING  N  N   4  
BOU  N1   C3    SING  N  N   5  
BOU  C3   S1    SING  N  N   6  
BOU  C3   C4    SING  N  N   7  
BOU  C4   N2    SING  N  N   8  
BOU  C5   C4    SING  N  N   9  
BOU  C5   O1    DOUB  N  N  10  
BOU  C6   C1    SING  N  N  11  
BOU  C8   C2    SING  N  N  12  
BOU  C8   O2    SING  N  N  13  
BOU  O3   C8    DOUB  N  N  14  
BOU  N2   C9    SING  N  N  15  
BOU  C9   C10   SING  N  N  16  
BOU  O4   C9    DOUB  N  N  17  
BOU  C10  C11   DOUB  Y  N  18  
BOU  C10  C15   SING  Y  N  19  
BOU  C11  C12   SING  Y  N  20  
BOU  C12  C13   DOUB  Y  N  21  
BOU  C14  C13   SING  Y  N  22  
BOU  C15  C14   DOUB  Y  N  23  
BOU  C16  C15   SING  N  N  24  
BOU  C16  C21   SING  Y  N  25  
BOU  C17  C16   DOUB  Y  N  26  
BOU  C18  C17   SING  Y  N  27  
BOU  C18  C19   DOUB  Y  N  28  
BOU  C19  C20   SING  Y  N  29  
BOU  C20  C21   DOUB  Y  N  30  
BOU  C21  C22   SING  N  N  31  
BOU  C22  O5    SING  N  N  32  
BOU  O6   C22   DOUB  N  N  33  
BOU  C2   H3    SING  N  N  34  
BOU  N1   HN4   SING  N  N  35  
BOU  C3   H5    SING  N  N  36  
BOU  C4   H6    SING  N  N  37  
BOU  C5   HO8   SING  N  N  38  
BOU  C6   H9    SING  N  N  39  
BOU  C6   H9A   SING  N  N  40  
BOU  C6   H9B   SING  N  N  41  
BOU  C7   H10   SING  N  N  42  
BOU  C7   H10A  SING  N  N  43  
BOU  C7   H10B  SING  N  N  44  
BOU  O2   HO12  SING  N  N  45  
BOU  N2   HN14  SING  N  N  46  
BOU  C11  H18   SING  N  N  47  
BOU  C12  H19   SING  N  N  48  
BOU  C13  H20   SING  N  N  49  
BOU  C14  H21   SING  N  N  50  
BOU  C17  H24   SING  N  N  51  
BOU  C18  H25   SING  N  N  52  
BOU  C19  H26   SING  N  N  53  
BOU  C20  H27   SING  N  N  54  
BOU  O5   HO30  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
BOU  SMILES            ACDLabs               12.01  "O=C(NC(C=O)C1SC(C(N1)C(=O)O)(C)C)c3ccccc3c2ccccc2C(=O)O"  
BOU  InChI             InChI                 1.03   "InChI=1S/C22H22N2O6S/c1-22(2)17(21(29)30)24-19(31-22)16(11-25)23-18(26)14-9-5-3-7-12(14)13-8-4-6-10-15(13)20(27)28/h3-11,16-17,19,24H,1-2H3,(H,23,26)(H,27,28)(H,29,30)/t16-,17+,19-/m1/s1"  
BOU  InChIKey          InChI                 1.03   RFZQTRAFQUXQJP-ZIFCJYIRSA-N  
BOU  SMILES_CANONICAL  CACTVS                3.370  "CC1(C)S[C@@H](N[C@H]1C(O)=O)[C@H](NC(=O)c2ccccc2c3ccccc3C(O)=O)C=O"  
BOU  SMILES            CACTVS                3.370  "CC1(C)S[CH](N[CH]1C(O)=O)[CH](NC(=O)c2ccccc2c3ccccc3C(O)=O)C=O"  
BOU  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.2  "CC1([C@@H](N[C@H](S1)[C@@H](C=O)NC(=O)c2ccccc2c3ccccc3C(=O)O)C(=O)O)C"  
BOU  SMILES            "OpenEye OEToolkits"  1.7.2  "CC1(C(NC(S1)C(C=O)NC(=O)c2ccccc2c3ccccc3C(=O)O)C(=O)O)C"  
#   #
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
BOU  "SYSTEMATIC NAME"  ACDLabs               12.01  "(2R,4S)-2-[(1R)-1-{[(2'-carboxybiphenyl-2-yl)carbonyl]amino}-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid"  
BOU  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.7.2  "(2R,4S)-2-[(1R)-1-[[2-(2-carboxyphenyl)phenyl]carbonylamino]-2-oxidanylidene-ethyl]-5,5-dimethyl-1,3-thiazolidine-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
BOU  "Create component"    2011-06-13  RCSB  
BOU  "Other modification"  2011-06-29  RCSB  
BOU  "Modify synonyms"     2020-06-05  PDBE  
#   #
loop_
_pdbx_chem_comp_synonyms.ordinal
_pdbx_chem_comp_synonyms.comp_id
_pdbx_chem_comp_synonyms.name
_pdbx_chem_comp_synonyms.provenance
_pdbx_chem_comp_synonyms.type
1  BOU  "CBAP, open form"                              ?  ?  
2  BOU  "benzoyl-6-amino penicilloic acid, open form"  ?  ?  
##
