data_TBH
#

_chem_comp.id                                   TBH
_chem_comp.name                                 "5-(2-{2-[(TERT-BUTOXY-HYDROXY-METHYL)-AMINO]-1-HYDROXY-3-PHENYL-PROPYLAMINO}-3-HYDROXY-3-PENTYLAMINO-PROPYL)-2-CARBOXYMETHOXY-BENZOIC ACID"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C31 H47 N3 O9"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        PNU177836
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2001-06-26
_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                       605.720
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    TBH
_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       1JF7
_chem_comp.pdbx_subcomponent_list               ?
_chem_comp.pdbx_processing_site                 PDBJ
#   #
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
TBH  O43   O43   O  0  1  N  N  N  23.302  14.405  44.037  -4.383  -3.355   1.925  O43   TBH   1  
TBH  C27   C27   C  0  1  N  N  N  23.269  13.945  45.170  -3.190  -3.359   2.155  C27   TBH   2  
TBH  O42   O42   O  0  1  N  N  N  23.836  14.449  46.142  -2.744  -3.653   3.393  O42   TBH   3  
TBH  C6    C6    C  0  1  Y  N  N  22.459  12.717  45.324  -2.230  -3.044   1.082  C6    TBH   4  
TBH  C5    C5    C  0  1  Y  N  N  21.400  12.600  44.483  -0.857  -3.053   1.342  C5    TBH   5  
TBH  C1    C1    C  0  1  Y  N  N  22.788  11.663  46.302  -2.689  -2.738  -0.207  C1    TBH   6  
TBH  O9    O9    O  0  1  N  N  N  23.866  11.799  47.126  -4.019  -2.731  -0.472  O9    TBH   7  
TBH  C23   C23   C  0  1  N  N  N  24.836  10.755  47.121  -4.163  -2.388  -1.852  C23   TBH   8  
TBH  C24   C24   C  0  1  N  N  N  25.875  10.938  48.180  -5.626  -2.363  -2.214  C24   TBH   9  
TBH  O25   O25   O  0  1  N  N  N  26.878  10.268  48.116  -6.460  -2.613  -1.376  O25   TBH  10  
TBH  O26   O26   O  0  1  N  N  N  25.714  11.692  49.123  -6.003  -2.063  -3.467  O26   TBH  11  
TBH  C2    C2    C  0  1  Y  N  N  21.948  10.564  46.355  -1.777  -2.442  -1.209  C2    TBH  12  
TBH  C3    C3    C  0  1  Y  N  N  20.860  10.497  45.473  -0.424  -2.450  -0.937  C3    TBH  13  
TBH  C4    C4    C  0  1  Y  N  N  20.591  11.499  44.541   0.035  -2.752   0.335  C4    TBH  14  
TBH  C7    C7    C  0  1  N  N  N  19.417  11.458  43.643   1.515  -2.756   0.618  C7    TBH  15  
TBH  C8    C8    C  0  1  N  N  S  19.409  11.884  42.219   1.953  -1.361   1.068  C8    TBH  16  
TBH  C11   C11   C  0  1  N  N  R  20.339  10.883  41.553   3.427  -1.396   1.474  C11   TBH  17  
TBH  N13   N13   N  0  1  N  N  N  19.921   9.546  41.855   4.227  -1.941   0.369  N13   TBH  18  
TBH  C15   C15   C  0  1  N  N  N  20.528   8.439  41.507   5.478  -1.172   0.333  C15   TBH  19  
TBH  C16   C16   C  0  1  N  N  N  20.799   7.624  42.546   6.363  -1.691  -0.802  C16   TBH  20  
TBH  C17   C17   C  0  1  N  N  N  19.717   6.700  43.066   7.666  -0.890  -0.839  C17   TBH  21  
TBH  C18   C18   C  0  1  N  N  N  20.156   5.248  42.890   8.552  -1.409  -1.974  C18   TBH  22  
TBH  C19   C19   C  0  1  N  N  N  19.392   4.330  41.973   9.855  -0.608  -2.011  C19   TBH  23  
TBH  O14   O14   O  0  1  N  N  N  21.639  11.231  41.077   3.584  -2.222   2.629  O14   TBH  24  
TBH  N10   N10   N  0  1  N  N  N  18.122  11.571  41.632   1.771  -0.411  -0.038  N10   TBH  25  
TBH  C12   C12   C  0  1  N  N  S  17.816  12.255  40.402   1.655   0.923   0.567  C12   TBH  26  
TBH  O20   O20   O  0  1  N  N  N  18.863  12.951  39.731   2.908   1.602   0.466  O20   TBH  27  
TBH  C21   C21   C  0  1  N  N  S  16.571  11.955  39.588   0.579   1.725  -0.169  C21   TBH  28  
TBH  N22   N22   N  0  1  N  N  N  16.310  13.214  38.932   0.546   3.096   0.356  N22   TBH  29  
TBH  C35   C35   C  0  1  N  N  S  15.561  14.257  39.595  -0.312   3.071   1.549  C35   TBH  30  
TBH  O36   O36   O  0  1  N  N  N  15.304  14.177  40.995   0.413   2.510   2.645  O36   TBH  31  
TBH  O37   O37   O  0  1  N  N  N  15.454  15.467  38.870  -0.713   4.403   1.874  O37   TBH  32  
TBH  C38   C38   C  0  1  N  N  N  14.862  16.592  39.515  -1.968   4.302   2.551  C38   TBH  33  
TBH  C40   C40   C  0  1  N  N  N  13.479  16.245  40.071  -1.820   3.383   3.766  C40   TBH  34  
TBH  C39   C39   C  0  1  N  N  N  15.775  17.114  40.615  -2.411   5.692   3.014  C39   TBH  35  
TBH  C41   C41   C  0  1  N  N  N  14.759  17.636  38.407  -3.016   3.724   1.599  C41   TBH  36  
TBH  C28   C28   C  0  1  N  N  N  16.865  10.932  38.513   0.902   1.758  -1.664  C28   TBH  37  
TBH  C29   C29   C  0  1  Y  N  N  15.597  10.369  37.925  -0.196   2.484  -2.398  C29   TBH  38  
TBH  C30   C30   C  0  1  Y  N  N  14.808   9.509  38.674  -0.066   3.831  -2.679  C30   TBH  39  
TBH  C31   C31   C  0  1  Y  N  N  13.669   8.982  38.107  -1.073   4.497  -3.353  C31   TBH  40  
TBH  C32   C32   C  0  1  Y  N  N  13.282   9.297  36.822  -2.210   3.815  -3.745  C32   TBH  41  
TBH  C33   C33   C  0  1  Y  N  N  14.064  10.156  36.081  -2.339   2.468  -3.465  C33   TBH  42  
TBH  C34   C34   C  0  1  Y  N  N  15.235  10.672  36.627  -1.330   1.801  -2.796  C34   TBH  43  
TBH  H421  1H42  H  0  0  N  N  N  24.292  15.236  45.870  -3.373  -3.860   4.097  H421  TBH  44  
TBH  H51   1H5   H  0  1  N  N  N  21.195  13.380  43.765  -0.495  -3.288   2.332  H51   TBH  45  
TBH  H231  1H23  H  0  0  N  N  N  25.343  10.771  46.145  -3.728  -1.404  -2.029  H231  TBH  46  
TBH  H232  2H23  H  0  0  N  N  N  24.321   9.799  47.298  -3.650  -3.128  -2.466  H232  TBH  47  
TBH  H261  1H26  H  0  0  N  N  N  26.460  11.632  49.708  -6.941  -2.047  -3.699  H261  TBH  48  
TBH  H21   1H2   H  0  1  N  N  N  22.128   9.770  47.065  -2.126  -2.206  -2.203  H21   TBH  49  
TBH  H31   1H3   H  0  1  N  N  N  20.207   9.638  45.517   0.283  -2.218  -1.721  H31   TBH  50  
TBH  H71   1H7   H  0  1  N  N  N  18.786  12.237  44.094   2.057  -3.033  -0.287  H71   TBH  51  
TBH  H72   2H7   H  0  1  N  N  N  19.129  10.397  43.614   1.732  -3.477   1.406  H72   TBH  52  
TBH  H81   1H8   H  0  1  N  N  N  19.658  12.950  42.114   1.349  -1.048   1.919  H81   TBH  53  
TBH  H111  1H11  H  0  0  N  N  N  20.314  10.989  40.458   3.765  -0.385   1.702  H111  TBH  54  
TBH  H131  1H13  H  0  0  N  N  N  19.911   9.514  42.854   3.730  -1.726  -0.483  H131  TBH  55  
TBH  H151  1H15  H  0  0  N  N  N  21.490   8.723  41.057   6.001  -1.285   1.283  H151  TBH  56  
TBH  H152  2H15  H  0  0  N  N  N  19.876   7.896  40.807   5.252  -0.119   0.165  H152  TBH  57  
TBH  H161  1H16  H  0  0  N  N  N  20.986   8.313  43.383   5.840  -1.578  -1.751  H161  TBH  58  
TBH  H162  2H16  H  0  0  N  N  N  21.629   6.978  42.223   6.589  -2.744  -0.634  H162  TBH  59  
TBH  H171  1H17  H  0  0  N  N  N  18.788   6.872  42.503   8.189  -1.003   0.111  H171  TBH  60  
TBH  H172  2H17  H  0  0  N  N  N  19.544   6.903  44.133   7.441   0.163  -1.007  H172  TBH  61  
TBH  H181  1H18  H  0  0  N  N  N  19.995   4.809  43.886   8.029  -1.296  -2.923  H181  TBH  62  
TBH  H182  2H18  H  0  0  N  N  N  21.182   5.287  42.495   8.777  -2.462  -1.806  H182  TBH  63  
TBH  H191  1H19  H  0  0  N  N  N  18.432   4.063  42.439   9.629   0.445  -2.179  H191  TBH  64  
TBH  H192  2H19  H  0  0  N  N  N  19.980   3.418  41.795  10.378  -0.720  -1.062  H192  TBH  65  
TBH  H193  3H19  H  0  0  N  N  N  19.206   4.839  41.016  10.486  -0.977  -2.820  H193  TBH  66  
TBH  H141  1H14  H  0  0  N  N  N  21.620  11.308  40.130   3.275  -3.105   2.385  H141  TBH  67  
TBH  H101  1H10  H  0  0  N  N  N  18.110  10.590  41.441   2.630  -0.415  -0.568  H101  TBH  68  
TBH  H121  1H12  H  0  0  N  N  N  17.302  13.003  41.024   1.380   0.823   1.617  H121  TBH  69  
TBH  H201  1H20  H  0  0  N  N  N  18.613  13.106  38.828   3.114   1.669  -0.477  H201  TBH  70  
TBH  H211  1H21  H  0  0  N  N  N  15.749  11.567  40.208  -0.392   1.254  -0.017  H211  TBH  71  
TBH  H221  1H22  H  0  0  N  N  N  17.207  13.608  38.732   1.480   3.307   0.675  H221  TBH  72  
TBH  H351  1H35  H  0  0  N  N  N  14.507  13.946  39.552  -1.194   2.464   1.348  H351  TBH  73  
TBH  H361  1H36  H  0  0  N  N  N  16.128  14.159  41.468   1.140   3.118   2.839  H361  TBH  74  
TBH  H401  1H40  H  0  0  N  N  N  13.144  15.287  39.647  -0.978   3.717   4.373  H401  TBH  75  
TBH  H402  2H40  H  0  0  N  N  N  12.765  17.037  39.799  -2.733   3.417   4.360  H402  TBH  76  
TBH  H403  3H40  H  0  0  N  N  N  13.534  16.162  41.166  -1.643   2.362   3.429  H403  TBH  77  
TBH  H391  1H39  H  0  0  N  N  N  15.793  16.396  41.448  -2.516   6.346   2.149  H391  TBH  78  
TBH  H392  2H39  H  0  0  N  N  N  15.399  18.083  40.974  -3.368   5.615   3.530  H392  TBH  79  
TBH  H393  3H39  H  0  0  N  N  N  16.793  17.240  40.218  -1.664   6.104   3.693  H393  TBH  80  
TBH  H411  1H41  H  0  0  N  N  N  13.838  17.468  37.830  -2.768   2.687   1.372  H411  TBH  81  
TBH  H412  2H41  H  0  0  N  N  N  15.630  17.551  37.741  -3.998   3.768   2.069  H412  TBH  82  
TBH  H413  3H41  H  0  0  N  N  N  14.734  18.642  38.851  -3.029   4.304   0.676  H413  TBH  83  
TBH  H281  1H28  H  0  0  N  N  N  17.433  10.106  38.967   1.848   2.277  -1.820  H281  TBH  84  
TBH  H282  2H28  H  0  0  N  N  N  17.443  11.416  37.712   0.980   0.739  -2.042  H282  TBH  85  
TBH  H301  1H30  H  0  0  N  N  N  15.083   9.256  39.687   0.822   4.364  -2.372  H301  TBH  86  
TBH  H311  1H31  H  0  0  N  N  N  13.061   8.302  38.686  -0.972   5.550  -3.571  H311  TBH  87  
TBH  H321  1H32  H  0  0  N  N  N  12.380   8.877  36.403  -2.997   4.336  -4.271  H321  TBH  88  
TBH  H331  1H33  H  0  0  N  N  N  13.769  10.428  35.078  -3.228   1.935  -3.772  H331  TBH  89  
TBH  H341  1H34  H  0  0  N  N  N  15.866  11.315  36.031  -1.431   0.749  -2.577  H341  TBH  90  
#   #
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
TBH  O43  C27   DOUB  N  N   1  
TBH  C27  O42   SING  N  N   2  
TBH  C27  C6    SING  N  N   3  
TBH  O42  H421  SING  N  N   4  
TBH  C6   C5    DOUB  Y  N   5  
TBH  C6   C1    SING  Y  N   6  
TBH  C5   C4    SING  Y  N   7  
TBH  C5   H51   SING  N  N   8  
TBH  C1   O9    SING  N  N   9  
TBH  C1   C2    DOUB  Y  N  10  
TBH  O9   C23   SING  N  N  11  
TBH  C23  C24   SING  N  N  12  
TBH  C23  H231  SING  N  N  13  
TBH  C23  H232  SING  N  N  14  
TBH  C24  O25   DOUB  N  N  15  
TBH  C24  O26   SING  N  N  16  
TBH  O26  H261  SING  N  N  17  
TBH  C2   C3    SING  Y  N  18  
TBH  C2   H21   SING  N  N  19  
TBH  C3   C4    DOUB  Y  N  20  
TBH  C3   H31   SING  N  N  21  
TBH  C4   C7    SING  N  N  22  
TBH  C7   C8    SING  N  N  23  
TBH  C7   H71   SING  N  N  24  
TBH  C7   H72   SING  N  N  25  
TBH  C8   C11   SING  N  N  26  
TBH  C8   N10   SING  N  N  27  
TBH  C8   H81   SING  N  N  28  
TBH  C11  N13   SING  N  N  29  
TBH  C11  O14   SING  N  N  30  
TBH  C11  H111  SING  N  N  31  
TBH  N13  C15   SING  N  N  32  
TBH  N13  H131  SING  N  N  33  
TBH  C15  C16   SING  N  N  34  
TBH  C15  H151  SING  N  N  35  
TBH  C15  H152  SING  N  N  36  
TBH  C16  C17   SING  N  N  37  
TBH  C16  H161  SING  N  N  38  
TBH  C16  H162  SING  N  N  39  
TBH  C17  C18   SING  N  N  40  
TBH  C17  H171  SING  N  N  41  
TBH  C17  H172  SING  N  N  42  
TBH  C18  C19   SING  N  N  43  
TBH  C18  H181  SING  N  N  44  
TBH  C18  H182  SING  N  N  45  
TBH  C19  H191  SING  N  N  46  
TBH  C19  H192  SING  N  N  47  
TBH  C19  H193  SING  N  N  48  
TBH  O14  H141  SING  N  N  49  
TBH  N10  C12   SING  N  N  50  
TBH  N10  H101  SING  N  N  51  
TBH  C12  O20   SING  N  N  52  
TBH  C12  C21   SING  N  N  53  
TBH  C12  H121  SING  N  N  54  
TBH  O20  H201  SING  N  N  55  
TBH  C21  N22   SING  N  N  56  
TBH  C21  C28   SING  N  N  57  
TBH  C21  H211  SING  N  N  58  
TBH  N22  C35   SING  N  N  59  
TBH  N22  H221  SING  N  N  60  
TBH  C35  O36   SING  N  N  61  
TBH  C35  O37   SING  N  N  62  
TBH  C35  H351  SING  N  N  63  
TBH  O36  H361  SING  N  N  64  
TBH  O37  C38   SING  N  N  65  
TBH  C38  C40   SING  N  N  66  
TBH  C38  C39   SING  N  N  67  
TBH  C38  C41   SING  N  N  68  
TBH  C40  H401  SING  N  N  69  
TBH  C40  H402  SING  N  N  70  
TBH  C40  H403  SING  N  N  71  
TBH  C39  H391  SING  N  N  72  
TBH  C39  H392  SING  N  N  73  
TBH  C39  H393  SING  N  N  74  
TBH  C41  H411  SING  N  N  75  
TBH  C41  H412  SING  N  N  76  
TBH  C41  H413  SING  N  N  77  
TBH  C28  C29   SING  N  N  78  
TBH  C28  H281  SING  N  N  79  
TBH  C28  H282  SING  N  N  80  
TBH  C29  C30   DOUB  Y  N  81  
TBH  C29  C34   SING  Y  N  82  
TBH  C30  C31   SING  Y  N  83  
TBH  C30  H301  SING  N  N  84  
TBH  C31  C32   DOUB  Y  N  85  
TBH  C31  H311  SING  N  N  86  
TBH  C32  C33   SING  Y  N  87  
TBH  C32  H321  SING  N  N  88  
TBH  C33  C34   DOUB  Y  N  89  
TBH  C33  H331  SING  N  N  90  
TBH  C34  H341  SING  N  N  91  
#   #
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
TBH  SMILES            ACDLabs               10.04  "O=C(O)c1cc(ccc1OCC(=O)O)CC(NC(O)C(NC(O)OC(C)(C)C)Cc2ccccc2)C(O)NCCCCC"  
TBH  SMILES_CANONICAL  CACTVS                3.341  "CCCCCN[C@H](O)[C@H](Cc1ccc(OCC(O)=O)c(c1)C(O)=O)N[C@@H](O)[C@H](Cc2ccccc2)N[C@@H](O)OC(C)(C)C"  
TBH  SMILES            CACTVS                3.341  "CCCCCN[CH](O)[CH](Cc1ccc(OCC(O)=O)c(c1)C(O)=O)N[CH](O)[CH](Cc2ccccc2)N[CH](O)OC(C)(C)C"  
TBH  SMILES_CANONICAL  "OpenEye OEToolkits"  1.5.0  "CCCCCN[C@@H]([C@H](Cc1ccc(c(c1)C(=O)O)OCC(=O)O)N[C@H]([C@H](Cc2ccccc2)N[C@@H](O)OC(C)(C)C)O)O"  
TBH  SMILES            "OpenEye OEToolkits"  1.5.0  "CCCCCNC(C(Cc1ccc(c(c1)C(=O)O)OCC(=O)O)NC(C(Cc2ccccc2)NC(O)OC(C)(C)C)O)O"  
TBH  InChI             InChI                 1.03   "InChI=1S/C31H47N3O9/c1-5-6-10-15-32-27(37)23(18-21-13-14-25(42-19-26(35)36)22(16-21)29(39)40)33-28(38)24(17-20-11-8-7-9-12-20)34-30(41)43-31(2,3)4/h7-9,11-14,16,23-24,27-28,30,32-34,37-38,41H,5-6,10,15,17-19H2,1-4H3,(H,35,36)(H,39,40)/t23-,24-,27+,28-,30-/m0/s1"  
TBH  InChIKey          InChI                 1.03   WVFJFYADATXBBE-JIFQQKSFSA-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
TBH  "SYSTEMATIC NAME"  ACDLabs               10.04  "5-[(2S,3R)-2-{[(1S,2S)-2-{[(S)-tert-butoxy(hydroxy)methyl]amino}-1-hydroxy-3-phenylpropyl]amino}-3-hydroxy-3-(pentylamino)propyl]-2-(carboxymethoxy)benzoic acid"  
TBH  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.5.0  "2-(carboxymethyloxy)-5-[(2S,3R)-3-hydroxy-2-[[(1S,2S)-1-hydroxy-2-[[(S)-hydroxy-[(2-methylpropan-2-yl)oxy]methyl]amino]-3-phenyl-propyl]amino]-3-(pentylamino)propyl]benzoic 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
TBH  "Create component"   2001-06-26  PDBJ  
TBH  "Modify descriptor"  2011-06-04  RCSB  
TBH  "Modify synonyms"    2021-03-01  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     TBH
_pdbx_chem_comp_synonyms.name        PNU177836
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
