data_S49
#

_chem_comp.id                                   S49
_chem_comp.name                                 "(2S)-N-[(4-carbamimidoylphenyl)methyl]-1-[(2R)-3-phenyl-2-[(phenylmethyl)sulfonylamino]propanoyl]pyrrolidine-2-carboxamide"
_chem_comp.type                                 peptide-like
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C29 H33 N5 O4 S"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        ?
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2015-03-23
_chem_comp.pdbx_modified_date                   2020-09-03
_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                       547.668
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    S49
_chem_comp.pdbx_model_coordinates_details       ?
_chem_comp.pdbx_model_coordinates_missing_flag  Y
_chem_comp.pdbx_ideal_coordinates_details       Corina
_chem_comp.pdbx_ideal_coordinates_missing_flag  N
_chem_comp.pdbx_model_coordinates_db_code       4UFD
_chem_comp.pdbx_subcomponent_list               "PMS PRO DPN 00S"
_chem_comp.pdbx_processing_site                 EBI
#   #
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
S49  C7    C7    C  0  1  N  N  N  14.935  -15.298  21.371    4.390  -1.000  -0.237  C     PMS   1  
S49  S8    S8    S  0  1  N  N  N  15.601  -16.601  22.194    3.171  -1.156   1.098  S     PMS   2  
S49  C4    C4    C  0  1  Y  N  N  13.931  -15.711  20.317    4.925  -2.364  -0.591  C1    PMS   3  
S49  C5    C5    C  0  1  Y  N  N  14.352  -16.110  19.050    4.299  -3.121  -1.563  C2    PMS   4  
S49  C6    C6    C  0  1  Y  N  N  13.413  -16.490  18.091    4.790  -4.372  -1.887  C3    PMS   5  
S49  C1    C1    C  0  1  Y  N  N  12.056  -16.465  18.396    5.907  -4.866  -1.239  C4    PMS   6  
S49  C2    C2    C  0  1  Y  N  N  11.638  -16.059  19.660    6.533  -4.108  -0.267  C5    PMS   7  
S49  C3    C3    C  0  1  Y  N  N  12.572  -15.678  20.619    6.045  -2.855   0.054  C6    PMS   8  
S49  O12   O12   O  0  1  N  N  N  16.482  -17.338  21.340    1.963  -1.721   0.607  O2S   PMS   9  
S49  O13   O13   O  0  1  N  N  N  14.524  -17.368  22.749    3.786  -1.654   2.278  O1S   PMS  10  
S49  N21   N21   N  0  1  N  N  N  18.584  -13.778  21.747   -0.196   1.933  -0.108  N     PRO  11  
S49  C22   C22   C  0  1  N  N  S  18.510  -12.458  21.115   -1.661   1.993  -0.005  CA    PRO  12  
S49  C26   C26   C  0  1  N  N  N  17.219  -12.276  20.371   -2.243   0.612  -0.166  C     PRO  13  
S49  O30   O30   O  0  1  N  N  N  16.746  -13.193  19.712   -1.511  -0.337  -0.348  O     PRO  14  
S49  C23   C23   C  0  1  N  N  N  19.663  -12.416  20.122   -2.162   2.909  -1.142  CB    PRO  15  
S49  C24   C24   C  0  1  N  N  N  20.504  -13.651  20.368   -0.998   2.861  -2.166  CG    PRO  16  
S49  C25   C25   C  0  1  N  N  N  19.660  -14.608  21.194    0.235   2.784  -1.232  CD    PRO  17  
S49  N9    N9    N  0  1  N  N  N  16.437  -16.037  23.448    2.768   0.405   1.474  N     DPN  18  
S49  C10   C10   C  0  1  N  N  R  17.764  -15.456  23.326    2.110   1.253   0.477  CA    DPN  19  
S49  C11   C11   C  0  1  N  N  N  17.692  -14.098  22.683    0.619   1.222   0.697  C     DPN  20  
S49  O31   O31   O  0  1  N  N  N  16.828  -13.307  23.051    0.153   0.558   1.598  O     DPN  21  
S49  C14   C14   C  0  1  N  N  N  18.353  -15.350  24.738    2.616   2.690   0.614  CB    DPN  22  
S49  C15   C15   C  0  1  Y  N  N  19.760  -14.783  24.763    4.081   2.742   0.263  CG    DPN  23  
S49  C16   C16   C  0  1  Y  N  N  19.974  -13.519  25.301    4.471   2.991  -1.040  CD1   DPN  24  
S49  C20   C20   C  0  1  Y  N  N  20.842  -15.510  24.266    5.035   2.547   1.245  CD2   DPN  25  
S49  C17   C17   C  0  1  Y  N  N  21.254  -12.980  25.335    5.814   3.044  -1.361  CE1   DPN  26  
S49  C19   C19   C  0  1  Y  N  N  22.125  -14.966  24.308    6.378   2.601   0.924  CE2   DPN  27  
S49  C18   C18   C  0  1  Y  N  N  22.338  -13.700  24.840    6.768   2.849  -0.379  CZ    DPN  28  
S49  N27   N27   N  0  1  N  N  N  16.610  -11.098  20.480   -3.577   0.432  -0.106  N23   00S  29  
S49  C28   C28   C  0  1  N  N  N  15.351  -10.770  19.829   -4.143  -0.910  -0.262  C16   00S  30  
S49  C29   C29   C  0  1  Y  N  N  14.245  -10.776  20.857   -5.645  -0.838  -0.156  C17   00S  31  
S49  C33   C33   C  0  1  Y  N  N  13.914   -9.619  21.546   -6.406  -0.636  -1.293  C22   00S  32  
S49  C34   C34   C  0  1  Y  N  N  12.902   -9.643  22.494   -7.782  -0.568  -1.202  C21   00S  33  
S49  C35   C35   C  0  1  Y  N  N  12.220  -10.815  22.765   -8.403  -0.704   0.039  C24   00S  34  
S49  C37   C37   C  0  1  N  N  N  11.128  -10.813  23.791   -9.879  -0.633   0.143  C27   00S  35  
S49  N39   N39   N  0  1  N  N  N  10.829   -9.731  24.374  -10.599  -0.443  -0.925  N35   00S  36  
S49  N38   N38   N  0  1  N  N  N  10.502  -11.884  24.071  -10.490  -0.769   1.370  N34   00S  37  
S49  C36   C36   C  0  1  Y  N  N  12.551  -11.975  22.075   -7.630  -0.909   1.181  C19   00S  38  
S49  C32   C32   C  0  1  Y  N  N  13.561  -11.950  21.127   -6.256  -0.980   1.077  C18   00S  39  
S49  H72C  H72C  H  0  0  N  N  N  15.747  -14.741  20.881    3.914  -0.558  -1.113  H2A   PMS  40  
S49  H71C  H71C  H  0  0  N  N  N  14.430  -14.646  22.099    5.209  -0.362   0.092  H1    PMS  41  
S49  H5    H5    H  0  1  N  N  N  15.405  -16.125  18.811    3.427  -2.736  -2.069  H2    PMS  42  
S49  H6    H6    H  0  1  N  N  N  13.740  -16.804  17.111    4.301  -4.964  -2.647  H3    PMS  43  
S49  H1    H1    H  0  1  N  N  N  11.329  -16.760  17.654    6.290  -5.843  -1.492  H4    PMS  44  
S49  H2    H2    H  0  1  N  N  N  10.585  -16.040  19.898    7.406  -4.493   0.239  H5    PMS  45  
S49  H3    H3    H  0  1  N  N  N  12.243  -15.357  21.596    6.536  -2.262   0.811  H6    PMS  46  
S49  H22   H22   H  0  1  N  N  N  18.632  -11.661  21.864   -1.949   2.407   0.961  HA    PRO  47  
S49  H231  H231  H  0  0  N  N  N  19.275  -12.422  19.093   -3.078   2.513  -1.581  HB2   PRO  48  
S49  H232  H232  H  0  0  N  N  N  20.266  -11.510  20.282   -2.315   3.925  -0.779  HB3   PRO  49  
S49  H241  H241  H  0  0  N  N  N  20.777  -14.119  19.411   -1.067   1.973  -2.795  HG2   PRO  50  
S49  H242  H242  H  0  0  N  N  N  21.418  -13.382  20.918   -0.973   3.766  -2.772  HG3   PRO  51  
S49  H251  H251  H  0  0  N  N  N  20.259  -15.054  22.002    0.503   3.778  -0.874  HD2   PRO  52  
S49  H252  H252  H  0  0  N  N  N  19.247  -15.406  20.560    1.078   2.328  -1.752  HD3   PRO  53  
S49  H9    H9    H  0  1  N  N  N  15.865  -15.329  23.863    2.968   0.759   2.355  H     DPN  54  
S49  H10   H10   H  0  1  N  N  N  18.407  -16.111  22.720    2.337   0.881  -0.522  HA    DPN  55  
S49  H141  H141  H  0  0  N  N  N  18.374  -16.356  25.183    2.057   3.338  -0.061  HB2   DPN  56  
S49  H142  H142  H  0  0  N  N  N  17.703  -14.697  25.339    2.477   3.028   1.641  HB3   DPN  57  
S49  H16   H16   H  0  1  N  N  N  19.142  -12.954  25.694    3.726   3.143  -1.807  HD1   DPN  58  
S49  H20   H20   H  0  1  N  N  N  20.686  -16.494  23.849    4.730   2.353   2.262  HD2   DPN  59  
S49  H17   H17   H  0  1  N  N  N  21.409  -11.995  25.749    6.119   3.238  -2.379  HE1   DPN  60  
S49  H19   H19   H  0  1  N  N  N  22.960  -15.533  23.924    7.123   2.448   1.690  HE2   DPN  61  
S49  H18   H18   H  0  1  N  N  N  23.332  -13.280  24.869    7.817   2.891  -0.630  HZ    DPN  62  
S49  H27   H27   H  0  1  N  N  N  17.044  -10.395  21.044   -4.163   1.191   0.040  HN23  00S  63  
S49  H281  H281  H  0  0  N  N  N  15.422   -9.772  19.371   -3.867  -1.310  -1.237  H16   00S  64  
S49  H282  H282  H  0  0  N  N  N  15.134  -11.516  19.050   -3.754  -1.561   0.521  H16A  00S  65  
S49  H33   H33   H  0  1  N  N  N  14.444   -8.700  21.345   -5.924  -0.530  -2.253  H22   00S  66  
S49  H34   H34   H  0  1  N  N  N  12.644   -8.739  23.025   -8.375  -0.409  -2.090  H21   00S  67  
S49  H39   H39   H  0  1  N  N  N  10.085   -9.853  25.031  -11.565  -0.396  -0.857  HN35  00S  68  
S49  H381  H381  H  0  0  N  N  N   9.771  -11.872  24.754   -9.954  -0.910   2.166  HN34  00S  69  
S49  H382  H382  H  0  0  N  N  N  10.740  -12.738  23.609  -11.457  -0.722   1.439  HN3A  00S  70  
S49  H36   H36   H  0  1  N  N  N  12.022  -12.894  22.277   -8.106  -1.015   2.145  H19   00S  71  
S49  H32   H32   H  0  1  N  N  N  13.817  -12.854  20.594   -5.656  -1.142   1.961  H18   00S  72  
#   #
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
S49  C7   S8    SING  N  N   1  
S49  C7   C4    SING  N  N   2  
S49  S8   O12   DOUB  N  N   3  
S49  S8   O13   DOUB  N  N   4  
S49  S8   N9    SING  N  N   5  
S49  C4   C5    SING  Y  N   6  
S49  C4   C3    DOUB  Y  N   7  
S49  C5   C6    DOUB  Y  N   8  
S49  C6   C1    SING  Y  N   9  
S49  C1   C2    DOUB  Y  N  10  
S49  C2   C3    SING  Y  N  11  
S49  C15  C16   SING  Y  N  12  
S49  C15  C20   DOUB  Y  N  13  
S49  C15  C14   SING  N  N  14  
S49  C16  C17   DOUB  Y  N  15  
S49  C17  C18   SING  Y  N  16  
S49  C18  C19   DOUB  Y  N  17  
S49  C19  C20   SING  Y  N  18  
S49  N9   C10   SING  N  N  19  
S49  C10  C14   SING  N  N  20  
S49  C10  C11   SING  N  N  21  
S49  C11  O31   DOUB  N  N  22  
S49  C11  N21   SING  N  N  23  
S49  N21  C22   SING  N  N  24  
S49  N21  C25   SING  N  N  25  
S49  C22  C26   SING  N  N  26  
S49  C22  C23   SING  N  N  27  
S49  C26  O30   DOUB  N  N  28  
S49  C26  N27   SING  N  N  29  
S49  C23  C24   SING  N  N  30  
S49  C24  C25   SING  N  N  31  
S49  N27  C28   SING  N  N  32  
S49  C28  C29   SING  N  N  33  
S49  C29  C33   SING  Y  N  34  
S49  C29  C32   DOUB  Y  N  35  
S49  C33  C34   DOUB  Y  N  36  
S49  C34  C35   SING  Y  N  37  
S49  C35  C37   SING  N  N  38  
S49  C35  C36   DOUB  Y  N  39  
S49  C37  N38   SING  N  N  40  
S49  C37  N39   DOUB  N  N  41  
S49  C36  C32   SING  Y  N  42  
S49  C7   H71C  SING  N  N  43  
S49  C7   H72C  SING  N  N  44  
S49  N9   H9    SING  N  N  45  
S49  C5   H5    SING  N  N  46  
S49  C3   H3    SING  N  N  47  
S49  C6   H6    SING  N  N  48  
S49  C1   H1    SING  N  N  49  
S49  C2   H2    SING  N  N  50  
S49  C16  H16   SING  N  N  51  
S49  C20  H20   SING  N  N  52  
S49  C14  H141  SING  N  N  53  
S49  C14  H142  SING  N  N  54  
S49  C17  H17   SING  N  N  55  
S49  C18  H18   SING  N  N  56  
S49  C19  H19   SING  N  N  57  
S49  C10  H10   SING  N  N  58  
S49  C22  H22   SING  N  N  59  
S49  C25  H251  SING  N  N  60  
S49  C25  H252  SING  N  N  61  
S49  C23  H231  SING  N  N  62  
S49  C23  H232  SING  N  N  63  
S49  N27  H27   SING  N  N  64  
S49  C24  H241  SING  N  N  65  
S49  C24  H242  SING  N  N  66  
S49  C28  H281  SING  N  N  67  
S49  C28  H282  SING  N  N  68  
S49  C33  H33   SING  N  N  69  
S49  C32  H32   SING  N  N  70  
S49  C34  H34   SING  N  N  71  
S49  C36  H36   SING  N  N  72  
S49  N38  H381  SING  N  N  73  
S49  N38  H382  SING  N  N  74  
S49  N39  H39   SING  N  N  75  
#   #
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
S49  SMILES            ACDLabs               12.01  "C(S(=O)(=O)NC(Cc1ccccc1)C(N3C(C(=O)NCc2ccc(/C(N)=N)cc2)CCC3)=O)c4ccccc4"  
S49  InChI             InChI                 1.03   "InChI=1S/C29H33N5O4S/c30-27(31)24-15-13-22(14-16-24)19-32-28(35)26-12-7-17-34(26)29(36)25(18-21-8-3-1-4-9-21)33-39(37,38)20-23-10-5-2-6-11-23/h1-6,8-11,13-16,25-26,33H,7,12,17-20H2,(H3,30,31)(H,32,35)/t25-,26+/m1/s1"  
S49  InChIKey          InChI                 1.03   VAMQUIIDPUWWSK-FTJBHMTQSA-N  
S49  SMILES_CANONICAL  CACTVS                3.385  "NC(=N)c1ccc(CNC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc3ccccc3)N[S](=O)(=O)Cc4ccccc4)cc1"  
S49  SMILES            CACTVS                3.385  "NC(=N)c1ccc(CNC(=O)[CH]2CCCN2C(=O)[CH](Cc3ccccc3)N[S](=O)(=O)Cc4ccccc4)cc1"  
S49  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.6  "[H]/N=C(/c1ccc(cc1)CNC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc3ccccc3)NS(=O)(=O)Cc4ccccc4)\N"  
S49  SMILES            "OpenEye OEToolkits"  1.7.6  "c1ccc(cc1)CC(C(=O)N2CCCC2C(=O)NCc3ccc(cc3)C(=N)N)NS(=O)(=O)Cc4ccccc4"  
#   #
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
S49  "SYSTEMATIC NAME"  ACDLabs               12.01  "N-(benzylsulfonyl)-D-phenylalanyl-N-(4-carbamimidoylbenzyl)-L-prolinamide"  
S49  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.7.6  "(2S)-N-[(4-carbamimidoylphenyl)methyl]-1-[(2R)-3-phenyl-2-[(phenylmethyl)sulfonylamino]propanoyl]pyrrolidine-2-carboxamide"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
S49  "Create component"    2015-03-23  EBI   
S49  "Other modification"  2015-03-26  EBI   
S49  "Other modification"  2015-07-10  RCSB  
S49  "Initial release"     2015-07-15  RCSB  
S49  "Other modification"  2019-12-12  RCSB  
S49  "Other modification"  2020-09-03  RCSB  
##
