data_15U
#

_chem_comp.id                                   15U
_chem_comp.name                                 
;(2R,4R)-4-methyl-1-(N~2~-{[(3S)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonyl}-L-arginyl)piperidine-2-carboxylic
acid
;

_chem_comp.type                                 peptide-like
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C23 H36 N6 O5 S"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        S-argatroban
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2012-10-16
_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                       508.634
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    15U
_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       4HFP
_chem_comp.pdbx_subcomponent_list               "15Y ARG MCP"
_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
15U  S    S    S  0  1  N  N  N   2.627  13.756   0.106   0.930  -1.336  -2.070  S     15Y   1  
15U  O1   O1   O  0  1  N  N  N   1.796  12.587   0.188   1.964  -1.580  -1.126  O1    15Y   2  
15U  O2   O2   O  0  1  N  N  N   2.519  14.499   1.336   1.060  -1.622  -3.456  O2    15Y   3  
15U  C1   C1   C  0  1  N  N  N   2.859  12.535  -4.232   0.216  -2.450   2.069  C1    15Y   4  
15U  C2   C2   C  0  1  N  N  S   3.206  13.656  -5.211  -0.421  -3.814   2.359  C2    15Y   5  
15U  C3   C3   C  0  1  N  N  N   2.180  14.779  -5.095  -1.788  -3.852   1.672  C3    15Y   6  
15U  C4   C4   C  0  1  Y  N  N   2.018  15.182  -3.641  -1.655  -3.362   0.252  C4    15Y   7  
15U  C5   C5   C  0  1  Y  N  N   1.504  16.435  -3.308  -2.691  -3.627  -0.630  C5    15Y   8  
15U  C6   C6   C  0  1  Y  N  N   1.357  16.810  -1.970  -2.623  -3.197  -1.940  C6    15Y   9  
15U  C7   C7   C  0  1  Y  N  N   1.709  15.964  -0.914  -1.515  -2.494  -2.378  C7    15Y  10  
15U  C8   C8   C  0  1  Y  N  N   2.227  14.690  -1.137  -0.480  -2.230  -1.507  C8    15Y  11  
15U  C9   C9   C  0  1  Y  N  N   2.410  14.244  -2.548  -0.541  -2.666  -0.183  C9    15Y  12  
15U  C10  C10  C  0  1  N  N  N   3.304  13.130  -6.640  -0.596  -3.993   3.869  C10   15Y  13  
15U  N    N    N  0  1  N  N  N   2.910  13.024  -2.861   0.545  -2.380   0.643  N     15Y  14  
15U  N1   N1   N  0  1  N  N  N   4.146  13.289  -0.092   0.565   0.276  -1.958  N     ARG  15  
15U  CA   CA   C  0  1  N  N  S   5.221  14.265  -0.031   0.347   0.888  -0.645  CA    ARG  16  
15U  C    C    C  0  1  N  N  N   5.782  14.569  -1.402  -0.872   1.773  -0.700  C     ARG  17  
15U  O    O    O  0  1  N  N  N   5.719  13.709  -2.264  -1.255   2.212  -1.763  O     ARG  18  
15U  CB   CB   C  0  1  N  N  N   6.286  13.781   0.959   1.569   1.726  -0.263  CB    ARG  19  
15U  CG   CG   C  0  1  N  N  N   7.159  12.658   0.411   2.800   0.822  -0.175  CG    ARG  20  
15U  CD   CD   C  0  1  N  N  N   8.411  12.495   1.256   4.007   1.646   0.275  CD    ARG  21  
15U  NE   NE   N  0  1  N  N  N   8.707  11.093   1.473   5.186   0.781   0.359  NE    ARG  22  
15U  CZ   CZ   C  0  1  N  N  N   9.512  10.378   0.684   6.397   1.304   0.746  CZ    ARG  23  
15U  NH1  NH1  N  0  1  N  N  N   9.637   9.072   0.924   6.502   2.640   1.054  NH1   ARG  24  
15U  NH2  NH2  N  0  1  N  N  N  10.149  10.912  -0.274   7.446   0.534   0.821  NH2   ARG  25  
15U  N2   N2   N  0  1  N  N  N   6.333  15.765  -1.651  -1.536   2.076   0.433  N     MCP  26  
15U  C11  C11  C  0  1  N  N  R   6.421  16.796  -0.597  -2.800   2.823   0.383  C1    MCP  27  
15U  C21  C21  C  0  1  N  N  N   5.855  18.129  -1.110  -3.869   2.035   1.146  C2    MCP  28  
15U  C31  C31  C  0  1  N  N  R   6.396  18.520  -2.484  -3.368   1.742   2.562  C3    MCP  29  
15U  C41  C41  C  0  1  N  N  N   6.145  17.369  -3.452  -2.099   0.890   2.490  C4    MCP  30  
15U  C51  C51  C  0  1  N  N  N   6.918  16.153  -2.946  -1.013   1.660   1.742  C5    MCP  31  
15U  C61  C61  C  0  1  N  N  N   7.828  16.905  -0.060  -3.228   2.996  -1.052  C6    MCP  32  
15U  O11  O11  O  0  1  N  N  N   8.602  15.936  -0.216  -3.355   2.029  -1.765  O1    MCP  33  
15U  O21  O21  O  0  1  N  N  N   8.178  17.951   0.530  -3.468   4.224  -1.537  O2    MCP  34  
15U  C71  C71  C  0  1  N  N  N   5.805  19.833  -2.986  -3.057   3.060   3.275  C7    MCP  35  
15U  H1   H1   H  0  1  N  N  N   1.845  12.166  -4.448  -0.487  -1.656   2.322  H1    15Y  36  
15U  H2   H2   H  0  1  N  N  N   3.581  11.714  -4.351   1.125  -2.335   2.659  H2    15Y  37  
15U  H3   H3   H  0  1  N  N  N   4.189  14.062  -4.929   0.212  -4.609   1.965  H3    15Y  38  
15U  H4   H4   H  0  1  N  N  N   2.522  15.647  -5.678  -2.165  -4.875   1.670  H4    15Y  39  
15U  H5   H5   H  0  1  N  N  N   1.213  14.431  -5.487  -2.484  -3.211   2.213  H5    15Y  40  
15U  H6   H6   H  0  1  N  N  N   1.217  17.121  -4.091  -3.558  -4.174  -0.290  H6    15Y  41  
15U  H7   H7   H  0  1  N  N  N   0.958  17.788  -1.744  -3.434  -3.408  -2.622  H7    15Y  42  
15U  H8   H8   H  0  1  N  N  N   1.576  16.307   0.101  -1.461  -2.155  -3.402  H8    15Y  43  
15U  H9   H9   H  0  1  N  N  N   4.051  12.324  -6.684  -1.074  -4.952   4.069  H9    15Y  44  
15U  H10  H10  H  0  1  N  N  N   2.325  12.740  -6.955   0.380  -3.965   4.353  H10   15Y  45  
15U  H11  H11  H  0  1  N  N  N   3.606  13.947  -7.311  -1.219  -3.188   4.260  H11   15Y  46  
15U  H12  H12  H  0  1  N  N  N   2.416  12.359  -2.301   0.952  -1.487   0.410  H12   15Y  47  
15U  H13  H13  H  0  1  N  N  N   4.200  12.856  -0.992   0.496   0.815  -2.762  H     ARG  48  
15U  H14  H14  H  0  1  N  N  N   4.809  15.203   0.370   0.195   0.106   0.099  HA    ARG  49  
15U  H15  H15  H  0  1  N  N  N   6.934  14.632   1.217   1.734   2.493  -1.020  HB2   ARG  50  
15U  H16  H16  H  0  1  N  N  N   5.780  13.418   1.865   1.396   2.200   0.703  HB3   ARG  51  
15U  H17  H17  H  0  1  N  N  N   6.589  11.717   0.424   2.615   0.025   0.545  HG2   ARG  52  
15U  H18  H18  H  0  1  N  N  N   7.449  12.897  -0.623   3.002   0.386  -1.154  HG3   ARG  53  
15U  H19  H19  H  0  1  N  N  N   9.259  12.967   0.738   4.192   2.443  -0.446  HD2   ARG  54  
15U  H20  H20  H  0  1  N  N  N   8.256  12.985   2.228   3.806   2.082   1.253  HD3   ARG  55  
15U  H21  H21  H  0  1  N  N  N   8.285  10.636   2.256   5.112  -0.162   0.142  HE    ARG  56  
15U  H22  H22  H  0  1  N  N  N   9.134   8.652   1.680   5.721   3.213   0.998  HH11  ARG  57  
15U  H23  H23  H  0  1  N  N  N  10.233   8.513   0.348   7.356   3.009   1.327  HH12  ARG  58  
15U  H24  H24  H  0  1  N  N  N   9.967  11.893  -0.344   7.372  -0.409   0.604  HH21  ARG  59  
15U  H26  H26  H  0  1  N  N  N   5.779  16.475   0.236  -2.665   3.801   0.844  H1    MCP  60  
15U  H27  H27  H  0  1  N  N  N   6.117  18.920  -0.392  -4.786   2.622   1.199  H21   MCP  61  
15U  H28  H28  H  0  1  N  N  N   4.760  18.042  -1.176  -4.068   1.096   0.629  H22   MCP  62  
15U  H29  H29  H  0  1  N  N  N   7.484  18.653  -2.392  -4.137   1.203   3.115  H3    MCP  63  
15U  H30  H30  H  0  1  N  N  N   6.496  17.643  -4.458  -1.754   0.661   3.498  H41   MCP  64  
15U  H31  H31  H  0  1  N  N  N   5.070  17.139  -3.489  -2.318  -0.037   1.961  H42   MCP  65  
15U  H32  H32  H  0  1  N  N  N   6.826  15.324  -3.663  -0.141   1.020   1.602  H51   MCP  66  
15U  H33  H33  H  0  1  N  N  N   7.980  16.410  -2.817  -0.731   2.544   2.314  H52   MCP  67  
15U  H34  H34  H  0  1  N  N  N   9.081  17.868   0.814  -3.740   4.285  -2.463  HO2   MCP  68  
15U  H35  H35  H  0  1  N  N  N   6.011  20.631  -2.257  -3.960   3.667   3.327  H71   MCP  69  
15U  H36  H36  H  0  1  N  N  N   6.260  20.094  -3.953  -2.700   2.852   4.284  H72   MCP  70  
15U  H37  H37  H  0  1  N  N  N   4.718  19.722  -3.111  -2.288   3.600   2.721  H73   MCP  71  
#   #
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
15U  C10  C2   SING  N  N   1  
15U  C2   C3   SING  N  N   2  
15U  C2   C1   SING  N  N   3  
15U  C3   C4   SING  N  N   4  
15U  C1   N    SING  N  N   5  
15U  C4   C5   DOUB  Y  N   6  
15U  C4   C9   SING  Y  N   7  
15U  C41  C51  SING  N  N   8  
15U  C41  C31  SING  N  N   9  
15U  C5   C6   SING  Y  N  10  
15U  C71  C31  SING  N  N  11  
15U  C51  N2   SING  N  N  12  
15U  N    C9   SING  N  N  13  
15U  C9   C8   DOUB  Y  N  14  
15U  C31  C21  SING  N  N  15  
15U  O    C    DOUB  N  N  16  
15U  C6   C7   DOUB  Y  N  17  
15U  N2   C    SING  N  N  18  
15U  N2   C11  SING  N  N  19  
15U  C    CA   SING  N  N  20  
15U  C8   C7   SING  Y  N  21  
15U  C8   S    SING  N  N  22  
15U  C21  C11  SING  N  N  23  
15U  C11  C61  SING  N  N  24  
15U  NH2  CZ   DOUB  N  N  25  
15U  O11  C61  DOUB  N  N  26  
15U  N1   CA   SING  N  N  27  
15U  N1   S    SING  N  N  28  
15U  C61  O21  SING  N  N  29  
15U  CA   CB   SING  N  N  30  
15U  S    O1   DOUB  N  N  31  
15U  S    O2   DOUB  N  N  32  
15U  CG   CB   SING  N  N  33  
15U  CG   CD   SING  N  N  34  
15U  CZ   NH1  SING  N  N  35  
15U  CZ   NE   SING  N  N  36  
15U  CD   NE   SING  N  N  37  
15U  C1   H1   SING  N  N  38  
15U  C1   H2   SING  N  N  39  
15U  C2   H3   SING  N  N  40  
15U  C3   H4   SING  N  N  41  
15U  C3   H5   SING  N  N  42  
15U  C5   H6   SING  N  N  43  
15U  C6   H7   SING  N  N  44  
15U  C7   H8   SING  N  N  45  
15U  C10  H9   SING  N  N  46  
15U  C10  H10  SING  N  N  47  
15U  C10  H11  SING  N  N  48  
15U  N    H12  SING  N  N  49  
15U  N1   H13  SING  N  N  50  
15U  CA   H14  SING  N  N  51  
15U  CB   H15  SING  N  N  52  
15U  CB   H16  SING  N  N  53  
15U  CG   H17  SING  N  N  54  
15U  CG   H18  SING  N  N  55  
15U  CD   H19  SING  N  N  56  
15U  CD   H20  SING  N  N  57  
15U  NE   H21  SING  N  N  58  
15U  NH1  H22  SING  N  N  59  
15U  NH1  H23  SING  N  N  60  
15U  NH2  H24  SING  N  N  61  
15U  C11  H26  SING  N  N  62  
15U  C21  H27  SING  N  N  63  
15U  C21  H28  SING  N  N  64  
15U  C31  H29  SING  N  N  65  
15U  C41  H30  SING  N  N  66  
15U  C41  H31  SING  N  N  67  
15U  C51  H32  SING  N  N  68  
15U  C51  H33  SING  N  N  69  
15U  O21  H34  SING  N  N  70  
15U  C71  H35  SING  N  N  71  
15U  C71  H36  SING  N  N  72  
15U  C71  H37  SING  N  N  73  
#   #
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
15U  SMILES            ACDLabs               12.01  "O=C(N1C(C(=O)O)CC(C)CC1)C(NS(=O)(=O)c3cccc2c3NCC(C)C2)CCCNC(=[N@H])N"  
15U  InChI             InChI                 1.03   "InChI=1S/C23H36N6O5S/c1-14-8-10-29(18(12-14)22(31)32)21(30)17(6-4-9-26-23(24)25)28-35(33,34)19-7-3-5-16-11-15(2)13-27-20(16)19/h3,5,7,14-15,17-18,27-28H,4,6,8-13H2,1-2H3,(H,31,32)(H4,24,25,26)/t14-,15+,17+,18-/m1/s1"  
15U  InChIKey          InChI                 1.03   KXNPVXPOPUZYGB-MXSMSXNCSA-N  
15U  SMILES_CANONICAL  CACTVS                3.370  "C[C@@H]1CCN([C@H](C1)C(O)=O)C(=O)[C@H](CCCNC(N)=N)N[S](=O)(=O)c2cccc3C[C@H](C)CNc23"  
15U  SMILES            CACTVS                3.370  "C[CH]1CCN([CH](C1)C(O)=O)C(=O)[CH](CCCNC(N)=N)N[S](=O)(=O)c2cccc3C[CH](C)CNc23"  
15U  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.6  "[H]/N=C(\N)/NCCC[C@@H](C(=O)N1CC[C@H](C[C@@H]1C(=O)O)C)NS(=O)(=O)c2cccc3c2NC[C@H](C3)C"  
15U  SMILES            "OpenEye OEToolkits"  1.7.6  "CC1CCN(C(C1)C(=O)O)C(=O)C(CCCNC(=N)N)NS(=O)(=O)c2cccc3c2NCC(C3)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
15U  "SYSTEMATIC NAME"  ACDLabs               12.01  "(2R,4R)-4-methyl-1-(N~2~-{[(3S)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonyl}-L-arginyl)piperidine-2-carboxylic acid"  
15U  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.7.6  "(2R,4R)-1-[(2S)-5-carbamimidamido-2-[[(3S)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonylamino]pentanoyl]-4-methyl-piperidine-2-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
15U  "Create component"  2012-10-16  RCSB  
15U  "Initial release"   2013-03-13  RCSB  
15U  "Modify synonyms"   2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     15U
_pdbx_chem_comp_synonyms.name        S-argatroban
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
