data_SKN
# 
_chem_comp.id                                    SKN 
_chem_comp.name                                  "((R)-2-(3-ethylphenyl)-1-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)ethyl)boronic acid" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H27 B N4 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "[(1~{R})-2-(3-ethylphenyl)-1-[[(2~{S})-3-phenyl-2-(pyrazin-2-ylcarbonylamino)propanoyl]amino]ethyl]boronic acid; [2-(3-ethylphenyl)-1-[(2S)-3-phenyl-2-[(pyrazin-2-yl)formamido]propanamido]ethyl]boronic acid" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2020-11-23 
_chem_comp.pdbx_modified_date                    2024-09-27 
_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                        446.307 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     SKN 
_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        7B12 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBE 
_chem_comp.pdbx_pcm                              Y 
# 
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.pdbx_backbone_atom_flag 
_chem_comp_atom.pdbx_n_terminal_atom_flag 
_chem_comp_atom.pdbx_c_terminal_atom_flag 
_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 
SKN C1  C1  C 0 1 N N R N N N -14.077 17.748 -90.368 2.481  0.472  0.237  C1  SKN 1  
SKN O4  O1  O 0 1 N N N N N N -14.057 17.434 -87.696 2.985  2.730  1.403  O4  SKN 2  
SKN N6  N1  N 0 1 N N N N N N -14.138 19.205 -90.333 1.118  0.854  -0.140 N6  SKN 3  
SKN C7  C2  C 0 1 Y N N N N N -13.616 17.843 -92.891 4.831  0.349  -0.545 C7  SKN 4  
SKN C8  C3  C 0 1 Y N N N N N -14.958 18.014 -93.206 5.278  -0.938 -0.781 C8  SKN 5  
SKN C9  C4  C 0 1 Y N N N N N -15.368 18.305 -94.501 6.564  -1.298 -0.425 C9  SKN 6  
SKN C10 C5  C 0 1 Y N N N N N -14.405 18.419 -95.490 7.403  -0.372 0.168  C10 SKN 7  
SKN C11 C6  C 0 1 Y N N N N N -13.065 18.295 -95.183 6.956  0.914  0.403  C11 SKN 8  
SKN C12 C7  C 0 1 Y N N N N N -12.676 18.024 -93.889 5.671  1.276  0.042  C12 SKN 9  
SKN C13 C8  C 0 1 N N N N N N -15.125 19.793 -89.644 0.085  0.036  0.146  C13 SKN 10 
SKN C14 C9  C 0 1 N N S N N N -15.000 21.305 -89.471 -1.317 0.430  -0.242 C14 SKN 11 
SKN C19 C10 C 0 1 Y N N N N N -17.244 23.634 -91.430 -4.374 -1.825 -0.040 C19 SKN 12 
SKN C20 C11 C 0 1 Y N N N N N -14.057 21.037 -87.105 -3.039 2.202  -0.037 C20 SKN 13 
SKN C21 C12 C 0 1 Y N N N N N -12.702 21.187 -87.370 -3.137 3.026  -1.143 C21 SKN 14 
SKN C22 C13 C 0 1 Y N N N N N -11.750 20.627 -86.531 -4.377 3.450  -1.582 C22 SKN 15 
SKN C24 C14 C 0 1 Y N N N N N -13.472 19.756 -85.139 -5.423 2.223  0.189  C24 SKN 16 
SKN C27 C15 C 0 1 Y N N N N N -17.518 24.993 -91.400 -5.593 -1.979 -0.700 C27 SKN 17 
SKN C30 C16 C 0 1 Y N N N N N -19.394 23.237 -92.076 -4.905 -3.575 1.342  C30 SKN 18 
SKN C32 C17 C 0 1 N N N N N N -16.825 18.547 -94.815 7.051  -2.701 -0.681 C32 SKN 19 
SKN C33 C18 C 0 1 N N N N N N -17.090 19.523 -95.928 7.690  -2.773 -2.069 C33 SKN 20 
SKN B2  B1  B 0 1 N N N N N N -13.343 17.273 -89.014 2.934  1.313  1.483  B2  SKN 21 
SKN O3  O2  O 0 1 N N N N N N -11.961 17.820 -88.848 3.294  0.657  2.690  O3  SKN 22 
SKN C5  C19 C 0 1 N N N N N N -13.202 17.309 -91.541 3.428  0.742  -0.933 C5  SKN 23 
SKN O15 O3  O 0 1 N N N N N N -16.098 19.188 -89.188 0.284  -1.016 0.715  O15 SKN 24 
SKN N16 N2  N 0 1 N N N N N N -16.081 21.907 -90.222 -2.251 -0.618 0.176  N16 SKN 25 
SKN C17 C20 C 0 1 N N N N N N -15.099 21.689 -87.985 -1.686 1.746  0.445  C17 SKN 26 
SKN C18 C21 C 0 1 N N N N N N -15.978 23.109 -90.801 -3.429 -0.765 -0.463 C18 SKN 27 
SKN C23 C22 C 0 1 Y N N N N N -12.138 19.907 -85.420 -5.520 3.048  -0.916 C23 SKN 28 
SKN C25 C23 C 0 1 Y N N N N N -14.429 20.313 -85.975 -4.182 1.801  0.629  C25 SKN 29 
SKN O26 O4  O 0 1 N N N N N N -14.946 23.776 -90.774 -3.716 -0.028 -1.385 O26 SKN 30 
SKN N28 N3  N 0 1 Y N N N N N -18.743 25.472 -91.651 -6.432 -2.925 -0.319 N28 SKN 31 
SKN C29 C24 C 0 1 Y N N N N N -19.678 24.581 -91.980 -6.117 -3.725 0.684  C29 SKN 32 
SKN N31 N4  N 0 1 Y N N N N N -18.175 22.747 -91.807 -4.064 -2.629 0.973  N31 SKN 33 
SKN H1  H1  H 0 1 N N N N N N -15.077 17.294 -90.430 2.505  -0.589 0.487  H1  SKN 34 
SKN H2  H2  H 0 1 N N N N N N -13.504 17.112 -86.994 3.276  3.160  2.219  H2  SKN 35 
SKN H3  H3  H 0 1 N N N N N N -13.456 19.755 -90.815 0.958  1.696  -0.595 H3  SKN 36 
SKN H4  H4  H 0 1 N N N N N N -15.699 17.919 -92.427 4.623  -1.661 -1.243 H4  SKN 37 
SKN H5  H5  H 0 1 N N N N N N -14.705 18.607 -96.510 8.406  -0.655 0.449  H5  SKN 38 
SKN H6  H6  H 0 1 N N N N N N -12.321 18.410 -95.957 7.611  1.638  0.865  H6  SKN 39 
SKN H7  H7  H 0 1 N N N N N N -11.625 17.952 -93.652 5.322  2.282  0.226  H7  SKN 40 
SKN H8  H8  H 0 1 N N N N N N -14.028 21.637 -89.865 -1.373 0.556  -1.323 H8  SKN 41 
SKN H9  H9  H 0 1 N N N N N N -12.386 21.746 -88.239 -2.244 3.340  -1.663 H9  SKN 42 
SKN H10 H10 H 0 1 N N N N N N -10.700 20.755 -86.748 -4.454 4.094  -2.445 H10 SKN 43 
SKN H11 H11 H 0 1 N N N N N N -13.778 19.202 -84.264 -6.316 1.910  0.710  H11 SKN 44 
SKN H12 H12 H 0 1 N N N N N N -16.721 25.684 -91.168 -5.851 -1.324 -1.520 H12 SKN 45 
SKN H13 H13 H 0 1 N N N N N N -20.177 22.557 -92.377 -4.652 -4.231 2.162  H13 SKN 46 
SKN H14 H14 H 0 1 N N N N N N -17.310 18.930 -93.905 7.790  -2.973 0.073  H14 SKN 47 
SKN H15 H15 H 0 1 N N N N N N -17.277 17.584 -95.093 6.210  -3.393 -0.632 H15 SKN 48 
SKN H16 H16 H 0 1 N N N N N N -18.175 19.627 -96.075 8.042  -3.788 -2.255 H16 SKN 49 
SKN H17 H17 H 0 1 N N N N N N -16.660 20.502 -95.667 6.951  -2.502 -2.824 H17 SKN 50 
SKN H18 H18 H 0 1 N N N N N N -16.628 19.155 -96.856 8.531  -2.082 -2.119 H18 SKN 51 
SKN H19 H19 H 0 1 N N N N N N -11.590 17.502 -88.034 3.559  1.257  3.400  H19 SKN 52 
SKN H20 H20 H 0 1 N N N N N N -13.224 16.210 -91.589 3.114  0.158  -1.798 H20 SKN 53 
SKN H21 H21 H 0 1 N N N N N N -12.174 17.647 -91.343 3.404  1.803  -1.182 H21 SKN 54 
SKN H22 H22 H 0 1 N N N N N N -16.940 21.404 -90.312 -2.023 -1.207 0.912  H22 SKN 55 
SKN H23 H23 H 0 1 N N N N N N -14.986 22.780 -87.903 -1.717 1.596  1.525  H23 SKN 56 
SKN H24 H24 H 0 1 N N N N N N -16.093 21.394 -87.618 -0.940 2.503  0.205  H24 SKN 57 
SKN H25 H25 H 0 1 N N N N N N -11.394 19.464 -84.774 -6.489 3.379  -1.258 H25 SKN 58 
SKN H26 H26 H 0 1 N N N N N N -15.477 20.183 -85.746 -4.106 1.157  1.493  H26 SKN 59 
SKN H27 H27 H 0 1 N N N N N N -20.684 24.922 -92.176 -6.803 -4.501 0.990  H27 SKN 60 
# 
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 
SKN C33 C32 SING N N 1  
SKN C10 C11 DOUB Y N 2  
SKN C10 C9  SING Y N 3  
SKN C11 C12 SING Y N 4  
SKN C32 C9  SING N N 5  
SKN C9  C8  DOUB Y N 6  
SKN C12 C7  DOUB Y N 7  
SKN C8  C7  SING Y N 8  
SKN C7  C5  SING N N 9  
SKN C30 C29 DOUB Y N 10 
SKN C30 N31 SING Y N 11 
SKN C29 N28 SING Y N 12 
SKN N31 C19 DOUB Y N 13 
SKN N28 C27 DOUB Y N 14 
SKN C5  C1  SING N N 15 
SKN C19 C27 SING Y N 16 
SKN C19 C18 SING N N 17 
SKN C18 O26 DOUB N N 18 
SKN C18 N16 SING N N 19 
SKN C1  N6  SING N N 20 
SKN C1  B2  SING N N 21 
SKN N6  C13 SING N N 22 
SKN N16 C14 SING N N 23 
SKN C13 C14 SING N N 24 
SKN C13 O15 DOUB N N 25 
SKN C14 C17 SING N N 26 
SKN B2  O3  SING N N 27 
SKN B2  O4  SING N N 28 
SKN C17 C20 SING N N 29 
SKN C21 C20 DOUB Y N 30 
SKN C21 C22 SING Y N 31 
SKN C20 C25 SING Y N 32 
SKN C22 C23 DOUB Y N 33 
SKN C25 C24 DOUB Y N 34 
SKN C23 C24 SING Y N 35 
SKN C1  H1  SING N N 36 
SKN O4  H2  SING N N 37 
SKN N6  H3  SING N N 38 
SKN C8  H4  SING N N 39 
SKN C10 H5  SING N N 40 
SKN C11 H6  SING N N 41 
SKN C12 H7  SING N N 42 
SKN C14 H8  SING N N 43 
SKN C21 H9  SING N N 44 
SKN C22 H10 SING N N 45 
SKN C24 H11 SING N N 46 
SKN C27 H12 SING N N 47 
SKN C30 H13 SING N N 48 
SKN C32 H14 SING N N 49 
SKN C32 H15 SING N N 50 
SKN C33 H16 SING N N 51 
SKN C33 H17 SING N N 52 
SKN C33 H18 SING N N 53 
SKN O3  H19 SING N N 54 
SKN C5  H20 SING N N 55 
SKN C5  H21 SING N N 56 
SKN N16 H22 SING N N 57 
SKN C17 H23 SING N N 58 
SKN C17 H24 SING N N 59 
SKN C23 H25 SING N N 60 
SKN C25 H26 SING N N 61 
SKN C29 H27 SING N N 62 
# 
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 
SKN InChI            InChI                1.03  "InChI=1S/C24H27BN4O4/c1-2-17-9-6-10-19(13-17)15-22(25(32)33)29-23(30)20(14-18-7-4-3-5-8-18)28-24(31)21-16-26-11-12-27-21/h3-13,16,20,22,32-33H,2,14-15H2,1H3,(H,28,31)(H,29,30)/t20-,22-/m0/s1" 
SKN InChIKey         InChI                1.03  RQXXOBNVVACHIB-UNMCSNQZSA-N                                                                                                                                                                      
SKN SMILES_CANONICAL CACTVS               3.385 "CCc1cccc(C[C@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)c3cnccn3)B(O)O)c1"                                                                                                                                  
SKN SMILES           CACTVS               3.385 "CCc1cccc(C[CH](NC(=O)[CH](Cc2ccccc2)NC(=O)c3cnccn3)B(O)O)c1"                                                                                                                                    
SKN SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "B([C@H](Cc1cccc(c1)CC)NC(=O)[C@H](Cc2ccccc2)NC(=O)c3cnccn3)(O)O"                                                                                                                                
SKN SMILES           "OpenEye OEToolkits" 2.0.7 "B(C(Cc1cccc(c1)CC)NC(=O)C(Cc2ccccc2)NC(=O)c3cnccn3)(O)O"                                                                                                                                        
# 
_pdbx_chem_comp_identifier.comp_id           SKN 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   2.0.7 
_pdbx_chem_comp_identifier.identifier        "[(1~{R})-2-(3-ethylphenyl)-1-[[(2~{S})-3-phenyl-2-(pyrazin-2-ylcarbonylamino)propanoyl]amino]ethyl]boronic acid" 
# 
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 SKN "[(1~{R})-2-(3-ethylphenyl)-1-[[(2~{S})-3-phenyl-2-(pyrazin-2-ylcarbonylamino)propanoyl]amino]ethyl]boronic acid" PDB    ? 
2 SKN "[2-(3-ethylphenyl)-1-[(2S)-3-phenyl-2-[(pyrazin-2-yl)formamido]propanamido]ethyl]boronic acid"                   AUTHOR ? 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
SKN "Create component" 2020-11-23 PDBE 
SKN "Initial release"  2021-12-01 RCSB 
SKN "Modify PCM"       2024-09-27 PDBE 
# 
_pdbx_chem_comp_pcm.pcm_id                             1 
_pdbx_chem_comp_pcm.comp_id                            SKN 
_pdbx_chem_comp_pcm.modified_residue_id                THR 
_pdbx_chem_comp_pcm.type                               None 
_pdbx_chem_comp_pcm.category                           "Covalent chemical modification" 
_pdbx_chem_comp_pcm.position                           "Amino-acid side chain" 
_pdbx_chem_comp_pcm.polypeptide_position               "Any position" 
_pdbx_chem_comp_pcm.comp_id_linking_atom               B2 
_pdbx_chem_comp_pcm.modified_residue_id_linking_atom   OG1 
_pdbx_chem_comp_pcm.uniprot_specific_ptm_accession     ? 
_pdbx_chem_comp_pcm.uniprot_generic_ptm_accession      ? 
# 
