data_IRK
# 
_chem_comp.id                                    IRK 
_chem_comp.name                                  "(1R,2S)-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]-2-{[N-({[(1R,2S)-2-propylcyclopropyl]methoxy}carbonyl)-L-leucyl]amino}propane-1-sulfonic acid" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H37 N3 O8 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2022-01-27 
_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                        491.599 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     IRK 
_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        7TQ8 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
_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 
IRK C02 C1  C 0 1 N N N N N N -21.450 23.096 2.452  -2.520  -0.163 -0.155 C02 IRK 1  
IRK C04 C2  C 0 1 N N S N N N -20.977 25.477 1.854  -0.181  -0.234 0.521  C04 IRK 2  
IRK C05 C3  C 0 1 N N N N N N -21.226 26.502 0.752  -0.016  -1.594 1.203  C05 IRK 3  
IRK C06 C4  C 0 1 N N N N N N -20.564 26.081 -0.587 -1.296  -1.941 1.966  C06 IRK 4  
IRK C07 C5  C 0 1 N N N N N N -19.018 26.183 -0.519 -1.179  -3.352 2.544  C07 IRK 5  
IRK C08 C6  C 0 1 N N N N N N -21.117 26.957 -1.732 -1.499  -0.939 3.104  C08 IRK 6  
IRK C09 C7  C 0 1 N N N N N N -21.556 25.988 3.166  1.121   0.163  -0.127 C09 IRK 7  
IRK C11 C8  C 0 1 N N S N N N -21.001 27.086 5.395  3.518   0.586  -0.019 C11 IRK 8  
IRK C12 C9  C 0 1 N N N N N N -20.274 26.284 6.496  3.836   -0.521 -1.025 C12 IRK 9  
IRK C13 C10 C 0 1 N N S N N N -20.761 24.743 6.587  3.996   -1.851 -0.286 C13 IRK 10 
IRK C14 C11 C 0 1 N N N N N N -20.184 24.111 7.507  4.302   -2.966 -1.262 C14 IRK 11 
IRK C16 C12 C 0 1 N N N N N N -22.637 23.651 7.577  5.771   -3.252 0.514  C16 IRK 12 
IRK C17 C13 C 0 1 N N N N N N -22.419 24.709 6.919  5.232   -1.810 0.641  C17 IRK 13 
IRK C19 C14 C 0 1 N N R N N N -20.635 28.560 5.491  3.445   1.931  -0.746 C19 IRK 14 
IRK C23 C15 C 0 1 N N N N N N -22.236 21.032 3.297  -4.852  -0.050 -0.651 C23 IRK 15 
IRK C24 C16 C 0 1 N N R N N N -23.264 19.885 3.072  -5.796  -0.171 -1.849 C24 IRK 16 
IRK C25 C17 C 0 1 N N N N N N -22.748 18.518 3.560  -6.603  1.068  -2.241 C25 IRK 17 
IRK C26 C18 C 0 1 N N R N N N -22.959 18.767 2.061  -7.300  -0.119 -1.572 C26 IRK 18 
IRK C27 C19 C 0 1 N N N N N N -21.692 18.913 1.186  -7.744  0.052  -0.118 C27 IRK 19 
IRK C28 C20 C 0 1 N N N N N N -22.041 19.611 -0.146 -9.269  -0.044 -0.036 C28 IRK 20 
IRK C29 C21 C 0 1 N N N N N N -23.052 18.787 -0.977 -9.714  0.126  1.418  C29 IRK 21 
IRK N03 N1  N 0 1 N N N N N N -21.623 24.227 1.545  -1.227  -0.324 -0.500 N03 IRK 22 
IRK N10 N2  N 0 1 N N N N N N -20.590 26.584 4.094  2.231   0.308  0.623  N10 IRK 23 
IRK N15 N3  N 0 1 N N N N N N -21.319 23.293 8.271  5.302   -3.731 -0.792 N15 IRK 24 
IRK O01 O1  O 0 1 N N N N N N -20.650 23.138 3.354  -2.818  0.057  1.003  O01 IRK 25 
IRK O18 O2  O 0 1 N N N N N N -19.029 24.046 7.769  3.728   -3.144 -2.316 O18 IRK 26 
IRK O20 O3  O 0 1 N N N N N N -21.345 29.275 4.505  4.694   2.193  -1.388 O20 IRK 27 
IRK O21 O4  O 0 1 N N N N N N -22.717 25.898 3.439  1.168   0.353  -1.324 O21 IRK 28 
IRK O22 O5  O 0 1 N N N N N N -22.284 21.973 2.236  -3.482  -0.239 -1.094 O22 IRK 29 
IRK H1  H1  H 0 1 N N N N N N -19.893 25.329 1.971  -0.460  0.513  1.264  H1  IRK 30 
IRK H2  H2  H 0 1 N N N N N N -20.810 27.471 1.066  0.176   -2.358 0.450  H2  IRK 31 
IRK H3  H3  H 0 1 N N N N N N -22.310 26.602 0.597  0.822   -1.552 1.900  H3  IRK 32 
IRK H4  H4  H 0 1 N N N N N N -20.832 25.034 -0.791 -2.147  -1.895 1.286  H4  IRK 33 
IRK H5  H5  H 0 1 N N N N N N -18.644 25.553 0.302  -0.328  -3.398 3.223  H5  IRK 34 
IRK H6  H6  H 0 1 N N N N N N -18.586 25.840 -1.471 -2.091  -3.599 3.087  H6  IRK 35 
IRK H7  H7  H 0 1 N N N N N N -18.727 27.229 -0.340 -1.035  -4.066 1.733  H7  IRK 36 
IRK H8  H8  H 0 1 N N N N N N -22.213 26.871 -1.763 -1.582  0.067  2.693  H8  IRK 37 
IRK H9  H9  H 0 1 N N N N N N -20.836 28.006 -1.559 -2.411  -1.186 3.648  H9  IRK 38 
IRK H10 H10 H 0 1 N N N N N N -20.695 26.618 -2.690 -0.648  -0.984 3.784  H10 IRK 39 
IRK H11 H11 H 0 1 N N N N N N -22.087 26.970 5.523  4.301   0.625  0.738  H11 IRK 40 
IRK H12 H12 H 0 1 N N N N N N -19.195 26.298 6.284  3.022   -0.602 -1.746 H12 IRK 41 
IRK H13 H13 H 0 1 N N N N N N -20.464 26.769 7.465  4.762   -0.282 -1.548 H13 IRK 42 
IRK H14 H14 H 0 1 N N N N N N -20.622 24.287 5.595  3.097   -2.079 0.286  H14 IRK 43 
IRK H15 H15 H 0 1 N N N N N N -23.426 23.824 8.324  6.860   -3.252 0.547  H15 IRK 44 
IRK H16 H16 H 0 1 N N N N N N -22.944 22.839 6.901  5.369   -3.878 1.311  H16 IRK 45 
IRK H17 H17 H 0 1 N N N N N N -22.705 25.590 7.512  5.965   -1.087 0.282  H17 IRK 46 
IRK H18 H18 H 0 1 N N N N N N -22.993 24.697 5.981  4.942   -1.591 1.669  H18 IRK 47 
IRK H19 H19 H 0 1 N N N N N N -19.920 28.969 6.220  2.652   1.897  -1.493 H19 IRK 48 
IRK H21 H21 H 0 1 N N N N N N -21.225 20.603 3.352  -4.956  0.939  -0.206 H21 IRK 49 
IRK H22 H22 H 0 1 N N N N N N -22.469 21.544 4.242  -5.103  -0.810 0.088  H22 IRK 50 
IRK H23 H23 H 0 1 N N N N N N -24.322 20.120 3.260  -5.455  -0.824 -2.653 H23 IRK 51 
IRK H24 H24 H 0 1 N N N N N N -23.420 17.839 4.105  -6.462  1.970  -1.645 H24 IRK 52 
IRK H25 H25 H 0 1 N N N N N N -21.729 18.427 3.964  -6.793  1.230  -3.302 H25 IRK 53 
IRK H26 H26 H 0 1 N N N N N N -23.824 18.274 1.594  -7.948  -0.737 -2.192 H26 IRK 54 
IRK H27 H27 H 0 1 N N N N N N -21.279 17.915 0.976  -7.298  -0.733 0.493  H27 IRK 55 
IRK H28 H28 H 0 1 N N N N N N -20.945 19.513 1.726  -7.421  1.026  0.249  H28 IRK 56 
IRK H29 H29 H 0 1 N N N N N N -21.119 19.741 -0.733 -9.716  0.741  -0.646 H29 IRK 57 
IRK H30 H30 H 0 1 N N N N N N -22.478 20.596 0.072  -9.592  -1.018 -0.403 H30 IRK 58 
IRK H31 H31 H 0 1 N N N N N N -23.274 19.316 -1.915 -10.800 0.058  1.476  H31 IRK 59 
IRK H32 H32 H 0 1 N N N N N N -22.621 17.801 -1.206 -9.267  -0.659 2.029  H32 IRK 60 
IRK H33 H33 H 0 1 N N N N N N -23.980 18.657 -0.401 -9.390  1.100  1.785  H33 IRK 61 
IRK H34 H34 H 0 1 N N N N N N -22.182 24.135 0.721  -0.990  -0.499 -1.424 H34 IRK 62 
IRK H35 H35 H 0 1 N N N N N N -19.628 26.647 3.827  2.178   0.228  1.589  H35 IRK 63 
IRK H36 H36 H 0 1 N N N N N N -21.196 22.673 9.046  5.668   -4.500 -1.256 H36 IRK 64 
IRK H37 H37 H 0 1 N N N N N N -21.121 30.197 4.559  4.946   1.528  -2.043 H37 IRK 65 
IRK S1  S1  S 0 1 N Y N N N N ?       ?      ?      3.092   3.247  0.451  S1  IRK 66 
IRK O2  O6  O 0 1 N Y N N N N ?       ?      ?      1.737   2.876  1.036  O2  IRK 67 
IRK O3  O7  O 0 1 N Y N N N N ?       ?      ?      3.983   3.168  1.556  O3  IRK 68 
IRK O1  O8  O 0 1 N Y N N N N ?       ?      ?      2.861   4.480  -0.217 O1  IRK 69 
IRK H20 H20 H 0 1 N Y N N N N ?       ?      ?      1.412   3.498  1.701  H20 IRK 70 
# 
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 
IRK C08 C06 SING N N 1  
IRK C29 C28 SING N N 2  
IRK C06 C07 SING N N 3  
IRK C06 C05 SING N N 4  
IRK C28 C27 SING N N 5  
IRK C05 C04 SING N N 6  
IRK C27 C26 SING N N 7  
IRK N03 C04 SING N N 8  
IRK N03 C02 SING N N 9  
IRK C04 C09 SING N N 10 
IRK C26 C24 SING N N 11 
IRK C26 C25 SING N N 12 
IRK O22 C02 SING N N 13 
IRK O22 C23 SING N N 14 
IRK C02 O01 DOUB N N 15 
IRK C24 C23 SING N N 16 
IRK C24 C25 SING N N 17 
IRK C09 O21 DOUB N N 18 
IRK C09 N10 SING N N 19 
IRK N10 C11 SING N N 20 
IRK O20 C19 SING N N 21 
IRK C11 C19 SING N N 22 
IRK C11 C12 SING N N 23 
IRK C12 C13 SING N N 24 
IRK C13 C17 SING N N 25 
IRK C13 C14 SING N N 26 
IRK C17 C16 SING N N 27 
IRK C14 O18 DOUB N N 28 
IRK C14 N15 SING N N 29 
IRK C16 N15 SING N N 30 
IRK C04 H1  SING N N 31 
IRK C05 H2  SING N N 32 
IRK C05 H3  SING N N 33 
IRK C06 H4  SING N N 34 
IRK C07 H5  SING N N 35 
IRK C07 H6  SING N N 36 
IRK C07 H7  SING N N 37 
IRK C08 H8  SING N N 38 
IRK C08 H9  SING N N 39 
IRK C08 H10 SING N N 40 
IRK C11 H11 SING N N 41 
IRK C12 H12 SING N N 42 
IRK C12 H13 SING N N 43 
IRK C13 H14 SING N N 44 
IRK C16 H15 SING N N 45 
IRK C16 H16 SING N N 46 
IRK C17 H17 SING N N 47 
IRK C17 H18 SING N N 48 
IRK C19 H19 SING N N 49 
IRK C23 H21 SING N N 50 
IRK C23 H22 SING N N 51 
IRK C24 H23 SING N N 52 
IRK C25 H24 SING N N 53 
IRK C25 H25 SING N N 54 
IRK C26 H26 SING N N 55 
IRK C27 H27 SING N N 56 
IRK C27 H28 SING N N 57 
IRK C28 H29 SING N N 58 
IRK C28 H30 SING N N 59 
IRK C29 H31 SING N N 60 
IRK C29 H32 SING N N 61 
IRK C29 H33 SING N N 62 
IRK N03 H34 SING N N 63 
IRK N10 H35 SING N N 64 
IRK N15 H36 SING N N 65 
IRK O20 H37 SING N N 66 
IRK C19 S1  SING N N 67 
IRK S1  O2  SING N N 68 
IRK S1  O3  DOUB N N 69 
IRK S1  O1  DOUB N N 70 
IRK O2  H20 SING N N 71 
# 
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 
IRK SMILES           ACDLabs              12.01 "CC(C)CC(NC(=O)OCC1CC1CCC)C(=O)NC(CC1CCNC1=O)C(O)S(=O)(=O)O"                                                                                                                                                              
IRK InChI            InChI                1.03  "InChI=1S/C21H37N3O8S/c1-4-5-13-9-15(13)11-32-21(28)24-16(8-12(2)3)19(26)23-17(20(27)33(29,30)31)10-14-6-7-22-18(14)25/h12-17,20,27H,4-11H2,1-3H3,(H,22,25)(H,23,26)(H,24,28)(H,29,30,31)/t13-,14-,15-,16-,17-,20+/m0/s1" 
IRK InChIKey         InChI                1.03  ZYXQADHLOGEXOL-CLTKYUOCSA-N                                                                                                                                                                                               
IRK SMILES_CANONICAL CACTVS               3.385 "CCC[C@H]1C[C@H]1COC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C[C@@H]2CCNC2=O)[C@H](O)[S](O)(=O)=O"                                                                                                                                 
IRK SMILES           CACTVS               3.385 "CCC[CH]1C[CH]1COC(=O)N[CH](CC(C)C)C(=O)N[CH](C[CH]2CCNC2=O)[CH](O)[S](O)(=O)=O"                                                                                                                                          
IRK SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "CCC[C@H]1C[C@H]1COC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C[C@@H]2CCNC2=O)C(O)S(=O)(=O)O"                                                                                                                                       
IRK SMILES           "OpenEye OEToolkits" 2.0.7 "CCCC1CC1COC(=O)NC(CC(C)C)C(=O)NC(CC2CCNC2=O)C(O)S(=O)(=O)O"                                                                                                                                                              
# 
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 
IRK "SYSTEMATIC NAME" ACDLabs              12.01 "(1R,2S)-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]-2-{[N-({[(1R,2S)-2-propylcyclopropyl]methoxy}carbonyl)-L-leucyl]amino}propane-1-sulfonic acid"                                         
IRK "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "(2~{S})-2-[[(2~{S})-4-methyl-2-[[(1~{R},2~{S})-2-propylcyclopropyl]methoxycarbonylamino]pentanoyl]amino]-1-oxidanyl-3-[(3~{S})-2-oxidanylidenepyrrolidin-3-yl]propane-1-sulfonic 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 
IRK "Create component" 2022-01-27 RCSB 
IRK "Initial release"  2022-03-02 RCSB 
IRK "Modify PCM"       2024-09-27 PDBE 
# 
_pdbx_chem_comp_pcm.pcm_id                             1 
_pdbx_chem_comp_pcm.comp_id                            IRK 
_pdbx_chem_comp_pcm.modified_residue_id                CYS 
_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               C19 
_pdbx_chem_comp_pcm.modified_residue_id_linking_atom   SG 
_pdbx_chem_comp_pcm.uniprot_specific_ptm_accession     ? 
_pdbx_chem_comp_pcm.uniprot_generic_ptm_accession      ? 
# 
