data_I6I
# 
_chem_comp.id                                    I6I 
_chem_comp.name                                  "N-{4-[4-(2-amino-4-oxo-1,4-dihydro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)butyl]-2-fluorobenzoyl}-D-gamma-glutamyl-L-gamma-glutamyl-D-glutamic acid" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C32 H38 F N7 O12" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2023-07-27 
_chem_comp.pdbx_modified_date                    2024-02-16 
_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                        731.682 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     I6I 
_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        8TLC 
_chem_comp.pdbx_subcomponent_list                ? 
_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.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 
I6I C02 C1  C 0 1 N N N N N N -39.106 63.609 3.618 -10.894 -0.393 -0.807 C02 I6I 1  
I6I C04 C2  C 0 1 N N N N N N -36.937 64.834 3.499 -8.678  0.223  -1.106 C04 I6I 2  
I6I C05 C3  C 0 1 Y N N N N N -37.643 64.580 7.128 -8.561  -2.476 1.248  C05 I6I 3  
I6I C06 C4  C 0 1 Y N N N N N -36.432 65.267 7.130 -7.238  -2.214 1.161  C06 I6I 4  
I6I C08 C5  C 0 1 Y N N N N N -36.907 64.912 5.032 -8.264  -0.779 -0.192 C08 I6I 5  
I6I C09 C6  C 0 1 Y N N N N N -37.940 64.357 5.772 -9.233  -1.580 0.400  C09 I6I 6  
I6I C12 C7  C 0 1 Y N N N N N -38.425 72.436 3.024 -0.041  4.114  0.258  C12 I6I 7  
I6I C14 C8  C 0 1 Y N N N N N -38.736 71.094 3.231 -0.122  3.127  1.242  C14 I6I 8  
I6I C15 C9  C 0 1 Y N N N N N -36.302 72.105 4.099 -2.426  4.001  -0.038 C15 I6I 9  
I6I C16 C10 C 0 1 Y N N N N N -37.823 70.255 3.868 -1.348  2.590  1.577  C16 I6I 10 
I6I C17 C11 C 0 1 N N N N N N -39.427 73.392 2.317 1.269   4.688  -0.110 C17 I6I 11 
I6I N19 N1  N 0 1 N N N N N N -40.667 73.802 3.006 2.389   4.261  0.505  N19 I6I 12 
I6I C20 C12 C 0 1 N N R N N N -41.605 74.719 2.323 3.689   4.831  0.141  C20 I6I 13 
I6I C21 C13 C 0 1 N N N N N N -41.789 75.989 3.198 4.796   3.826  0.465  C21 I6I 14 
I6I O24 O1  O 0 1 N N N N N N -41.577 78.738 2.910 6.550   1.857  0.751  O24 I6I 15 
I6I C26 C14 C 0 1 N N N N N N -42.927 74.005 2.067 3.918   6.099  0.922  C26 I6I 16 
I6I C29 C15 C 0 1 N N N N N N -34.796 66.133 5.502 -5.744  -0.610 -0.071 C29 I6I 17 
I6I C30 C16 C 0 1 N N N N N N -34.857 67.607 5.947 -5.465  0.610  0.809  C30 I6I 18 
I6I C31 C17 C 0 1 N N N N N N -36.010 68.414 5.311 -4.110  1.212  0.431  C31 I6I 19 
I6I C32 C18 C 0 1 N N N N N N -35.564 69.867 5.020 -3.831  2.432  1.311  C32 I6I 20 
I6I C33 C19 C 0 1 Y N N N N N -36.606 70.762 4.307 -2.497  3.025  0.939  C33 I6I 21 
I6I C34 C20 C 0 1 N N S N N N -39.346 80.487 2.803 6.845   -0.539 -0.449 C34 I6I 22 
I6I C13 C21 C 0 1 Y N N N N N -37.212 72.940 3.460 -1.204  4.549  -0.384 C13 I6I 23 
I6I C22 C22 C 0 1 N N N N N N -40.443 76.721 3.449 4.635   2.587  -0.419 C22 I6I 24 
I6I C23 C23 C 0 1 N N N N N N -40.526 78.230 3.132 5.726   1.597  -0.099 C23 I6I 25 
I6I C35 C24 C 0 1 N N N N N N -39.277 81.298 4.124 6.377   -1.949 -0.816 C35 I6I 26 
I6I C36 C25 C 0 1 N N N N N N -40.451 82.295 4.284 5.198   -2.343 0.075  C36 I6I 27 
I6I C37 C26 C 0 1 N N N N N N -40.750 82.594 5.779 4.738   -3.732 -0.286 C37 I6I 28 
I6I C40 C27 C 0 1 N N N N N N -38.207 80.837 1.850 8.081   -0.197 -1.240 C40 I6I 29 
I6I C43 C28 C 0 1 N N R N N N -42.931 83.793 5.166 3.257   -5.642 0.021  C43 I6I 30 
I6I C44 C29 C 0 1 N N N N N N -43.108 85.311 5.286 1.786   -5.810 0.409  C44 I6I 31 
I6I C45 C30 C 0 1 N N N N N N -43.848 85.915 4.079 0.926   -4.865 -0.433 C45 I6I 32 
I6I C46 C31 C 0 1 N N N N N N -44.709 87.126 4.458 -0.522  -5.030 -0.051 C46 I6I 33 
I6I C49 C32 C 0 1 N N N N N N -44.254 83.057 5.358 4.090   -6.657 0.760  C49 I6I 34 
I6I F24 F1  F 0 1 N N N N N N -36.913 74.262 3.259 -1.136  5.504  -1.337 F24 I6I 35 
I6I N01 N2  N 0 1 N N N N N N -39.077 63.685 5.083 -10.560 -1.371 0.077  N01 I6I 36 
I6I N03 N3  N 0 1 N N N N N N -38.031 64.188 2.838 -9.984  0.371  -1.373 N03 I6I 37 
I6I N07 N4  N 0 1 Y N N N N N -36.024 65.446 5.882 -7.041  -1.186 0.291  N07 I6I 38 
I6I N11 N5  N 0 1 N N N N N N -40.212 62.958 2.939 -12.213 -0.201 -1.122 N11 I6I 39 
I6I N25 N6  N 0 1 N N N N N N -39.286 79.039 3.107 5.785   0.424  -0.759 N25 I6I 40 
I6I N39 N7  N 0 1 N N N N N N -41.964 83.324 6.173 3.704   -4.292 0.372  N39 I6I 41 
I6I O10 O2  O 0 1 N N N N N N -36.066 65.301 2.852 -7.853  0.945  -1.644 O10 I6I 42 
I6I O18 O3  O 0 1 N N N N N N -39.193 73.801 1.228 1.337   5.547  -0.967 O18 I6I 43 
I6I O27 O4  O 0 1 N N N N N N -43.442 73.291 2.972 5.050   6.798  0.749  O27 I6I 44 
I6I O28 O5  O 0 1 N N N N N N -43.504 74.131 0.955 3.081   6.487  1.702  O28 I6I 45 
I6I O38 O6  O 0 1 N N N N N N -39.988 82.227 6.614 5.298   -4.345 -1.170 O38 I6I 46 
I6I O41 O7  O 0 1 N N N N N N -37.245 80.038 1.701 9.186   -0.948 -1.116 O41 I6I 47 
I6I O42 O8  O 0 1 N N N N N N -38.230 81.918 1.211 8.077   0.753  -1.987 O42 I6I 48 
I6I O47 O9  O 0 1 N N N N N N -45.950 87.106 4.236 -0.834  -5.821 0.808  O47 I6I 49 
I6I O48 O10 O 0 1 N N N N N N -44.181 88.140 4.991 -1.466  -4.298 -0.663 O48 I6I 50 
I6I O50 O11 O 0 1 N N N N N N -45.069 83.451 6.233 3.858   -7.968 0.592  O50 I6I 51 
I6I O51 O12 O 0 1 N N N N N N -44.532 82.055 4.644 4.968   -6.290 1.505  O51 I6I 52 
I6I H1  H1  H 0 1 N N N N N N -38.229 64.282 7.985 -9.020  -3.237 1.860  H1  I6I 53 
I6I H2  H2  H 0 1 N N N N N N -35.907 65.602 8.012 -6.461  -2.737 1.698  H2  I6I 54 
I6I H3  H3  H 0 1 N N N N N N -39.686 70.703 2.897 0.772   2.785  1.741  H3  I6I 55 
I6I H4  H4  H 0 1 N N N N N N -35.355 72.500 4.436 -3.326  4.335  -0.532 H4  I6I 56 
I6I H5  H5  H 0 1 N N N N N N -38.061 69.213 4.020 -1.411  1.827  2.339  H5  I6I 57 
I6I H6  H6  H 0 1 N N N N N N -40.870 73.463 3.925 2.336   3.575  1.190  H6  I6I 58 
I6I H7  H7  H 0 1 N N N N N N -41.176 75.024 1.357 3.701   5.054  -0.926 H7  I6I 59 
I6I H8  H8  H 0 1 N N N N N N -42.477 76.677 2.685 5.768   4.283  0.277  H8  I6I 60 
I6I H9  H9  H 0 1 N N N N N N -42.219 75.694 4.167 4.727   3.536  1.513  H9  I6I 61 
I6I H10 H10 H 0 1 N N N N N N -33.939 65.642 5.986 -5.760  -0.307 -1.118 H10 I6I 62 
I6I H11 H11 H 0 1 N N N N N N -34.676 66.087 4.410 -4.961  -1.354 0.080  H11 I6I 63 
I6I H12 H12 H 0 1 N N N N N N -33.907 68.089 5.674 -6.248  1.354  0.658  H12 I6I 64 
I6I H13 H13 H 0 1 N N N N N N -34.980 67.632 7.040 -5.449  0.307  1.856  H13 I6I 65 
I6I H14 H14 H 0 1 N N N N N N -36.864 68.430 6.004 -3.327  0.469  0.582  H14 I6I 66 
I6I H15 H15 H 0 1 N N N N N N -36.311 67.933 4.369 -4.126  1.515  -0.616 H15 I6I 67 
I6I H16 H16 H 0 1 N N N N N N -34.666 69.824 4.386 -4.614  3.176  1.160  H16 I6I 68 
I6I H17 H17 H 0 1 N N N N N N -35.312 70.341 5.980 -3.815  2.129  2.358  H17 I6I 69 
I6I H18 H18 H 0 1 N N N N N N -40.301 80.714 2.307 7.072   -0.497 0.616  H18 I6I 70 
I6I H19 H19 H 0 1 N N N N N N -39.670 76.268 2.811 3.663   2.131  -0.231 H19 I6I 71 
I6I H20 H20 H 0 1 N N N N N N -40.165 76.597 4.506 4.703   2.878  -1.467 H20 I6I 72 
I6I H21 H21 H 0 1 N N N N N N -39.297 80.594 4.969 6.065   -1.967 -1.860 H21 I6I 73 
I6I H22 H22 H 0 1 N N N N N N -38.333 81.863 4.140 7.196   -2.653 -0.669 H22 I6I 74 
I6I H23 H23 H 0 1 N N N N N N -40.191 83.236 3.777 5.510   -2.325 1.120  H23 I6I 75 
I6I H24 H24 H 0 1 N N N N N N -41.350 81.864 3.820 4.379   -1.639 -0.072 H24 I6I 76 
I6I H25 H25 H 0 1 N N N N N N -42.547 83.565 4.161 3.368   -5.794 -1.053 H25 I6I 77 
I6I H26 H26 H 0 1 N N N N N N -42.114 85.777 5.360 1.478   -6.839 0.230  H26 I6I 78 
I6I H27 H27 H 0 1 N N N N N N -43.684 85.528 6.198 1.660   -5.571 1.465  H27 I6I 79 
I6I H28 H28 H 0 1 N N N N N N -44.499 85.143 3.643 1.234   -3.836 -0.254 H28 I6I 80 
I6I H29 H29 H 0 1 N N N N N N -43.104 86.232 3.333 1.052   -5.104 -1.489 H29 I6I 81 
I6I H30 H30 H 0 1 N N N N N N -39.821 63.286 5.619 -11.251 -1.919 0.480  H30 I6I 82 
I6I H31 H31 H 0 1 N N N N N N -40.228 62.912 1.940 -12.895 -0.759 -0.715 H31 I6I 83 
I6I H32 H32 H 0 1 N N N N N N -40.958 62.556 3.470 -12.466 0.492  -1.751 H32 I6I 84 
I6I H33 H33 H 0 1 N N N N N N -38.405 78.606 3.296 5.125   0.216  -1.439 H33 I6I 85 
I6I H34 H34 H 0 1 N N N N N N -42.136 83.505 7.141 3.257   -3.802 1.079  H34 I6I 86 
I6I H35 H35 H 0 1 N N N N N N -44.259 72.921 2.658 5.152   7.605  1.272  H35 I6I 87 
I6I H36 H36 H 0 1 N N N N N N -36.627 80.399 1.076 9.954   -0.690 -1.643 H36 I6I 88 
I6I H37 H37 H 0 1 N N N N N N -44.850 88.793 5.161 -2.381  -4.439 -0.384 H37 I6I 89 
I6I H38 H38 H 0 1 N N N N N N -45.836 82.891 6.227 4.418   -8.580 1.088  H38 I6I 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 
I6I O28 C26 DOUB N N 1  
I6I O42 C40 DOUB N N 2  
I6I O18 C17 DOUB N N 3  
I6I O41 C40 SING N N 4  
I6I C40 C34 SING N N 5  
I6I C26 C20 SING N N 6  
I6I C26 O27 SING N N 7  
I6I C17 N19 SING N N 8  
I6I C17 C12 SING N N 9  
I6I C20 N19 SING N N 10 
I6I C20 C21 SING N N 11 
I6I C34 N25 SING N N 12 
I6I C34 C35 SING N N 13 
I6I N03 C04 SING N N 14 
I6I N03 C02 DOUB N N 15 
I6I O10 C04 DOUB N N 16 
I6I O24 C23 DOUB N N 17 
I6I N11 C02 SING N N 18 
I6I C12 C14 DOUB Y N 19 
I6I C12 C13 SING Y N 20 
I6I N25 C23 SING N N 21 
I6I C23 C22 SING N N 22 
I6I C21 C22 SING N N 23 
I6I C14 C16 SING Y N 24 
I6I F24 C13 SING N N 25 
I6I C13 C15 DOUB Y N 26 
I6I C04 C08 SING N N 27 
I6I C02 N01 SING N N 28 
I6I C16 C33 DOUB Y N 29 
I6I C45 C46 SING N N 30 
I6I C45 C44 SING N N 31 
I6I C15 C33 SING Y N 32 
I6I C35 C36 SING N N 33 
I6I O47 C46 DOUB N N 34 
I6I C36 C37 SING N N 35 
I6I C33 C32 SING N N 36 
I6I C46 O48 SING N N 37 
I6I O51 C49 DOUB N N 38 
I6I C32 C31 SING N N 39 
I6I C08 C09 DOUB Y N 40 
I6I C08 N07 SING Y N 41 
I6I N01 C09 SING N N 42 
I6I C43 C44 SING N N 43 
I6I C43 C49 SING N N 44 
I6I C43 N39 SING N N 45 
I6I C31 C30 SING N N 46 
I6I C49 O50 SING N N 47 
I6I C29 N07 SING N N 48 
I6I C29 C30 SING N N 49 
I6I C09 C05 SING Y N 50 
I6I C37 N39 SING N N 51 
I6I C37 O38 DOUB N N 52 
I6I N07 C06 SING Y N 53 
I6I C05 C06 DOUB Y N 54 
I6I C05 H1  SING N N 55 
I6I C06 H2  SING N N 56 
I6I C14 H3  SING N N 57 
I6I C15 H4  SING N N 58 
I6I C16 H5  SING N N 59 
I6I N19 H6  SING N N 60 
I6I C20 H7  SING N N 61 
I6I C21 H8  SING N N 62 
I6I C21 H9  SING N N 63 
I6I C29 H10 SING N N 64 
I6I C29 H11 SING N N 65 
I6I C30 H12 SING N N 66 
I6I C30 H13 SING N N 67 
I6I C31 H14 SING N N 68 
I6I C31 H15 SING N N 69 
I6I C32 H16 SING N N 70 
I6I C32 H17 SING N N 71 
I6I C34 H18 SING N N 72 
I6I C22 H19 SING N N 73 
I6I C22 H20 SING N N 74 
I6I C35 H21 SING N N 75 
I6I C35 H22 SING N N 76 
I6I C36 H23 SING N N 77 
I6I C36 H24 SING N N 78 
I6I C43 H25 SING N N 79 
I6I C44 H26 SING N N 80 
I6I C44 H27 SING N N 81 
I6I C45 H28 SING N N 82 
I6I C45 H29 SING N N 83 
I6I N01 H30 SING N N 84 
I6I N11 H31 SING N N 85 
I6I N11 H32 SING N N 86 
I6I N25 H33 SING N N 87 
I6I N39 H34 SING N N 88 
I6I O27 H35 SING N N 89 
I6I O41 H36 SING N N 90 
I6I O48 H37 SING N N 91 
I6I O50 H38 SING N N 92 
# 
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 
I6I SMILES           ACDLabs              12.01 "O=C(O)C(CCC(=O)O)NC(=O)CCC(NC(=O)CCC(NC(=O)c1ccc(cc1F)CCCCn1ccc2NC(N)=NC(=O)c21)C(=O)O)C(=O)O"                                                                                                                                                                                                                            
I6I InChI            InChI                1.06  "InChI=1S/C32H38FN7O12/c33-18-15-16(3-1-2-13-40-14-12-19-26(40)28(46)39-32(34)38-19)4-5-17(18)27(45)37-22(31(51)52)7-10-24(42)35-20(29(47)48)6-9-23(41)36-21(30(49)50)8-11-25(43)44/h4-5,12,14-15,20-22H,1-3,6-11,13H2,(H,35,42)(H,36,41)(H,37,45)(H,43,44)(H,47,48)(H,49,50)(H,51,52)(H3,34,38,39,46)/t20-,21+,22+/m0/s1" 
I6I InChIKey         InChI                1.06  CLRLOXIKNFTIBU-BHDDXSALSA-N                                                                                                                                                                                                                                                                                                
I6I SMILES_CANONICAL CACTVS               3.385 "NC1=NC(=O)c2n(CCCCc3ccc(c(F)c3)C(=O)N[C@H](CCC(=O)N[C@@H](CCC(=O)N[C@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)ccc2N1"                                                                                                                                                                                                             
I6I SMILES           CACTVS               3.385 "NC1=NC(=O)c2n(CCCCc3ccc(c(F)c3)C(=O)N[CH](CCC(=O)N[CH](CCC(=O)N[CH](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)ccc2N1"                                                                                                                                                                                                                 
I6I SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "c1cc(c(cc1CCCCn2ccc3c2C(=O)N=C(N3)N)F)C(=O)N[C@H](CCC(=O)N[C@@H](CCC(=O)N[C@H](CCC(=O)O)C(=O)O)C(=O)O)C(=O)O"                                                                                                                                                                                                             
I6I SMILES           "OpenEye OEToolkits" 2.0.7 "c1cc(c(cc1CCCCn2ccc3c2C(=O)N=C(N3)N)F)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)O)C(=O)O)C(=O)O)C(=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 
I6I "SYSTEMATIC NAME" ACDLabs              12.01 "N-{4-[4-(2-amino-4-oxo-1,4-dihydro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)butyl]-2-fluorobenzoyl}-D-gamma-glutamyl-L-gamma-glutamyl-D-glutamic acid"                                                                                                            
I6I "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "(2~{R})-2-[[(4~{S})-4-[[(4~{R})-4-[[4-[4-(2-azanyl-4-oxidanylidene-1~{H}-pyrrolo[3,2-d]pyrimidin-5-yl)butyl]-2-fluoranyl-phenyl]carbonylamino]-5-oxidanyl-5-oxidanylidene-pentanoyl]amino]-5-oxidanyl-5-oxidanylidene-pentanoyl]amino]pentanedioic 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 
I6I "Create component" 2023-07-27 RCSB 
I6I "Initial release"  2024-02-21 RCSB 
# 
