data_9UY
# 
_chem_comp.id                                    9UY 
_chem_comp.name                                  "3-[5-[[(3~{R},4~{R})-3-ethenyl-4-methyl-5-oxidanylidene-3,4-dihydropyrrol-2-yl]methyl]-2-[[5-[(4-ethenyl-3-methyl-5-oxidanylidene-pyrrol-2-yl)methyl]-3-(3-hydroxy-3-oxopropyl)-4-methyl-1~{H}-pyrrol-2-yl]methyl]-4-methyl-1~{H}-pyrrol-3-yl]propanoic acid" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C33 H38 N4 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "Billeverdin IXa, bound form" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2017-06-13 
_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                        586.678 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     9UY 
_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        5VIV 
_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 
9UY O2D O1  O 0 1 N N N N N N 7.643  3.674  -10.173 -2.066  4.781  -0.712 O2D 9UY 1  
9UY CGD C1  C 0 1 N N N N N N 7.035  2.602  -10.266 -1.098  4.319  0.095  CGD 9UY 2  
9UY O1D O2  O 0 1 N N N N N N 7.260  1.788  -11.194 -0.906  4.840  1.168  O1D 9UY 3  
9UY CBD C2  C 0 1 N N N N N N 5.942  2.297  -9.257  -0.250  3.151  -0.339 CBD 9UY 4  
9UY CAD C3  C 0 1 N N N N N N 4.564  2.495  -9.930  0.770   2.828  0.755  CAD 9UY 5  
9UY C3D C4  C 0 1 Y N N N N N 3.474  2.407  -8.902  1.619   1.661  0.322  C3D 9UY 6  
9UY C2D C5  C 0 1 Y N N N N N 2.665  3.515  -8.397  2.829   1.730  -0.396 C2D 9UY 7  
9UY CMD C6  C 0 1 N N N N N N 2.706  4.948  -8.793  3.513   2.986  -0.873 CMD 9UY 8  
9UY C1D C7  C 0 1 Y N N N N N 1.760  2.896  -7.424  3.263   0.466  -0.580 C1D 9UY 9  
9UY CHD C8  C 0 1 N N N N N N 0.806  3.727  -6.644  4.523   0.060  -1.299 CHD 9UY 10 
9UY C4C C9  C 0 1 N N N N N N 0.145  3.435  -5.498  5.687   0.114  -0.344 C4C 9UY 11 
9UY C3C C10 C 0 1 N N R N N N -0.903 4.358  -4.931  7.119   -0.224 -0.698 C3C 9UY 12 
9UY CAC C11 C 0 1 N N N N N N -0.178 5.575  -4.429  7.232   -1.661 -1.139 CAC 9UY 13 
9UY CBC C12 C 0 1 N N N N N N 0.490  5.499  -3.299  7.700   -1.946 -2.329 CBC 9UY 14 
9UY C2C C13 C 0 1 N N R N N N -1.492 3.576  -3.766  7.873   -0.000 0.630  C2C 9UY 15 
9UY CMC C14 C 0 1 N N N N N N -2.986 3.249  -3.811  8.924   1.100  0.478  CMC 9UY 16 
9UY C1C C15 C 0 1 N N N N N N -0.589 2.381  -3.708  6.768   0.438  1.571  C1C 9UY 17 
9UY OC  O3  O 0 1 N N N N N N -0.619 1.581  -2.799  6.908   0.725  2.741  OC  9UY 18 
9UY NC  N1  N 0 1 N N N N N N 0.249  2.353  -4.739  5.612   0.461  0.893  NC  9UY 19 
9UY C4D C16 C 0 1 Y N N N N N 2.983  1.244  -8.174  1.362   0.357  0.555  C4D 9UY 20 
9UY ND  N2  N 0 1 Y N N N N N 1.968  1.557  -7.303  2.365   -0.381 -0.001 ND  9UY 21 
9UY CHA C17 C 0 1 N N N N N N 3.557  -0.092 -8.431  0.171   -0.189 1.299  CHA 9UY 22 
9UY C1A C18 C 0 1 Y N N N N N 3.192  -1.391 -7.847  -0.992  -0.331 0.351  C1A 9UY 23 
9UY C2A C19 C 0 1 Y N N N N N 3.787  -2.645 -8.317  -1.233  -1.388 -0.451 C2A 9UY 24 
9UY CAA C20 C 0 1 N N N N N N 4.814  -2.884 -9.386  -0.394  -2.635 -0.559 CAA 9UY 25 
9UY CBA C21 C 0 1 N N N N N N 6.151  -2.908 -8.671  -0.890  -3.673 0.451  CBA 9UY 26 
9UY CGA C22 C 0 1 N N N N N N 7.338  -3.199 -9.535  -0.051  -4.920 0.342  CGA 9UY 27 
9UY O2A O4  O 0 1 N N N N N N 7.175  -3.314 -10.761 0.850   -4.974 -0.461 O2A 9UY 28 
9UY O1A O5  O 0 1 N N N N N N 8.405  -3.282 -8.994  -0.305  -5.971 1.137  O1A 9UY 29 
9UY C3A C23 C 0 1 Y N N N N N 3.195  -3.658 -7.477  -2.414  -1.113 -1.168 C3A 9UY 30 
9UY CMA C24 C 0 1 N N N N N N 3.420  -5.125 -7.564  -3.071  -2.011 -2.184 CMA 9UY 31 
9UY C4A C25 C 0 1 Y N N N N N 2.326  -2.889 -6.589  -2.850  0.102  -0.777 C4A 9UY 32 
9UY NA  N3  N 0 1 Y N N N N N 2.320  -1.560 -6.837  -1.984  0.585  0.159  NA  9UY 33 
9UY CHB C26 C 0 1 N N N N N N 1.488  -3.447 -5.525  -4.084  0.804  -1.283 CHB 9UY 34 
9UY C1B C27 C 0 1 N N N N N N 1.883  -4.583 -4.640  -5.284  0.338  -0.500 C1B 9UY 35 
9UY C2B C28 C 0 1 N N N N N N 0.900  -5.258 -3.763  -6.607  0.787  -0.715 C2B 9UY 36 
9UY CMB C29 C 0 1 N N N N N N -0.544 -4.868 -3.604  -7.052  1.793  -1.744 CMB 9UY 37 
9UY C3B C30 C 0 1 N N N N N N 1.656  -6.367 -3.153  -7.407  0.140  0.184  C3B 9UY 38 
9UY CAB C31 C 0 1 N N N N N N 1.036  -7.298 -2.143  -8.809  0.273  0.341  CAB 9UY 39 
9UY CBB C32 C 0 1 N N N N N N 1.481  -8.419 -1.577  -9.450  -0.441 1.281  CBB 9UY 40 
9UY C4B C33 C 0 1 N N N N N N 3.010  -6.171 -3.743  -6.478  -0.743 0.972  C4B 9UY 41 
9UY OB  O6  O 0 1 N N N N N N 3.998  -6.924 -3.502  -6.781  -1.492 1.876  OB  9UY 42 
9UY NB  N4  N 0 1 N N N N N N 3.114  -5.140 -4.623  -5.243  -0.544 0.471  NB  9UY 43 
9UY H1  H1  H 0 1 N N N N N N 8.264  3.750  -10.888 -2.584  5.532  -0.391 H1  9UY 44 
9UY H2  H2  H 0 1 N N N N N N 6.038  1.257  -8.913  -0.886  2.283  -0.510 H2  9UY 45 
9UY H3  H3  H 0 1 N N N N N N 6.034  2.977  -8.398  0.274   3.405  -1.260 H3  9UY 46 
9UY H4  H4  H 0 1 N N N N N N 4.532  3.484  -10.411 1.407   3.696  0.926  H4  9UY 47 
9UY H5  H5  H 0 1 N N N N N N 4.413  1.713  -10.689 0.247   2.575  1.677  H5  9UY 48 
9UY H6  H6  H 0 1 N N N N N N 2.020  5.116  -9.637  4.199   3.339  -0.104 H6  9UY 49 
9UY H7  H7  H 0 1 N N N N N N 2.399  5.573  -7.941  4.068   2.773  -1.786 H7  9UY 50 
9UY H8  H8  H 0 1 N N N N N N 3.730  5.216  -9.094  2.765   3.753  -1.073 H8  9UY 51 
9UY H9  H9  H 0 1 N N N N N N 1.374  4.638  -6.404  4.412   -0.955 -1.681 H9  9UY 52 
9UY H10 H10 H 0 1 N N N N N N 0.009  3.970  -7.362  4.703   0.743  -2.130 H10 9UY 53 
9UY H11 H11 H 0 1 N N N N N N -1.670 4.615  -5.677  7.492   0.445  -1.473 H11 9UY 54 
9UY H12 H12 H 0 1 N N N N N N -0.205 6.499  -4.988  6.928   -2.455 -0.474 H12 9UY 55 
9UY H13 H13 H 0 1 N N N N N N 1.017  6.364  -2.924  8.005   -1.151 -2.994 H13 9UY 56 
9UY H14 H14 H 0 1 N N N N N N 0.512  4.572  -2.746  7.781   -2.975 -2.645 H14 9UY 57 
9UY H15 H15 H 0 1 N N N N N N -1.317 4.167  -2.855  8.330   -0.928 0.976  H15 9UY 58 
9UY H16 H16 H 0 1 N N N N N N -3.266 2.685  -2.909  8.436   2.032  0.190  H16 9UY 59 
9UY H17 H17 H 0 1 N N N N N N -3.565 4.184  -3.853  9.443   1.241  1.427  H17 9UY 60 
9UY H18 H18 H 0 1 N N N N N N -3.202 2.643  -4.704  9.642   0.813  -0.290 H18 9UY 61 
9UY H19 H19 H 0 1 N N N N N N 1.479  0.926  -6.700  2.430   -1.348 0.016  H19 9UY 62 
9UY H20 H20 H 0 1 N N N N N N 3.434  -0.237 -9.514  0.420   -1.164 1.718  H20 9UY 63 
9UY H21 H21 H 0 1 N N N N N N 4.625  0.021  -8.195  -0.099  0.494  2.105  H21 9UY 64 
9UY H22 H22 H 0 1 N N N N N N 4.791  -2.073 -10.129 -0.476  -3.042 -1.567 H22 9UY 65 
9UY H23 H23 H 0 1 N N N N N N 4.630  -3.846 -9.887  0.647   -2.392 -0.349 H23 9UY 66 
9UY H24 H24 H 0 1 N N N N N N 6.103  -3.680 -7.889  -0.808  -3.266 1.459  H24 9UY 67 
9UY H25 H25 H 0 1 N N N N N N 6.304  -1.923 -8.205  -1.931  -3.916 0.240  H25 9UY 68 
9UY H26 H26 H 0 1 N N N N N N 9.078  -3.445 -9.644  0.259   -6.749 1.031  H26 9UY 69 
9UY H27 H27 H 0 1 N N N N N N 4.260  -5.407 -6.912  -3.784  -2.666 -1.683 H27 9UY 70 
9UY H28 H28 H 0 1 N N N N N N 2.512  -5.655 -7.241  -3.593  -1.403 -2.923 H28 9UY 71 
9UY H29 H29 H 0 1 N N N N N N 3.655  -5.399 -8.603  -2.311  -2.614 -2.681 H29 9UY 72 
9UY H30 H30 H 0 1 N N N N N N 1.784  -0.856 -6.371  -2.059  1.439  0.612  H30 9UY 73 
9UY H31 H31 H 0 1 N N N N N N 1.273  -2.607 -4.848  -3.966  1.881  -1.161 H31 9UY 74 
9UY H32 H32 H 0 1 N N N N N N 0.559  -3.767 -6.019  -4.226  0.572  -2.339 H32 9UY 75 
9UY H33 H33 H 0 1 N N N N N N -1.031 -5.547 -2.888  -7.307  1.277  -2.670 H33 9UY 76 
9UY H34 H34 H 0 1 N N N N N N -0.606 -3.835 -3.230  -7.926  2.329  -1.375 H34 9UY 77 
9UY H35 H35 H 0 1 N N N N N N -1.052 -4.937 -4.578  -6.245  2.501  -1.934 H35 9UY 78 
9UY H36 H36 H 0 1 N N N N N N 0.049  -7.002 -1.818  -9.362  0.949  -0.295 H36 9UY 79 
9UY H37 H37 H 0 1 N N N N N N 0.865  -8.944 -0.862  -8.897  -1.116 1.916  H37 9UY 80 
9UY H38 H38 H 0 1 N N N N N N 2.458  -8.802 -1.833  -10.519 -0.340 1.400  H38 9UY 81 
# 
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 
9UY O1D CGD DOUB N N 1  
9UY O2A CGA DOUB N N 2  
9UY CGD O2D SING N N 3  
9UY CGD CBD SING N N 4  
9UY CAD CBD SING N N 5  
9UY CAD C3D SING N N 6  
9UY CGA O1A SING N N 7  
9UY CGA CBA SING N N 8  
9UY CAA CBA SING N N 9  
9UY CAA C2A SING N N 10 
9UY C3D C2D SING Y N 11 
9UY C3D C4D DOUB Y N 12 
9UY CMD C2D SING N N 13 
9UY CHA C4D SING N N 14 
9UY CHA C1A SING N N 15 
9UY C2D C1D DOUB Y N 16 
9UY C2A C1A DOUB Y N 17 
9UY C2A C3A SING Y N 18 
9UY C4D ND  SING Y N 19 
9UY C1A NA  SING Y N 20 
9UY CMA C3A SING N N 21 
9UY C3A C4A DOUB Y N 22 
9UY C1D ND  SING Y N 23 
9UY C1D CHD SING N N 24 
9UY NA  C4A SING Y N 25 
9UY CHD C4C SING N N 26 
9UY C4A CHB SING N N 27 
9UY CHB C1B SING N N 28 
9UY C4C C3C SING N N 29 
9UY C4C NC  DOUB N N 30 
9UY C3C CAC SING N N 31 
9UY C3C C2C SING N N 32 
9UY NC  C1C SING N N 33 
9UY C1B NB  DOUB N N 34 
9UY C1B C2B SING N N 35 
9UY NB  C4B SING N N 36 
9UY CAC CBC DOUB N N 37 
9UY CMC C2C SING N N 38 
9UY C2C C1C SING N N 39 
9UY C2B CMB SING N N 40 
9UY C2B C3B DOUB N N 41 
9UY C4B OB  DOUB N N 42 
9UY C4B C3B SING N N 43 
9UY C1C OC  DOUB N N 44 
9UY C3B CAB SING N N 45 
9UY CAB CBB DOUB N N 46 
9UY O2D H1  SING N N 47 
9UY CBD H2  SING N N 48 
9UY CBD H3  SING N N 49 
9UY CAD H4  SING N N 50 
9UY CAD H5  SING N N 51 
9UY CMD H6  SING N N 52 
9UY CMD H7  SING N N 53 
9UY CMD H8  SING N N 54 
9UY CHD H9  SING N N 55 
9UY CHD H10 SING N N 56 
9UY C3C H11 SING N N 57 
9UY CAC H12 SING N N 58 
9UY CBC H13 SING N N 59 
9UY CBC H14 SING N N 60 
9UY C2C H15 SING N N 61 
9UY CMC H16 SING N N 62 
9UY CMC H17 SING N N 63 
9UY CMC H18 SING N N 64 
9UY ND  H19 SING N N 65 
9UY CHA H20 SING N N 66 
9UY CHA H21 SING N N 67 
9UY CAA H22 SING N N 68 
9UY CAA H23 SING N N 69 
9UY CBA H24 SING N N 70 
9UY CBA H25 SING N N 71 
9UY O1A H26 SING N N 72 
9UY CMA H27 SING N N 73 
9UY CMA H28 SING N N 74 
9UY CMA H29 SING N N 75 
9UY NA  H30 SING N N 76 
9UY CHB H31 SING N N 77 
9UY CHB H32 SING N N 78 
9UY CMB H33 SING N N 79 
9UY CMB H34 SING N N 80 
9UY CMB H35 SING N N 81 
9UY CAB H36 SING N N 82 
9UY CBB H37 SING N N 83 
9UY CBB H38 SING N N 84 
# 
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 
9UY InChI            InChI                1.03  "InChI=1S/C33H38N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,19-20,34-35H,1-2,9-15H2,3-6H3,(H,38,39)(H,40,41)/t19-,20-/m1/s1" 
9UY InChIKey         InChI                1.03  IAVYOZQSRLDKLE-WOJBJXKFSA-N                                                                                                                                                                                                     
9UY SMILES_CANONICAL CACTVS               3.385 "C[C@@H]1[C@@H](C=C)C(=NC1=O)Cc2[nH]c(Cc3[nH]c(CC4=NC(=O)C(=C4C)C=C)c(C)c3CCC(O)=O)c(CCC(O)=O)c2C"                                                                                                                              
9UY SMILES           CACTVS               3.385 "C[CH]1[CH](C=C)C(=NC1=O)Cc2[nH]c(Cc3[nH]c(CC4=NC(=O)C(=C4C)C=C)c(C)c3CCC(O)=O)c(CCC(O)=O)c2C"                                                                                                                                  
9UY SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "Cc1c(c([nH]c1CC2=NC(=O)[C@@H]([C@H]2C=C)C)Cc3c(c(c([nH]3)CC4=NC(=O)C(=C4C)C=C)C)CCC(=O)O)CCC(=O)O"                                                                                                                             
9UY SMILES           "OpenEye OEToolkits" 2.0.6 "Cc1c(c([nH]c1CC2=NC(=O)C(C2C=C)C)Cc3c(c(c([nH]3)CC4=NC(=O)C(=C4C)C=C)C)CCC(=O)O)CCC(=O)O"                                                                                                                                      
# 
_pdbx_chem_comp_identifier.comp_id           9UY 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   2.0.6 
_pdbx_chem_comp_identifier.identifier        "3-[5-[[(3~{R},4~{R})-3-ethenyl-4-methyl-5-oxidanylidene-3,4-dihydropyrrol-2-yl]methyl]-2-[[5-[(4-ethenyl-3-methyl-5-oxidanylidene-pyrrol-2-yl)methyl]-3-(3-hydroxy-3-oxopropyl)-4-methyl-1~{H}-pyrrol-2-yl]methyl]-4-methyl-1~{H}-pyrrol-3-yl]propanoic 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 
9UY "Create component" 2017-06-13 RCSB 
9UY "Modify synonyms"  2017-06-13 RCSB 
9UY "Initial release"  2017-06-21 RCSB 
9UY "Modify synonyms"  2021-03-13 RCSB 
9UY "Modify PCM"       2024-09-27 PDBE 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      9UY 
_pdbx_chem_comp_synonyms.name         "Billeverdin IXa, bound form" 
_pdbx_chem_comp_synonyms.provenance   PDB 
_pdbx_chem_comp_synonyms.type         ? 
# 
loop_
_pdbx_chem_comp_pcm.pcm_id 
_pdbx_chem_comp_pcm.comp_id 
_pdbx_chem_comp_pcm.modified_residue_id 
_pdbx_chem_comp_pcm.type 
_pdbx_chem_comp_pcm.category 
_pdbx_chem_comp_pcm.position 
_pdbx_chem_comp_pcm.polypeptide_position 
_pdbx_chem_comp_pcm.comp_id_linking_atom 
_pdbx_chem_comp_pcm.modified_residue_id_linking_atom 
_pdbx_chem_comp_pcm.uniprot_specific_ptm_accession 
_pdbx_chem_comp_pcm.uniprot_generic_ptm_accession 
1 9UY CYS None "Covalent chemical modification" "Amino-acid side chain" "Any position" CAB SG ? ? 
2 9UY CYS None "Covalent chemical modification" "Amino-acid side chain" "Any position" CBC SG ? ? 
# 
