data_QU4
#

_chem_comp.id                                   QU4
_chem_comp.name                                 "3,3'-[(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylene]bis(6-hydroxybenzoic acid)"
_chem_comp.type                                 non-polymer
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C22 H14 O9"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "Aurintricarboxylic acid"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2019-12-19
_chem_comp.pdbx_modified_date                   2021-02-26
_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                       422.341
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    QU4
_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       6VBA
_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.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
QU4  CAJ  C1   C  0  1  Y  N  N   -6.617  11.239   -6.206   3.674  -1.019  -1.904  CAJ  QU4   1  
QU4  CAK  C2   C  0  1  Y  N  N  -10.882  12.223  -11.295  -1.583  -2.967  -1.886  CAK  QU4   2  
QU4  CAL  C3   C  0  1  Y  N  N   -7.053  10.479   -7.289   2.331  -0.791  -1.824  CAL  QU4   3  
QU4  CAM  C4   C  0  1  Y  N  N   -9.721  11.906  -10.611  -0.713  -1.918  -1.814  CAM  QU4   4  
QU4  CAN  C5   C  0  1  N  N  N   -6.553   7.940  -11.741   0.308   3.642  -0.218  CAN  QU4   5  
QU4  CAO  C6   C  0  1  N  N  N   -7.212   9.060  -11.240   0.743   2.366  -0.355  CAO  QU4   6  
QU4  CAP  C7   C  0  1  Y  N  N   -8.093  12.403   -8.208   2.587   0.008   0.453  CAP  QU4   7  
QU4  CAQ  C8   C  0  1  Y  N  N  -10.379   9.620  -10.429  -1.414  -1.474   0.467  CAQ  QU4   8  
QU4  CAR  C9   C  0  1  N  N  N   -7.274   8.010   -9.097  -1.548   1.514  -0.348  CAR  QU4   9  
QU4  CAS  C10  C  0  1  N  N  N   -8.016  14.557   -7.111   4.832   0.072   1.517  CAS  QU4  10  
QU4  CAT  C11  C  0  1  N  N  N  -12.456   8.873  -11.387  -3.161  -2.878   1.540  CAT  QU4  11  
QU4  CAU  C12  C  0  1  N  N  N   -6.337   5.832   -8.690  -3.474   3.064  -0.128  CAU  QU4  12  
QU4  CAV  C13  C  0  1  N  N  N   -8.264  10.270   -9.442   0.323  -0.031  -0.567  CAV  QU4  13  
QU4  CAW  C14  C  0  1  Y  N  N   -6.934  12.593   -6.147   4.502  -0.743  -0.820  CAW  QU4  14  
QU4  CAX  C15  C  0  1  Y  N  N  -11.793  11.213  -11.549  -2.388  -3.291  -0.799  CAX  QU4  15  
QU4  CAY  C16  C  0  1  Y  N  N   -7.807  11.037   -8.327   1.769  -0.274  -0.645  CAY  QU4  16  
QU4  CAZ  C17  C  0  1  Y  N  N   -9.444  10.615  -10.147  -0.616  -1.157  -0.637  CAZ  QU4  17  
QU4  CBA  C18  C  0  1  Y  N  N   -7.679  13.197   -7.149   3.957  -0.221   0.366  CBA  QU4  18  
QU4  CBB  C19  C  0  1  Y  N  N  -11.548   9.905  -11.137  -2.308  -2.537   0.386  CBB  QU4  19  
QU4  CBC  C20  C  0  1  N  N  N   -6.606   6.881   -9.584  -2.028   2.809  -0.207  CBC  QU4  20  
QU4  CBD  C21  C  0  1  N  N  N   -6.241   6.847  -10.936  -1.072   3.917  -0.139  CBD  QU4  21  
QU4  CBE  C22  C  0  1  N  N  N   -7.578   9.121   -9.899  -0.166   1.290  -0.422  CBE  QU4  22  
QU4  OAA  O1   O  0  1  N  N  N   -8.697  15.059   -8.035   6.028  -0.130   1.438  OAA  QU4  23  
QU4  OAB  O2   O  0  1  N  N  N  -12.767   8.133  -10.435  -3.082  -2.154   2.673  OAB  QU4  24  
QU4  OAC  O3   O  0  1  N  N  N   -6.507   6.023   -7.465  -3.929   4.325   0.009  OAC  QU4  25  
QU4  OAD  O4   O  0  1  N  N  N   -5.654   5.885  -11.441  -1.467   5.067  -0.015  OAD  QU4  26  
QU4  OAE  O5   O  0  1  N  N  N   -7.656  15.281   -6.153   4.305   0.563   2.656  OAE  QU4  27  
QU4  OAF  O6   O  0  1  N  N  N  -12.938   8.659  -12.534  -3.934  -3.813   1.469  OAF  QU4  28  
QU4  OAG  O7   O  0  1  N  N  N   -5.934   4.708   -9.083  -4.259   2.137  -0.185  OAG  QU4  29  
QU4  OAH  O8   O  0  1  N  N  N   -6.546  13.394   -5.123   5.832  -0.978  -0.908  OAH  QU4  30  
QU4  OAI  O9   O  0  1  N  N  N  -12.942  11.453  -12.232  -3.248  -4.333  -0.881  OAI  QU4  31  
QU4  H1   H1   H  0  1  N  N  N   -6.037  10.781   -5.418   4.097  -1.420  -2.813  H1   QU4  32  
QU4  H2   H2   H  0  1  N  N  N  -11.072  13.234  -11.623  -1.651  -3.546  -2.795  H2   QU4  33  
QU4  H3   H3   H  0  1  N  N  N   -6.802   9.429   -7.328   1.698  -1.008  -2.671  H3   QU4  34  
QU4  H4   H4   H  0  1  N  N  N   -8.999  12.688  -10.428  -0.096  -1.673  -2.665  H4   QU4  35  
QU4  H5   H5   H  0  1  N  N  N   -6.276   7.918  -12.785   1.022   4.450  -0.164  H5   QU4  36  
QU4  H7   H7   H  0  1  N  N  N   -7.440   9.886  -11.897   1.804   2.170  -0.415  H7   QU4  37  
QU4  H8   H8   H  0  1  N  N  N   -8.673  12.868   -8.991   2.159   0.402   1.363  H8   QU4  38  
QU4  H9   H9   H  0  1  N  N  N  -10.196   8.610  -10.094  -1.343  -0.891   1.373  H9   QU4  39  
QU4  H10  H10  H  0  1  N  N  N   -7.569   8.027   -8.058  -2.235   0.682  -0.401  H10  QU4  40  
QU4  H12  H12  H  0  1  N  N  N  -13.369   7.463  -10.737  -3.660  -2.415   3.402  H12  QU4  41  
QU4  H13  H13  H  0  1  N  N  N   -6.289   5.231   -6.987  -4.888   4.443   0.057  H13  QU4  42  
QU4  H14  H14  H  0  1  N  N  N   -7.979  16.165   -6.285   4.918   0.739   3.383  H14  QU4  43  
QU4  H15  H15  H  0  1  N  N  N   -6.045  12.886   -4.495   6.343  -0.226  -1.237  H15  QU4  44  
QU4  H16  H16  H  0  1  N  N  N  -13.303  10.632  -12.544  -2.870  -5.178  -0.601  H16  QU4  45  
#   #
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
QU4  OAF  CAT  DOUB  N  N   1  
QU4  OAI  CAX  SING  N  N   2  
QU4  CAN  CAO  DOUB  N  N   3  
QU4  CAN  CBD  SING  N  N   4  
QU4  CAX  CAK  DOUB  Y  N   5  
QU4  CAX  CBB  SING  Y  N   6  
QU4  OAD  CBD  DOUB  N  N   7  
QU4  CAT  CBB  SING  N  N   8  
QU4  CAT  OAB  SING  N  N   9  
QU4  CAK  CAM  SING  Y  N  10  
QU4  CAO  CBE  SING  N  N  11  
QU4  CBB  CAQ  DOUB  Y  N  12  
QU4  CBD  CBC  SING  N  N  13  
QU4  CAM  CAZ  DOUB  Y  N  14  
QU4  CAQ  CAZ  SING  Y  N  15  
QU4  CAZ  CAV  SING  N  N  16  
QU4  CBE  CAV  DOUB  N  Z  17  
QU4  CBE  CAR  SING  N  N  18  
QU4  CBC  CAR  DOUB  N  N  19  
QU4  CBC  CAU  SING  N  N  20  
QU4  CAV  CAY  SING  N  N  21  
QU4  OAG  CAU  DOUB  N  N  22  
QU4  CAU  OAC  SING  N  N  23  
QU4  CAY  CAP  DOUB  Y  N  24  
QU4  CAY  CAL  SING  Y  N  25  
QU4  CAP  CBA  SING  Y  N  26  
QU4  OAA  CAS  DOUB  N  N  27  
QU4  CAL  CAJ  DOUB  Y  N  28  
QU4  CBA  CAS  SING  N  N  29  
QU4  CBA  CAW  DOUB  Y  N  30  
QU4  CAS  OAE  SING  N  N  31  
QU4  CAJ  CAW  SING  Y  N  32  
QU4  CAW  OAH  SING  N  N  33  
QU4  CAJ  H1   SING  N  N  34  
QU4  CAK  H2   SING  N  N  35  
QU4  CAL  H3   SING  N  N  36  
QU4  CAM  H4   SING  N  N  37  
QU4  CAN  H5   SING  N  N  38  
QU4  CAO  H7   SING  N  N  39  
QU4  CAP  H8   SING  N  N  40  
QU4  CAQ  H9   SING  N  N  41  
QU4  CAR  H10  SING  N  N  42  
QU4  OAB  H12  SING  N  N  43  
QU4  OAC  H13  SING  N  N  44  
QU4  OAE  H14  SING  N  N  45  
QU4  OAH  H15  SING  N  N  46  
QU4  OAI  H16  SING  N  N  47  
#   #
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
QU4  SMILES            ACDLabs               12.01  "c1c(O)c(cc(c1)/C(c2ccc(c(c2)C(O)=O)O)=C3/C=CC(C(=C3)C(O)=O)=O)C(O)=O"  
QU4  InChI             InChI                 1.03   "InChI=1S/C22H14O9/c23-16-4-1-10(7-13(16)20(26)27)19(11-2-5-17(24)14(8-11)21(28)29)12-3-6-18(25)15(9-12)22(30)31/h1-9,23-24H,(H,26,27)(H,28,29)(H,30,31)"  
QU4  InChIKey          InChI                 1.03   GIXWDMTZECRIJT-UHFFFAOYSA-N  
QU4  SMILES_CANONICAL  CACTVS                3.385  "OC(=O)c1cc(ccc1O)C(\c2ccc(O)c(c2)C(O)=O)=C3/C=CC(=O)C(=C3)C(O)=O"  
QU4  SMILES            CACTVS                3.385  "OC(=O)c1cc(ccc1O)C(c2ccc(O)c(c2)C(O)=O)=C3C=CC(=O)C(=C3)C(O)=O"  
QU4  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.7  "c1cc(c(cc1C(=C2C=CC(=O)C(=C2)C(=O)O)c3ccc(c(c3)C(=O)O)O)C(=O)O)O"  
QU4  SMILES            "OpenEye OEToolkits"  2.0.7  "c1cc(c(cc1C(=C2C=CC(=O)C(=C2)C(=O)O)c3ccc(c(c3)C(=O)O)O)C(=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
QU4  "SYSTEMATIC NAME"  ACDLabs               12.01  "3,3'-[(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylene]bis(6-hydroxybenzoic acid)"  
QU4  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  2.0.7  "5-[(3-carboxy-4-oxidanylidene-cyclohexa-2,5-dien-1-ylidene)-(3-carboxy-4-oxidanyl-phenyl)methyl]-2-oxidanyl-benzoic acid"  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     QU4
_pdbx_chem_comp_synonyms.name        "Aurintricarboxylic acid"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
QU4  "Create component"  2019-12-19  RCSB  
QU4  "Modify synonyms"   2020-06-05  PDBE  
QU4  "Initial release"   2021-03-03  RCSB  
##
