data_AOQ
#

_chem_comp.id                                   AOQ
_chem_comp.name                                 "2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C22 H19 Cl O3"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        Atovaquone
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2014-06-03
_chem_comp.pdbx_modified_date                   2021-03-01
_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                       366.837
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    AOQ
_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       4PD4
_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
AOQ  O1   O1   O   0  1  N  N  N  199.993  -27.813  79.126  -1.984  -1.796   0.006  O1   AOQ   1  
AOQ  O2   O2   O   0  1  N  N  N  200.516  -30.794  83.463  -5.041   2.520  -0.002  O2   AOQ   2  
AOQ  C1   C1   C   0  1  N  N  N  200.121  -28.488  80.194  -2.698  -0.811   0.004  C1   AOQ   3  
AOQ  C2   C2   C   0  1  N  N  N  200.135  -27.926  81.484  -2.101   0.527   0.000  C2   AOQ   4  
AOQ  C3   C3   C   0  1  N  N  N  200.256  -28.739  82.603  -2.875   1.632  -0.002  C3   AOQ   5  
AOQ  C4   C4   C   0  1  N  N  N  200.389  -30.093  82.442  -4.353   1.520  -0.001  C4   AOQ   6  
AOQ  C5   C5   C   0  1  Y  N  N  200.502  -32.054  81.008  -6.368   0.048   0.003  C5   AOQ   7  
AOQ  C6   C6   C   0  1  Y  N  N  200.504  -32.629  79.745  -6.936  -1.216   0.000  C6   AOQ   8  
AOQ  C7   C7   C   0  1  Y  N  N  200.374  -31.796  78.650  -6.136  -2.342  -0.004  C7   AOQ   9  
AOQ  C8   C8   C   0  1  Y  N  N  200.251  -30.427  78.802  -4.754  -2.224  -0.004  C8   AOQ  10  
AOQ  C9   C9   C   0  1  Y  N  N  200.254  -29.864  80.059  -4.170  -0.964  -0.002  C9   AOQ  11  
AOQ  C10  C10  C   0  1  Y  N  N  200.379  -30.668  81.172  -4.984   0.183   0.002  C10  AOQ  12  
AOQ  O6   O3   O   0  1  N  N  N  200.263  -28.217  83.875  -2.296   2.855  -0.005  O6   AOQ  13  
AOQ  C11  C11  C   0  1  N  N  N  200.575  -25.531  80.742  -0.023   0.006   1.250  C11  AOQ  14  
AOQ  C12  C12  C   0  1  N  N  N  200.109  -24.114  81.004   1.500   0.153   1.249  C12  AOQ  15  
AOQ  C13  C13  C   0  1  N  N  N  198.588  -24.088  81.125   2.076  -0.520   0.002  C13  AOQ  16  
AOQ  C14  C14  C   0  1  N  N  N  198.203  -24.843  82.381   1.499   0.146  -1.249  C14  AOQ  17  
AOQ  C15  C15  C   0  1  N  N  N  198.505  -26.289  82.078  -0.024  -0.000  -1.248  C15  AOQ  18  
AOQ  C16  C16  C   0  1  N  N  N  199.986  -26.483  81.789  -0.600   0.672  -0.001  C16  AOQ  19  
AOQ  CL   CL1  CL  0  0  N  N  N  196.289  -18.577  81.615   8.056   0.056  -0.002  CL   AOQ  20  
AOQ  C17  C17  C   0  1  Y  N  N  198.078  -22.715  81.240   3.576  -0.375   0.001  C17  AOQ  21  
AOQ  C18  C18  C   0  1  Y  N  N  198.923  -21.624  81.090   4.149   0.883   0.003  C18  AOQ  22  
AOQ  C19  C19  C   0  1  Y  N  N  198.377  -20.353  81.210   5.525   1.016   0.002  C19  AOQ  23  
AOQ  C20  C20  C   0  1  Y  N  N  197.008  -20.203  81.460   6.328  -0.110  -0.001  C20  AOQ  24  
AOQ  C21  C21  C   0  1  Y  N  N  196.169  -21.302  81.599   5.754  -1.369  -0.003  C21  AOQ  25  
AOQ  C22  C22  C   0  1  Y  N  N  196.720  -22.570  81.488   4.379  -1.501   0.003  C22  AOQ  26  
AOQ  H1   H1   H   0  1  N  N  N  200.597  -32.685  81.879  -6.998   0.925   0.006  H1   AOQ  27  
AOQ  H2   H2   H   0  1  N  N  N  200.604  -33.697  79.621  -8.011  -1.321   0.001  H2   AOQ  28  
AOQ  H3   H3   H   0  1  N  N  N  200.368  -32.222  77.658  -6.590  -3.322  -0.005  H3   AOQ  29  
AOQ  H4   H4   H   0  1  N  N  N  200.152  -29.796  77.931  -4.135  -3.108  -0.007  H4   AOQ  30  
AOQ  H5   H5   H   0  1  N  N  N  200.368  -28.920  84.506  -2.927   3.588  -0.006  H5   AOQ  31  
AOQ  H6   H6   H   0  1  N  N  N  200.245  -25.843  79.740  -0.287  -1.052   1.253  H6   AOQ  32  
AOQ  H7   H7   H   0  1  N  N  N  201.673  -25.568  80.794  -0.434   0.485   2.139  H7   AOQ  33  
AOQ  H8   H8   H   0  1  N  N  N  200.557  -23.749  81.940   1.763   1.210   1.247  H8   AOQ  34  
AOQ  H9   H9   H   0  1  N  N  N  200.421  -23.466  80.171   1.911  -0.322   2.140  H9   AOQ  35  
AOQ  H10  H10  H   0  1  N  N  N  198.145  -24.584  80.249   1.813  -1.577   0.004  H10  AOQ  36  
AOQ  H11  H11  H   0  1  N  N  N  198.798  -24.496  83.238   1.762   1.204  -1.252  H11  AOQ  37  
AOQ  H12  H12  H   0  1  N  N  N  197.133  -24.709  82.599   1.910  -0.332  -2.138  H12  AOQ  38  
AOQ  H13  H13  H   0  1  N  N  N  197.922  -26.603  81.199  -0.435   0.474  -2.139  H13  AOQ  39  
AOQ  H14  H14  H   0  1  N  N  N  198.223  -26.905  82.944  -0.287  -1.058  -1.246  H14  AOQ  40  
AOQ  H15  H15  H   0  1  N  N  N  200.523  -26.290  82.730  -0.337   1.730  -0.003  H15  AOQ  41  
AOQ  H16  H16  H   0  1  N  N  N  199.975  -21.760  80.886   3.522   1.762   0.005  H16  AOQ  42  
AOQ  H17  H17  H   0  1  N  N  N  199.007  -19.482  81.111   5.972   1.999   0.004  H17  AOQ  43  
AOQ  H18  H18  H   0  1  N  N  N  195.114  -21.172  81.789   6.381  -2.248  -0.006  H18  AOQ  44  
AOQ  H19  H19  H   0  1  N  N  N  196.093  -23.443  81.594   3.930  -2.483   0.006  H19  AOQ  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
AOQ  C7   C8   DOUB  Y  N   1  
AOQ  C7   C6   SING  Y  N   2  
AOQ  C8   C9   SING  Y  N   3  
AOQ  O1   C1   DOUB  N  N   4  
AOQ  C6   C5   DOUB  Y  N   5  
AOQ  C9   C1   SING  N  N   6  
AOQ  C9   C10  DOUB  Y  N   7  
AOQ  C1   C2   SING  N  N   8  
AOQ  C11  C12  SING  N  N   9  
AOQ  C11  C16  SING  N  N  10  
AOQ  C12  C13  SING  N  N  11  
AOQ  C5   C10  SING  Y  N  12  
AOQ  C18  C19  DOUB  Y  N  13  
AOQ  C18  C17  SING  Y  N  14  
AOQ  C13  C17  SING  N  N  15  
AOQ  C13  C14  SING  N  N  16  
AOQ  C10  C4   SING  N  N  17  
AOQ  C19  C20  SING  Y  N  18  
AOQ  C17  C22  DOUB  Y  N  19  
AOQ  C20  C21  DOUB  Y  N  20  
AOQ  C20  CL   SING  N  N  21  
AOQ  C2   C16  SING  N  N  22  
AOQ  C2   C3   DOUB  N  N  23  
AOQ  C22  C21  SING  Y  N  24  
AOQ  C16  C15  SING  N  N  25  
AOQ  C15  C14  SING  N  N  26  
AOQ  C4   C3   SING  N  N  27  
AOQ  C4   O2   DOUB  N  N  28  
AOQ  C3   O6   SING  N  N  29  
AOQ  C5   H1   SING  N  N  30  
AOQ  C6   H2   SING  N  N  31  
AOQ  C7   H3   SING  N  N  32  
AOQ  C8   H4   SING  N  N  33  
AOQ  O6   H5   SING  N  N  34  
AOQ  C11  H6   SING  N  N  35  
AOQ  C11  H7   SING  N  N  36  
AOQ  C12  H8   SING  N  N  37  
AOQ  C12  H9   SING  N  N  38  
AOQ  C13  H10  SING  N  N  39  
AOQ  C14  H11  SING  N  N  40  
AOQ  C14  H12  SING  N  N  41  
AOQ  C15  H13  SING  N  N  42  
AOQ  C15  H14  SING  N  N  43  
AOQ  C16  H15  SING  N  N  44  
AOQ  C18  H16  SING  N  N  45  
AOQ  C19  H17  SING  N  N  46  
AOQ  C21  H18  SING  N  N  47  
AOQ  C22  H19  SING  N  N  48  
#   #
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
AOQ  SMILES            ACDLabs               12.01  "Clc1ccc(cc1)C4CCC(C=3C(=O)c2ccccc2C(=O)C=3O)CC4"  
AOQ  InChI             InChI                 1.03   "InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,26H,5-8H2/t13-,15-"  
AOQ  InChIKey          InChI                 1.03   KUCQYCKVKVOKAY-CTYIDZIISA-N  
AOQ  SMILES_CANONICAL  CACTVS                3.385  "OC1=C([C@H]2CC[C@@H](CC2)c3ccc(Cl)cc3)C(=O)c4ccccc4C1=O"  
AOQ  SMILES            CACTVS                3.385  "OC1=C([CH]2CC[CH](CC2)c3ccc(Cl)cc3)C(=O)c4ccccc4C1=O"  
AOQ  SMILES_CANONICAL  "OpenEye OEToolkits"  1.9.2  "c1ccc2c(c1)C(=O)C(=C(C2=O)O)C3CCC(CC3)c4ccc(cc4)Cl"  
AOQ  SMILES            "OpenEye OEToolkits"  1.9.2  "c1ccc2c(c1)C(=O)C(=C(C2=O)O)C3CCC(CC3)c4ccc(cc4)Cl"  
#   #
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
AOQ  "SYSTEMATIC NAME"  ACDLabs               12.01  "2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione"  
AOQ  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.9.2  "2-[4-(4-chlorophenyl)cyclohexyl]-3-oxidanyl-naphthalene-1,4-dione"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
AOQ  "Create component"   2014-06-03  RCSB  
AOQ  "Initial release"    2014-06-11  RCSB  
AOQ  "Modify descriptor"  2014-09-05  RCSB  
AOQ  "Modify synonyms"    2016-04-12  RCSB  
AOQ  "Modify synonyms"    2021-03-01  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     AOQ
_pdbx_chem_comp_synonyms.name        Atovaquone
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
