data_VAK
#

_chem_comp.id                                   VAK
_chem_comp.name                                 "methyl (1R,2R,4S)-2-ethyl-2,4,5,7-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C22 H20 O8"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        Aklavinone
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2009-07-31
_chem_comp.pdbx_modified_date                   2020-06-17
_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                       412.389
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    VAK
_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       3IHG
_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
VAK  C1    C1    C  0  1  Y  N  N  12.596  70.916   5.097  -4.600   2.124  -0.504  C1    VAK   1  
VAK  C2    C2    C  0  1  Y  N  N  13.167  69.869   5.813  -5.880   1.783  -0.094  C2    VAK   2  
VAK  C3    C3    C  0  1  Y  N  N  12.830  68.529   5.543  -6.152   0.515   0.375  C3    VAK   3  
VAK  C4    C4    C  0  1  Y  N  N  11.895  68.238   4.544  -5.143  -0.444   0.443  C4    VAK   4  
VAK  C5    C5    C  0  1  N  N  N  10.407  68.939   2.855  -2.765  -1.112   0.095  C5    VAK   5  
VAK  C6    C6    C  0  1  Y  N  N   8.878  69.621   1.143  -0.308  -1.511   0.284  C6    VAK   6  
VAK  C7    C7    C  0  1  N  N  S   7.318  70.243  -0.696   2.107  -2.041   0.521  C7    VAK   7  
VAK  C8    C8    C  0  1  N  N  N   7.320  71.392  -1.710   3.428  -1.305   0.732  C8    VAK   8  
VAK  C9    C9    C  0  1  N  N  R   6.988  72.747  -1.044   3.688  -0.419  -0.492  C9    VAK   9  
VAK  C10   C10   C  0  1  N  N  R   8.075  73.166  -0.082   2.676   0.720  -0.511  C10   VAK  10  
VAK  C11   C11   C  0  1  Y  N  N   9.549  72.320   1.672   0.223   1.042  -0.674  C11   VAK  11  
VAK  C12   C12   C  0  1  N  N  N  11.068  71.639   3.404  -2.211   1.528  -0.889  C12   VAK  12  
VAK  C13   C13   C  0  1  N  N  N   6.840  73.901  -2.029   5.108   0.146  -0.428  C13   VAK  13  
VAK  C14   C14   C  0  1  N  N  N   9.302  73.626  -0.883   2.969   1.664   0.626  C14   VAK  14  
VAK  C15   C15   C  0  1  N  N  N  11.454  74.913  -0.928   3.986   3.605   1.562  C15   VAK  15  
VAK  C16   C16   C  0  1  Y  N  N  11.318  69.271   3.840  -3.850  -0.115   0.032  C16   VAK  16  
VAK  O16   O16   O  0  1  N  N  N  10.186  74.642  -0.341   3.746   2.740   0.422  O16   VAK  17  
VAK  C17   C17   C  0  1  Y  N  N   9.810  69.956   2.123  -1.365  -0.666  -0.048  C17   VAK  18  
VAK  O17   O17   O  0  1  N  N  N   9.630  73.139  -1.953   2.505   1.453   1.721  O17   VAK  19  
VAK  C18   C18   C  0  1  Y  N  N  10.141  71.300   2.391  -1.092   0.628  -0.535  C18   VAK  20  
VAK  O18   O18   O  0  1  N  N  N  11.380  72.836   3.669  -2.009   2.539  -1.533  O18   VAK  21  
VAK  C19   C19   C  0  1  Y  N  N   8.611  72.031   0.694   1.275   0.192  -0.337  C19   VAK  22  
VAK  O19   O19   O  0  1  N  N  N  11.550  66.954   4.233  -5.416  -1.689   0.905  O19   VAK  23  
VAK  C20   C20   C  0  1  Y  N  N   8.264  70.616   0.397   1.014  -1.074   0.146  C20   VAK  24  
VAK  O20   O20   O  0  1  N  N  N  10.127  67.738   2.649  -3.020  -2.289   0.263  O20   VAK  25  
VAK  C21   C21   C  0  1  Y  N  N  11.666  70.602   4.115  -3.581   1.181  -0.450  C21   VAK  26  
VAK  O21   O21   O  0  1  N  N  N   8.577  68.311   0.895  -0.561  -2.761   0.743  O21   VAK  27  
VAK  C22   C22   C  0  1  N  N  N   6.363  73.403  -3.357   6.117  -1.004  -0.456  C22   VAK  28  
VAK  O22   O22   O  0  1  N  N  N   6.008  69.910  -0.213   2.265  -3.002  -0.526  O22   VAK  29  
VAK  O23   O23   O  0  1  N  N  N   5.765  72.627  -0.332   3.530  -1.189  -1.686  O23   VAK  30  
VAK  H1    H1    H  0  1  N  N  N  12.868  71.942   5.299  -4.397   3.119  -0.870  H1    VAK  31  
VAK  H2    H2    H  0  1  N  N  N  13.883  70.088   6.591  -6.671   2.517  -0.141  H2    VAK  32  
VAK  H3    H3    H  0  1  N  N  N  13.291  67.730   6.104  -7.153   0.263   0.692  H3    VAK  33  
VAK  H7    H7    H  0  1  N  N  N   7.653  69.317  -1.187   1.831  -2.555   1.441  H7    VAK  34  
VAK  H8    H8    H  0  1  N  N  N   8.319  71.458  -2.166   3.365  -0.686   1.627  H8    VAK  35  
VAK  H8A   H8A   H  0  1  N  N  N   6.563  71.183  -2.481   4.238  -2.027   0.841  H8A   VAK  36  
VAK  H10   H10   H  0  1  N  N  N   7.622  73.931   0.566   2.759   1.258  -1.455  H10   VAK  37  
VAK  H11   H11   H  0  1  N  N  N   9.818  73.346   1.873   0.436   2.033  -1.048  H11   VAK  38  
VAK  H13   H13   H  0  1  N  N  N   6.110  74.622  -1.632   5.278   0.800  -1.283  H13   VAK  39  
VAK  H13A  H13A  H  0  0  N  N  N   7.816  74.391  -2.158   5.231   0.715   0.494  H13A  VAK  40  
VAK  H15   H15   H  0  1  N  N  N  11.956  75.713  -0.364   4.627   4.434   1.261  H15   VAK  41  
VAK  H15A  H15A  H  0  0  N  N  N  12.072  74.003  -0.903   3.036   3.996   1.929  H15A  VAK  42  
VAK  H15B  H15B  H  0  0  N  N  N  11.314  75.232  -1.971   4.475   3.037   2.353  H15B  VAK  43  
VAK  HO19  HO19  H  0  0  N  N  N  10.907  66.959   3.534  -5.689  -2.312   0.218  HO19  VAK  44  
VAK  HO21  HO21  H  0  0  N  N  N   9.075  67.755   1.482  -0.620  -3.431   0.048  HO21  VAK  45  
VAK  H22   H22   H  0  1  N  N  N   6.263  74.250  -4.052   5.946  -1.658   0.399  H22   VAK  46  
VAK  H22A  H22A  H  0  0  N  N  N   7.089  72.682  -3.760   5.993  -1.572  -1.378  H22A  VAK  47  
VAK  H22B  H22B  H  0  0  N  N  N   5.386  72.912  -3.235   7.128  -0.601  -0.410  H22B  VAK  48  
VAK  HO22  HO22  H  0  0  N  N  N   6.072  69.195   0.409   1.470  -3.522  -0.705  HO22  VAK  49  
VAK  HO23  HO23  H  0  0  N  N  N   5.555  73.457   0.080   4.131  -1.944  -1.750  HO23  VAK  50  
#   #
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
VAK  C21  C1    DOUB  Y  N   1  
VAK  C1   C2    SING  Y  N   2  
VAK  C1   H1    SING  N  N   3  
VAK  C3   C2    DOUB  Y  N   4  
VAK  C2   H2    SING  N  N   5  
VAK  C4   C3    SING  Y  N   6  
VAK  C3   H3    SING  N  N   7  
VAK  C16  C4    DOUB  Y  N   8  
VAK  O19  C4    SING  N  N   9  
VAK  C17  C5    SING  N  N  10  
VAK  O20  C5    DOUB  N  N  11  
VAK  C5   C16   SING  N  N  12  
VAK  C20  C6    DOUB  Y  N  13  
VAK  O21  C6    SING  N  N  14  
VAK  C6   C17   SING  Y  N  15  
VAK  C8   C7    SING  N  N  16  
VAK  C7   O22   SING  N  N  17  
VAK  C7   C20   SING  N  N  18  
VAK  C7   H7    SING  N  N  19  
VAK  C8   C9    SING  N  N  20  
VAK  C8   H8    SING  N  N  21  
VAK  C8   H8A   SING  N  N  22  
VAK  C13  C9    SING  N  N  23  
VAK  C9   O23   SING  N  N  24  
VAK  C9   C10   SING  N  N  25  
VAK  C14  C10   SING  N  N  26  
VAK  C10  C19   SING  N  N  27  
VAK  C10  H10   SING  N  N  28  
VAK  C19  C11   DOUB  Y  N  29  
VAK  C11  C18   SING  Y  N  30  
VAK  C11  H11   SING  N  N  31  
VAK  C18  C12   SING  N  N  32  
VAK  C12  O18   DOUB  N  N  33  
VAK  C12  C21   SING  N  N  34  
VAK  C22  C13   SING  N  N  35  
VAK  C13  H13   SING  N  N  36  
VAK  C13  H13A  SING  N  N  37  
VAK  O17  C14   DOUB  N  N  38  
VAK  C14  O16   SING  N  N  39  
VAK  C15  O16   SING  N  N  40  
VAK  C15  H15   SING  N  N  41  
VAK  C15  H15A  SING  N  N  42  
VAK  C15  H15B  SING  N  N  43  
VAK  C16  C21   SING  Y  N  44  
VAK  C17  C18   DOUB  Y  N  45  
VAK  C20  C19   SING  Y  N  46  
VAK  O19  HO19  SING  N  N  47  
VAK  O21  HO21  SING  N  N  48  
VAK  C22  H22   SING  N  N  49  
VAK  C22  H22A  SING  N  N  50  
VAK  C22  H22B  SING  N  N  51  
VAK  O22  HO22  SING  N  N  52  
VAK  O23  HO23  SING  N  N  53  
#   #
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
VAK  SMILES            ACDLabs               11.02  "O=C(OC)C4c2c(c(O)c1C(=O)c3c(C(=O)c1c2)cccc3O)C(O)CC4(O)CC"  
VAK  SMILES_CANONICAL  CACTVS                3.352  "CC[C@@]1(O)C[C@H](O)c2c(O)c3C(=O)c4c(O)cccc4C(=O)c3cc2[C@H]1C(=O)OC"  
VAK  SMILES            CACTVS                3.352  "CC[C]1(O)C[CH](O)c2c(O)c3C(=O)c4c(O)cccc4C(=O)c3cc2[CH]1C(=O)OC"  
VAK  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.0  "CC[C@]1(C[C@@H](c2c(cc3c(c2O)C(=O)c4c(cccc4O)C3=O)[C@H]1C(=O)OC)O)O"  
VAK  SMILES            "OpenEye OEToolkits"  1.7.0  "CCC1(CC(c2c(cc3c(c2O)C(=O)c4c(cccc4O)C3=O)C1C(=O)OC)O)O"  
VAK  InChI             InChI                 1.03   "InChI=1S/C22H20O8/c1-3-22(29)8-13(24)15-10(17(22)21(28)30-2)7-11-16(20(15)27)19(26)14-9(18(11)25)5-4-6-12(14)23/h4-7,13,17,23-24,27,29H,3,8H2,1-2H3/t13-,17-,22+/m0/s1"  
VAK  InChIKey          InChI                 1.03   RACGRCLGVYXIAO-YOKWENHESA-N  
#   #
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
VAK  "SYSTEMATIC NAME"  ACDLabs               11.02  "methyl (1R,2R,4S)-2-ethyl-2,4,5,7-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate"  
VAK  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.6.1  "methyl (1R,2R,4S)-2-ethyl-2,4,5,7-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
VAK  "Create component"      2009-07-31  RCSB  
VAK  "Modify aromatic_flag"  2011-06-04  RCSB  
VAK  "Modify descriptor"     2011-06-04  RCSB  
VAK  "Modify synonyms"       2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     VAK
_pdbx_chem_comp_synonyms.name        Aklavinone
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
