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 ? ##