data_WIN # _chem_comp.id WIN _chem_comp.name "methyl (5beta,7alpha,9beta,10alpha,11alpha,12alpha,13beta,15alpha)-15-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-3,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-21-oate" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C28 H36 O11" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "Bruceantin; Picras-3-en-21-oic acid; (11beta,12alpha,15beta)-15-[(3,4-Dimethyl-1-oxo-2-pentenyl)oxy]-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxopicras-3-en-21-oic acid methyl ester" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-02-16 _chem_comp.pdbx_modified_date 2020-05-26 _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 548.579 _chem_comp.one_letter_code ? _chem_comp.three_letter_code WIN _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 3G71 _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 WIN C1D C1D C 0 1 N N N 65.281 126.848 92.975 7.090 3.490 -0.075 C1D WIN 1 WIN C2C C2C C 0 1 N N N 66.270 127.448 93.978 6.792 2.008 0.160 C2C WIN 2 WIN C1E C1E C 0 1 N N N 67.693 127.548 93.407 7.608 1.506 1.354 C1E WIN 3 WIN C1V C1V C 0 1 N N N 66.185 126.623 95.283 5.323 1.830 0.445 C1V WIN 4 WIN C1B C1B C 0 1 N N N 65.939 127.362 96.613 4.697 2.520 1.630 C1B WIN 5 WIN C1N C1N C 0 1 N N N 66.368 125.231 95.165 4.579 1.064 -0.349 C1N WIN 6 WIN C1W C1W C 0 1 N N N 66.329 124.046 95.899 3.119 1.035 -0.184 C1W WIN 7 WIN O1G O1G O 0 1 N N N 66.251 122.884 95.460 2.586 1.754 0.638 O1G WIN 8 WIN O1T O1T O 0 1 N N N 66.163 124.175 97.213 2.371 0.211 -0.945 O1T WIN 9 WIN C2F C2F C 0 1 N N R 66.019 122.855 97.693 0.929 0.235 -0.727 C2F WIN 10 WIN C2K C2K C 0 1 N N S 64.723 122.925 98.503 0.321 -1.097 -1.073 C2K WIN 11 WIN C2M C2M C 0 1 N N R 64.756 121.899 99.647 -1.237 -0.990 -1.019 C2M WIN 12 WIN C1O C1O C 0 1 N N N 63.480 122.480 100.277 -1.583 -2.474 -1.168 C1O WIN 13 WIN O1S O1S O 0 1 N N N 62.581 122.596 99.146 -0.495 -3.211 -0.563 O1S WIN 14 WIN C2L C2L C 0 1 N N S 63.294 122.824 97.924 0.520 -2.268 -0.112 C2L WIN 15 WIN C2A C2A C 0 1 N N N 62.682 124.080 97.366 1.902 -2.869 -0.235 C2A WIN 16 WIN O1J O1J O 0 1 N N N 61.474 124.098 97.508 2.818 -2.199 -0.649 O1J WIN 17 WIN O1R O1R O 0 1 N N N 63.379 125.165 96.932 2.112 -4.148 0.115 O1R WIN 18 WIN C1A C1A C 0 1 N N N 62.717 126.386 96.526 3.463 -4.658 -0.029 C1A WIN 19 WIN C2E C2E C 0 1 N N S 62.845 121.545 97.236 0.195 -1.887 1.327 C2E WIN 20 WIN O1M O1M O 0 1 N N N 63.230 121.445 95.874 1.096 -0.908 1.831 O1M WIN 21 WIN C2D C2D C 0 1 N N R 63.324 120.342 98.059 -1.254 -1.413 1.464 C2D WIN 22 WIN O1L O1L O 0 1 N N N 62.298 119.853 98.897 -2.095 -2.563 1.517 O1L WIN 23 WIN C2J C2J C 0 1 N N R 64.515 120.477 99.057 -1.621 -0.449 0.345 C2J WIN 24 WIN C2I C2I C 0 1 N N S 64.857 119.339 100.047 -3.051 0.058 0.436 C2I WIN 25 WIN C1F C1F C 0 1 N N N 63.867 119.477 101.211 -4.092 -1.056 0.430 C1F WIN 26 WIN C1P C1P C 0 1 N N N 64.565 117.991 99.356 -3.216 0.864 1.741 C1P WIN 27 WIN C1X C1X C 0 1 N N N 65.487 116.907 99.835 -4.662 1.309 1.811 C1X WIN 28 WIN O1H O1H O 0 1 N N N 65.065 115.798 99.546 -5.277 1.273 2.858 O1H WIN 29 WIN C2B C2B C 0 1 N N N 66.757 117.081 100.388 -5.302 1.786 0.576 C2B WIN 30 WIN O1K O1K O 0 1 N N N 67.470 115.993 100.827 -6.519 2.386 0.631 O1K WIN 31 WIN C1Y C1Y C 0 1 N N N 67.309 118.331 100.645 -4.691 1.634 -0.603 C1Y WIN 32 WIN C1C C1C C 0 1 N N N 68.834 118.273 100.965 -5.406 2.135 -1.831 C1C WIN 33 WIN C2H C2H C 0 1 N N R 66.370 119.556 100.434 -3.339 1.011 -0.730 C2H WIN 34 WIN C1Q C1Q C 0 1 N N N 66.666 120.821 101.270 -3.149 0.274 -2.050 C1Q WIN 35 WIN C2G C2G C 0 1 N N R 66.200 121.947 100.350 -1.662 -0.111 -2.171 C2G WIN 36 WIN O1U O1U O 0 1 N N N 67.291 121.808 99.344 -0.896 1.120 -2.188 O1U WIN 37 WIN C1Z C1Z C 0 1 N N N 67.438 122.615 98.235 0.301 1.276 -1.640 C1Z WIN 38 WIN O1I O1I O 0 1 N N N 68.393 122.636 97.434 0.931 2.292 -1.874 O1I WIN 39 WIN H1D H1D H 0 1 N N N 65.321 127.417 92.035 6.510 3.847 -0.925 H1D WIN 40 WIN H1DA H1DA H 0 0 N N N 65.548 125.799 92.780 6.821 4.060 0.814 H1DA WIN 41 WIN H1DB H1DB H 0 0 N N N 64.263 126.896 93.390 8.153 3.618 -0.281 H1DB WIN 42 WIN H2C H2C H 0 1 N N N 65.997 128.490 94.199 7.061 1.438 -0.729 H2C WIN 43 WIN H1E H1E H 0 1 N N N 68.362 127.984 94.163 7.339 2.076 2.243 H1E WIN 44 WIN H1EA H1EA H 0 0 N N N 68.051 126.544 93.136 7.395 0.450 1.521 H1EA WIN 45 WIN H1EB H1EB H 0 0 N N N 67.685 128.188 92.513 8.670 1.635 1.147 H1EB WIN 46 WIN H1B H1B H 0 1 N N N 65.906 126.634 97.437 4.241 3.455 1.306 H1B WIN 47 WIN H1BA H1BA H 0 0 N N N 66.754 128.079 96.790 3.933 1.875 2.064 H1BA WIN 48 WIN H1BB H1BB H 0 0 N N N 64.981 127.900 96.561 5.463 2.728 2.376 H1BB WIN 49 WIN H1N H1N H 0 1 N N N 66.632 125.000 94.144 5.048 0.464 -1.115 H1N WIN 50 WIN H2F H2F H 0 1 N N N 65.824 121.950 97.098 0.737 0.514 0.311 H2F WIN 51 WIN H2K H2K H 0 1 N N N 64.801 124.000 98.724 0.632 -1.398 -2.091 H2K WIN 52 WIN H1O H1O H 0 1 N N N 63.072 121.817 101.054 -2.525 -2.721 -0.702 H1O WIN 53 WIN H1OA H1OA H 0 0 N N N 63.668 123.456 100.749 -1.632 -2.719 -2.236 H1OA WIN 54 WIN H1A H1A H 0 1 N N N 63.469 127.125 96.214 3.769 -4.587 -1.072 H1A WIN 55 WIN H1AA H1AA H 0 0 N N N 62.041 126.174 95.685 4.141 -4.070 0.590 H1AA WIN 56 WIN H1AB H1AB H 0 0 N N N 62.137 126.787 97.370 3.494 -5.701 0.289 H1AB WIN 57 WIN H2E H2E H 0 1 N N N 61.746 121.561 97.200 0.305 -2.792 1.953 H2E WIN 58 WIN HO1M HO1M H 0 0 N N N 62.915 120.624 95.515 0.919 -0.642 2.744 HO1M WIN 59 WIN H2D H2D H 0 1 N N N 63.655 119.711 97.221 -1.343 -0.885 2.427 H2D WIN 60 WIN HO1L HO1L H 0 0 N N N 62.621 119.110 99.394 -1.905 -3.155 2.258 HO1L WIN 61 WIN H2J H2J H 0 1 N N N 65.291 120.296 98.299 -0.985 0.465 0.512 H2J WIN 62 WIN H1F H1F H 0 1 N N N 64.061 118.689 101.954 -3.924 -1.715 1.282 H1F WIN 63 WIN H1FA H1FA H 0 0 N N N 63.990 120.463 101.682 -5.089 -0.621 0.498 H1FA WIN 64 WIN H1FB H1FB H 0 0 N N N 62.839 119.378 100.832 -4.007 -1.628 -0.494 H1FB WIN 65 WIN H1P H1P H 0 1 N N N 63.529 117.697 99.580 -2.979 0.229 2.593 H1P WIN 66 WIN H1PA H1PA H 0 0 N N N 64.699 118.114 98.271 -2.556 1.730 1.718 H1PA WIN 67 WIN H1C H1C H 0 1 N N N 69.208 119.289 101.158 -6.365 2.566 -1.542 H1C WIN 68 WIN H1CA H1CA H 0 0 N N N 68.998 117.647 101.855 -4.798 2.895 -2.320 H1CA WIN 69 WIN H2H H2H H 0 1 N N N 66.754 119.800 99.433 -2.595 1.816 -0.680 H2H WIN 70 WIN H1Q H1Q H 0 1 N N N 66.117 120.819 102.223 -3.769 -0.613 -2.112 H1Q WIN 71 WIN H1QA H1QA H 0 0 N N N 67.735 120.909 101.514 -3.388 0.935 -2.891 H1QA WIN 72 WIN H2G H2G H 0 1 N N N 66.049 122.884 100.905 -1.516 -0.661 -3.116 H2G WIN 73 WIN H35 H35 H 0 1 N N N 66.997 115.197 100.614 -6.884 2.454 1.524 H35 WIN 74 WIN H36 H36 H 0 1 N N N 69.372 117.841 100.108 -5.573 1.305 -2.517 H36 WIN 75 # 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 WIN C1D C2C SING N N 1 WIN C1D H1D SING N N 2 WIN C1D H1DA SING N N 3 WIN C1D H1DB SING N N 4 WIN C2C C1V SING N N 5 WIN C2C H2C SING N N 6 WIN C1E C2C SING N N 7 WIN C1E H1E SING N N 8 WIN C1E H1EA SING N N 9 WIN C1E H1EB SING N N 10 WIN C1V C1B SING N N 11 WIN C1B H1B SING N N 12 WIN C1B H1BA SING N N 13 WIN C1B H1BB SING N N 14 WIN C1N C1V DOUB N E 15 WIN C1N C1W SING N N 16 WIN C1N H1N SING N N 17 WIN C1W O1T SING N N 18 WIN O1G C1W DOUB N N 19 WIN O1T C2F SING N N 20 WIN C2F C1Z SING N N 21 WIN C2F C2K SING N N 22 WIN C2F H2F SING N N 23 WIN C2K C2M SING N N 24 WIN C2K H2K SING N N 25 WIN C2M C1O SING N N 26 WIN C2M C2G SING N N 27 WIN C1O H1O SING N N 28 WIN C1O H1OA SING N N 29 WIN O1S C1O SING N N 30 WIN C2L C2K SING N N 31 WIN C2L O1S SING N N 32 WIN C2A C2L SING N N 33 WIN C2A O1J DOUB N N 34 WIN O1R C2A SING N N 35 WIN C1A O1R SING N N 36 WIN C1A H1A SING N N 37 WIN C1A H1AA SING N N 38 WIN C1A H1AB SING N N 39 WIN C2E C2L SING N N 40 WIN C2E C2D SING N N 41 WIN C2E H2E SING N N 42 WIN O1M C2E SING N N 43 WIN O1M HO1M SING N N 44 WIN C2D O1L SING N N 45 WIN C2D C2J SING N N 46 WIN C2D H2D SING N N 47 WIN O1L HO1L SING N N 48 WIN C2J C2M SING N N 49 WIN C2J C2I SING N N 50 WIN C2J H2J SING N N 51 WIN C2I C2H SING N N 52 WIN C2I C1F SING N N 53 WIN C1F H1F SING N N 54 WIN C1F H1FA SING N N 55 WIN C1F H1FB SING N N 56 WIN C1P C2I SING N N 57 WIN C1P C1X SING N N 58 WIN C1P H1P SING N N 59 WIN C1P H1PA SING N N 60 WIN C1X C2B SING N N 61 WIN O1H C1X DOUB N N 62 WIN C2B C1Y DOUB N N 63 WIN C2B O1K SING N N 64 WIN C1Y C1C SING N N 65 WIN C1C H1C SING N N 66 WIN C1C H1CA SING N N 67 WIN C2H C1Y SING N N 68 WIN C2H C1Q SING N N 69 WIN C2H H2H SING N N 70 WIN C1Q H1Q SING N N 71 WIN C1Q H1QA SING N N 72 WIN C2G C1Q SING N N 73 WIN C2G H2G SING N N 74 WIN O1U C2G SING N N 75 WIN C1Z O1U SING N N 76 WIN O1I C1Z DOUB N N 77 WIN O1K H35 SING N N 78 WIN C1C H36 SING N N 79 # 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 WIN SMILES ACDLabs 12.01 "O=C(OC)C15OCC24C1C(OC(=O)\C=C(/C)C(C)C)C(=O)OC2CC3C(=C(O)C(=O)CC3(C)C4C(O)C5O)C" WIN SMILES_CANONICAL CACTVS 3.370 "COC(=O)[C@@]12OC[C@@]34[C@@H](C[C@H]5C(=C(O)C(=O)C[C@]5(C)[C@H]3[C@@H](O)[C@@H]1O)C)OC(=O)[C@H](OC(=O)\C=C(C)\C(C)C)[C@@H]24" WIN SMILES CACTVS 3.370 "COC(=O)[C]12OC[C]34[CH](C[CH]5C(=C(O)C(=O)C[C]5(C)[CH]3[CH](O)[CH]1O)C)OC(=O)[CH](OC(=O)C=C(C)C(C)C)[CH]24" WIN SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "CC1=C(C(=O)C[C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4[C@H](C(=O)O3)OC(=O)/C=C(\C)/C(C)C)(OC5)C(=O)OC)O)O)C)O" WIN SMILES "OpenEye OEToolkits" 1.7.0 "CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C(C)C)(OC5)C(=O)OC)O)O)C)O" WIN InChI InChI 1.03 "InChI=1S/C28H36O11/c1-11(2)12(3)7-17(30)39-20-22-27-10-37-28(22,25(35)36-6)23(33)19(32)21(27)26(5)9-15(29)18(31)13(4)14(26)8-16(27)38-24(20)34/h7,11,14,16,19-23,31-33H,8-10H2,1-6H3/b12-7+/t14-,16+,19+,20+,21+,22+,23-,26-,27+,28-/m0/s1" WIN InChIKey InChI 1.03 IRQXZTBHNKVIRL-GOTQHHPNSA-N # _pdbx_chem_comp_identifier.comp_id WIN _pdbx_chem_comp_identifier.type "SYSTEMATIC NAME" _pdbx_chem_comp_identifier.program ACDLabs _pdbx_chem_comp_identifier.program_version 12.01 _pdbx_chem_comp_identifier.identifier "methyl (5beta,7alpha,9beta,10alpha,11alpha,12alpha,13beta,15alpha)-15-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-3,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-21-oate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site WIN "Create component" 2009-02-16 RCSB WIN "Modify descriptor" 2011-06-04 RCSB WIN "Modify synonyms" 2020-05-26 PDBE # loop_ _pdbx_chem_comp_synonyms.ordinal _pdbx_chem_comp_synonyms.comp_id _pdbx_chem_comp_synonyms.name _pdbx_chem_comp_synonyms.provenance _pdbx_chem_comp_synonyms.type 1 WIN Bruceantin ? ? 2 WIN "Picras-3-en-21-oic acid" ? ? 3 WIN "(11beta,12alpha,15beta)-15-[(3,4-Dimethyl-1-oxo-2-pentenyl)oxy]-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxopicras-3-en-21-oic acid methyl ester" ? ? #