data_SMQ # _chem_comp.id SMQ _chem_comp.name "SIMOCYCLINONE C4" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C37 H38 O15" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2010-12-17 _chem_comp.pdbx_modified_date 2011-06-04 _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 722.689 _chem_comp.one_letter_code ? _chem_comp.three_letter_code SMQ _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 2Y31 _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # 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 SMQ O4 O4 O 0 1 N N N 33.846 -24.034 -5.902 13.962 5.483 -0.299 O4 SMQ 1 SMQ C1A C1A C 0 1 Y N N 44.285 -35.626 1.331 -1.385 -1.555 0.122 C1A SMQ 2 SMQ O1A O1A O 0 1 N N N 46.086 -34.360 2.262 -0.960 0.139 -1.496 O1A SMQ 3 SMQ C1B C1B C 0 1 Y N N 45.637 -35.452 1.611 -1.691 -0.326 -0.449 C1B SMQ 4 SMQ O1B O1B O 0 1 N N N 48.353 -34.700 1.728 -2.519 2.798 0.280 O1B SMQ 5 SMQ C1C C1C C 0 1 Y N N 46.571 -36.379 1.211 -2.740 0.424 0.050 C1C SMQ 6 SMQ O1C O1C O 0 1 N N N 50.699 -37.210 2.151 -4.182 1.612 -2.980 O1C SMQ 7 SMQ C1D C1D C 0 1 N N S 48.049 -36.097 1.579 -3.072 1.768 -0.543 C1D SMQ 8 SMQ O1D O1D O 0 1 N N N 51.706 -39.399 -1.207 -8.646 0.817 -1.301 O1D SMQ 9 SMQ C1E C1E C 0 1 N N S 48.995 -36.681 0.572 -4.591 1.950 -0.631 C1E SMQ 10 SMQ O1E O1E O 0 1 N N N 48.655 -41.152 -1.100 -7.999 0.494 2.300 O1E SMQ 11 SMQ C1F C1F C 0 1 N N S 50.485 -36.582 0.895 -5.180 2.002 -2.034 C1F SMQ 12 SMQ O1F O1F O 0 1 N N N 49.816 -39.744 0.633 -6.707 -0.554 0.212 O1F SMQ 13 SMQ C1G C1G C 0 1 N N N 51.391 -37.227 -0.189 -6.379 1.059 -2.148 C1G SMQ 14 SMQ O1G O1G O 0 1 N N N 46.790 -39.622 -0.175 -4.885 0.831 2.806 O1G SMQ 15 SMQ C1H C1H C 0 1 N N R 50.769 -38.345 -1.085 -7.374 1.410 -1.031 C1H SMQ 16 SMQ O1H O1H O 0 1 N N N 48.674 -36.385 -0.744 -5.182 2.833 0.338 O1H SMQ 17 SMQ C1I C1I C 0 1 N N N 50.249 -37.686 -2.393 -7.506 2.932 -0.955 C1I SMQ 18 SMQ C1J C1J C 0 1 N N N 49.476 -38.597 -3.312 -8.253 3.357 0.273 C1J SMQ 19 SMQ C1K C1K C 0 1 N N N 49.408 -38.246 -4.775 -8.914 4.711 0.275 C1K SMQ 20 SMQ C1L C1L C 0 1 N N N 48.917 -39.770 -2.851 -8.363 2.600 1.357 C1L SMQ 21 SMQ C1M C1M C 0 1 N N N 49.044 -40.067 -1.508 -7.749 1.269 1.400 C1M SMQ 22 SMQ C1N C1N C 0 1 N N R 49.572 -39.018 -0.515 -6.807 0.869 0.287 C1N SMQ 23 SMQ C1O C1O C 0 1 N N R 48.519 -37.900 -0.213 -5.429 1.452 0.549 C1O SMQ 24 SMQ C1P C1P C 0 1 N N N 47.109 -38.444 0.075 -4.621 0.740 1.626 C1P SMQ 25 SMQ C1Q C1Q C 0 1 Y N N 46.156 -37.520 0.517 -3.488 -0.072 1.126 C1Q SMQ 26 SMQ C1R C1R C 0 1 Y N N 44.809 -37.719 0.217 -3.172 -1.301 1.698 C1R SMQ 27 SMQ C1S C1S C 0 1 Y N N 43.870 -36.761 0.627 -2.122 -2.040 1.187 C1S SMQ 28 SMQ C2A C2A C 0 1 N N R 43.278 -34.572 1.811 -0.244 -2.371 -0.429 C2A SMQ 29 SMQ O2A O2A O 0 1 N N N 42.000 -35.167 1.972 -0.459 -3.752 -0.132 O2A SMQ 30 SMQ C2B C2B C 0 1 N N N 43.106 -33.523 0.742 1.068 -1.911 0.212 C2B SMQ 31 SMQ O2B O2B O 0 1 N N N 39.965 -32.299 2.308 2.946 -5.096 -0.556 O2B SMQ 32 SMQ C2C C2C C 0 1 N N R 42.049 -32.495 1.174 2.214 -2.785 -0.308 C2C SMQ 33 SMQ O2C O2C O 0 1 N N N 38.734 -32.060 0.421 2.572 -6.543 1.073 O2C SMQ 34 SMQ C2D C2D C 0 1 N N R 40.784 -33.156 1.535 1.902 -4.253 -0.003 C2D SMQ 35 SMQ O2D O2D O 0 1 N N N 41.875 -31.703 0.016 3.432 -2.411 0.340 O2D SMQ 36 SMQ C2E C2E C 0 1 N N R 41.091 -34.282 2.531 0.557 -4.622 -0.635 C2E SMQ 37 SMQ C2F C2F C 0 1 N N N 39.866 -35.107 2.904 0.209 -6.070 -0.284 C2F SMQ 38 SMQ C2G C2G C 0 1 N N N 38.967 -31.703 1.584 3.201 -6.249 0.084 C2G SMQ 39 SMQ C2H C2H C 0 1 N N N 38.201 -30.524 2.258 4.272 -7.176 -0.432 C2H SMQ 40 SMQ C3A C3A C 0 1 N N N 41.674 -30.397 0.374 4.170 -1.449 -0.252 C3A SMQ 41 SMQ O3A O3A O 0 1 N N N 41.936 -29.960 1.506 3.790 -0.942 -1.291 O3A SMQ 42 SMQ C3B C3B C 0 1 N N N 41.139 -29.623 -0.627 5.390 -1.028 0.336 C3B SMQ 43 SMQ O3B O3B O 0 1 N N N 34.936 -25.928 -6.657 13.605 4.015 1.331 O3B SMQ 44 SMQ C3C C3C C 0 1 N N N 40.730 -28.303 -0.592 6.133 -0.060 -0.260 C3C SMQ 45 SMQ C3D C3D C 0 1 N N N 39.796 -28.213 -1.802 7.346 0.357 0.325 C3D SMQ 46 SMQ C3E C3E C 0 1 N N N 39.236 -26.835 -2.056 8.091 1.327 -0.272 C3E SMQ 47 SMQ C3F C3F C 0 1 N N N 38.471 -26.888 -3.377 9.303 1.745 0.312 C3F SMQ 48 SMQ C3G C3G C 0 1 N N N 37.715 -25.640 -3.656 10.048 2.715 -0.285 C3G SMQ 49 SMQ C3H C3H C 0 1 N N N 36.697 -25.892 -4.773 11.261 3.133 0.300 C3H SMQ 50 SMQ C3I C3I C 0 1 N N N 35.715 -24.877 -4.833 12.004 4.101 -0.296 C3I SMQ 51 SMQ C3J C3J C 0 1 N N N 34.773 -24.935 -5.854 13.224 4.521 0.293 C3J SMQ 52 SMQ HO4 HO4 H 0 1 N N N 33.274 -24.207 -6.640 14.776 5.702 0.175 HO4 SMQ 53 SMQ HO1A HO1A H 0 0 N N N 46.192 -34.562 3.184 -1.301 -0.125 -2.361 HO1A SMQ 54 SMQ HO1B HO1B H 0 0 N N N 48.420 -34.487 2.651 -1.558 2.754 0.372 HO1B SMQ 55 SMQ HO1C HO1C H 0 0 N N N 50.747 -38.151 2.031 -4.485 1.621 -3.898 HO1C SMQ 56 SMQ H1D H1D H 0 1 N N N 48.185 -36.583 2.556 -2.644 1.837 -1.543 H1D SMQ 57 SMQ HO1D HO1D H 0 0 N N N 51.916 -39.532 -2.124 -9.047 1.106 -2.132 HO1D SMQ 58 SMQ H1F H1F H 0 1 N N N 50.763 -35.518 0.924 -5.503 3.021 -2.251 H1F SMQ 59 SMQ HO1F HO1F H 0 0 N N N 49.872 -40.668 0.418 -7.552 -1.000 0.060 HO1F SMQ 60 SMQ H1G H1G H 0 1 N N N 51.706 -36.417 -0.864 -6.856 1.187 -3.119 H1G SMQ 61 SMQ H1GA H1GA H 0 0 N N N 52.192 -37.729 0.374 -6.046 0.027 -2.035 H1GA SMQ 62 SMQ H1I H1I H 0 1 N N N 49.581 -36.860 -2.106 -6.510 3.375 -0.937 H1I SMQ 63 SMQ H1IA H1IA H 0 0 N N N 51.141 -37.370 -2.953 -8.039 3.288 -1.836 H1IA SMQ 64 SMQ H1K H1K H 0 1 N N N 49.391 -37.152 -4.890 -9.932 4.619 -0.102 H1K SMQ 65 SMQ H1KA H1KA H 0 0 N N N 50.289 -38.655 -5.291 -8.937 5.102 1.292 H1KA SMQ 66 SMQ H1KB H1KB H 0 0 N N N 48.494 -38.674 -5.212 -8.350 5.392 -0.363 H1KB SMQ 67 SMQ H1L H1L H 0 1 N N N 48.395 -40.437 -3.521 -8.907 2.967 2.215 H1L SMQ 68 SMQ H1R H1R H 0 1 N N N 44.493 -38.599 -0.324 -3.745 -1.676 2.533 H1R SMQ 69 SMQ H1S H1S H 0 1 N N N 42.824 -36.900 0.398 -1.871 -2.994 1.627 H1S SMQ 70 SMQ H2A H2A H 0 1 N N N 43.650 -34.146 2.754 -0.189 -2.236 -1.509 H2A SMQ 71 SMQ H2B H2B H 0 1 N N N 44.065 -33.010 0.580 1.256 -0.870 -0.050 H2B SMQ 72 SMQ H2BA H2BA H 0 0 N N N 42.777 -34.008 -0.189 0.998 -2.008 1.295 H2BA SMQ 73 SMQ H2C H2C H 0 1 N N N 42.354 -31.918 2.059 2.316 -2.650 -1.385 H2C SMQ 74 SMQ H2D H2D H 0 1 N N N 40.309 -33.473 0.595 1.850 -4.398 1.077 H2D SMQ 75 SMQ H2E H2E H 0 1 N N N 41.480 -33.784 3.432 0.623 -4.516 -1.718 H2E SMQ 76 SMQ H2F H2F H 0 1 N N N 39.873 -35.306 3.986 -0.749 -6.333 -0.733 H2F SMQ 77 SMQ H2FA H2FA H 0 0 N N N 38.955 -34.550 2.639 0.984 -6.734 -0.667 H2FA SMQ 78 SMQ H2FB H2FB H 0 0 N N N 39.886 -36.061 2.356 0.144 -6.176 0.799 H2FB SMQ 79 SMQ H2H H2H H 0 1 N N N 38.021 -30.761 3.317 4.333 -8.053 0.212 H2H SMQ 80 SMQ H2HA H2HA H 0 0 N N N 38.803 -29.606 2.185 4.024 -7.487 -1.447 H2HA SMQ 81 SMQ H2HB H2HB H 0 0 N N N 37.239 -30.373 1.747 5.231 -6.658 -0.434 H2HB SMQ 82 SMQ H3B H3B H 0 1 N N N 41.021 -30.118 -1.580 5.728 -1.478 1.258 H3B SMQ 83 SMQ H3C H3C H 0 1 N N N 41.001 -27.530 0.112 5.795 0.389 -1.182 H3C SMQ 84 SMQ H3D H3D H 0 1 N N N 39.558 -29.065 -2.422 7.685 -0.092 1.247 H3D SMQ 85 SMQ H3E H3E H 0 1 N N N 39.354 -25.970 -1.420 7.753 1.777 -1.194 H3E SMQ 86 SMQ H3F H3F H 0 1 N N N 38.479 -27.742 -4.038 9.641 1.295 1.234 H3F SMQ 87 SMQ H3G H3G H 0 1 N N N 37.861 -24.698 -3.148 9.710 3.165 -1.206 H3G SMQ 88 SMQ H3H H3H H 0 1 N N N 36.726 -26.744 -5.436 11.599 2.683 1.222 H3H SMQ 89 SMQ H3I H3I H 0 1 N N N 35.697 -24.079 -4.106 11.666 4.551 -1.217 H3I SMQ 90 # 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 SMQ O4 C3J SING N N 1 SMQ O4 HO4 SING N N 2 SMQ C1S C1A DOUB Y N 3 SMQ C1A C1B SING Y N 4 SMQ C1A C2A SING N N 5 SMQ C1B O1A SING N N 6 SMQ O1A HO1A SING N N 7 SMQ C1C C1B DOUB Y N 8 SMQ C1D O1B SING N N 9 SMQ O1B HO1B SING N N 10 SMQ C1Q C1C SING Y N 11 SMQ C1C C1D SING N N 12 SMQ C1F O1C SING N N 13 SMQ O1C HO1C SING N N 14 SMQ C1E C1D SING N N 15 SMQ C1D H1D SING N N 16 SMQ O1D C1H SING N N 17 SMQ O1D HO1D SING N N 18 SMQ O1H C1E SING N N 19 SMQ C1O C1E SING N N 20 SMQ C1E C1F SING N N 21 SMQ C1M O1E DOUB N N 22 SMQ C1G C1F SING N N 23 SMQ C1F H1F SING N N 24 SMQ C1N O1F SING N N 25 SMQ O1F HO1F SING N N 26 SMQ C1H C1G SING N N 27 SMQ C1G H1G SING N N 28 SMQ C1G H1GA SING N N 29 SMQ O1G C1P DOUB N N 30 SMQ C1I C1H SING N N 31 SMQ C1H C1N SING N N 32 SMQ O1H C1O SING N N 33 SMQ C1J C1I SING N N 34 SMQ C1I H1I SING N N 35 SMQ C1I H1IA SING N N 36 SMQ C1K C1J SING N N 37 SMQ C1J C1L DOUB N N 38 SMQ C1K H1K SING N N 39 SMQ C1K H1KA SING N N 40 SMQ C1K H1KB SING N N 41 SMQ C1L C1M SING N N 42 SMQ C1L H1L SING N N 43 SMQ C1M C1N SING N N 44 SMQ C1N C1O SING N N 45 SMQ C1O C1P SING N N 46 SMQ C1P C1Q SING N N 47 SMQ C1R C1Q DOUB Y N 48 SMQ C1R C1S SING Y N 49 SMQ C1R H1R SING N N 50 SMQ C1S H1S SING N N 51 SMQ C2B C2A SING N N 52 SMQ C2A O2A SING N N 53 SMQ C2A H2A SING N N 54 SMQ O2A C2E SING N N 55 SMQ C2B C2C SING N N 56 SMQ C2B H2B SING N N 57 SMQ C2B H2BA SING N N 58 SMQ C2D O2B SING N N 59 SMQ C2G O2B SING N N 60 SMQ O2D C2C SING N N 61 SMQ C2C C2D SING N N 62 SMQ C2C H2C SING N N 63 SMQ O2C C2G DOUB N N 64 SMQ C2D C2E SING N N 65 SMQ C2D H2D SING N N 66 SMQ O2D C3A SING N N 67 SMQ C2E C2F SING N N 68 SMQ C2E H2E SING N N 69 SMQ C2F H2F SING N N 70 SMQ C2F H2FA SING N N 71 SMQ C2F H2FB SING N N 72 SMQ C2G C2H SING N N 73 SMQ C2H H2H SING N N 74 SMQ C2H H2HA SING N N 75 SMQ C2H H2HB SING N N 76 SMQ C3B C3A SING N N 77 SMQ C3A O3A DOUB N N 78 SMQ C3B C3C DOUB N E 79 SMQ C3B H3B SING N N 80 SMQ O3B C3J DOUB N N 81 SMQ C3D C3C SING N N 82 SMQ C3C H3C SING N N 83 SMQ C3E C3D DOUB N N 84 SMQ C3D H3D SING N E 85 SMQ C3F C3E SING N N 86 SMQ C3E H3E SING N N 87 SMQ C3G C3F DOUB N N 88 SMQ C3F H3F SING N E 89 SMQ C3H C3G SING N N 90 SMQ C3G H3G SING N N 91 SMQ C3I C3H DOUB N N 92 SMQ C3H H3H SING N E 93 SMQ C3J C3I SING N N 94 SMQ C3I H3I SING N N 95 # 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 SMQ SMILES ACDLabs 12.01 "O=C(O)CCCCCCCCC(=O)OC1CC(OC(C)C1OC(=O)C)c6ccc5C(=O)C34OC4(C(O)CC2(O)CC(=CC(=O)C23O)C)C(O)c5c6O" SMQ SMILES_CANONICAL CACTVS 3.352 "C[C@H]1O[C@H](C[C@@H](OC(=O)\C=C\C=C\C=C\C=C\C(O)=O)[C@@H]1OC(C)=O)c2ccc3C(=O)[C@@]45O[C@@]4([C@@H](O)C[C@]6(O)CC(=CC(=O)[C@]56O)C)[C@@H](O)c3c2O" SMQ SMILES CACTVS 3.352 "C[CH]1O[CH](C[CH](OC(=O)C=CC=CC=CC=CC(O)=O)[CH]1OC(C)=O)c2ccc3C(=O)[C]45O[C]4([CH](O)C[C]6(O)CC(=CC(=O)[C]56O)C)[CH](O)c3c2O" SMQ SMILES_CANONICAL "OpenEye OEToolkits" 1.6.1 "C[C@@H]1[C@H]([C@@H](C[C@@H](O1)c2ccc3c(c2O)[C@@H]([C@@]45[C@H](C[C@@]6(CC(=CC(=O)[C@@]6([C@]4(C3=O)O5)O)C)O)O)O)OC(=O)C=C\C=C\C=C\C=C\C(=O)O)OC(=O)C" SMQ SMILES "OpenEye OEToolkits" 1.6.1 "CC1C(C(CC(O1)c2ccc3c(c2O)C(C45C(CC6(CC(=CC(=O)C6(C4(C3=O)O5)O)C)O)O)O)OC(=O)C=CC=CC=CC=CC(=O)O)OC(=O)C" SMQ InChI InChI 1.03 ;InChI=1S/C37H38O15/c1-18-14-25(39)36(48)34(47,16-18)17-26(40)35-33(46)29-22(32(45)37(35,36)52-35)13-12-21(30(29)44)23-15-24(31(19(2)49-23)50-20(3)38)51-28(43)11-9-7-5-4-6-8-10-27(41)42/h4-14,19,23-24,26,31,33,40,44,46-48H,15-17H2,1-3H3,(H,41,42)/b6-4+,7-5+,10-8+,11-9+/t19-,23-,24-,26+,31-,33+,34-,35+,36-,37-/m1/s1 ; SMQ InChIKey InChI 1.03 FTHVOUWMLYLIFE-WSOZGFGQSA-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 SMQ "SYSTEMATIC NAME" ACDLabs 12.01 "(1R)-4-O-acetyl-1,5-anhydro-3-O-(9-carboxynonanoyl)-2,6-dideoxy-1-[(4aR,6S,6aS,7S,12aS,12bR)-4a,6,7,8,12b-pentahydroxy-3-methyl-1,12-dioxo-1,4,4a,5,6,7,12,12b-octahydro-6a,12a-epoxytetraphen-9-yl]-D-arabino-hexitol" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site SMQ "Create component" 2010-12-17 EBI SMQ "Modify aromatic_flag" 2011-06-04 RCSB SMQ "Modify descriptor" 2011-06-04 RCSB #