data_LSD # _chem_comp.id LSD _chem_comp.name "Lasalocid A" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C34 H54 O8" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "6-[(3R,4S,5S,7R)-7-{(2S,3S,5S)-5-ethyl-5-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]-3-methyltetrahydrofuran-2-yl}-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxy-3-methylbenzoic acid" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2015-01-09 _chem_comp.pdbx_modified_date 2021-03-13 _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 590.788 _chem_comp.one_letter_code ? _chem_comp.three_letter_code LSD _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 4RZM _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 LSD O1 O1 O 0 1 N N N 2.630 5.822 54.969 4.168 -1.942 -1.043 O1 LSD 1 LSD C1 C1 C 0 1 N N N 1.965 4.786 54.976 5.237 -1.475 -1.384 C1 LSD 2 LSD O2 O2 O 0 1 N N N 2.229 3.927 55.831 5.558 -1.409 -2.691 O2 LSD 3 LSD C2 C2 C 0 1 Y N N 0.884 4.536 53.933 6.180 -0.974 -0.368 C2 LSD 4 LSD C3 C3 C 0 1 Y N N 0.534 3.225 53.613 7.135 -1.834 0.193 C3 LSD 5 LSD O3 O3 O 0 1 N N N 1.149 2.190 54.233 7.197 -3.131 -0.198 O3 LSD 6 LSD C4 C4 C 0 1 Y N N -0.399 2.916 52.657 8.017 -1.351 1.148 C4 LSD 7 LSD C34 C34 C 0 1 N N N -0.725 1.480 52.326 9.047 -2.270 1.754 C34 LSD 8 LSD C5 C5 C 0 1 Y N N -1.033 3.937 51.991 7.954 -0.030 1.544 C5 LSD 9 LSD C6 C6 C 0 1 Y N N -0.710 5.239 52.278 7.011 0.823 0.993 C6 LSD 10 LSD C7 C7 C 0 1 Y N N 0.229 5.549 53.258 6.130 0.362 0.039 C7 LSD 11 LSD C8 C8 C 0 1 N N N 0.468 7.032 53.479 5.107 1.295 -0.557 C8 LSD 12 LSD C9 C9 C 0 1 N N N 0.002 7.521 54.830 3.787 1.157 0.204 C9 LSD 13 LSD C10 C10 C 0 1 N N R -1.437 7.299 55.189 2.749 2.104 -0.401 C10 LSD 14 LSD C33 C33 C 0 1 N N N -1.610 7.761 56.643 2.437 1.670 -1.835 C33 LSD 15 LSD C11 C11 C 0 1 N N S -2.369 8.095 54.290 1.468 2.058 0.435 C11 LSD 16 LSD O4 O4 O 0 1 N N N -2.213 9.502 54.626 0.951 0.726 0.442 O4 LSD 17 LSD C12 C12 C 0 1 N N S -3.830 7.639 54.465 0.430 3.005 -0.170 C12 LSD 18 LSD C32 C32 C 0 1 N N N -4.078 6.200 54.018 0.984 4.431 -0.178 C32 LSD 19 LSD C13 C13 C 0 1 N N N -4.696 8.534 53.655 -0.831 2.960 0.653 C13 LSD 20 LSD O5 O5 O 0 1 N N N -4.382 8.858 52.533 -0.781 2.645 1.818 O5 LSD 21 LSD C14 C14 C 0 1 N N R -5.923 9.111 54.237 -2.155 3.309 0.023 C14 LSD 22 LSD C30 C30 C 0 1 N N N -7.046 9.139 53.169 -3.115 3.816 1.102 C30 LSD 23 LSD C31 C31 C 0 1 N N N -7.644 7.740 52.881 -2.569 5.113 1.702 C31 LSD 24 LSD C15 C15 C 0 1 N N S -5.466 10.453 54.802 -2.747 2.065 -0.642 C15 LSD 25 LSD O6 O6 O 0 1 N N N -5.454 11.513 53.834 -3.141 1.107 0.353 O6 LSD 26 LSD C16 C16 C 0 1 N N S -6.332 10.885 55.978 -4.053 2.427 -1.394 C16 LSD 27 LSD C29 C29 C 0 1 N N N -5.956 10.139 57.265 -3.756 2.906 -2.816 C29 LSD 28 LSD C17 C17 C 0 1 N N N -6.058 12.362 55.952 -4.777 1.053 -1.406 C17 LSD 29 LSD C18 C18 C 0 1 N N S -5.857 12.712 54.465 -4.342 0.442 -0.056 C18 LSD 30 LSD C27 C27 C 0 1 N N N -7.193 13.160 53.939 -5.437 0.661 0.990 C27 LSD 31 LSD C28 C28 C 0 1 N N N -7.584 14.479 54.586 -5.798 2.146 1.048 C28 LSD 32 LSD C19 C19 C 0 1 N N R -4.840 13.794 54.128 -4.075 -1.055 -0.226 C19 LSD 33 LSD C20 C20 C 0 1 N N N -3.418 13.419 54.533 -3.756 -1.674 1.137 C20 LSD 34 LSD O7 O7 O 0 1 N N N -4.890 13.990 52.710 -5.234 -1.686 -0.775 O7 LSD 35 LSD C23 C23 C 0 1 N N S -3.986 14.934 52.098 -5.082 -3.089 -1.000 C23 LSD 36 LSD C24 C24 C 0 1 N N N -4.494 16.289 52.491 -3.914 -3.329 -1.957 C24 LSD 37 LSD C22 C22 C 0 1 N N R -2.532 14.758 52.536 -4.804 -3.790 0.332 C22 LSD 38 LSD C21 C21 C 0 1 N N N -2.464 14.492 54.033 -3.549 -3.183 0.968 C21 LSD 39 LSD O8 O8 O 0 1 N N N -2.023 13.589 51.920 -5.918 -3.611 1.209 O8 LSD 40 LSD C25 C25 C 0 1 N N N -1.640 15.976 52.240 -4.580 -5.284 0.086 C25 LSD 41 LSD C26 C26 C 0 1 N N N -1.190 16.133 50.806 -4.301 -5.984 1.418 C26 LSD 42 LSD H1 H1 H 0 1 N N N 2.947 4.230 56.374 4.906 -1.747 -3.321 H1 LSD 43 LSD H2 H2 H 0 1 N N N 1.769 2.525 54.870 7.786 -3.288 -0.949 H2 LSD 44 LSD H3 H3 H 0 1 N N N -0.059 1.128 51.524 9.959 -2.236 1.158 H3 LSD 45 LSD H4 H4 H 0 1 N N N -0.583 0.856 53.221 9.266 -1.948 2.772 H4 LSD 46 LSD H5 H5 H 0 1 N N N -1.771 1.409 51.992 8.660 -3.288 1.770 H5 LSD 47 LSD H6 H6 H 0 1 N N N -1.782 3.716 51.245 8.641 0.340 2.291 H6 LSD 48 LSD H7 H7 H 0 1 N N N -1.193 6.038 51.734 6.970 1.855 1.309 H7 LSD 49 LSD H8 H8 H 0 1 N N N 1.547 7.228 53.391 5.465 2.322 -0.481 H8 LSD 50 LSD H9 H9 H 0 1 N N N -0.071 7.592 52.701 4.951 1.041 -1.605 H9 LSD 51 LSD H10 H10 H 0 1 N N N 0.613 7.015 55.592 3.430 0.130 0.128 H10 LSD 52 LSD H11 H11 H 0 1 N N N 0.188 8.604 54.870 3.943 1.411 1.252 H11 LSD 53 LSD H12 H12 H 0 1 N N N -1.679 6.229 55.115 3.143 3.120 -0.407 H12 LSD 54 LSD H13 H13 H 0 1 N N N -0.936 7.185 57.294 3.349 1.703 -2.431 H13 LSD 55 LSD H14 H14 H 0 1 N N N -1.367 8.831 56.719 2.043 0.654 -1.830 H14 LSD 56 LSD H15 H15 H 0 1 N N N -2.651 7.598 56.958 1.697 2.345 -2.266 H15 LSD 57 LSD H16 H16 H 0 1 N N N -2.075 7.931 53.243 1.690 2.367 1.456 H16 LSD 58 LSD H17 H17 H 0 1 N N N -1.305 9.757 54.510 0.731 0.385 -0.436 H17 LSD 59 LSD H18 H18 H 0 1 N N N -4.102 7.732 55.527 0.208 2.696 -1.192 H18 LSD 60 LSD H19 H19 H 0 1 N N N -3.446 5.519 54.606 1.890 4.466 -0.782 H19 LSD 61 LSD H20 H20 H 0 1 N N N -5.136 5.945 54.175 0.240 5.108 -0.600 H20 LSD 62 LSD H21 H21 H 0 1 N N N -3.831 6.100 52.951 1.214 4.737 0.842 H21 LSD 63 LSD H22 H22 H 0 1 N N N -6.259 8.478 55.071 -2.008 4.087 -0.726 H22 LSD 64 LSD H23 H23 H 0 1 N N N -6.630 9.541 52.234 -4.093 4.004 0.659 H23 LSD 65 LSD H24 H24 H 0 1 N N N -7.852 9.798 53.525 -3.210 3.065 1.886 H24 LSD 66 LSD H25 H25 H 0 1 N N N -8.432 7.827 52.118 -1.564 4.940 2.088 H25 LSD 67 LSD H26 H26 H 0 1 N N N -6.851 7.071 52.514 -2.535 5.884 0.933 H26 LSD 68 LSD H27 H27 H 0 1 N N N -8.073 7.327 53.806 -3.218 5.439 2.515 H27 LSD 69 LSD H28 H28 H 0 1 N N N -4.442 10.317 55.181 -2.025 1.625 -1.329 H28 LSD 70 LSD H29 H29 H 0 1 N N N -7.390 10.698 55.744 -4.629 3.171 -0.844 H29 LSD 71 LSD H30 H30 H 0 1 N N N -6.602 10.478 58.088 -3.245 2.116 -3.366 H30 LSD 72 LSD H31 H31 H 0 1 N N N -6.091 9.058 57.115 -4.690 3.153 -3.319 H31 LSD 73 LSD H32 H32 H 0 1 N N N -4.905 10.346 57.515 -3.120 3.790 -2.777 H32 LSD 74 LSD H33 H33 H 0 1 N N N -5.151 12.596 56.529 -5.858 1.185 -1.441 H33 LSD 75 LSD H34 H34 H 0 1 N N N -6.911 12.919 56.367 -4.435 0.442 -2.240 H34 LSD 76 LSD H35 H35 H 0 1 N N N -7.131 13.292 52.849 -6.320 0.083 0.717 H35 LSD 77 LSD H36 H36 H 0 1 N N N -7.952 12.399 54.173 -5.077 0.335 1.966 H36 LSD 78 LSD H37 H37 H 0 1 N N N -8.561 14.803 54.198 -4.955 2.709 1.449 H37 LSD 79 LSD H38 H38 H 0 1 N N N -7.647 14.348 55.676 -6.029 2.504 0.045 H38 LSD 80 LSD H39 H39 H 0 1 N N N -6.826 15.241 54.352 -6.666 2.284 1.692 H39 LSD 81 LSD H40 H40 H 0 1 N N N -5.123 14.721 54.647 -3.229 -1.199 -0.898 H40 LSD 82 LSD H41 H41 H 0 1 N N N -3.150 12.450 54.087 -2.847 -1.225 1.538 H41 LSD 83 LSD H42 H42 H 0 1 N N N -3.353 13.348 55.629 -4.584 -1.494 1.822 H42 LSD 84 LSD H43 H43 H 0 1 N N N -4.036 14.838 51.003 -5.998 -3.488 -1.436 H43 LSD 85 LSD H44 H44 H 0 1 N N N -5.540 16.397 52.168 -3.798 -4.400 -2.128 H44 LSD 86 LSD H45 H45 H 0 1 N N N -4.435 16.400 53.584 -4.112 -2.830 -2.906 H45 LSD 87 LSD H46 H46 H 0 1 N N N -3.880 17.064 52.010 -2.998 -2.930 -1.521 H46 LSD 88 LSD H47 H47 H 0 1 N N N -1.438 14.180 54.279 -2.690 -3.363 0.322 H47 LSD 89 LSD H48 H48 H 0 1 N N N -2.698 15.430 54.558 -3.377 -3.639 1.942 H48 LSD 90 LSD H49 H49 H 0 1 N N N -1.118 13.462 52.180 -5.810 -4.030 2.073 H49 LSD 91 LSD H50 H50 H 0 1 N N N -0.741 15.896 52.868 -5.471 -5.714 -0.371 H50 LSD 92 LSD H51 H51 H 0 1 N N N -2.202 16.880 52.518 -3.728 -5.419 -0.580 H51 LSD 93 LSD H52 H52 H 0 1 N N N -0.562 17.032 50.714 -3.411 -5.553 1.876 H52 LSD 94 LSD H53 H53 H 0 1 N N N -0.610 15.248 50.505 -5.154 -5.849 2.085 H53 LSD 95 LSD H54 H54 H 0 1 N N N -2.071 16.233 50.154 -4.142 -7.048 1.243 H54 LSD 96 # # 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 LSD C26 C25 SING N N 1 LSD O8 C22 SING N N 2 LSD C5 C6 DOUB Y N 3 LSD C5 C4 SING Y N 4 LSD C23 C24 SING N N 5 LSD C23 C22 SING N N 6 LSD C23 O7 SING N N 7 LSD C25 C22 SING N N 8 LSD C6 C7 SING Y N 9 LSD C34 C4 SING N N 10 LSD O5 C13 DOUB N N 11 LSD C22 C21 SING N N 12 LSD C4 C3 DOUB Y N 13 LSD O7 C19 SING N N 14 LSD C31 C30 SING N N 15 LSD C30 C14 SING N N 16 LSD C7 C8 SING N N 17 LSD C7 C2 DOUB Y N 18 LSD C8 C9 SING N N 19 LSD C3 C2 SING Y N 20 LSD C3 O3 SING N N 21 LSD C13 C14 SING N N 22 LSD C13 C12 SING N N 23 LSD O6 C18 SING N N 24 LSD O6 C15 SING N N 25 LSD C2 C1 SING N N 26 LSD C27 C18 SING N N 27 LSD C27 C28 SING N N 28 LSD C32 C12 SING N N 29 LSD C21 C20 SING N N 30 LSD C19 C18 SING N N 31 LSD C19 C20 SING N N 32 LSD C14 C15 SING N N 33 LSD C11 C12 SING N N 34 LSD C11 O4 SING N N 35 LSD C11 C10 SING N N 36 LSD C18 C17 SING N N 37 LSD C15 C16 SING N N 38 LSD C9 C10 SING N N 39 LSD O1 C1 DOUB N N 40 LSD C1 O2 SING N N 41 LSD C10 C33 SING N N 42 LSD C17 C16 SING N N 43 LSD C16 C29 SING N N 44 LSD O2 H1 SING N N 45 LSD O3 H2 SING N N 46 LSD C34 H3 SING N N 47 LSD C34 H4 SING N N 48 LSD C34 H5 SING N N 49 LSD C5 H6 SING N N 50 LSD C6 H7 SING N N 51 LSD C8 H8 SING N N 52 LSD C8 H9 SING N N 53 LSD C9 H10 SING N N 54 LSD C9 H11 SING N N 55 LSD C10 H12 SING N N 56 LSD C33 H13 SING N N 57 LSD C33 H14 SING N N 58 LSD C33 H15 SING N N 59 LSD C11 H16 SING N N 60 LSD O4 H17 SING N N 61 LSD C12 H18 SING N N 62 LSD C32 H19 SING N N 63 LSD C32 H20 SING N N 64 LSD C32 H21 SING N N 65 LSD C14 H22 SING N N 66 LSD C30 H23 SING N N 67 LSD C30 H24 SING N N 68 LSD C31 H25 SING N N 69 LSD C31 H26 SING N N 70 LSD C31 H27 SING N N 71 LSD C15 H28 SING N N 72 LSD C16 H29 SING N N 73 LSD C29 H30 SING N N 74 LSD C29 H31 SING N N 75 LSD C29 H32 SING N N 76 LSD C17 H33 SING N N 77 LSD C17 H34 SING N N 78 LSD C27 H35 SING N N 79 LSD C27 H36 SING N N 80 LSD C28 H37 SING N N 81 LSD C28 H38 SING N N 82 LSD C28 H39 SING N N 83 LSD C19 H40 SING N N 84 LSD C20 H41 SING N N 85 LSD C20 H42 SING N N 86 LSD C23 H43 SING N N 87 LSD C24 H44 SING N N 88 LSD C24 H45 SING N N 89 LSD C24 H46 SING N N 90 LSD C21 H47 SING N N 91 LSD C21 H48 SING N N 92 LSD O8 H49 SING N N 93 LSD C25 H50 SING N N 94 LSD C25 H51 SING N N 95 LSD C26 H52 SING N N 96 LSD C26 H53 SING N N 97 LSD C26 H54 SING N N 98 # # 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 LSD SMILES ACDLabs 12.01 "O=C(O)c1c(O)c(ccc1CCC(C)C(O)C(C(=O)C(CC)C2OC(CC2C)(C3OC(C)C(O)(CC)CC3)CC)C)C" LSD InChI InChI 1.03 "InChI=1S/C34H54O8/c1-9-25(31-21(6)18-34(11-3,42-31)26-16-17-33(40,10-2)23(8)41-26)30(37)22(7)28(35)19(4)12-14-24-15-13-20(5)29(36)27(24)32(38)39/h13,15,19,21-23,25-26,28,31,35-36,40H,9-12,14,16-18H2,1-8H3,(H,38,39)/t19-,21+,22+,23+,25+,26-,28+,31+,33-,34+/m1/s1" LSD InChIKey InChI 1.03 BBMULGJBVDDDNI-OWKLGTHSSA-N LSD SMILES_CANONICAL CACTVS 3.385 "CC[C@H]([C@H]1O[C@@](CC)(C[C@@H]1C)[C@H]2CC[C@](O)(CC)[C@H](C)O2)C(=O)[C@@H](C)[C@@H](O)[C@H](C)CCc3ccc(C)c(O)c3C(O)=O" LSD SMILES CACTVS 3.385 "CC[CH]([CH]1O[C](CC)(C[CH]1C)[CH]2CC[C](O)(CC)[CH](C)O2)C(=O)[CH](C)[CH](O)[CH](C)CCc3ccc(C)c(O)c3C(O)=O" LSD SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CC[C@H]([C@@H]1[C@H](C[C@@](O1)(CC)[C@H]2CC[C@@]([C@@H](O2)C)(CC)O)C)C(=O)[C@@H](C)[C@H]([C@H](C)CCc3ccc(c(c3C(=O)O)O)C)O" LSD SMILES "OpenEye OEToolkits" 1.7.6 "CCC(C1C(CC(O1)(CC)C2CCC(C(O2)C)(CC)O)C)C(=O)C(C)C(C(C)CCc3ccc(c(c3C(=O)O)O)C)O" # # 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 LSD "SYSTEMATIC NAME" ACDLabs 12.01 "6-[(3R,4S,5S,7R)-7-{(2S,3S,5S)-5-ethyl-5-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]-3-methyltetrahydrofuran-2-yl}-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxy-3-methylbenzoic acid" LSD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "6-[(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-ethyl-5-[(2R,5R,6S)-5-ethyl-6-methyl-5-oxidanyl-oxan-2-yl]-3-methyl-oxolan-2-yl]-3,5-dimethyl-4-oxidanyl-6-oxidanylidene-nonyl]-3-methyl-2-oxidanyl-benzoic acid" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site LSD "Create component" 2015-01-09 RCSB LSD "Initial release" 2015-01-21 RCSB LSD "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id LSD _pdbx_chem_comp_synonyms.name "6-[(3R,4S,5S,7R)-7-{(2S,3S,5S)-5-ethyl-5-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]-3-methyltetrahydrofuran-2-yl}-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxy-3-methylbenzoic acid" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##