data_IVC # _chem_comp.id IVC _chem_comp.name "Isovaleryl-coenzyme A" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C26 H44 N7 O17 P3 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-oxidanyl-3-phosphonooxy-oxolan-2-yl]methoxy-oxidanyl-phosphoryl]oxy-oxidanyl-phosphoryl]oxy-3,3-dimethyl-2-oxidanyl-butanoyl]amino]propanoylamino]ethyl] 3-methylbutanethioate" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2015-07-16 _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 851.651 _chem_comp.one_letter_code ? _chem_comp.three_letter_code IVC _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 5CJV _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 IVC O9 O1 O 0 1 N N N -206.289 -101.747 -35.376 -8.963 1.819 -0.384 O9 IVC 1 IVC P1 P1 P 0 1 N N N -205.638 -103.094 -35.363 -9.332 0.283 -0.697 P1 IVC 2 IVC O5 O2 O 0 1 N N N -205.352 -103.636 -36.766 -10.109 -0.277 0.432 O5 IVC 3 IVC O6 O3 O 0 1 N N N -204.333 -103.113 -34.559 -10.212 0.206 -2.044 O6 IVC 4 IVC O2 O4 O 0 1 N N N -206.602 -104.178 -34.668 -7.978 -0.565 -0.891 O2 IVC 5 IVC C1 C1 C 0 1 N N S -208.043 -104.145 -34.582 -7.035 -0.778 0.162 C1 IVC 6 IVC C2 C2 C 0 1 N N R -208.671 -104.286 -35.967 -6.771 -2.291 0.356 C2 IVC 7 IVC O3 O5 O 0 1 N N N -207.835 -105.066 -36.814 -7.833 -3.069 -0.198 O3 IVC 8 IVC C4 C3 C 0 1 N N R -209.958 -105.044 -35.627 -5.459 -2.496 -0.444 C4 IVC 9 IVC N1 N1 N 0 1 Y N N -211.117 -104.196 -35.364 -4.728 -3.664 0.054 N1 IVC 10 IVC C7 C4 C 0 1 Y N N -211.668 -103.917 -34.141 -3.723 -3.653 0.975 C7 IVC 11 IVC N2 N2 N 0 1 Y N N -212.732 -103.153 -34.194 -3.300 -4.866 1.186 N2 IVC 12 IVC C8 C5 C 0 1 Y N N -212.893 -102.909 -35.550 -4.005 -5.729 0.415 C8 IVC 13 IVC C6 C6 C 0 1 Y N N -211.902 -103.542 -36.283 -4.933 -4.969 -0.316 C6 IVC 14 IVC N3 N3 N 0 1 Y N N -211.754 -103.521 -37.612 -5.756 -5.588 -1.156 N3 IVC 15 IVC C15 C7 C 0 1 Y N N -212.711 -102.788 -38.189 -5.704 -6.895 -1.305 C15 IVC 16 IVC N4 N4 N 0 1 Y N N -213.722 -102.128 -37.617 -4.849 -7.650 -0.641 N4 IVC 17 IVC C12 C8 C 0 1 Y N N -213.846 -102.168 -36.272 -3.991 -7.121 0.225 C12 IVC 18 IVC N5 N5 N 0 1 N N N -214.861 -101.509 -35.705 -3.098 -7.921 0.916 N5 IVC 19 IVC O1 O6 O 0 1 N N N -209.700 -105.817 -34.468 -4.716 -1.284 -0.191 O1 IVC 20 IVC C3 C9 C 0 1 N N R -208.426 -105.450 -33.894 -5.659 -0.200 -0.222 C3 IVC 21 IVC C5 C10 C 0 1 N N N -208.551 -105.368 -32.393 -5.248 0.876 0.785 C5 IVC 22 IVC O4 O7 O 0 1 N N N -209.468 -104.308 -32.049 -4.028 1.487 0.358 O4 IVC 23 IVC P2 P2 P 0 1 N N N -209.268 -103.417 -30.737 -3.302 2.665 1.181 P2 IVC 24 IVC O12 O8 O 0 1 N N N -208.199 -103.909 -29.836 -4.242 3.972 1.189 O12 IVC 25 IVC O10 O9 O 0 1 N N N -208.954 -101.988 -31.178 -3.064 2.220 2.572 O10 IVC 26 IVC O7 O10 O 0 1 N N N -210.656 -103.390 -29.954 -1.896 3.020 0.482 O7 IVC 27 IVC P3 P3 P 0 1 N N N -211.025 -103.649 -28.425 -0.554 3.756 0.981 P3 IVC 28 IVC O14 O11 O 0 1 N N N -210.197 -104.753 -27.884 0.340 2.723 1.834 O14 IVC 29 IVC O13 O12 O 0 1 N N N -212.499 -104.020 -28.355 -0.913 4.915 1.829 O13 IVC 30 IVC O8 O13 O 0 1 N N N -210.835 -102.277 -27.637 0.285 4.264 -0.296 O8 IVC 31 IVC C11 C11 C 0 1 N N N -209.865 -102.218 -26.582 1.476 5.047 -0.183 C11 IVC 32 IVC C9 C12 C 0 1 N N N -209.500 -100.766 -26.280 2.017 5.356 -1.581 C9 IVC 33 IVC C13 C13 C 0 1 N N N -208.685 -100.214 -27.455 2.334 4.047 -2.306 C13 IVC 34 IVC C14 C14 C 0 1 N N N -210.795 -99.958 -26.142 0.966 6.137 -2.373 C14 IVC 35 IVC C10 C15 C 0 1 N N R -208.672 -100.652 -24.975 3.291 6.194 -1.460 C10 IVC 36 IVC O11 O14 O 0 1 N N N -208.400 -99.285 -24.725 2.971 7.470 -0.902 O11 IVC 37 IVC C16 C16 C 0 1 N N N -209.390 -101.261 -23.782 4.275 5.487 -0.564 C16 IVC 38 IVC O15 O15 O 0 1 N N N -209.356 -102.473 -23.588 4.515 5.927 0.540 O15 IVC 39 IVC N6 N6 N 0 1 N N N -210.026 -100.414 -22.976 4.888 4.365 -0.990 N6 IVC 40 IVC C17 C17 C 0 1 N N N -210.703 -100.844 -21.764 5.763 3.619 -0.083 C17 IVC 41 IVC C18 C18 C 0 1 N N N -210.209 -100.088 -20.552 6.328 2.396 -0.809 C18 IVC 42 IVC C19 C19 C 0 1 N N N -211.093 -100.308 -19.354 7.228 1.629 0.125 C19 IVC 43 IVC O16 O16 O 0 1 N N N -212.193 -100.844 -19.460 7.402 2.022 1.259 O16 IVC 44 IVC N7 N7 N 0 1 N N N -210.612 -99.890 -18.188 7.841 0.507 -0.301 N7 IVC 45 IVC C20 C20 C 0 1 N N N -211.361 -100.023 -16.949 8.717 -0.239 0.606 C20 IVC 46 IVC C21 C21 C 0 1 N N N -211.070 -98.900 -15.976 9.282 -1.461 -0.120 C21 IVC 47 IVC S1 S1 S 0 1 N N N -212.350 -98.866 -14.693 10.363 -2.383 1.001 S1 IVC 48 IVC C22 C22 C 0 1 N N N -211.746 -97.611 -13.618 10.845 -3.660 -0.033 C22 IVC 49 IVC O17 O17 O 0 1 N N N -210.722 -97.016 -13.813 10.430 -3.707 -1.172 O17 IVC 50 IVC C23 C23 C 0 1 N N N -212.645 -97.358 -12.437 11.784 -4.725 0.472 C23 IVC 51 IVC C24 C24 C 0 1 N N N -211.899 -97.269 -11.110 12.051 -5.739 -0.642 C24 IVC 52 IVC C25 C25 C 0 1 N N N -210.805 -98.311 -10.986 13.100 -6.749 -0.171 C25 IVC 53 IVC C26 C26 C 0 1 N N N -211.284 -95.895 -10.976 10.753 -6.473 -0.985 C26 IVC 54 IVC H1 H1 H 0 1 N N N -206.411 -101.463 -36.274 -8.453 2.251 -1.083 H1 IVC 55 IVC H2 H2 H 0 1 N N N -203.632 -103.455 -35.101 -11.044 0.696 -1.999 H2 IVC 56 IVC H3 H3 H 0 1 N N N -208.427 -103.266 -34.043 -7.392 -0.329 1.089 H3 IVC 57 IVC H4 H4 H 0 1 N N N -208.900 -103.299 -36.396 -6.625 -2.528 1.410 H4 IVC 58 IVC H5 H5 H 0 1 N N N -206.974 -104.668 -36.864 -7.673 -4.022 -0.182 H5 IVC 59 IVC H6 H6 H 0 1 N N N -210.190 -105.712 -36.469 -5.672 -2.603 -1.508 H6 IVC 60 IVC H7 H7 H 0 1 N N N -211.261 -104.294 -33.214 -3.336 -2.769 1.459 H7 IVC 61 IVC H8 H8 H 0 1 N N N -212.660 -102.720 -39.266 -6.385 -7.366 -1.999 H8 IVC 62 IVC H9 H9 H 0 1 N N N -215.405 -101.060 -36.414 -3.094 -8.880 0.772 H9 IVC 63 IVC H10 H10 H 0 1 N N N -215.436 -102.153 -35.201 -2.477 -7.523 1.545 H10 IVC 64 IVC H11 H11 H 0 1 N N N -207.674 -106.212 -34.145 -5.702 0.225 -1.225 H11 IVC 65 IVC H12 H12 H 0 1 N N N -208.931 -106.324 -32.003 -6.030 1.633 0.848 H12 IVC 66 IVC H13 H13 H 0 1 N N N -207.565 -105.158 -31.953 -5.102 0.421 1.765 H13 IVC 67 IVC H14 H14 H 0 1 N N N -207.543 -103.231 -29.722 -4.440 4.319 0.308 H14 IVC 68 IVC H15 H15 H 0 1 N N N -210.761 -105.465 -27.605 0.612 1.938 1.340 H15 IVC 69 IVC H16 H16 H 0 1 N N N -210.284 -102.683 -25.677 1.250 5.980 0.333 H16 IVC 70 IVC H17 H17 H 0 1 N N N -208.961 -102.763 -26.889 2.224 4.491 0.381 H17 IVC 71 IVC H18 H18 H 0 1 N N N -208.413 -99.167 -27.254 1.411 3.493 -2.476 H18 IVC 72 IVC H19 H19 H 0 1 N N N -207.771 -100.813 -27.580 2.806 4.267 -3.263 H19 IVC 73 IVC H20 H20 H 0 1 N N N -209.286 -100.266 -28.375 3.010 3.448 -1.696 H20 IVC 74 IVC H21 H21 H 0 1 N N N -211.384 -100.350 -25.300 0.652 7.009 -1.799 H21 IVC 75 IVC H22 H22 H 0 1 N N N -210.550 -98.902 -25.958 1.393 6.461 -3.322 H22 IVC 76 IVC H23 H23 H 0 1 N N N -211.380 -100.042 -27.070 0.104 5.497 -2.562 H23 IVC 77 IVC H24 H24 H 0 1 N N N -207.728 -101.196 -25.124 3.731 6.330 -2.448 H24 IVC 78 IVC H25 H25 H 0 1 N N N -207.892 -99.204 -23.926 2.574 7.426 -0.022 H25 IVC 79 IVC H26 H26 H 0 1 N N N -210.039 -99.443 -23.214 4.749 4.051 -1.897 H26 IVC 80 IVC H27 H27 H 0 1 N N N -211.783 -100.670 -21.878 6.583 4.260 0.240 H27 IVC 81 IVC H28 H28 H 0 1 N N N -210.519 -101.918 -21.614 5.193 3.293 0.787 H28 IVC 82 IVC H29 H29 H 0 1 N N N -209.192 -100.429 -20.311 5.508 1.755 -1.132 H29 IVC 83 IVC H30 H30 H 0 1 N N N -210.189 -99.014 -20.787 6.899 2.722 -1.679 H30 IVC 84 IVC H31 H31 H 0 1 N N N -209.705 -99.470 -18.162 7.703 0.193 -1.209 H31 IVC 85 IVC H32 H32 H 0 1 N N N -212.436 -100.018 -17.183 9.537 0.403 0.929 H32 IVC 86 IVC H33 H33 H 0 1 N N N -211.094 -100.979 -16.475 8.146 -0.564 1.476 H33 IVC 87 IVC H34 H34 H 0 1 N N N -210.087 -99.064 -15.510 8.462 -2.103 -0.443 H34 IVC 88 IVC H35 H35 H 0 1 N N N -211.065 -97.941 -16.514 9.852 -1.136 -0.990 H35 IVC 89 IVC H36 H36 H 0 1 N N N -213.176 -96.409 -12.601 12.724 -4.265 0.778 H36 IVC 90 IVC H37 H37 H 0 1 N N N -213.373 -98.180 -12.372 11.333 -5.232 1.325 H37 IVC 91 IVC H38 H38 H 0 1 N N N -212.620 -97.415 -10.292 12.419 -5.219 -1.526 H38 IVC 92 IVC H39 H39 H 0 1 N N N -210.302 -98.201 -10.014 12.732 -7.269 0.713 H39 IVC 93 IVC H40 H40 H 0 1 N N N -211.246 -99.316 -11.059 13.290 -7.471 -0.965 H40 IVC 94 IVC H41 H41 H 0 1 N N N -210.073 -98.172 -11.795 14.024 -6.226 0.073 H41 IVC 95 IVC H42 H42 H 0 1 N N N -210.745 -95.826 -10.020 10.386 -6.993 -0.101 H42 IVC 96 IVC H43 H43 H 0 1 N N N -210.582 -95.725 -11.806 10.007 -5.753 -1.320 H43 IVC 97 IVC H44 H44 H 0 1 N N N -212.078 -95.134 -11.005 10.944 -7.195 -1.779 H44 IVC 98 # # 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 IVC C15 N4 DOUB Y N 1 IVC C15 N3 SING Y N 2 IVC N4 C12 SING Y N 3 IVC N3 C6 DOUB Y N 4 IVC O3 C2 SING N N 5 IVC O5 P1 DOUB N N 6 IVC C6 C8 SING Y N 7 IVC C6 N1 SING Y N 8 IVC C12 N5 SING N N 9 IVC C12 C8 DOUB Y N 10 IVC C2 C4 SING N N 11 IVC C2 C1 SING N N 12 IVC C4 N1 SING N N 13 IVC C4 O1 SING N N 14 IVC C8 N2 SING Y N 15 IVC O9 P1 SING N N 16 IVC N1 C7 SING Y N 17 IVC P1 O2 SING N N 18 IVC P1 O6 SING N N 19 IVC O2 C1 SING N N 20 IVC C1 C3 SING N N 21 IVC O1 C3 SING N N 22 IVC N2 C7 DOUB Y N 23 IVC C3 C5 SING N N 24 IVC C5 O4 SING N N 25 IVC O4 P2 SING N N 26 IVC O10 P2 DOUB N N 27 IVC P2 O7 SING N N 28 IVC P2 O12 SING N N 29 IVC O7 P3 SING N N 30 IVC P3 O13 DOUB N N 31 IVC P3 O14 SING N N 32 IVC P3 O8 SING N N 33 IVC O8 C11 SING N N 34 IVC C13 C9 SING N N 35 IVC C11 C9 SING N N 36 IVC C9 C14 SING N N 37 IVC C9 C10 SING N N 38 IVC C10 O11 SING N N 39 IVC C10 C16 SING N N 40 IVC C16 O15 DOUB N N 41 IVC C16 N6 SING N N 42 IVC N6 C17 SING N N 43 IVC C17 C18 SING N N 44 IVC C18 C19 SING N N 45 IVC O16 C19 DOUB N N 46 IVC C19 N7 SING N N 47 IVC N7 C20 SING N N 48 IVC C20 C21 SING N N 49 IVC C21 S1 SING N N 50 IVC S1 C22 SING N N 51 IVC O17 C22 DOUB N N 52 IVC C22 C23 SING N N 53 IVC C23 C24 SING N N 54 IVC C24 C25 SING N N 55 IVC C24 C26 SING N N 56 IVC O9 H1 SING N N 57 IVC O6 H2 SING N N 58 IVC C1 H3 SING N N 59 IVC C2 H4 SING N N 60 IVC O3 H5 SING N N 61 IVC C4 H6 SING N N 62 IVC C7 H7 SING N N 63 IVC C15 H8 SING N N 64 IVC N5 H9 SING N N 65 IVC N5 H10 SING N N 66 IVC C3 H11 SING N N 67 IVC C5 H12 SING N N 68 IVC C5 H13 SING N N 69 IVC O12 H14 SING N N 70 IVC O14 H15 SING N N 71 IVC C11 H16 SING N N 72 IVC C11 H17 SING N N 73 IVC C13 H18 SING N N 74 IVC C13 H19 SING N N 75 IVC C13 H20 SING N N 76 IVC C14 H21 SING N N 77 IVC C14 H22 SING N N 78 IVC C14 H23 SING N N 79 IVC C10 H24 SING N N 80 IVC O11 H25 SING N N 81 IVC N6 H26 SING N N 82 IVC C17 H27 SING N N 83 IVC C17 H28 SING N N 84 IVC C18 H29 SING N N 85 IVC C18 H30 SING N N 86 IVC N7 H31 SING N N 87 IVC C20 H32 SING N N 88 IVC C20 H33 SING N N 89 IVC C21 H34 SING N N 90 IVC C21 H35 SING N N 91 IVC C23 H36 SING N N 92 IVC C23 H37 SING N N 93 IVC C24 H38 SING N N 94 IVC C25 H39 SING N N 95 IVC C25 H40 SING N N 96 IVC C25 H41 SING N N 97 IVC C26 H42 SING N N 98 IVC C26 H43 SING N N 99 IVC C26 H44 SING N N 100 # # 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 IVC SMILES ACDLabs 12.01 "OP(OC1C(OC(C1O)n2cnc3c2ncnc3N)COP(OP(=O)(O)OCC(C)(C(O)C(=O)NCCC(NCCSC(CC(C)C)=O)=O)C)(O)=O)(O)=O" IVC InChI InChI 1.03 "InChI=1S/C26H44N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h12-15,19-21,25,36-37H,5-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21+,25-/m1/s1" IVC InChIKey InChI 1.03 UYVZIWWBJMYRCD-ZMHDXICWSA-N IVC SMILES_CANONICAL CACTVS 3.385 "CC(C)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)CO[P](O)(=O)O[P](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O[P](O)(O)=O)n2cnc3c(N)ncnc23" IVC SMILES CACTVS 3.385 "CC(C)CC(=O)SCCNC(=O)CCNC(=O)[CH](O)C(C)(C)CO[P](O)(=O)O[P](O)(=O)OC[CH]1O[CH]([CH](O)[CH]1O[P](O)(O)=O)n2cnc3c(N)ncnc23" IVC SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "CC(C)CC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)O" IVC SMILES "OpenEye OEToolkits" 1.9.2 "CC(C)CC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)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 IVC "SYSTEMATIC NAME" ACDLabs 12.01 "S-{(3S,5S,9R)-1-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-3,5,9-trihydroxy-8,8-dimethyl-3,5-dioxido-10,14-dioxo-2,4,6-trioxa-11,15-diaza-3lambda~5~,5lambda~5~-diphosphaheptadecan-17-yl} 3-methylbutanethioate (non-preferred name)" IVC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-oxidanyl-3-phosphonooxy-oxolan-2-yl]methoxy-oxidanyl-phosphoryl]oxy-oxidanyl-phosphoryl]oxy-3,3-dimethyl-2-oxidanyl-butanoyl]amino]propanoylamino]ethyl] 3-methylbutanethioate" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site IVC "Create component" 2015-07-16 RCSB IVC "Initial release" 2015-09-09 RCSB IVC "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id IVC _pdbx_chem_comp_synonyms.name "S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-oxidanyl-3-phosphonooxy-oxolan-2-yl]methoxy-oxidanyl-phosphoryl]oxy-oxidanyl-phosphoryl]oxy-3,3-dimethyl-2-oxidanyl-butanoyl]amino]propanoylamino]ethyl] 3-methylbutanethioate" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##