data_0E9 # _chem_comp.id 0E9 _chem_comp.name "benzyl [(1R,4S,6S,9R)-4,6-dibenzyl-5-hydroxy-1,9-bis(1-methylethyl)-2,8,11-trioxo-13-phenyl-12-oxa-3,7,10-triazatridec-1-yl]carbamate" _chem_comp.type peptide-like _chem_comp.pdbx_type HETAIN _chem_comp.formula "C43 H52 N4 O7" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms A-74704 _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2008-11-07 _chem_comp.pdbx_modified_date 2021-03-01 _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 736.896 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 0E9 _chem_comp.pdbx_model_coordinates_details "not provided" _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 9HVP _chem_comp.pdbx_subcomponent_list "PHQ VAL COR VAL PHQ" _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 0E9 C1 C1 C 0 1 N N N -12.083 14.594 33.261 -7.058 -0.798 0.377 C1 PHQ 1 0E9 O1 O1 O 0 1 N N N -12.600 15.649 33.662 -7.511 -0.465 1.454 O1 PHQ 2 0E9 O2 O2 O 0 1 N N N -12.601 13.312 33.668 -7.888 -1.055 -0.652 O2 PHQ 3 0E9 C2 C2 C 0 1 N N N -13.299 13.009 34.848 -9.311 -0.914 -0.401 C2 PHQ 4 0E9 C3 C3 C 0 1 Y N N -12.826 11.956 35.916 -10.077 -1.240 -1.658 C3 PHQ 5 0E9 C4 C4 C 0 1 Y N N -12.548 10.611 35.557 -10.483 -2.538 -1.903 C4 PHQ 6 0E9 C5 C5 C 0 1 Y N N -12.215 9.655 36.514 -11.186 -2.837 -3.055 C5 PHQ 7 0E9 C6 C6 C 0 1 Y N N -12.138 10.020 37.837 -11.482 -1.837 -3.963 C6 PHQ 8 0E9 C7 C7 C 0 1 Y N N -12.395 11.324 38.205 -11.077 -0.539 -3.717 C7 PHQ 9 0E9 C8 C8 C 0 1 Y N N -12.736 12.301 37.276 -10.378 -0.239 -2.563 C8 PHQ 10 0E9 N N1 N 0 1 N N N -10.976 14.541 32.506 -5.725 -0.904 0.209 N VAL 11 0E9 CA C9 C 0 1 N N S -10.225 15.690 32.020 -4.821 -0.618 1.327 CA VAL 12 0E9 C C10 C 0 1 N N N -10.159 15.551 30.515 -3.474 -0.206 0.791 C VAL 13 0E9 O O3 O 0 1 N N N -9.467 14.684 29.968 -3.153 -0.508 -0.338 O VAL 14 0E9 CB C11 C 0 1 N N N -8.749 15.738 32.572 -4.665 -1.872 2.190 CB VAL 15 0E9 CG1 C12 C 0 1 N N N -8.076 17.032 32.146 -3.777 -1.555 3.394 CG1 VAL 16 0E9 CG2 C13 C 0 1 N N N -8.665 15.646 34.076 -6.041 -2.330 2.678 CG2 VAL 17 0E9 C11 C14 C 0 1 N N N -12.397 16.245 27.955 -1.006 2.326 1.670 C1 COR 18 0E9 C21 C15 C 0 1 N N S -10.988 16.530 28.401 -1.364 0.991 1.013 C2 COR 19 0E9 N2 N2 N 0 1 N N N -10.920 16.447 29.878 -2.627 0.497 1.568 N2 COR 20 0E9 C31 C16 C 0 1 N N N -10.355 17.698 27.688 -0.254 -0.026 1.288 C3 COR 21 0E9 O3 O5 O 0 1 N N N -10.555 18.735 28.572 -0.615 -1.288 0.724 O3 COR 22 0E9 C41 C17 C 0 1 N N S -8.816 17.540 27.467 1.051 0.461 0.656 C4 COR 23 0E9 N4 N3 N 0 1 N N N -8.621 17.469 26.005 2.136 -0.458 1.007 N4 COR 24 0E9 C51 C18 C 0 1 N N N -7.911 18.643 28.082 0.895 0.508 -0.865 C5 COR 25 0E9 C1A C19 C 0 1 Y N N -12.730 14.826 28.435 -2.037 3.361 1.297 C1A COR 26 0E9 C2A C20 C 0 1 Y N N -12.145 13.740 27.794 -3.157 3.536 2.088 C2A COR 27 0E9 C3A C21 C 0 1 Y N N -12.295 12.483 28.330 -4.102 4.485 1.746 C3A COR 28 0E9 C4A C22 C 0 1 Y N N -13.033 12.300 29.488 -3.927 5.259 0.614 C4A COR 29 0E9 C5A C23 C 0 1 Y N N -13.628 13.379 30.108 -2.806 5.084 -0.176 C5A COR 30 0E9 C6A C24 C 0 1 Y N N -13.481 14.645 29.593 -1.859 4.138 0.168 C6A COR 31 0E9 C1B C25 C 0 1 Y N N -6.547 18.738 27.395 2.144 1.084 -1.481 C1B COR 32 0E9 C2B C26 C 0 1 Y N N -6.367 19.614 26.338 3.183 0.248 -1.845 C2B COR 33 0E9 C3B C27 C 0 1 Y N N -5.241 19.521 25.549 4.329 0.776 -2.410 C3B COR 34 0E9 C4B C28 C 0 1 Y N N -4.287 18.547 25.832 4.436 2.140 -2.611 C4B COR 35 0E9 C5B C29 C 0 1 Y N N -4.438 17.673 26.896 3.396 2.975 -2.247 C5B COR 36 0E9 C6B C30 C 0 1 Y N N -5.569 17.777 27.680 2.249 2.447 -1.686 C6B COR 37 0E9 N1 N4 N 0 1 N N N -7.043 16.775 23.406 5.764 -0.495 0.658 N VAL 38 0E9 CA1 C31 C 0 1 N N S -8.419 16.522 23.803 4.536 -0.990 1.285 CA VAL 39 0E9 C9 C32 C 0 1 N N N -8.366 16.331 25.321 3.412 -0.023 1.019 C VAL 40 0E9 O4 O6 O 0 1 N N N -7.988 15.256 25.827 3.654 1.148 0.816 O VAL 41 0E9 CB1 C33 C 0 1 N N N -9.121 15.306 23.167 4.750 -1.121 2.794 CB VAL 42 0E9 CG11 C34 C 0 0 N N N -10.599 15.507 23.407 3.490 -1.699 3.440 CG1 VAL 43 0E9 CG21 C35 C 0 0 N N N -8.755 15.111 21.691 5.934 -2.053 3.062 CG2 VAL 44 0E9 C12 C36 C 0 1 N N N -6.751 17.802 22.604 6.740 -1.359 0.314 C1 PHQ 45 0E9 O11 O8 O 0 1 N N N -7.563 18.410 21.875 6.602 -2.547 0.524 O1 PHQ 46 0E9 O21 O9 O 0 1 N N N -5.400 18.133 22.514 7.869 -0.904 -0.262 O2 PHQ 47 0E9 C22 C37 C 0 1 N N N -4.683 18.441 21.398 8.878 -1.890 -0.605 C2 PHQ 48 0E9 C32 C38 C 0 1 Y N N -3.283 17.845 21.482 10.061 -1.201 -1.235 C3 PHQ 49 0E9 C42 C39 C 0 1 Y N N -2.208 18.660 21.769 11.101 -0.753 -0.443 C4 PHQ 50 0E9 C52 C40 C 0 1 Y N N -0.979 18.067 21.960 12.186 -0.120 -1.020 C5 PHQ 51 0E9 C61 C41 C 0 1 Y N N -0.823 16.692 21.873 12.231 0.063 -2.390 C6 PHQ 52 0E9 C71 C42 C 0 1 Y N N -1.904 15.897 21.579 11.191 -0.386 -3.182 C7 PHQ 53 0E9 C81 C43 C 0 1 Y N N -3.138 16.468 21.374 10.108 -1.023 -2.605 C8 PHQ 54 0E9 H21 H2 H 0 1 N N N -13.349 13.961 35.396 -9.609 -1.598 0.393 H21 PHQ 55 0E9 H22 H3 H 0 1 N N N -14.197 12.518 34.446 -9.528 0.111 -0.099 H22 PHQ 56 0E9 H41 H4 H 0 1 N N N -12.596 10.322 34.517 -10.252 -3.319 -1.194 H41 PHQ 57 0E9 H51 H5 H 0 1 N N N -12.019 8.635 36.219 -11.502 -3.852 -3.247 H51 PHQ 58 0E9 H61 H6 H 0 1 N N N -11.877 9.287 38.586 -12.030 -2.071 -4.864 H61 PHQ 59 0E9 H71 H7 H 0 1 N N N -12.329 11.595 39.248 -11.308 0.242 -4.427 H71 PHQ 60 0E9 H81 H8 H 0 1 N N N -12.930 13.314 37.596 -10.064 0.776 -2.369 H81 PHQ 61 0E9 H H9 H 0 1 N N N -10.637 13.634 32.255 -5.363 -1.169 -0.651 H VAL 62 0E9 HA H11 H 0 1 N N N -10.727 16.609 32.356 -5.235 0.189 1.931 HA VAL 63 0E9 HB H12 H 0 1 N N N -8.243 14.858 32.148 -4.207 -2.665 1.599 HB VAL 64 0E9 HG11 H13 H 0 0 N N N -7.913 17.669 33.028 -4.238 -0.766 3.988 HG11 VAL 65 0E9 HG12 H14 H 0 0 N N N -7.108 16.804 31.675 -3.661 -2.450 4.006 HG12 VAL 66 0E9 HG13 H15 H 0 0 N N N -8.719 17.560 31.426 -2.798 -1.224 3.046 HG13 VAL 67 0E9 HG21 H16 H 0 0 N N N -8.645 14.589 34.379 -6.674 -2.556 1.819 HG21 VAL 68 0E9 HG22 H17 H 0 0 N N N -7.748 16.144 34.423 -5.930 -3.224 3.292 HG22 VAL 69 0E9 HG23 H18 H 0 0 N N N -9.542 16.138 34.523 -6.500 -1.537 3.269 HG23 VAL 70 0E9 H11 H20 H 0 1 N N N -13.094 16.973 28.395 -0.988 2.205 2.753 H11 COR 71 0E9 H12 H21 H 0 1 N N N -12.489 16.325 26.862 -0.025 2.650 1.323 H12 COR 72 0E9 H2 H22 H 0 1 N N N -10.292 15.747 28.064 -1.470 1.132 -0.062 H2 COR 73 0E9 HN22 H24 H 0 0 N N N -11.465 17.086 30.420 -2.853 0.677 2.494 HN22 COR 74 0E9 H3 H25 H 0 1 N N N -10.788 17.825 26.685 -0.119 -0.134 2.364 H3 COR 75 0E9 HO3 H26 H 0 1 N N N -10.601 18.393 29.457 -0.752 -1.267 -0.233 HO3 COR 76 0E9 H4 H27 H 0 1 N N N -8.496 16.635 28.004 1.285 1.458 1.028 H4 COR 77 0E9 HN42 H29 H 0 0 N N N -8.682 18.321 25.485 1.937 -1.381 1.231 HN42 COR 78 0E9 H511 H30 H 0 0 N N N -8.422 19.611 27.975 0.734 -0.501 -1.245 H51 COR 79 0E9 H52 H31 H 0 1 N N N -7.737 18.383 29.136 0.041 1.134 -1.123 H52 COR 80 0E9 H2A H32 H 0 1 N N N -11.579 13.882 26.885 -3.294 2.932 2.972 H2A COR 81 0E9 H3A H33 H 0 1 N N N -11.835 11.634 27.846 -4.978 4.622 2.364 H3A COR 82 0E9 H4A H34 H 0 1 N N N -13.143 11.310 29.906 -4.666 6.000 0.347 H4A COR 83 0E9 H5A H35 H 0 1 N N N -14.213 13.228 31.003 -2.670 5.689 -1.060 H5A COR 84 0E9 H6A H36 H 0 1 N N N -13.943 15.490 30.082 -0.982 4.004 -0.447 H6A COR 85 0E9 H2B H37 H 0 1 N N N -7.110 20.371 26.132 3.100 -0.817 -1.688 H2B COR 86 0E9 H3B H38 H 0 1 N N N -5.100 20.197 24.719 5.141 0.123 -2.694 H3B COR 87 0E9 H4B H39 H 0 1 N N N -3.409 18.471 25.208 5.331 2.552 -3.052 H4B COR 88 0E9 H5B H40 H 0 1 N N N -3.687 16.926 27.107 3.480 4.040 -2.404 H5B COR 89 0E9 H6B H41 H 0 1 N N N -5.701 17.112 28.520 1.435 3.099 -1.406 H6B COR 90 0E9 H1 H42 H 0 1 N N N -6.312 16.177 23.735 5.875 0.454 0.491 H VAL 91 0E9 HA1 H44 H 0 1 N N N -9.023 17.372 23.451 4.283 -1.965 0.868 HA VAL 92 0E9 HB1 H45 H 0 1 N N N -8.785 14.366 23.630 4.958 -0.139 3.218 HB VAL 93 0E9 HG14 H46 H 0 0 N N N -10.792 15.556 24.489 3.220 -2.630 2.941 HG11 VAL 94 0E9 HG15 H47 H 0 0 N N N -10.923 16.446 22.934 3.679 -1.895 4.496 HG12 VAL 95 0E9 HG16 H48 H 0 0 N N N -11.158 14.665 22.973 2.672 -0.985 3.344 HG13 VAL 96 0E9 HG24 H49 H 0 0 N N N -9.674 15.064 21.088 6.832 -1.640 2.602 HG21 VAL 97 0E9 HG25 H50 H 0 0 N N N -8.137 15.955 21.352 6.087 -2.146 4.137 HG22 VAL 98 0E9 HG26 H51 H 0 0 N N N -8.192 14.173 21.574 5.727 -3.035 2.638 HG23 VAL 99 0E9 H211 H54 H 0 0 N N N -5.197 18.032 20.515 9.198 -2.411 0.297 H21 PHQ 100 0E9 H221 H55 H 0 0 N N N -4.600 19.535 21.318 8.458 -2.608 -1.310 H22 PHQ 101 0E9 H411 H56 H 0 0 N N N -2.326 19.731 21.842 11.066 -0.896 0.627 H41 PHQ 102 0E9 H512 H57 H 0 0 N N N -0.121 18.685 22.182 12.999 0.231 -0.402 H51 PHQ 103 0E9 H611 H58 H 0 0 N N N 0.147 16.247 22.036 13.079 0.558 -2.841 H61 PHQ 104 0E9 H711 H59 H 0 0 N N N -1.785 14.826 21.509 11.226 -0.243 -4.252 H71 PHQ 105 0E9 H811 H60 H 0 0 N N N -3.989 15.849 21.131 9.297 -1.377 -3.224 H81 PHQ 106 # # 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 0E9 C1 O1 DOUB N N 1 0E9 C1 O2 SING N N 2 0E9 O2 C2 SING N N 3 0E9 C2 C3 SING N N 4 0E9 C2 H21 SING N N 5 0E9 C2 H22 SING N N 6 0E9 C3 C4 DOUB Y N 7 0E9 C3 C8 SING Y N 8 0E9 C4 C5 SING Y N 9 0E9 C4 H41 SING N N 10 0E9 C5 C6 DOUB Y N 11 0E9 C5 H51 SING N N 12 0E9 C6 C7 SING Y N 13 0E9 C6 H61 SING N N 14 0E9 C7 C8 DOUB Y N 15 0E9 C7 H71 SING N N 16 0E9 C8 H81 SING N N 17 0E9 N CA SING N N 18 0E9 N H SING N N 19 0E9 CA C SING N N 20 0E9 CA CB SING N N 21 0E9 CA HA SING N N 22 0E9 C O DOUB N N 23 0E9 CB CG1 SING N N 24 0E9 CB CG2 SING N N 25 0E9 CB HB SING N N 26 0E9 CG1 HG11 SING N N 27 0E9 CG1 HG12 SING N N 28 0E9 CG1 HG13 SING N N 29 0E9 CG2 HG21 SING N N 30 0E9 CG2 HG22 SING N N 31 0E9 CG2 HG23 SING N N 32 0E9 C11 C21 SING N N 33 0E9 C11 C1A SING N N 34 0E9 C11 H11 SING N N 35 0E9 C11 H12 SING N N 36 0E9 C21 N2 SING N N 37 0E9 C21 C31 SING N N 38 0E9 C21 H2 SING N N 39 0E9 N2 HN22 SING N N 40 0E9 C31 O3 SING N N 41 0E9 C31 C41 SING N N 42 0E9 C31 H3 SING N N 43 0E9 O3 HO3 SING N N 44 0E9 C41 N4 SING N N 45 0E9 C41 C51 SING N N 46 0E9 C41 H4 SING N N 47 0E9 N4 HN42 SING N N 48 0E9 C51 C1B SING N N 49 0E9 C51 H511 SING N N 50 0E9 C51 H52 SING N N 51 0E9 C1A C2A DOUB Y N 52 0E9 C1A C6A SING Y N 53 0E9 C2A C3A SING Y N 54 0E9 C2A H2A SING N N 55 0E9 C3A C4A DOUB Y N 56 0E9 C3A H3A SING N N 57 0E9 C4A C5A SING Y N 58 0E9 C4A H4A SING N N 59 0E9 C5A C6A DOUB Y N 60 0E9 C5A H5A SING N N 61 0E9 C6A H6A SING N N 62 0E9 C1B C2B DOUB Y N 63 0E9 C1B C6B SING Y N 64 0E9 C2B C3B SING Y N 65 0E9 C2B H2B SING N N 66 0E9 C3B C4B DOUB Y N 67 0E9 C3B H3B SING N N 68 0E9 C4B C5B SING Y N 69 0E9 C4B H4B SING N N 70 0E9 C5B C6B DOUB Y N 71 0E9 C5B H5B SING N N 72 0E9 C6B H6B SING N N 73 0E9 N1 CA1 SING N N 74 0E9 N1 H1 SING N N 75 0E9 CA1 C9 SING N N 76 0E9 CA1 CB1 SING N N 77 0E9 CA1 HA1 SING N N 78 0E9 C9 O4 DOUB N N 79 0E9 CB1 CG11 SING N N 80 0E9 CB1 CG21 SING N N 81 0E9 CB1 HB1 SING N N 82 0E9 CG11 HG14 SING N N 83 0E9 CG11 HG15 SING N N 84 0E9 CG11 HG16 SING N N 85 0E9 CG21 HG24 SING N N 86 0E9 CG21 HG25 SING N N 87 0E9 CG21 HG26 SING N N 88 0E9 C12 O11 DOUB N N 89 0E9 C12 O21 SING N N 90 0E9 O21 C22 SING N N 91 0E9 C22 C32 SING N N 92 0E9 C22 H211 SING N N 93 0E9 C22 H221 SING N N 94 0E9 C32 C42 DOUB Y N 95 0E9 C32 C81 SING Y N 96 0E9 C42 C52 SING Y N 97 0E9 C42 H411 SING N N 98 0E9 C52 C61 DOUB Y N 99 0E9 C52 H512 SING N N 100 0E9 C61 C71 SING Y N 101 0E9 C61 H611 SING N N 102 0E9 C71 C81 DOUB Y N 103 0E9 C71 H711 SING N N 104 0E9 C81 H811 SING N N 105 0E9 C1 N SING N N 106 0E9 C N2 SING N N 107 0E9 N4 C9 SING N N 108 0E9 N1 C12 SING N N 109 # # 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 0E9 SMILES ACDLabs 10.04 "O=C(OCc1ccccc1)NC(C(=O)NC(Cc2ccccc2)C(O)C(NC(=O)C(NC(=O)OCc3ccccc3)C(C)C)Cc4ccccc4)C(C)C" 0E9 SMILES_CANONICAL CACTVS 3.352 "CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](Cc2ccccc2)[C@@H](O)[C@H](Cc3ccccc3)NC(=O)[C@@H](NC(=O)OCc4ccccc4)C(C)C" 0E9 SMILES CACTVS 3.352 "CC(C)[CH](NC(=O)OCc1ccccc1)C(=O)N[CH](Cc2ccccc2)[CH](O)[CH](Cc3ccccc3)NC(=O)[CH](NC(=O)OCc4ccccc4)C(C)C" 0E9 InChI InChI 1.03 "InChI=1S/C43H52N4O7/c1-29(2)37(46-42(51)53-27-33-21-13-7-14-22-33)40(49)44-35(25-31-17-9-5-10-18-31)39(48)36(26-32-19-11-6-12-20-32)45-41(50)38(30(3)4)47-43(52)54-28-34-23-15-8-16-24-34/h5-24,29-30,35-39,48H,25-28H2,1-4H3,(H,44,49)(H,45,50)(H,46,51)(H,47,52)/t35-,36-,37-,38-/m0/s1" 0E9 InChIKey InChI 1.03 GEANBHANAKKWSL-ZQWQDMLBSA-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 0E9 "SYSTEMATIC NAME" ACDLabs 10.04 "benzyl [(1R,4S,6S,9R)-4,6-dibenzyl-5-hydroxy-1,9-bis(1-methylethyl)-2,8,11-trioxo-13-phenyl-12-oxa-3,7,10-triazatridec-1-yl]carbamate (non-preferred name)" 0E9 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "phenylmethyl N-[(2S)-1-[[(2S,4S)-3-hydroxy-4-[[(2S)-3-methyl-2-phenylmethoxycarbonylamino-butanoyl]amino]-1,5-diphenyl-pentan-2-yl]amino]-3-methyl-1-oxo-butan-2-yl]carbamate" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 0E9 "Create component" 2008-11-07 RCSB 0E9 "Modify aromatic_flag" 2011-06-04 RCSB 0E9 "Modify descriptor" 2011-06-04 RCSB 0E9 "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 0E9 _pdbx_chem_comp_synonyms.name A-74704 _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##