data_18C # _chem_comp.id 18C _chem_comp.name "N-((E,2S,3R)-1,3-DIHYDROXYOCTADEC-4-EN-2-YL)STEARAMIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C36 H71 N O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "C18-CERAMIDE; N-STEAROYL-D-ERYTHRO-SPHINGOSINE; (2S,3R,4E)-2-STEAROYLAMINOOCTADEC-4-ENE-1,3-DIOL; (2S,3R,4E)-2-STEAROYLAMINO-1,3-OCTADEC-4-ENEDIOL" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2007-07-16 _chem_comp.pdbx_modified_date 2020-05-26 _chem_comp.pdbx_ambiguous_flag ? _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 565.954 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 18C _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details "OpenEye/OEToolkits V1.4.2" _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code ? _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 18C O19 O19 O 0 1 N N N 17.784 -0.775 -0.607 -13.003 -1.185 3.345 O19 18C 1 18C C19 C19 C 0 1 N N N 17.624 -1.974 -0.941 -14.070 -1.008 3.929 C19 18C 2 18C N2 N2 N 0 1 N N N 18.349 -3.029 -0.478 -14.412 0.117 4.659 N2 18C 3 18C C2 C2 C 0 1 N N S 19.562 -2.984 0.370 -13.529 1.249 4.825 C2 18C 4 18C C1 C1 C 0 1 N N N 19.954 -4.382 0.852 -14.379 2.521 4.943 C1 18C 5 18C O1 O1 O 0 1 N N N 20.244 -5.257 -0.252 -15.211 2.669 3.801 O1 18C 6 18C C3 C3 C 0 1 N N R 20.784 -2.237 -0.200 -12.622 0.989 6.051 C3 18C 7 18C C4 C4 C 0 1 N N N 20.763 -2.017 -1.706 -11.597 2.065 6.282 C4 18C 8 18C C5 C5 C 0 1 N N N 20.623 -0.789 -2.262 -10.268 1.915 6.388 C5 18C 9 18C C6 C6 C 0 1 N N N 20.566 -0.521 -3.766 -9.244 2.988 6.619 C6 18C 10 18C C7 C7 C 0 1 N N N 21.941 -0.245 -4.368 -8.477 2.748 7.920 C7 18C 11 18C C8 C8 C 0 1 N N N 22.001 -0.503 -5.884 -7.412 3.812 8.204 C8 18C 12 18C C9 C9 C 0 1 N N N 23.408 -0.275 -6.473 -6.568 3.593 9.463 C9 18C 13 18C C10 C10 C 0 1 N N N 23.619 -0.756 -7.911 -5.538 4.698 9.707 C10 18C 14 18C C11 C11 C 0 1 N N N 22.294 -0.971 -8.646 -4.709 4.416 10.963 C11 18C 15 18C C12 C12 C 0 1 N N N 22.350 -2.003 -9.785 -3.658 5.505 11.188 C12 18C 16 18C C13 C13 C 0 1 N N N 21.008 -2.125 -10.526 -2.845 5.312 12.471 C13 18C 17 18C C14 C14 C 0 1 N N N 20.232 -3.381 -10.126 -1.845 6.440 12.734 C14 18C 18 18C C15 C15 C 0 1 N N N 18.952 -3.543 -10.949 -1.054 6.190 14.020 C15 18C 19 18C C16 C16 C 0 1 N N N 18.645 -5.012 -11.276 -0.080 7.334 14.305 C16 18C 20 18C C17 C17 C 0 1 N N N 17.281 -5.183 -11.946 0.735 7.069 15.571 C17 18C 21 18C C18 C18 C 0 1 N N N 17.246 -6.468 -12.737 1.728 8.188 15.840 C18 18C 22 18C O3 O3 O 0 1 N N N 20.651 -1.010 0.470 -13.433 0.958 7.233 O3 18C 23 18C C20 C20 C 0 1 N N N 16.580 -2.401 -1.959 -15.170 -2.051 3.903 C20 18C 24 18C C21 C21 C 0 1 N N N 16.638 -1.571 -3.250 -14.783 -3.290 3.095 C21 18C 25 18C C22 C22 C 0 1 N N N 16.003 -2.343 -4.419 -15.892 -4.347 3.084 C22 18C 26 18C C23 C23 C 0 1 N N N 15.889 -1.518 -5.694 -15.525 -5.604 2.289 C23 18C 27 18C C24 C24 C 0 1 N N N 17.258 -1.292 -6.319 -16.623 -6.669 2.298 C24 18C 28 18C C25 C25 C 0 1 N N N 17.127 -1.034 -7.811 -16.215 -7.891 1.472 C25 18C 29 18C C26 C26 C 0 1 N N N 17.945 0.184 -8.217 -17.299 -8.972 1.505 C26 18C 30 18C C27 C27 C 0 1 N N N 17.824 0.444 -9.712 -16.903 -10.179 0.652 C27 18C 31 18C C28 C28 C 0 1 N N N 18.585 1.686 -10.162 -17.920 -11.323 0.707 C28 18C 32 18C C29 C29 C 0 1 N N N 20.002 1.731 -9.611 -17.489 -12.559 -0.087 C29 18C 33 18C C30 C30 C 0 1 N N N 21.019 1.766 -10.751 -18.506 -13.694 0.062 C30 18C 34 18C C31 C31 C 0 1 N N N 22.351 2.398 -10.310 -18.094 -14.918 -0.755 C31 18C 35 18C C32 C32 C 0 1 N N N 23.603 1.557 -10.606 -19.083 -16.087 -0.682 C32 18C 36 18C C33 C33 C 0 1 N N N 23.849 1.289 -12.097 -18.643 -17.346 -1.437 C33 18C 37 18C C34 C34 C 0 1 N N N 23.349 -0.077 -12.571 -19.593 -18.529 -1.231 C34 18C 38 18C C35 C35 C 0 1 N N N 23.644 -0.231 -14.053 -19.059 -19.791 -1.909 C35 18C 39 18C C36 C36 C 0 1 N N N 22.366 -0.226 -14.878 -19.968 -20.984 -1.660 C36 18C 40 18C H361 1H36 H 0 0 N N N 21.495 -0.225 -14.206 -20.973 -20.801 -2.053 H361 18C 41 18C H362 2H36 H 0 0 N N N 22.342 0.673 -15.511 -20.052 -21.197 -0.589 H362 18C 42 18C H363 3H36 H 0 0 N N N 22.337 -1.123 -15.514 -19.568 -21.876 -2.153 H363 18C 43 18C H351 1H35 H 0 0 N N N 24.279 0.607 -14.377 -18.972 -19.626 -2.989 H351 18C 44 18C H352 2H35 H 0 0 N N N 24.152 -1.194 -14.207 -18.055 -20.020 -1.533 H352 18C 45 18C H341 1H34 H 0 0 N N N 23.861 -0.872 -12.009 -20.587 -18.298 -1.628 H341 18C 46 18C H342 2H34 H 0 0 N N N 22.265 -0.153 -12.401 -19.715 -18.715 -0.157 H342 18C 47 18C H331 1H33 H 0 0 N N N 23.322 2.063 -12.674 -18.520 -17.131 -2.505 H331 18C 48 18C H332 2H33 H 0 0 N N N 24.938 1.305 -12.252 -17.654 -17.640 -1.062 H332 18C 49 18C H321 1H32 H 0 0 N N N 24.475 2.100 -10.213 -20.075 -15.761 -1.013 H321 18C 50 18C H322 2H32 H 0 0 N N N 23.447 0.578 -10.130 -19.186 -16.351 0.379 H322 18C 51 18C H311 1H31 H 0 0 N N N 22.458 3.354 -10.843 -17.952 -14.627 -1.803 H311 18C 52 18C H312 2H31 H 0 0 N N N 22.298 2.499 -9.216 -17.121 -15.277 -0.397 H312 18C 53 18C H301 1H30 H 0 0 N N N 21.211 0.735 -11.084 -18.597 -13.969 1.120 H301 18C 54 18C H302 2H30 H 0 0 N N N 20.602 2.378 -11.564 -19.486 -13.337 -0.273 H302 18C 55 18C H291 1H29 H 0 0 N N N 20.120 2.634 -8.995 -16.507 -12.897 0.264 H291 18C 56 18C H292 2H29 H 0 0 N N N 20.177 0.830 -9.005 -17.387 -12.308 -1.148 H292 18C 57 18C H281 1H28 H 0 0 N N N 18.638 1.684 -11.261 -18.892 -10.969 0.343 H281 18C 58 18C H282 2H28 H 0 0 N N N 18.048 2.567 -9.780 -18.060 -11.604 1.758 H282 18C 59 18C H271 1H27 H 0 0 N N N 18.232 -0.425 -10.249 -16.757 -9.866 -0.389 H271 18C 60 18C H272 2H27 H 0 0 N N N 16.759 0.608 -9.935 -15.937 -10.564 1.003 H272 18C 61 18C H261 1H26 H 0 0 N N N 17.575 1.063 -7.669 -17.466 -9.292 2.541 H261 18C 62 18C H262 2H26 H 0 0 N N N 19.002 -0.004 -7.976 -18.240 -8.546 1.140 H262 18C 63 18C H251 1H25 H 0 0 N N N 17.493 -1.913 -8.362 -16.032 -7.589 0.434 H251 18C 64 18C H252 2H25 H 0 0 N N N 16.069 -0.847 -8.048 -15.275 -8.300 1.861 H252 18C 65 18C H241 1H24 H 0 0 N N N 17.732 -0.421 -5.843 -16.831 -6.986 3.326 H241 18C 66 18C H242 2H24 H 0 0 N N N 17.872 -2.192 -6.166 -17.550 -6.246 1.894 H242 18C 67 18C H231 1H23 H 0 0 N N N 15.252 -2.055 -6.412 -15.325 -5.305 1.253 H231 18C 68 18C H232 2H23 H 0 0 N N N 15.451 -0.541 -5.443 -14.593 -6.028 2.681 H232 18C 69 18C H221 1H22 H 0 0 N N N 16.630 -3.221 -4.632 -16.795 -3.913 2.637 H221 18C 70 18C H222 2H22 H 0 0 N N N 14.983 -2.619 -4.114 -16.152 -4.631 4.111 H222 18C 71 18C H211 1H21 H 0 0 N N N 16.087 -0.631 -3.098 -14.573 -2.980 2.064 H211 18C 72 18C H212 2H21 H 0 0 N N N 17.691 -1.363 -3.492 -13.859 -3.720 3.495 H212 18C 73 18C H201 1H20 H 0 0 N N N 16.756 -3.456 -2.216 -16.067 -1.595 3.467 H201 18C 74 18C H202 2H20 H 0 0 N N N 15.589 -2.247 -1.507 -15.421 -2.323 4.935 H202 18C 75 18C HN2 HN2 H 0 1 N N N 18.026 -3.938 -0.741 -15.327 0.149 5.099 HN2 18C 76 18C H2 H2 H 0 1 N N N 19.250 -2.361 1.221 -12.899 1.309 3.928 H2 18C 77 18C H11 1H1 H 0 1 N N N 20.850 -4.301 1.485 -15.040 2.468 5.816 H11 18C 78 18C H12 2H1 H 0 1 N N N 19.109 -4.804 1.416 -13.750 3.413 5.043 H12 18C 79 18C HO1 HO1 H 0 1 N N N 20.308 -4.748 -1.052 -14.814 2.136 3.094 HO1 18C 80 18C H3 H3 H 0 1 N N N 21.722 -2.792 -0.052 -12.150 0.004 5.972 H3 18C 81 18C HO3 HO3 H 0 1 N N N 20.621 -1.162 1.407 -13.231 1.771 7.717 HO3 18C 82 18C H4 H4 H 0 1 N N N 20.864 -2.873 -2.357 -11.986 3.080 6.356 H4 18C 83 18C H5 H5 H 0 1 N N N 20.546 0.058 -1.597 -9.870 0.907 6.277 H5 18C 84 18C H61 1H6 H 0 1 N N N 20.142 -1.407 -4.261 -8.555 2.977 5.766 H61 18C 85 18C H62 2H6 H 0 1 N N N 19.947 0.375 -3.922 -9.697 3.984 6.630 H62 18C 86 18C H71 1H7 H 0 1 N N N 22.190 0.811 -4.188 -9.184 2.747 8.761 H71 18C 87 18C H72 2H7 H 0 1 N N N 22.654 -0.932 -3.889 -8.018 1.752 7.909 H72 18C 88 18C H81 1H8 H 0 1 N N N 21.712 -1.548 -6.070 -7.909 4.788 8.277 H81 18C 89 18C H82 2H8 H 0 1 N N N 21.317 0.208 -6.370 -6.737 3.875 7.342 H82 18C 90 18C H91 1H9 H 0 1 N N N 23.598 0.808 -6.458 -6.045 2.633 9.356 H91 18C 91 18C H92 2H9 H 0 1 N N N 24.094 -0.871 -5.853 -7.218 3.490 10.339 H92 18C 92 18C H101 1H10 H 0 0 N N N 24.202 0.003 -8.453 -6.044 5.663 9.821 H101 18C 93 18C H102 2H10 H 0 0 N N N 24.148 -1.720 -7.873 -4.873 4.778 8.838 H102 18C 94 18C H111 1H11 H 0 0 N N N 21.556 -1.323 -7.910 -5.372 4.359 11.834 H111 18C 95 18C H112 2H11 H 0 0 N N N 22.032 -0.008 -9.108 -4.222 3.440 10.858 H112 18C 96 18C H121 1H12 H 0 0 N N N 23.120 -1.689 -10.505 -2.980 5.549 10.326 H121 18C 97 18C H122 2H12 H 0 0 N N N 22.583 -2.983 -9.343 -4.158 6.480 11.245 H122 18C 98 18C H131 1H13 H 0 0 N N N 20.395 -1.244 -10.284 -3.547 5.253 13.313 H131 18C 99 18C H132 2H13 H 0 0 N N N 21.223 -2.191 -11.603 -2.318 4.351 12.432 H132 18C 100 18C H141 1H14 H 0 0 N N N 20.872 -4.260 -10.293 -1.145 6.525 11.895 H141 18C 101 18C H142 2H14 H 0 0 N N N 19.950 -3.288 -9.067 -2.379 7.395 12.812 H142 18C 102 18C H151 1H15 H 0 0 N N N 18.111 -3.132 -10.371 -1.747 6.080 14.863 H151 18C 103 18C H152 2H15 H 0 0 N N N 19.095 -3.010 -11.900 -0.499 5.248 13.932 H152 18C 104 18C H161 1H16 H 0 0 N N N 19.420 -5.388 -11.960 -0.637 8.272 14.417 H161 18C 105 18C H162 2H16 H 0 0 N N N 18.631 -5.574 -10.330 0.598 7.461 13.452 H162 18C 106 18C H171 1H17 H 0 0 N N N 16.499 -5.212 -11.173 0.063 6.969 16.432 H171 18C 107 18C H172 2H17 H 0 0 N N N 17.107 -4.337 -12.627 1.278 6.122 15.473 H172 18C 108 18C H181 1H18 H 0 0 N N N 17.237 -6.237 -13.812 1.213 9.145 15.977 H181 18C 109 18C H182 2H18 H 0 0 N N N 18.135 -7.070 -12.498 2.300 7.977 16.749 H182 18C 110 18C H183 3H18 H 0 0 N N N 16.339 -7.034 -12.477 2.434 8.294 15.011 H183 18C 111 # 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 18C O19 C19 DOUB N N 1 18C C19 C20 SING N N 2 18C C19 N2 SING N N 3 18C N2 C2 SING N N 4 18C N2 HN2 SING N N 5 18C C2 C1 SING N N 6 18C C2 C3 SING N N 7 18C C2 H2 SING N N 8 18C C1 O1 SING N N 9 18C C1 H11 SING N N 10 18C C1 H12 SING N N 11 18C O1 HO1 SING N N 12 18C C3 O3 SING N N 13 18C C3 C4 SING N N 14 18C C3 H3 SING N N 15 18C C4 C5 DOUB N E 16 18C C4 H4 SING N N 17 18C C5 C6 SING N N 18 18C C5 H5 SING N N 19 18C C6 C7 SING N N 20 18C C6 H61 SING N N 21 18C C6 H62 SING N N 22 18C C7 C8 SING N N 23 18C C7 H71 SING N N 24 18C C7 H72 SING N N 25 18C C8 C9 SING N N 26 18C C8 H81 SING N N 27 18C C8 H82 SING N N 28 18C C9 C10 SING N N 29 18C C9 H91 SING N N 30 18C C9 H92 SING N N 31 18C C10 C11 SING N N 32 18C C10 H101 SING N N 33 18C C10 H102 SING N N 34 18C C11 C12 SING N N 35 18C C11 H111 SING N N 36 18C C11 H112 SING N N 37 18C C12 C13 SING N N 38 18C C12 H121 SING N N 39 18C C12 H122 SING N N 40 18C C13 C14 SING N N 41 18C C13 H131 SING N N 42 18C C13 H132 SING N N 43 18C C14 C15 SING N N 44 18C C14 H141 SING N N 45 18C C14 H142 SING N N 46 18C C15 C16 SING N N 47 18C C15 H151 SING N N 48 18C C15 H152 SING N N 49 18C C16 C17 SING N N 50 18C C16 H161 SING N N 51 18C C16 H162 SING N N 52 18C C17 C18 SING N N 53 18C C17 H171 SING N N 54 18C C17 H172 SING N N 55 18C C18 H181 SING N N 56 18C C18 H182 SING N N 57 18C C18 H183 SING N N 58 18C O3 HO3 SING N N 59 18C C20 C21 SING N N 60 18C C20 H201 SING N N 61 18C C20 H202 SING N N 62 18C C21 C22 SING N N 63 18C C21 H211 SING N N 64 18C C21 H212 SING N N 65 18C C22 C23 SING N N 66 18C C22 H221 SING N N 67 18C C22 H222 SING N N 68 18C C23 C24 SING N N 69 18C C23 H231 SING N N 70 18C C23 H232 SING N N 71 18C C24 C25 SING N N 72 18C C24 H241 SING N N 73 18C C24 H242 SING N N 74 18C C25 C26 SING N N 75 18C C25 H251 SING N N 76 18C C25 H252 SING N N 77 18C C26 C27 SING N N 78 18C C26 H261 SING N N 79 18C C26 H262 SING N N 80 18C C27 C28 SING N N 81 18C C27 H271 SING N N 82 18C C27 H272 SING N N 83 18C C28 C29 SING N N 84 18C C28 H281 SING N N 85 18C C28 H282 SING N N 86 18C C29 C30 SING N N 87 18C C29 H291 SING N N 88 18C C29 H292 SING N N 89 18C C30 C31 SING N N 90 18C C30 H301 SING N N 91 18C C30 H302 SING N N 92 18C C31 C32 SING N N 93 18C C31 H311 SING N N 94 18C C31 H312 SING N N 95 18C C32 C33 SING N N 96 18C C32 H321 SING N N 97 18C C32 H322 SING N N 98 18C C33 C34 SING N N 99 18C C33 H331 SING N N 100 18C C33 H332 SING N N 101 18C C34 C35 SING N N 102 18C C34 H341 SING N N 103 18C C34 H342 SING N N 104 18C C35 C36 SING N N 105 18C C35 H351 SING N N 106 18C C35 H352 SING N N 107 18C C36 H361 SING N N 108 18C C36 H362 SING N N 109 18C C36 H363 SING N N 110 # 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 18C SMILES ACDLabs 10.04 "O=C(NC(CO)C(O)/C=C/CCCCCCCCCCCCC)CCCCCCCCCCCCCCCCC" 18C SMILES_CANONICAL CACTVS 3.341 "CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)\C=C\CCCCCCCCCCCCC" 18C SMILES CACTVS 3.341 "CCCCCCCCCCCCCCCCCC(=O)N[CH](CO)[CH](O)C=CCCCCCCCCCCCCC" 18C SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](\C=C\CCCCCCCCCCCCC)O" 18C SMILES "OpenEye OEToolkits" 1.5.0 "CCCCCCCCCCCCCCCCCC(=O)NC(CO)C(C=CCCCCCCCCCCCCC)O" 18C InChI InChI 1.03 "InChI=1S/C36H71NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38-39H,3-28,30,32-33H2,1-2H3,(H,37,40)/b31-29+/t34-,35+/m0/s1" 18C InChIKey InChI 1.03 VODZWWMEJITOND-NXCSZAMKSA-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 18C "SYSTEMATIC NAME" ACDLabs 10.04 "N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)heptadec-3-en-1-yl]octadecanamide" 18C "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octadecanamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 18C "Create component" 2007-07-16 RCSB 18C "Modify descriptor" 2011-06-04 RCSB 18C "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 18C C18-CERAMIDE ? ? 2 18C N-STEAROYL-D-ERYTHRO-SPHINGOSINE ? ? 3 18C "(2S,3R,4E)-2-STEAROYLAMINOOCTADEC-4-ENE-1,3-DIOL" ? ? 4 18C "(2S,3R,4E)-2-STEAROYLAMINO-1,3-OCTADEC-4-ENEDIOL" ? ? #