data_M8B # _chem_comp.id M8B _chem_comp.name "methyl N-[(2S)-1-[2-[(4-bromophenyl)methyl]-2-[3-[(3Z,8S,11R)-8-tert-butyl-11-oxidanyl-7,10-bis(oxidanylidene)-6,9-diazabicyclo[11.2.2]heptadeca-1(15),3,13,16-tetraen-11-yl]propyl]hydrazinyl]-3,3-dimethyl-1-oxidanylidene-butan-2-yl]carbamate" _chem_comp.type non-polymer _chem_comp.pdbx_type HETAIN _chem_comp.formula "C37 H52 Br N5 O6" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-03-01 _chem_comp.pdbx_modified_date 2014-09-05 _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 742.743 _chem_comp.one_letter_code ? _chem_comp.three_letter_code M8B _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 3ZPU _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 M8B C19 C19 C 0 1 N N N 20.007 18.079 6.837 5.616 2.891 -4.233 C19 M8B 1 M8B O5 O5 O 0 1 N N N 18.596 17.903 6.606 4.442 2.240 -3.680 O5 M8B 2 M8B C18 C18 C 0 1 N N N 18.105 18.817 5.703 4.165 2.478 -2.384 C18 M8B 3 M8B O4 O4 O 0 1 N N N 18.846 19.593 5.053 4.884 3.211 -1.733 O4 M8B 4 M8B N4 N4 N 0 1 N N N 16.807 18.823 5.492 3.090 1.904 -1.808 N4 M8B 5 M8B C13 C13 C 0 1 N N S 16.059 19.816 4.681 2.788 2.164 -0.398 C13 M8B 6 M8B C14 C14 C 0 1 N N N 15.313 19.124 3.533 1.712 3.247 -0.298 C14 M8B 7 M8B C16 C16 C 0 1 N N N 16.407 18.620 2.637 0.442 2.772 -1.006 C16 M8B 8 M8B C17 C17 C 0 1 N N N 14.387 17.941 4.016 1.403 3.523 1.175 C17 M8B 9 M8B C15 C15 C 0 1 N N N 14.483 20.172 2.694 2.217 4.530 -0.962 C15 M8B 10 M8B C12 C12 C 0 1 N N N 15.216 20.662 5.695 2.288 0.898 0.249 C12 M8B 11 M8B O3 O3 O 0 1 N N N 14.093 20.322 6.093 1.956 -0.045 -0.438 O3 M8B 12 M8B N3 N3 N 0 1 N N N 15.882 21.745 6.176 2.210 0.813 1.592 N3 M8B 13 M8B N2 N2 N 0 1 N N N 15.371 22.438 7.171 1.868 -0.370 2.184 N2 M8B 14 M8B C10 C10 C 0 1 N N N 16.253 22.325 8.360 2.945 -0.851 3.059 C10 M8B 15 M8B C11 C11 C 0 1 Y N N 16.336 21.010 8.896 4.160 -1.178 2.228 C11 M8B 16 M8B C20 C20 C 0 1 Y N N 15.173 20.321 9.272 5.110 -0.205 1.980 C20 M8B 17 M8B C21 C21 C 0 1 Y N N 15.316 19.000 9.755 6.224 -0.504 1.219 C21 M8B 18 M8B C22 C22 C 0 1 Y N N 16.538 18.406 9.913 6.387 -1.777 0.703 C22 M8B 19 M8B BR1 BR1 BR 0 0 N N N 16.614 16.514 10.707 7.911 -2.188 -0.339 BR1 M8B 20 M8B C23 C23 C 0 1 Y N N 17.676 19.113 9.559 5.436 -2.751 0.951 C23 M8B 21 M8B C24 C24 C 0 1 Y N N 17.565 20.395 9.001 4.326 -2.452 1.718 C24 M8B 22 M8B C9 C9 C 0 1 N N N 15.287 23.837 6.816 0.606 -0.243 2.924 C9 M8B 23 M8B C8 C8 C 0 1 N N N 13.880 24.253 6.359 -0.543 -0.019 1.938 C8 M8B 24 M8B C7 C7 C 0 1 N N N 13.434 23.631 5.004 -0.739 -1.276 1.089 C7 M8B 25 M8B C1 C1 C 0 1 N N R 12.126 24.305 4.571 -1.853 -1.032 0.064 C1 M8B 26 M8B C25 C25 C 0 1 N N N 11.665 23.625 3.194 -2.123 -2.327 -0.702 C25 M8B 27 M8B O1 O1 O 0 1 N N N 12.436 25.691 4.393 -1.436 -0.012 -0.844 O1 M8B 28 M8B C2 C2 C 0 1 N N N 11.047 24.330 5.532 -3.097 -0.594 0.790 C2 M8B 29 M8B O2 O2 O 0 1 N N N 10.507 23.324 6.004 -3.681 -1.375 1.514 O2 M8B 30 M8B N1 N1 N 0 1 N N N 10.350 25.523 5.762 -3.550 0.690 0.638 N1 M8B 31 M8B C3 C3 C 0 1 N N S 9.049 25.641 6.511 -4.799 0.997 1.386 C3 M8B 32 M8B C4 C4 C 0 1 N N N 9.209 26.148 7.922 -4.697 2.389 2.014 C4 M8B 33 M8B C6 C6 C 0 1 N N N 9.982 27.497 7.970 -4.341 3.412 0.933 C6 M8B 34 M8B C35 C35 C 0 1 N N N 7.757 26.449 8.484 -6.040 2.762 2.647 C35 M8B 35 M8B C5 C5 C 0 1 N N N 9.896 25.130 8.777 -3.610 2.385 3.091 C5 M8B 36 M8B C34 C34 C 0 1 N N N 8.181 26.495 5.681 -5.942 0.961 0.402 C34 M8B 37 M8B O6 O6 O 0 1 N N N 8.538 27.595 5.244 -6.278 1.965 -0.188 O6 M8B 38 M8B N5 N5 N 0 1 N N N 6.893 26.137 5.284 -6.592 -0.220 0.187 N5 M8B 39 M8B C37 C37 C 0 1 N N N 6.018 26.937 4.386 -7.715 -0.175 -0.776 C37 M8B 40 M8B C36 C36 C 0 1 N N N 5.138 26.013 3.744 -8.569 -1.403 -0.613 C36 M8B 41 M8B C33 C33 C 0 1 N N N 5.358 25.399 2.506 -8.501 -2.391 -1.470 C33 M8B 42 M8B C32 C32 C 0 1 N N N 6.463 25.568 1.657 -7.567 -2.333 -2.651 C32 M8B 43 M8B C29 C29 C 0 1 Y N N 7.764 25.053 2.056 -6.144 -2.339 -2.151 C29 M8B 44 M8B C28 C28 C 0 1 Y N N 8.924 25.822 1.821 -5.200 -1.530 -2.751 C28 M8B 45 M8B C27 C27 C 0 1 Y N N 10.230 25.371 2.164 -3.895 -1.522 -2.287 C27 M8B 46 M8B C26 C26 C 0 1 Y N N 10.342 24.117 2.798 -3.536 -2.328 -1.224 C26 M8B 47 M8B C31 C31 C 0 1 Y N N 9.183 23.350 3.020 -4.479 -3.144 -0.626 C31 M8B 48 M8B C30 C30 C 0 1 Y N N 7.929 23.796 2.662 -5.781 -3.152 -1.093 C30 M8B 49 M8B H191 H191 H 0 0 N N N 20.356 17.330 7.563 5.724 2.615 -5.282 H191 M8B 50 M8B H192 H192 H 0 0 N N N 20.552 17.954 5.890 5.503 3.973 -4.152 H192 M8B 51 M8B H193 H193 H 0 0 N N N 20.190 19.088 7.235 6.501 2.576 -3.681 H193 M8B 52 M8B H4 H4 H 0 1 N N N 16.275 18.091 5.917 2.516 1.319 -2.327 H4 M8B 53 M8B H13 H13 H 0 1 N N N 16.792 20.500 4.227 3.691 2.500 0.111 H13 M8B 54 M8B H161 H161 H 0 0 N N N 15.965 18.102 1.773 0.126 1.818 -0.584 H161 M8B 55 M8B H162 H162 H 0 0 N N N 17.012 19.468 2.285 -0.348 3.510 -0.867 H162 M8B 56 M8B H163 H163 H 0 0 N N N 17.046 17.921 3.196 0.643 2.650 -2.070 H163 M8B 57 M8B H171 H171 H 0 0 N N N 13.884 17.490 3.148 2.314 3.834 1.686 H171 M8B 58 M8B H172 H172 H 0 0 N N N 14.999 17.179 4.521 0.658 4.316 1.247 H172 M8B 59 M8B H173 H173 H 0 0 N N N 13.632 18.329 4.716 1.016 2.617 1.641 H173 M8B 60 M8B H151 H151 H 0 0 N N N 13.957 19.655 1.878 2.438 4.333 -2.011 H151 M8B 61 M8B H152 H152 H 0 0 N N N 13.749 20.666 3.348 1.451 5.302 -0.890 H152 M8B 62 M8B H153 H153 H 0 0 N N N 15.164 20.926 2.272 3.122 4.868 -0.458 H153 M8B 63 M8B H3 H3 H 0 1 N N N 16.758 22.014 5.775 2.397 1.592 2.139 H3 M8B 64 M8B H101 H101 H 0 0 N N N 17.265 22.645 8.072 3.199 -0.078 3.783 H101 M8B 65 M8B H102 H102 H 0 0 N N N 15.866 22.994 9.143 2.614 -1.747 3.584 H102 M8B 66 M8B H91C H91C H 0 0 N N N 15.564 24.439 7.694 0.424 -1.155 3.492 H91C M8B 67 M8B H92C H92C H 0 0 N N N 15.995 24.035 5.998 0.669 0.604 3.607 H92C M8B 68 M8B H20 H20 H 0 1 N N N 14.201 20.785 9.195 4.982 0.789 2.382 H20 M8B 69 M8B H24 H24 H 0 1 N N N 18.450 20.905 8.651 3.585 -3.213 1.915 H24 M8B 70 M8B H21 H21 H 0 1 N N N 14.428 18.440 10.008 6.966 0.256 1.025 H21 M8B 71 M8B H23 H23 H 0 1 N N N 18.651 18.676 9.713 5.563 -3.745 0.549 H23 M8B 72 M8B H81C H81C H 0 0 N N N 13.162 23.944 7.133 -1.458 0.194 2.490 H81C M8B 73 M8B H82C H82C H 0 0 N N N 13.861 25.348 6.258 -0.305 0.824 1.289 H82C M8B 74 M8B H71C H71C H 0 0 N N N 14.210 23.802 4.243 0.189 -1.512 0.568 H71C M8B 75 M8B H72C H72C H 0 0 N N N 13.272 22.550 5.126 -1.015 -2.111 1.734 H72C M8B 76 M8B H1 H1 H 0 1 N N N 11.655 26.159 4.123 -2.089 0.199 -1.524 H1 M8B 77 M8B H251 H251 H 0 0 N N N 12.393 23.870 2.407 -1.420 -2.405 -1.531 H251 M8B 78 M8B H252 H252 H 0 0 N N N 11.621 22.534 3.326 -1.985 -3.181 -0.037 H252 M8B 79 M8B HA HA H 0 1 N N N 10.749 26.365 5.399 -3.100 1.351 0.083 HA M8B 80 M8B HB HB H 0 1 N N N 8.598 24.639 6.563 -4.961 0.255 2.170 HB M8B 81 M8B H61C H61C H 0 0 N N N 10.076 27.830 9.014 -5.182 3.524 0.248 H61C M8B 82 M8B H62C H62C H 0 0 N N N 10.984 27.361 7.537 -4.122 4.372 1.400 H62C M8B 83 M8B H63C H63C H 0 0 N N N 9.433 28.255 7.392 -3.466 3.068 0.382 H63C M8B 84 M8B H351 H351 H 0 0 N N N 7.833 26.822 9.516 -6.293 2.034 3.417 H351 M8B 85 M8B H352 H352 H 0 0 N N N 7.270 27.208 7.854 -5.968 3.754 3.094 H352 M8B 86 M8B H353 H353 H 0 0 N N N 7.160 25.525 8.472 -6.814 2.765 1.880 H353 M8B 87 M8B H51C H51C H 0 0 N N N 10.002 25.521 9.800 -2.671 2.042 2.657 H51C M8B 88 M8B H52C H52C H 0 0 N N N 9.300 24.206 8.797 -3.482 3.395 3.481 H52C M8B 89 M8B H53C H53C H 0 0 N N N 10.892 24.915 8.362 -3.902 1.717 3.900 H53C M8B 90 M8B H5 H5 H 0 1 N N N 6.528 25.273 5.631 -6.336 -1.042 0.642 H5 M8B 91 M8B H371 H371 H 0 0 N N N 5.440 27.667 4.971 -8.324 0.712 -0.575 H371 M8B 92 M8B H372 H372 H 0 0 N N N 6.625 27.466 3.637 -7.326 -0.115 -1.792 H372 M8B 93 M8B H36 H36 H 0 1 N N N 4.222 25.766 4.260 -9.247 -1.477 0.232 H36 M8B 94 M8B H33 H33 H 0 1 N N N 4.591 24.719 2.165 -9.134 -3.262 -1.332 H33 M8B 95 M8B H321 H321 H 0 0 N N N 6.208 25.086 0.702 -7.728 -3.205 -3.287 H321 M8B 96 M8B H322 H322 H 0 0 N N N 6.583 26.650 1.501 -7.752 -1.428 -3.227 H322 M8B 97 M8B H28 H28 H 0 1 N N N 8.816 26.793 1.362 -5.471 -0.895 -3.580 H28 M8B 98 M8B H30 H30 H 0 1 N N N 7.066 23.174 2.849 -6.519 -3.790 -0.632 H30 M8B 99 M8B H27 H27 H 0 1 N N N 11.103 25.968 1.946 -3.157 -0.896 -2.763 H27 M8B 100 M8B H31 H31 H 0 1 N N N 9.279 22.380 3.486 -4.200 -3.779 0.200 H31 M8B 101 # 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 M8B C19 O5 SING N N 1 M8B O5 C18 SING N N 2 M8B C18 O4 DOUB N N 3 M8B C18 N4 SING N N 4 M8B N4 C13 SING N N 5 M8B C13 C14 SING N N 6 M8B C13 C12 SING N N 7 M8B C14 C16 SING N N 8 M8B C14 C17 SING N N 9 M8B C14 C15 SING N N 10 M8B C12 O3 DOUB N N 11 M8B C12 N3 SING N N 12 M8B N3 N2 SING N N 13 M8B N2 C10 SING N N 14 M8B N2 C9 SING N N 15 M8B C10 C11 SING N N 16 M8B C11 C20 SING Y N 17 M8B C11 C24 DOUB Y N 18 M8B C20 C21 DOUB Y N 19 M8B C21 C22 SING Y N 20 M8B C22 BR1 SING N N 21 M8B C22 C23 DOUB Y N 22 M8B C23 C24 SING Y N 23 M8B C9 C8 SING N N 24 M8B C8 C7 SING N N 25 M8B C7 C1 SING N N 26 M8B C1 O1 SING N N 27 M8B C1 C2 SING N N 28 M8B C1 C25 SING N N 29 M8B C25 C26 SING N N 30 M8B C2 O2 DOUB N N 31 M8B C2 N1 SING N N 32 M8B N1 C3 SING N N 33 M8B C3 C4 SING N N 34 M8B C3 C34 SING N N 35 M8B C4 C6 SING N N 36 M8B C4 C35 SING N N 37 M8B C4 C5 SING N N 38 M8B C34 O6 DOUB N N 39 M8B C34 N5 SING N N 40 M8B N5 C37 SING N N 41 M8B C37 C36 SING N N 42 M8B C36 C33 DOUB N Z 43 M8B C33 C32 SING N N 44 M8B C32 C29 SING N N 45 M8B C29 C28 SING Y N 46 M8B C29 C30 DOUB Y N 47 M8B C28 C27 DOUB Y N 48 M8B C27 C26 SING Y N 49 M8B C26 C31 DOUB Y N 50 M8B C31 C30 SING Y N 51 M8B C19 H191 SING N N 52 M8B C19 H192 SING N N 53 M8B C19 H193 SING N N 54 M8B N4 H4 SING N N 55 M8B C13 H13 SING N N 56 M8B C16 H161 SING N N 57 M8B C16 H162 SING N N 58 M8B C16 H163 SING N N 59 M8B C17 H171 SING N N 60 M8B C17 H172 SING N N 61 M8B C17 H173 SING N N 62 M8B C15 H151 SING N N 63 M8B C15 H152 SING N N 64 M8B C15 H153 SING N N 65 M8B N3 H3 SING N N 66 M8B C10 H101 SING N N 67 M8B C10 H102 SING N N 68 M8B C9 H91C SING N N 69 M8B C9 H92C SING N N 70 M8B C20 H20 SING N N 71 M8B C24 H24 SING N N 72 M8B C21 H21 SING N N 73 M8B C23 H23 SING N N 74 M8B C8 H81C SING N N 75 M8B C8 H82C SING N N 76 M8B C7 H71C SING N N 77 M8B C7 H72C SING N N 78 M8B O1 H1 SING N N 79 M8B C25 H251 SING N N 80 M8B C25 H252 SING N N 81 M8B N1 HA SING N N 82 M8B C3 HB SING N N 83 M8B C6 H61C SING N N 84 M8B C6 H62C SING N N 85 M8B C6 H63C SING N N 86 M8B C35 H351 SING N N 87 M8B C35 H352 SING N N 88 M8B C35 H353 SING N N 89 M8B C5 H51C SING N N 90 M8B C5 H52C SING N N 91 M8B C5 H53C SING N N 92 M8B N5 H5 SING N N 93 M8B C37 H371 SING N N 94 M8B C37 H372 SING N N 95 M8B C36 H36 SING N N 96 M8B C33 H33 SING N N 97 M8B C32 H321 SING N N 98 M8B C32 H322 SING N N 99 M8B C28 H28 SING N N 100 M8B C30 H30 SING N N 101 M8B C27 H27 SING N N 102 M8B C31 H31 SING N N 103 # 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 M8B SMILES ACDLabs 12.01 "O=C(OC)NC(C(=O)NN(Cc1ccc(Br)cc1)CCCC3(O)C(=O)NC(C(=O)NCC=CCc2ccc(cc2)C3)C(C)(C)C)C(C)(C)C" M8B InChI InChI 1.03 ;InChI=1S/C37H52BrN5O6/c1-35(2,3)29-31(44)39-21-9-8-11-25-12-14-26(15-13-25)23-37(48,33(46)40-29)20-10-22-43(24-27-16-18-28(38)19-17-27)42-32(45)30(36(4,5)6)41-34(47)49-7/h8-9,12-19,29-30,48H,10-11,20-24H2,1-7H3,(H,39,44)(H,40,46)(H,41,47)(H,42,45)/b9-8-/t29-,30-,37-/m1/s1 ; M8B InChIKey InChI 1.03 SFNMYSUIYNOTIA-HIOXXDBGSA-N M8B SMILES_CANONICAL CACTVS 3.385 "COC(=O)N[C@H](C(=O)NN(CCC[C@@]1(O)Cc2ccc(C\C=C/CNC(=O)[C@@H](NC1=O)C(C)(C)C)cc2)Cc3ccc(Br)cc3)C(C)(C)C" M8B SMILES CACTVS 3.385 "COC(=O)N[CH](C(=O)NN(CCC[C]1(O)Cc2ccc(CC=CCNC(=O)[CH](NC1=O)C(C)(C)C)cc2)Cc3ccc(Br)cc3)C(C)(C)C" M8B SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "CC(C)(C)[C@H]1C(=O)NC/C=C\Cc2ccc(cc2)C[C@@](C(=O)N1)(CCCN(Cc3ccc(cc3)Br)NC(=O)[C@H](C(C)(C)C)NC(=O)OC)O" M8B SMILES "OpenEye OEToolkits" 1.9.2 "CC(C)(C)C1C(=O)NCC=CCc2ccc(cc2)CC(C(=O)N1)(CCCN(Cc3ccc(cc3)Br)NC(=O)C(C(C)(C)C)NC(=O)OC)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 M8B "SYSTEMATIC NAME" ACDLabs 12.01 "methyl {(2S)-1-[2-(4-bromobenzyl)-2-{3-[(3R,6S,10Z)-6-tert-butyl-3-hydroxy-4,7-dioxo-5,8-diazabicyclo[11.2.2]heptadeca-1(15),10,13,16-tetraen-3-yl]propyl}hydrazinyl]-3,3-dimethyl-1-oxobutan-2-yl}carbamate" M8B "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "methyl N-[(2S)-1-[2-[(4-bromophenyl)methyl]-2-[3-[(3Z,8S,11R)-8-tert-butyl-11-oxidanyl-7,10-bis(oxidanylidene)-6,9-diazabicyclo[11.2.2]heptadeca-1(15),3,13,16-tetraen-11-yl]propyl]hydrazinyl]-3,3-dimethyl-1-oxidanylidene-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 M8B "Create component" 2013-03-01 EBI M8B "Initial release" 2013-11-06 RCSB M8B "Modify descriptor" 2014-09-05 RCSB #