data_690 # _chem_comp.id 690 _chem_comp.name "5-cyclopropyl-2-(4-fluorophenyl)-6-[{2-[(3R)-1-hydroxy-1,3-dihydro-2,1-benzoxaborol-3-yl]ethyl}(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C29 H28 B F N2 O6 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-04-26 _chem_comp.pdbx_modified_date 2013-05-03 _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 562.417 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 690 _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 4KB7 _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 690 O27 O27 O 0 1 N N N 6.295 43.523 55.264 -1.384 -3.341 2.000 O27 690 1 690 S24 S24 S 0 1 N N N 6.208 44.296 54.056 -2.483 -2.488 1.714 S24 690 2 690 O26 O26 O 0 1 N N N 4.815 44.510 53.777 -3.750 -3.021 1.352 O26 690 3 690 C25 C25 C 0 1 N N N 6.926 45.760 54.302 -2.668 -1.230 3.008 C25 690 4 690 N11 N11 N 0 1 N N N 6.944 43.409 52.907 -2.002 -1.637 0.377 N11 690 5 690 C10 C10 C 0 1 Y N N 6.023 42.984 51.899 -0.641 -1.434 0.130 C10 690 6 690 C9 C9 C 0 1 Y N N 5.422 41.758 52.201 -0.032 -0.265 0.556 C9 690 7 690 C8 C8 C 0 1 Y N N 4.523 41.197 51.322 1.319 -0.058 0.313 C8 690 8 690 O7 O7 O 0 1 Y N N 3.899 40.051 51.516 2.156 0.960 0.605 O7 690 9 690 C28 C28 C 0 1 Y N N 5.704 43.644 50.682 0.093 -2.412 -0.536 C28 690 10 690 C31 C31 C 0 1 N N N 6.327 44.957 50.320 -0.582 -3.679 -0.994 C31 690 11 690 C32 C32 C 0 1 N N N 5.690 45.842 49.244 -0.053 -5.002 -0.438 C32 690 12 690 C33 C33 C 0 1 N N N 6.950 45.040 48.929 0.219 -4.620 -1.896 C33 690 13 690 C29 C29 C 0 1 Y N N 4.783 43.047 49.799 1.436 -2.222 -0.779 C29 690 14 690 C30 C30 C 0 1 Y N N 4.215 41.829 50.145 2.053 -1.045 -0.364 C30 690 15 690 C5 C5 C 0 1 Y N N 3.229 40.895 49.543 3.431 -0.524 -0.456 C5 690 16 690 C3 C3 C 0 1 N N N 2.623 41.175 48.210 4.591 -1.185 -1.063 C3 690 17 690 N2 N2 N 0 1 N N N 2.724 40.223 47.277 5.379 -1.984 -0.315 N2 690 18 690 C1 C1 C 0 1 N N N 2.185 40.377 45.938 6.538 -2.644 -0.921 C1 690 19 690 O4 O4 O 0 1 N N N 2.087 42.248 47.995 4.843 -1.013 -2.241 O4 690 20 690 C6 C6 C 0 1 Y N N 3.073 39.731 50.471 3.401 0.714 0.165 C6 690 21 690 C34 C34 C 0 1 Y N N 2.213 38.526 50.419 4.555 1.618 0.321 C34 690 22 690 C35 C35 C 0 1 Y N N 1.052 38.504 49.650 5.806 1.252 -0.184 C35 690 23 690 C36 C36 C 0 1 Y N N 0.247 37.368 49.652 6.881 2.102 -0.036 C36 690 24 690 C40 C40 C 0 1 Y N N 2.544 37.440 51.220 4.401 2.847 0.968 C40 690 25 690 C39 C39 C 0 1 Y N N 1.738 36.310 51.224 5.483 3.688 1.111 C39 690 26 690 C37 C37 C 0 1 Y N N 0.591 36.273 50.438 6.723 3.317 0.613 C37 690 27 690 F38 F38 F 0 1 N N N -0.187 35.180 50.448 7.781 4.145 0.757 F38 690 28 690 C12 C12 C 0 1 N N N 8.223 43.937 52.338 -3.002 -1.096 -0.547 C12 690 29 690 C13 C13 C 0 1 N N N 9.411 43.120 52.837 -3.303 0.358 -0.180 C13 690 30 690 C14 C14 C 0 1 N N R 10.722 43.368 52.076 -4.347 0.923 -1.145 C14 690 31 690 O15 O15 O 0 1 N N N 10.546 43.845 50.729 -5.582 0.229 -0.969 O15 690 32 690 B16 B16 B 0 1 N N N 11.412 44.957 50.436 -6.582 1.164 -0.587 B16 690 33 690 O17 O17 O 0 1 N N N 12.344 44.862 49.222 -7.946 0.877 -0.316 O17 690 34 690 C18 C18 C 0 1 Y N N 12.000 45.317 51.750 -5.893 2.573 -0.521 C18 690 35 690 C19 C19 C 0 1 Y N N 12.830 46.384 52.074 -6.363 3.844 -0.209 C19 690 36 690 C20 C20 C 0 1 Y N N 13.257 46.506 53.400 -5.497 4.920 -0.238 C20 690 37 690 C21 C21 C 0 1 Y N N 12.848 45.575 54.363 -4.169 4.732 -0.577 C21 690 38 690 C22 C22 C 0 1 Y N N 12.011 44.515 54.007 -3.698 3.469 -0.888 C22 690 39 690 C23 C23 C 0 1 Y N N 11.590 44.408 52.684 -4.553 2.386 -0.862 C23 690 40 690 H1 H1 H 0 1 N N N 6.384 46.308 55.087 -1.760 -0.630 3.064 H1 690 41 690 H2 H2 H 0 1 N N N 7.969 45.608 54.615 -3.515 -0.587 2.771 H2 690 42 690 H3 H3 H 0 1 N N N 6.904 46.340 53.368 -2.841 -1.719 3.967 H3 690 43 690 H4 H4 H 0 1 N N N 5.663 41.251 53.124 -0.609 0.486 1.076 H4 690 44 690 H5 H5 H 0 1 N N N 6.864 45.485 51.122 -1.655 -3.601 -1.174 H5 690 45 690 H6 H6 H 0 1 N N N 5.742 46.937 49.331 0.784 -4.956 0.258 H6 690 46 690 H7 H7 H 0 1 N N N 4.728 45.555 48.794 -0.777 -5.795 -0.252 H7 690 47 690 H8 H8 H 0 1 N N N 6.896 44.176 48.250 -0.327 -5.163 -2.668 H8 690 48 690 H9 H9 H 0 1 N N N 7.910 45.558 48.787 1.234 -4.324 -2.158 H9 690 49 690 H10 H10 H 0 1 N N N 4.523 43.529 48.868 2.005 -2.978 -1.299 H10 690 50 690 H11 H11 H 0 1 N N N 3.190 39.370 47.511 5.179 -2.121 0.624 H11 690 51 690 H12 H12 H 0 1 N N N 2.389 39.468 45.353 7.222 -1.891 -1.312 H12 690 52 690 H13 H13 H 0 1 N N N 1.099 40.539 45.997 7.050 -3.243 -0.168 H13 690 53 690 H14 H14 H 0 1 N N N 2.659 41.241 45.449 6.205 -3.289 -1.734 H14 690 54 690 H15 H15 H 0 1 N N N 0.778 39.363 49.056 5.930 0.306 -0.689 H15 690 55 690 H16 H16 H 0 1 N N N -0.645 37.337 49.043 7.848 1.821 -0.425 H16 690 56 690 H17 H17 H 0 1 N N N 3.428 37.475 51.839 3.435 3.137 1.356 H17 690 57 690 H18 H18 H 0 1 N N N 2.001 35.460 51.837 5.365 4.638 1.611 H18 690 58 690 H19 H19 H 0 1 N N N 8.350 44.985 52.646 -2.618 -1.142 -1.566 H19 690 59 690 H20 H20 H 0 1 N N N 8.181 43.880 51.240 -3.917 -1.685 -0.477 H20 690 60 690 H21 H21 H 0 1 N N N 9.157 42.054 52.745 -3.687 0.404 0.839 H21 690 61 690 H22 H22 H 0 1 N N N 9.577 43.367 53.896 -2.388 0.947 -0.250 H22 690 62 690 H23 H23 H 0 1 N N N 11.280 42.421 52.051 -4.002 0.795 -2.171 H23 690 63 690 H24 H24 H 0 1 N N N 12.220 44.024 48.792 -8.178 -0.057 -0.412 H24 690 64 690 H25 H25 H 0 1 N N N 13.136 47.098 51.324 -7.400 3.989 0.055 H25 690 65 690 H26 H26 H 0 1 N N N 13.905 47.322 53.683 -5.858 5.909 0.004 H26 690 66 690 H27 H27 H 0 1 N N N 13.181 45.677 55.385 -3.496 5.576 -0.598 H27 690 67 690 H28 H28 H 0 1 N N N 11.696 43.792 54.744 -2.660 3.330 -1.152 H28 690 68 # 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 690 C1 N2 SING N N 1 690 N2 C3 SING N N 2 690 O4 C3 DOUB N N 3 690 C3 C5 SING N N 4 690 C33 C32 SING N N 5 690 C33 C31 SING N N 6 690 O17 B16 SING N N 7 690 C32 C31 SING N N 8 690 C5 C30 SING Y N 9 690 C5 C6 DOUB Y N 10 690 C35 C36 DOUB Y N 11 690 C35 C34 SING Y N 12 690 C36 C37 SING Y N 13 690 C29 C30 DOUB Y N 14 690 C29 C28 SING Y N 15 690 C30 C8 SING Y N 16 690 C31 C28 SING N N 17 690 C34 C6 SING N N 18 690 C34 C40 DOUB Y N 19 690 B16 O15 SING N N 20 690 B16 C18 SING N N 21 690 C37 F38 SING N N 22 690 C37 C39 DOUB Y N 23 690 C6 O7 SING Y N 24 690 C28 C10 DOUB Y N 25 690 O15 C14 SING N N 26 690 C40 C39 SING Y N 27 690 C8 O7 SING Y N 28 690 C8 C9 DOUB Y N 29 690 C18 C19 DOUB Y N 30 690 C18 C23 SING Y N 31 690 C10 C9 SING Y N 32 690 C10 N11 SING N N 33 690 C19 C20 SING Y N 34 690 C14 C23 SING N N 35 690 C14 C13 SING N N 36 690 C12 C13 SING N N 37 690 C12 N11 SING N N 38 690 C23 C22 DOUB Y N 39 690 N11 S24 SING N N 40 690 C20 C21 DOUB Y N 41 690 O26 S24 DOUB N N 42 690 C22 C21 SING Y N 43 690 S24 C25 SING N N 44 690 S24 O27 DOUB N N 45 690 C25 H1 SING N N 46 690 C25 H2 SING N N 47 690 C25 H3 SING N N 48 690 C9 H4 SING N N 49 690 C31 H5 SING N N 50 690 C32 H6 SING N N 51 690 C32 H7 SING N N 52 690 C33 H8 SING N N 53 690 C33 H9 SING N N 54 690 C29 H10 SING N N 55 690 N2 H11 SING N N 56 690 C1 H12 SING N N 57 690 C1 H13 SING N N 58 690 C1 H14 SING N N 59 690 C35 H15 SING N N 60 690 C36 H16 SING N N 61 690 C40 H17 SING N N 62 690 C39 H18 SING N N 63 690 C12 H19 SING N N 64 690 C12 H20 SING N N 65 690 C13 H21 SING N N 66 690 C13 H22 SING N N 67 690 C14 H23 SING N N 68 690 O17 H24 SING N N 69 690 C19 H25 SING N N 70 690 C20 H26 SING N N 71 690 C21 H27 SING N N 72 690 C22 H28 SING N N 73 # 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 690 SMILES ACDLabs 12.01 "O=S(=O)(N(c3c(cc1c(oc(c1C(=O)NC)c2ccc(F)cc2)c3)C4CC4)CCC6OB(O)c5ccccc56)C" 690 InChI InChI 1.03 "InChI=1S/C29H28BFN2O6S/c1-32-29(34)27-22-15-21(17-7-8-17)24(16-26(22)38-28(27)18-9-11-19(31)12-10-18)33(40(2,36)37)14-13-25-20-5-3-4-6-23(20)30(35)39-25/h3-6,9-12,15-17,25,35H,7-8,13-14H2,1-2H3,(H,32,34)/t25-/m1/s1" 690 InChIKey InChI 1.03 NPAMWFMDBHAIAJ-RUZDIDTESA-N 690 SMILES_CANONICAL CACTVS 3.370 "CNC(=O)c1c(oc2cc(N(CC[C@H]3OB(O)c4ccccc34)[S](C)(=O)=O)c(cc12)C5CC5)c6ccc(F)cc6" 690 SMILES CACTVS 3.370 "CNC(=O)c1c(oc2cc(N(CC[CH]3OB(O)c4ccccc34)[S](C)(=O)=O)c(cc12)C5CC5)c6ccc(F)cc6" 690 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "B1(c2ccccc2[C@H](O1)CCN(c3cc4c(cc3C5CC5)c(c(o4)c6ccc(cc6)F)C(=O)NC)S(=O)(=O)C)O" 690 SMILES "OpenEye OEToolkits" 1.7.6 "B1(c2ccccc2C(O1)CCN(c3cc4c(cc3C5CC5)c(c(o4)c6ccc(cc6)F)C(=O)NC)S(=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 690 "SYSTEMATIC NAME" ACDLabs 12.01 "5-cyclopropyl-2-(4-fluorophenyl)-6-[{2-[(3R)-1-hydroxy-1,3-dihydro-2,1-benzoxaborol-3-yl]ethyl}(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide" 690 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-[methylsulfonyl-[2-[(3R)-1-oxidanyl-3H-2,1-benzoxaborol-3-yl]ethyl]amino]-1-benzofuran-3-carboxamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 690 "Create component" 2013-04-26 RCSB 690 "Initial release" 2013-05-08 RCSB #