data_592 # _chem_comp.id 592 _chem_comp.name "N-benzyl-6-[(3-endo)-3-{[(3-methoxy-2-methylphenyl)carbonyl]amino}-8-azabicyclo[3.2.1]oct-8-yl]pyridine-3-carboxamide" _chem_comp.type non-polymer _chem_comp.pdbx_type HETAIN _chem_comp.formula "C29 H32 N4 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-06-05 _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 484.589 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 592 _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 4AWQ _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 592 C20 C20 C 0 1 N N N 10.012 19.714 15.655 5.453 2.728 -1.265 C20 592 1 592 C13 C13 C 0 1 Y N N 9.625 20.902 16.548 5.975 1.563 -0.464 C13 592 2 592 C14 C14 C 0 1 Y N N 9.055 20.648 17.794 7.311 1.510 -0.103 C14 592 3 592 O2 O2 O 0 1 N N N 8.752 19.354 18.157 8.153 2.512 -0.471 O2 592 4 592 C19 C19 C 0 1 N N N 8.178 19.156 19.450 9.518 2.393 -0.065 C19 592 5 592 C15 C15 C 0 1 Y N N 8.742 21.760 18.619 7.790 0.437 0.634 C15 592 6 592 C16 C16 C 0 1 Y N N 9.006 23.073 18.267 6.937 -0.585 1.011 C16 592 7 592 C1 C1 C 0 1 Y N N 9.589 23.321 17.018 5.605 -0.544 0.656 C1 592 8 592 C12 C12 C 0 1 Y N N 9.915 22.240 16.183 5.112 0.536 -0.080 C12 592 9 592 C10 C10 C 0 1 N N N 10.570 22.585 14.853 3.683 0.588 -0.456 C10 592 10 592 O1 O1 O 0 1 N N N 10.053 22.256 13.774 3.279 1.470 -1.188 O1 592 11 592 N1 N1 N 0 1 N N N 11.704 23.323 14.989 2.829 -0.344 0.013 N1 592 12 592 C4 C4 C 0 1 N N N 12.544 23.775 13.864 1.413 -0.292 -0.360 C4 592 13 592 C5 C5 C 0 1 N N N 11.802 24.907 13.074 1.032 -1.582 -1.092 C5 592 14 592 C3 C3 C 0 1 N N N 13.941 24.208 14.486 0.559 -0.144 0.903 C3 592 15 592 C2 C2 C 0 1 N N S 13.925 25.708 14.922 0.695 -1.420 1.748 C2 592 16 592 C8 C8 C 0 1 N N N 12.855 26.056 15.989 2.200 -1.760 1.853 C8 592 17 592 C7 C7 C 0 1 N N N 11.588 26.288 15.200 2.491 -2.646 0.624 C7 592 18 592 C6 C6 C 0 1 N N R 11.978 26.304 13.689 1.136 -2.761 -0.112 C6 592 19 592 N4 N4 N 0 1 N N N 13.447 26.449 13.742 0.122 -2.539 0.953 N4 592 20 592 C21 C21 C 0 1 Y N N 14.274 26.955 12.755 -1.100 -2.185 0.408 C21 592 21 592 C26 C26 C 0 1 Y N N 15.691 26.960 12.962 -1.539 -2.807 -0.759 C26 592 22 592 C25 C25 C 0 1 Y N N 16.491 27.450 11.926 -2.748 -2.455 -1.295 C25 592 23 592 N2 N2 N 0 1 Y N N 13.724 27.337 11.601 -1.841 -1.262 1.008 N2 592 24 592 C23 C23 C 0 1 Y N N 14.477 27.830 10.600 -3.010 -0.894 0.526 C23 592 25 592 C24 C24 C 0 1 Y N N 15.872 27.861 10.747 -3.508 -1.472 -0.643 C24 592 26 592 C27 C27 C 0 1 N N N 16.727 28.453 9.614 -4.818 -1.059 -1.182 C27 592 27 592 O3 O3 O 0 1 N N N 16.149 28.881 8.629 -5.246 -1.572 -2.198 O3 592 28 592 N3 N3 N 0 1 N N N 18.082 28.504 9.831 -5.540 -0.114 -0.548 N3 592 29 592 C11 C11 C 0 1 N N N 18.973 29.123 8.847 -6.841 0.296 -1.083 C11 592 30 592 C17 C17 C 0 1 Y N N 19.229 28.322 7.567 -7.437 1.357 -0.196 C17 592 31 592 C18 C18 C 0 1 Y N N 19.815 28.978 6.476 -7.175 2.692 -0.442 C18 592 32 592 C22 C22 C 0 1 Y N N 20.060 28.243 5.304 -7.722 3.666 0.373 C22 592 33 592 C28 C28 C 0 1 Y N N 19.722 26.884 5.270 -8.532 3.305 1.433 C28 592 34 592 C9 C9 C 0 1 Y N N 19.151 26.230 6.367 -8.795 1.970 1.679 C9 592 35 592 C29 C29 C 0 1 Y N N 18.908 26.962 7.529 -8.252 0.997 0.862 C29 592 36 592 H201 H201 H 0 0 N N N 9.174 19.469 14.986 5.424 2.460 -2.321 H201 592 37 592 H202 H202 H 0 0 N N N 10.895 19.979 15.054 4.448 2.980 -0.927 H202 592 38 592 H203 H203 H 0 0 N N N 10.245 18.843 16.285 6.109 3.587 -1.126 H203 592 39 592 H15 H15 H 0 1 N N N 8.272 21.572 19.573 8.832 0.398 0.915 H15 592 40 592 H191 H191 H 0 0 N N N 7.988 18.084 19.607 9.571 2.350 1.023 H191 592 41 592 H192 H192 H 0 0 N N N 8.873 19.522 20.220 9.944 1.482 -0.485 H192 592 42 592 H193 H193 H 0 0 N N N 7.230 19.710 19.519 10.080 3.256 -0.422 H193 592 43 592 H16 H16 H 0 1 N N N 8.768 23.885 18.938 7.316 -1.418 1.584 H16 592 44 592 H1 H1 H 0 1 N N N 9.786 24.334 16.700 4.942 -1.344 0.951 H1 592 45 592 HA HA H 0 1 N N N 11.987 23.576 15.914 3.152 -1.048 0.597 HA 592 46 592 H4 H4 H 0 1 N N N 12.722 22.934 13.178 1.241 0.561 -1.015 H4 592 47 592 H51C H51C H 0 0 N N N 12.194 24.928 12.046 0.010 -1.503 -1.462 H51C 592 48 592 H52C H52C H 0 0 N N N 10.728 24.669 13.052 1.713 -1.742 -1.929 H52C 592 49 592 H31C H31C H 0 0 N N N 14.152 23.581 15.365 0.906 0.714 1.479 H31C 592 50 592 H32C H32C H 0 0 N N N 14.730 24.062 13.733 -0.484 -0.001 0.623 H32C 592 51 592 H6 H6 H 0 1 N N N 11.466 27.096 13.123 1.019 -3.722 -0.612 H6 592 52 592 H2 H2 H 0 1 N N N 14.925 26.035 15.243 0.227 -1.316 2.727 H2 592 53 592 H81C H81C H 0 0 N N N 12.725 25.222 16.695 2.798 -0.850 1.815 H81C 592 54 592 H82C H82C H 0 0 N N N 13.139 26.963 16.542 2.402 -2.309 2.773 H82C 592 55 592 H71C H71C H 0 0 N N N 10.870 25.478 15.395 3.233 -2.171 -0.019 H71C 592 56 592 H72C H72C H 0 0 N N N 11.139 27.252 15.483 2.836 -3.631 0.939 H72C 592 57 592 H26 H26 H 0 1 N N N 16.125 26.599 13.883 -0.929 -3.560 -1.237 H26 592 58 592 H25 H25 H 0 1 N N N 17.564 27.509 12.037 -3.109 -2.923 -2.199 H25 592 59 592 H23 H23 H 0 1 N N N 14.014 28.197 9.696 -3.587 -0.140 1.039 H23 592 60 592 H3 H3 H 0 1 N N N 18.464 28.115 10.669 -5.199 0.295 0.263 H3 592 61 592 H111 H111 H 0 0 N N N 18.533 30.088 8.556 -6.710 0.695 -2.089 H111 592 62 592 H112 H112 H 0 0 N N N 19.944 29.295 9.335 -7.507 -0.566 -1.118 H112 592 63 592 H18 H18 H 0 1 N N N 20.073 30.025 6.535 -6.542 2.974 -1.270 H18 592 64 592 H29 H29 H 0 1 N N N 18.475 26.481 8.394 -8.460 -0.046 1.051 H29 592 65 592 H22 H22 H 0 1 N N N 20.503 28.719 4.442 -7.516 4.708 0.181 H22 592 66 592 H28 H28 H 0 1 N N N 19.908 26.322 4.367 -8.959 4.065 2.070 H28 592 67 592 H9 H9 H 0 1 N N N 18.903 25.180 6.315 -9.428 1.688 2.507 H9 592 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 592 C20 C13 SING N N 1 592 C13 C14 SING Y N 2 592 C13 C12 DOUB Y N 3 592 C14 O2 SING N N 4 592 C14 C15 DOUB Y N 5 592 O2 C19 SING N N 6 592 C15 C16 SING Y N 7 592 C16 C1 DOUB Y N 8 592 C1 C12 SING Y N 9 592 C12 C10 SING N N 10 592 C10 O1 DOUB N N 11 592 C10 N1 SING N N 12 592 N1 C4 SING N N 13 592 C4 C5 SING N N 14 592 C4 C3 SING N N 15 592 C5 C6 SING N N 16 592 C3 C2 SING N N 17 592 C2 C8 SING N N 18 592 C2 N4 SING N N 19 592 C8 C7 SING N N 20 592 C7 C6 SING N N 21 592 C6 N4 SING N N 22 592 N4 C21 SING N N 23 592 C21 C26 SING Y N 24 592 C21 N2 DOUB Y N 25 592 C26 C25 DOUB Y N 26 592 C25 C24 SING Y N 27 592 N2 C23 SING Y N 28 592 C23 C24 DOUB Y N 29 592 C24 C27 SING N N 30 592 C27 O3 DOUB N N 31 592 C27 N3 SING N N 32 592 N3 C11 SING N N 33 592 C11 C17 SING N N 34 592 C17 C18 SING Y N 35 592 C17 C29 DOUB Y N 36 592 C18 C22 DOUB Y N 37 592 C22 C28 SING Y N 38 592 C28 C9 DOUB Y N 39 592 C9 C29 SING Y N 40 592 C20 H201 SING N N 41 592 C20 H202 SING N N 42 592 C20 H203 SING N N 43 592 C15 H15 SING N N 44 592 C19 H191 SING N N 45 592 C19 H192 SING N N 46 592 C19 H193 SING N N 47 592 C16 H16 SING N N 48 592 C1 H1 SING N N 49 592 N1 HA SING N N 50 592 C4 H4 SING N N 51 592 C5 H51C SING N N 52 592 C5 H52C SING N N 53 592 C3 H31C SING N N 54 592 C3 H32C SING N N 55 592 C6 H6 SING N N 56 592 C2 H2 SING N N 57 592 C8 H81C SING N N 58 592 C8 H82C SING N N 59 592 C7 H71C SING N N 60 592 C7 H72C SING N N 61 592 C26 H26 SING N N 62 592 C25 H25 SING N N 63 592 C23 H23 SING N N 64 592 N3 H3 SING N N 65 592 C11 H111 SING N N 66 592 C11 H112 SING N N 67 592 C18 H18 SING N N 68 592 C29 H29 SING N N 69 592 C22 H22 SING N N 70 592 C28 H28 SING N N 71 592 C9 H9 SING N N 72 # 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 592 SMILES ACDLabs 12.01 "O=C(NCc1ccccc1)c2ccc(nc2)N3C5CCC3CC(NC(=O)c4cccc(OC)c4C)C5" 592 InChI InChI 1.03 "InChI=1S/C29H32N4O3/c1-19-25(9-6-10-26(19)36-2)29(35)32-22-15-23-12-13-24(16-22)33(23)27-14-11-21(18-30-27)28(34)31-17-20-7-4-3-5-8-20/h3-11,14,18,22-24H,12-13,15-17H2,1-2H3,(H,31,34)(H,32,35)/t22-,23+,24-" 592 InChIKey InChI 1.03 JXXRMCOYDPMQEY-BKFWDETESA-N 592 SMILES_CANONICAL CACTVS 3.385 "COc1cccc(C(=O)NC2C[C@@H]3CC[C@H](C2)N3c4ccc(cn4)C(=O)NCc5ccccc5)c1C" 592 SMILES CACTVS 3.385 "COc1cccc(C(=O)NC2C[CH]3CC[CH](C2)N3c4ccc(cn4)C(=O)NCc5ccccc5)c1C" 592 SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "Cc1c(cccc1OC)C(=O)NC2C[C@H]3CC[C@@H](C2)N3c4ccc(cn4)C(=O)NCc5ccccc5" 592 SMILES "OpenEye OEToolkits" 1.9.2 "Cc1c(cccc1OC)C(=O)NC2CC3CCC(C2)N3c4ccc(cn4)C(=O)NCc5ccccc5" # 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 592 "SYSTEMATIC NAME" ACDLabs 12.01 "N-benzyl-6-{(3-endo)-3-[(3-methoxy-2-methylbenzoyl)amino]-8-azabicyclo[3.2.1]oct-8-yl}pyridine-3-carboxamide" 592 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "6-[(1S,5R)-3-[(3-methoxy-2-methyl-phenyl)carbonylamino]-8-azabicyclo[3.2.1]octan-8-yl]-N-(phenylmethyl)pyridine-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 592 "Create component" 2012-06-05 EBI 592 "Initial release" 2012-08-24 RCSB 592 "Modify descriptor" 2014-09-05 RCSB #