data_YAK # _chem_comp.id YAK _chem_comp.name "N-{3-[(4aR,7aS)-1-(4-fluorobenzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[b]pyridin-3-yl]-1,1-dioxido-2H-1,2,4-benzothiadiazin-7-yl}methanesulfonamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C23 H23 F N4 O6 S2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-04-17 _chem_comp.pdbx_modified_date 2011-06-04 _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 534.580 _chem_comp.one_letter_code ? _chem_comp.three_letter_code YAK _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 3H2L _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 YAK F34 F34 F 0 1 N N N 90.917 9.896 50.206 7.217 4.128 -0.475 F34 YAK 1 YAK C11 C11 C 0 1 Y N N 92.142 10.211 50.661 6.549 3.077 0.048 C11 YAK 2 YAK C5 C5 C 0 1 Y N N 93.147 10.655 49.779 7.115 1.814 0.023 C5 YAK 3 YAK C6 C6 C 0 1 Y N N 92.396 10.091 52.030 5.300 3.263 0.616 C6 YAK 4 YAK C2 C2 C 0 1 Y N N 93.658 10.410 52.533 4.618 2.188 1.152 C2 YAK 5 YAK C8 C8 C 0 1 Y N N 94.654 10.856 51.666 5.182 0.926 1.121 C8 YAK 6 YAK C1 C1 C 0 1 Y N N 94.413 10.968 50.289 6.431 0.739 0.559 C1 YAK 7 YAK C23 C23 C 0 1 N N N 96.006 11.173 52.224 4.437 -0.246 1.706 C23 YAK 8 YAK N26 N26 N 0 1 N N N 96.583 9.927 52.733 3.545 -0.813 0.691 N26 YAK 9 YAK C21 C21 C 0 1 N N S 97.318 9.096 51.791 4.099 -1.750 -0.280 C21 YAK 10 YAK C19 C19 C 0 1 N N N 98.746 9.605 51.525 5.210 -2.569 0.415 C19 YAK 11 YAK C17 C17 C 0 1 N N N 99.437 8.410 50.877 4.560 -3.882 0.883 C17 YAK 12 YAK C20 C20 C 0 1 N N R 97.461 7.607 52.196 3.065 -2.804 -0.707 C20 YAK 13 YAK C18 C18 C 0 1 N N N 98.770 7.174 51.495 3.078 -3.817 0.458 C18 YAK 14 YAK C14 C14 C 0 1 N N N 97.425 7.363 53.708 1.700 -2.223 -0.885 C14 YAK 15 YAK O33 O33 O 0 1 N N N 97.812 6.130 54.160 0.843 -2.813 -1.738 O33 YAK 16 YAK C16 C16 C 0 1 N N N 96.385 9.573 54.073 2.253 -0.453 0.698 C16 YAK 17 YAK O28 O28 O 0 1 N N N 95.711 10.229 54.871 1.870 0.423 1.450 O28 YAK 18 YAK C13 C13 C 0 1 N N N 97.012 8.320 54.578 1.302 -1.114 -0.206 C13 YAK 19 YAK C15 C15 C 0 1 N N N 97.199 8.303 56.048 -0.063 -0.586 -0.372 C15 YAK 20 YAK N24 N24 N 0 1 N N N 96.661 9.226 56.802 -1.049 -1.259 0.135 N24 YAK 21 YAK C9 C9 C 0 1 Y N N 96.774 9.269 58.207 -2.375 -0.968 0.057 C9 YAK 22 YAK C3 C3 C 0 1 Y N N 96.225 10.380 58.886 -3.295 -1.635 0.872 C3 YAK 23 YAK N25 N25 N 0 1 N N N 98.023 7.252 56.521 -0.228 0.607 -1.056 N25 YAK 24 YAK S35 S35 S 0 1 N N N 98.109 6.891 58.161 -1.663 0.789 -1.893 S35 YAK 25 YAK O29 O29 O 0 1 N N N 99.503 6.843 58.567 -1.554 0.012 -3.077 O29 YAK 26 YAK O30 O30 O 0 1 N N N 97.175 5.811 58.395 -1.974 2.176 -1.886 O30 YAK 27 YAK C12 C12 C 0 1 Y N N 97.417 8.291 58.976 -2.851 -0.012 -0.851 C12 YAK 28 YAK C7 C7 C 0 1 Y N N 97.507 8.385 60.372 -4.185 0.290 -0.929 C7 YAK 29 YAK C10 C10 C 0 1 Y N N 96.942 9.487 61.031 -5.091 -0.370 -0.103 C10 YAK 30 YAK C4 C4 C 0 1 Y N N 96.305 10.487 60.281 -4.637 -1.332 0.790 C4 YAK 31 YAK N27 N27 N 0 1 N N N 97.020 9.653 62.456 -6.454 -0.066 -0.173 N27 YAK 32 YAK S36 S36 S 0 1 N N N 97.450 8.384 63.532 -7.162 0.841 1.018 S36 YAK 33 YAK O31 O31 O 0 1 N N N 96.997 8.753 64.869 -8.495 1.035 0.565 O31 YAK 34 YAK O32 O32 O 0 1 N N N 97.016 7.116 62.976 -6.891 0.123 2.213 O32 YAK 35 YAK C22 C22 C 0 1 N N N 99.229 8.409 63.586 -6.248 2.408 0.996 C22 YAK 36 YAK H5 H5 H 0 1 N N N 92.944 10.753 48.723 8.091 1.668 -0.416 H5 YAK 37 YAK H6 H6 H 0 1 N N N 91.617 9.752 52.697 4.859 4.249 0.641 H6 YAK 38 YAK H2 H2 H 0 1 N N N 93.862 10.312 53.589 3.644 2.333 1.595 H2 YAK 39 YAK H1 H1 H 0 1 N N N 95.200 11.294 49.625 6.872 -0.246 0.539 H1 YAK 40 YAK H23 H23 H 0 1 N N N 96.650 11.593 51.437 5.149 -1.006 2.028 H23 YAK 41 YAK H23A H23A H 0 0 N N N 95.923 11.915 53.031 3.849 0.087 2.561 H23A YAK 42 YAK H21 H21 H 0 1 N N N 96.689 9.168 50.892 4.482 -1.216 -1.150 H21 YAK 43 YAK H19 H19 H 0 1 N N N 98.744 10.480 50.858 6.014 -2.780 -0.290 H19 YAK 44 YAK H19A H19A H 0 0 N N N 99.254 9.945 52.440 5.600 -2.018 1.271 H19A YAK 45 YAK H17 H17 H 0 1 N N N 99.303 8.424 49.785 5.048 -4.732 0.406 H17 YAK 46 YAK H17A H17A H 0 0 N N N 100.523 8.420 51.054 4.634 -3.970 1.967 H17A YAK 47 YAK H20 H20 H 0 1 N N N 96.604 6.995 51.877 3.386 -3.286 -1.630 H20 YAK 48 YAK H18 H18 H 0 1 N N N 98.542 6.443 50.705 2.734 -4.794 0.118 H18 YAK 49 YAK H18A H18A H 0 0 N N N 99.449 6.712 52.227 2.460 -3.460 1.282 H18A YAK 50 YAK HO33 HO33 H 0 0 N N N 97.902 5.536 53.424 -0.002 -2.368 -1.888 HO33 YAK 51 YAK H3 H3 H 0 1 N N N 95.736 11.159 58.321 -2.953 -2.388 1.567 H3 YAK 52 YAK HN25 HN25 H 0 0 N N N 98.561 6.717 55.870 0.452 1.299 -1.050 HN25 YAK 53 YAK H7 H7 H 0 1 N N N 98.009 7.613 60.937 -4.532 1.038 -1.628 H7 YAK 54 YAK H4 H4 H 0 1 N N N 95.875 11.342 60.781 -5.342 -1.848 1.426 H4 YAK 55 YAK HN27 HN27 H 0 0 N N N 97.712 10.361 62.598 -6.985 -0.386 -0.919 HN27 YAK 56 YAK H22 H22 H 0 1 N N N 99.627 8.414 62.561 -6.420 2.916 0.047 H22 YAK 57 YAK H22A H22A H 0 0 N N N 99.567 9.312 64.115 -6.594 3.041 1.814 H22A YAK 58 YAK H22B H22B H 0 0 N N N 99.592 7.516 64.116 -5.183 2.210 1.115 H22B YAK 59 # 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 YAK F34 C11 SING N N 1 YAK C5 C11 DOUB Y N 2 YAK C11 C6 SING Y N 3 YAK C5 C1 SING Y N 4 YAK C5 H5 SING N N 5 YAK C6 C2 DOUB Y N 6 YAK C6 H6 SING N N 7 YAK C8 C2 SING Y N 8 YAK C2 H2 SING N N 9 YAK C1 C8 DOUB Y N 10 YAK C8 C23 SING N N 11 YAK C1 H1 SING N N 12 YAK C23 N26 SING N N 13 YAK C23 H23 SING N N 14 YAK C23 H23A SING N N 15 YAK C21 N26 SING N N 16 YAK N26 C16 SING N N 17 YAK C19 C21 SING N N 18 YAK C21 C20 SING N N 19 YAK C21 H21 SING N N 20 YAK C17 C19 SING N N 21 YAK C19 H19 SING N N 22 YAK C19 H19A SING N N 23 YAK C17 C18 SING N N 24 YAK C17 H17 SING N N 25 YAK C17 H17A SING N N 26 YAK C18 C20 SING N N 27 YAK C20 C14 SING N N 28 YAK C20 H20 SING N N 29 YAK C18 H18 SING N N 30 YAK C18 H18A SING N N 31 YAK C14 O33 SING N N 32 YAK C14 C13 DOUB N N 33 YAK O33 HO33 SING N N 34 YAK C16 C13 SING N N 35 YAK C16 O28 DOUB N N 36 YAK C13 C15 SING N N 37 YAK C15 N25 SING N N 38 YAK C15 N24 DOUB N N 39 YAK N24 C9 SING N N 40 YAK C9 C3 DOUB Y N 41 YAK C9 C12 SING Y N 42 YAK C3 C4 SING Y N 43 YAK C3 H3 SING N N 44 YAK N25 S35 SING N N 45 YAK N25 HN25 SING N N 46 YAK S35 O30 DOUB N N 47 YAK S35 O29 DOUB N N 48 YAK S35 C12 SING N N 49 YAK C12 C7 DOUB Y N 50 YAK C7 C10 SING Y N 51 YAK C7 H7 SING N N 52 YAK C4 C10 DOUB Y N 53 YAK C10 N27 SING N N 54 YAK C4 H4 SING N N 55 YAK N27 S36 SING N N 56 YAK N27 HN27 SING N N 57 YAK O32 S36 DOUB N N 58 YAK S36 C22 SING N N 59 YAK S36 O31 DOUB N N 60 YAK C22 H22 SING N N 61 YAK C22 H22A SING N N 62 YAK C22 H22B SING N N 63 # 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 YAK SMILES ACDLabs 10.04 "Fc1ccc(cc1)CN4C(=O)C(C3=Nc2c(cc(cc2)NS(=O)(=O)C)S(=O)(=O)N3)=C(O)C5CCCC45" YAK SMILES_CANONICAL CACTVS 3.341 "C[S](=O)(=O)Nc1ccc2N=C(N[S](=O)(=O)c2c1)C3=C(O)[C@@H]4CCC[C@@H]4N(Cc5ccc(F)cc5)C3=O" YAK SMILES CACTVS 3.341 "C[S](=O)(=O)Nc1ccc2N=C(N[S](=O)(=O)c2c1)C3=C(O)[CH]4CCC[CH]4N(Cc5ccc(F)cc5)C3=O" YAK SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CS(=O)(=O)Nc1ccc2c(c1)S(=O)(=O)NC(=N2)C3=C([C@@H]4CCC[C@@H]4N(C3=O)Cc5ccc(cc5)F)O" YAK SMILES "OpenEye OEToolkits" 1.5.0 "CS(=O)(=O)Nc1ccc2c(c1)S(=O)(=O)NC(=N2)C3=C(C4CCCC4N(C3=O)Cc5ccc(cc5)F)O" YAK InChI InChI 1.03 "InChI=1S/C23H23FN4O6S2/c1-35(31,32)26-15-9-10-17-19(11-15)36(33,34)27-22(25-17)20-21(29)16-3-2-4-18(16)28(23(20)30)12-13-5-7-14(24)8-6-13/h5-11,16,18,26,29H,2-4,12H2,1H3,(H,25,27)/t16-,18+/m1/s1" YAK InChIKey InChI 1.03 PAEBVIJMNXTTAT-AEFFLSMTSA-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 YAK "SYSTEMATIC NAME" ACDLabs 10.04 "N-{3-[(4aR,7aS)-1-(4-fluorobenzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[b]pyridin-3-yl]-1,1-dioxido-2H-1,2,4-benzothiadiazin-7-yl}methanesulfonamide" YAK "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "N-[3-[(4aR,7aS)-1-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-5,6,7,7a-tetrahydro-4aH-cyclopenta[e]pyridin-3-yl]-1,1-dioxo-2H-benzo[e][1,2,4]thiadiazin-7-yl]methanesulfonamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site YAK "Create component" 2009-04-17 RCSB YAK "Modify aromatic_flag" 2011-06-04 RCSB YAK "Modify descriptor" 2011-06-04 RCSB #