data_DWS # _chem_comp.id DWS _chem_comp.name "3-[(6aS,7S,9S,10aS)-9-cyano-7-methyl-8-oxo-2-(phenylamino)-6,6a,7,8,9,10-hexahydrobenzo[h]quinazolin-10a(5H)-yl]benzoic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C27 H24 N4 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2017-11-10 _chem_comp.pdbx_modified_date 2018-07-20 _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 452.504 _chem_comp.one_letter_code ? _chem_comp.three_letter_code DWS _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 6BL2 _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 DWS C4 C1 C 0 1 Y N N 35.215 218.893 44.712 2.300 3.393 0.845 C4 DWS 1 DWS C5 C2 C 0 1 Y N N 35.840 218.668 43.502 3.271 2.414 0.901 C5 DWS 2 DWS C6 C3 C 0 1 Y N N 36.647 219.638 42.946 2.966 1.111 0.550 C6 DWS 3 DWS C7 C4 C 0 1 Y N N 36.851 220.853 43.589 1.686 0.780 0.141 C7 DWS 4 DWS C8 C5 C 0 1 N N S 37.760 221.961 43.064 1.363 -0.641 -0.240 C8 DWS 5 DWS C10 C6 C 0 1 N N N 39.143 222.770 45.113 1.864 -0.242 -2.638 C10 DWS 6 DWS C13 C7 C 0 1 Y N N 36.537 225.367 44.168 -1.845 -0.806 -2.235 C13 DWS 7 DWS C15 C8 C 0 1 Y N N 35.149 224.517 42.558 -2.293 -0.837 0.020 C15 DWS 8 DWS C17 C9 C 0 1 Y N N 36.995 223.270 43.239 -0.083 -0.721 -0.636 C17 DWS 9 DWS C20 C10 C 0 1 Y N N 32.605 225.937 40.351 -5.495 -1.557 1.522 C20 DWS 10 DWS C21 C11 C 0 1 Y N N 31.646 226.928 40.205 -6.844 -1.501 1.233 C21 DWS 11 DWS C22 C12 C 0 1 Y N N 31.122 227.540 41.327 -7.295 -0.733 0.175 C22 DWS 12 DWS C24 C13 C 0 1 Y N N 32.522 226.189 42.720 -5.046 -0.069 -0.312 C24 DWS 13 DWS C26 C14 C 0 1 N N N 38.082 221.783 41.570 1.647 -1.550 0.956 C26 DWS 14 DWS C34 C15 C 0 1 N N N 39.463 220.570 39.819 3.426 -2.293 2.477 C34 DWS 15 DWS C23 C16 C 0 1 Y N N 31.557 227.169 42.586 -6.396 -0.018 -0.596 C23 DWS 16 DWS C36 C17 C 0 1 Y N N 36.208 221.043 44.806 0.706 1.749 0.080 C36 DWS 17 DWS C3 C18 C 0 1 Y N N 35.386 220.090 45.374 1.007 3.066 0.433 C3 DWS 18 DWS C12 C19 C 0 1 Y N N 37.362 224.262 44.136 -0.484 -0.741 -1.956 C12 DWS 19 DWS C19 C20 C 0 1 Y N N 33.058 225.565 41.606 -4.590 -0.840 0.750 C19 DWS 20 DWS C29 C21 C 0 1 N N N 40.095 220.259 42.241 4.021 -1.508 0.247 C29 DWS 21 DWS C2 C22 C 0 1 N N N 34.735 220.354 46.683 -0.039 4.107 0.376 C2 DWS 22 DWS C11 C23 C 0 1 N N N 38.568 224.167 45.009 0.485 -0.707 -3.105 C11 DWS 23 DWS C27 C24 C 0 1 N N S 39.090 220.708 41.219 3.089 -1.322 1.424 C27 DWS 24 DWS C30 C25 C 0 1 N N S 39.941 220.716 43.679 3.720 -0.786 -1.036 C30 DWS 25 DWS C9 C26 C 0 1 N N S 39.130 222.021 43.787 2.259 -1.057 -1.405 C9 DWS 26 DWS C32 C27 C 0 1 N N N 41.298 220.751 44.358 4.645 -1.293 -2.144 C32 DWS 27 DWS N35 N1 N 0 1 N N N 39.743 220.418 38.707 3.685 -3.043 3.290 N35 DWS 28 DWS N14 N2 N 0 1 Y N N 35.439 225.515 43.412 -2.711 -0.852 -1.238 N14 DWS 29 DWS N16 N3 N 0 1 Y N N 35.897 223.413 42.474 -1.006 -0.773 0.318 N16 DWS 30 DWS N18 N4 N 0 1 N N N 34.022 224.539 41.712 -3.224 -0.890 1.044 N18 DWS 31 DWS O37 O1 O 0 1 N N N 35.335 221.178 47.436 0.254 5.376 0.723 O37 DWS 32 DWS O33 O2 O 0 1 N N N 40.991 219.500 41.892 4.984 -2.231 0.337 O33 DWS 33 DWS O1 O3 O 0 1 N N N 33.650 219.753 46.941 -1.163 3.820 0.017 O1 DWS 34 DWS H1 H1 H 0 1 N N N 34.588 218.126 45.143 2.539 4.409 1.123 H1 DWS 35 DWS H2 H2 H 0 1 N N N 35.696 217.729 42.989 4.272 2.666 1.220 H2 DWS 36 DWS H3 H3 H 0 1 N N N 37.128 219.451 41.997 3.730 0.349 0.595 H3 DWS 37 DWS H4 H4 H 0 1 N N N 38.550 222.200 45.843 2.593 -0.401 -3.433 H4 DWS 38 DWS H5 H5 H 0 1 N N N 40.183 222.844 45.464 1.827 0.817 -2.382 H5 DWS 39 DWS H6 H6 H 0 1 N N N 36.792 226.167 44.847 -2.191 -0.817 -3.257 H6 DWS 40 DWS H7 H7 H 0 1 N N N 33.004 225.449 39.474 -5.144 -2.154 2.351 H7 DWS 41 DWS H8 H8 H 0 1 N N N 31.311 227.219 39.220 -7.548 -2.058 1.833 H8 DWS 42 DWS H9 H9 H 0 1 N N N 30.372 228.309 41.221 -8.350 -0.692 -0.050 H9 DWS 43 DWS H10 H10 H 0 1 N N N 32.862 225.906 43.705 -4.345 0.489 -0.915 H10 DWS 44 DWS H11 H11 H 0 1 N N N 38.471 222.741 41.196 0.958 -1.312 1.767 H11 DWS 45 DWS H12 H12 H 0 1 N N N 37.142 221.542 41.052 1.518 -2.591 0.662 H12 DWS 46 DWS H13 H13 H 0 1 N N N 31.143 227.644 43.463 -6.752 0.581 -1.422 H13 DWS 47 DWS H14 H14 H 0 1 N N N 36.357 221.976 45.330 -0.293 1.489 -0.239 H14 DWS 48 DWS H15 H15 H 0 1 N N N 39.344 224.831 44.601 0.114 -0.022 -3.867 H15 DWS 49 DWS H16 H16 H 0 1 N N N 38.292 224.504 46.019 0.569 -1.706 -3.533 H16 DWS 50 DWS H17 H17 H 0 1 N N N 38.413 219.843 41.284 3.191 -0.309 1.815 H17 DWS 51 DWS H18 H18 H 0 1 N N N 39.352 219.942 44.193 3.863 0.286 -0.898 H18 DWS 52 DWS H19 H19 H 0 1 N N N 39.701 222.698 43.134 2.125 -2.119 -1.608 H19 DWS 53 DWS H20 H20 H 0 1 N N N 41.179 221.083 45.400 4.489 -2.363 -2.286 H20 DWS 54 DWS H21 H21 H 0 1 N N N 41.742 219.745 44.343 4.423 -0.767 -3.072 H21 DWS 55 DWS H22 H22 H 0 1 N N N 41.957 221.451 43.823 5.682 -1.112 -1.863 H22 DWS 56 DWS H23 H23 H 0 1 N N N 33.891 223.742 41.123 -2.928 -0.962 1.965 H23 DWS 57 DWS H24 H24 H 0 1 N N N 34.845 221.285 48.243 -0.464 6.022 0.669 H24 DWS 58 # 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 DWS N35 C34 TRIP N N 1 DWS C34 C27 SING N N 2 DWS C21 C20 DOUB Y N 3 DWS C21 C22 SING Y N 4 DWS C20 C19 SING Y N 5 DWS C27 C26 SING N N 6 DWS C27 C29 SING N N 7 DWS C22 C23 DOUB Y N 8 DWS C26 C8 SING N N 9 DWS C19 N18 SING N N 10 DWS C19 C24 DOUB Y N 11 DWS N18 C15 SING N N 12 DWS O33 C29 DOUB N N 13 DWS C29 C30 SING N N 14 DWS N16 C15 DOUB Y N 15 DWS N16 C17 SING Y N 16 DWS C15 N14 SING Y N 17 DWS C23 C24 SING Y N 18 DWS C6 C5 DOUB Y N 19 DWS C6 C7 SING Y N 20 DWS C8 C17 SING N N 21 DWS C8 C7 SING N N 22 DWS C8 C9 SING N N 23 DWS C17 C12 DOUB Y N 24 DWS N14 C13 DOUB Y N 25 DWS C5 C4 SING Y N 26 DWS C7 C36 DOUB Y N 27 DWS C30 C9 SING N N 28 DWS C30 C32 SING N N 29 DWS C9 C10 SING N N 30 DWS C12 C13 SING Y N 31 DWS C12 C11 SING N N 32 DWS C4 C3 DOUB Y N 33 DWS C36 C3 SING Y N 34 DWS C11 C10 SING N N 35 DWS C3 C2 SING N N 36 DWS C2 O1 DOUB N N 37 DWS C2 O37 SING N N 38 DWS C4 H1 SING N N 39 DWS C5 H2 SING N N 40 DWS C6 H3 SING N N 41 DWS C10 H4 SING N N 42 DWS C10 H5 SING N N 43 DWS C13 H6 SING N N 44 DWS C20 H7 SING N N 45 DWS C21 H8 SING N N 46 DWS C22 H9 SING N N 47 DWS C24 H10 SING N N 48 DWS C26 H11 SING N N 49 DWS C26 H12 SING N N 50 DWS C23 H13 SING N N 51 DWS C36 H14 SING N N 52 DWS C11 H15 SING N N 53 DWS C11 H16 SING N N 54 DWS C27 H17 SING N N 55 DWS C30 H18 SING N N 56 DWS C9 H19 SING N N 57 DWS C32 H20 SING N N 58 DWS C32 H21 SING N N 59 DWS C32 H22 SING N N 60 DWS N18 H23 SING N N 61 DWS O37 H24 SING N N 62 # 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 DWS SMILES ACDLabs 12.01 "c1c(cc(cc1)C45c2c(cnc(n2)Nc3ccccc3)CCC4C(C(C(C5)C#N)=O)C)C(=O)O" DWS InChI InChI 1.03 "InChI=1S/C27H24N4O3/c1-16-22-11-10-18-15-29-26(30-21-8-3-2-4-9-21)31-24(18)27(22,13-19(14-28)23(16)32)20-7-5-6-17(12-20)25(33)34/h2-9,12,15-16,19,22H,10-11,13H2,1H3,(H,33,34)(H,29,30,31)/t16-,19-,22-,27+/m0/s1" DWS InChIKey InChI 1.03 MJZJSVVSZUVNQP-RIMKCHMMSA-N DWS SMILES_CANONICAL CACTVS 3.385 "C[C@H]1[C@@H]2CCc3cnc(Nc4ccccc4)nc3[C@]2(C[C@@H](C#N)C1=O)c5cccc(c5)C(O)=O" DWS SMILES CACTVS 3.385 "C[CH]1[CH]2CCc3cnc(Nc4ccccc4)nc3[C]2(C[CH](C#N)C1=O)c5cccc(c5)C(O)=O" DWS SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "C[C@H]1[C@@H]2CCc3cnc(nc3[C@]2(C[C@H](C1=O)C#N)c4cccc(c4)C(=O)O)Nc5ccccc5" DWS SMILES "OpenEye OEToolkits" 2.0.6 "CC1C2CCc3cnc(nc3C2(CC(C1=O)C#N)c4cccc(c4)C(=O)O)Nc5ccccc5" # 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 DWS "SYSTEMATIC NAME" ACDLabs 12.01 "3-[(6aS,7S,9S,10aS)-9-cyano-7-methyl-8-oxo-2-(phenylamino)-6,6a,7,8,9,10-hexahydrobenzo[h]quinazolin-10a(5H)-yl]benzoic acid" DWS "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "3-[(6~{a}~{S},7~{S},9~{S},10~{a}~{S})-9-cyano-7-methyl-8-oxidanylidene-2-phenylazanyl-5,6,6~{a},7,9,10-hexahydrobenzo[h]quinazolin-10~{a}-yl]benzoic acid" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site DWS "Create component" 2017-11-10 RCSB DWS "Modify formula" 2018-05-18 RCSB DWS "Initial release" 2018-07-25 RCSB #