data_3UW # _chem_comp.id 3UW _chem_comp.name "(4S,4a'S,10a'R)-2-amino-8'-(2-fluoropyridin-3-yl)-1-methyl-3',4',4a',10a'-tetrahydro-2'H-spiro[imidazole-4,10'-pyrano[3,2-b]chromen]-5(1H)-one" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H19 F N4 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2014-11-07 _chem_comp.pdbx_modified_date 2014-11-28 _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 382.388 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 3UW _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 4RRN _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 3UW C1 C1 C 0 1 Y N N 25.258 14.313 8.990 0.220 0.696 0.168 C1 3UW 1 3UW C2 C2 C 0 1 Y N N 26.101 13.220 8.655 0.478 2.034 -0.090 C2 3UW 2 3UW C3 C3 C 0 1 Y N N 27.505 13.348 8.796 -0.577 2.922 -0.276 C3 3UW 3 3UW C4 C4 C 0 1 Y N N 28.084 14.556 9.258 -1.880 2.480 -0.203 C4 3UW 4 3UW C5 C5 C 0 1 Y N N 27.243 15.653 9.597 -2.143 1.137 0.059 C5 3UW 5 3UW C6 C6 C 0 1 Y N N 25.838 15.522 9.447 -1.086 0.250 0.244 C6 3UW 6 3UW C7 C7 C 0 1 N N S 23.737 14.212 8.822 1.339 -0.289 0.361 C7 3UW 7 3UW C8 C8 C 0 1 N N R 23.291 12.761 8.621 2.652 0.436 0.646 C8 3UW 8 3UW C9 C9 C 0 1 N N S 24.248 11.993 7.688 2.804 1.572 -0.376 C9 3UW 9 3UW O10 O10 O 0 1 N N N 25.575 12.023 8.206 1.748 2.511 -0.163 O10 3UW 10 3UW O11 O11 O 0 1 N N N 21.936 12.693 8.177 3.742 -0.479 0.522 O11 3UW 11 3UW C12 C12 C 0 1 N N N 21.406 11.369 8.039 5.025 0.102 0.762 C12 3UW 12 3UW C13 C13 C 0 1 N N N 22.284 10.503 7.111 5.281 1.209 -0.264 C13 3UW 13 3UW C14 C14 C 0 1 N N N 23.767 10.531 7.558 4.152 2.265 -0.157 C14 3UW 14 3UW C15 C15 C 0 1 Y N N 27.781 16.896 10.026 -3.544 0.655 0.141 C15 3UW 15 3UW C16 C16 C 0 1 Y N N 27.334 17.599 11.178 -3.950 -0.470 -0.580 C16 3UW 16 3UW N17 N17 N 0 1 Y N N 27.828 18.799 11.559 -5.196 -0.899 -0.506 N17 3UW 17 3UW C18 C18 C 0 1 Y N N 28.795 19.372 10.810 -6.097 -0.292 0.242 C18 3UW 18 3UW C19 C19 C 0 1 Y N N 29.307 18.759 9.636 -5.772 0.828 0.984 C19 3UW 19 3UW C20 C20 C 0 1 Y N N 28.784 17.505 9.223 -4.476 1.314 0.946 C20 3UW 20 3UW F21 F21 F 0 1 N N N 26.379 17.078 11.970 -3.062 -1.123 -1.360 F21 3UW 21 3UW N22 N22 N 0 1 N N N 22.958 14.753 9.930 1.021 -1.220 1.449 N22 3UW 22 3UW C23 C23 C 0 1 N N N 22.265 15.761 9.528 0.988 -2.414 0.938 C23 3UW 23 3UW N24 N24 N 0 1 N N N 22.428 16.076 8.216 1.252 -2.424 -0.410 N24 3UW 24 3UW C25 C25 C 0 1 N N N 23.312 15.180 7.695 1.480 -1.170 -0.859 C25 3UW 25 3UW O26 O26 O 0 1 N N N 23.724 15.131 6.529 1.740 -0.827 -1.992 O26 3UW 26 3UW C27 C27 C 0 1 N N N 21.782 17.165 7.475 1.282 -3.627 -1.245 C27 3UW 27 3UW N28 N28 N 0 1 N N N 21.398 16.491 10.308 0.718 -3.547 1.668 N28 3UW 28 3UW H1 H1 H 0 1 N N N 28.143 12.513 8.548 -0.374 3.963 -0.479 H1 3UW 29 3UW H2 H2 H 0 1 N N N 29.156 14.644 9.352 -2.696 3.174 -0.348 H2 3UW 30 3UW H3 H3 H 0 1 N N N 25.199 16.359 9.686 -1.288 -0.792 0.448 H3 3UW 31 3UW H4 H4 H 0 1 N N N 23.351 12.272 9.605 2.632 0.849 1.655 H4 3UW 32 3UW H5 H5 H 0 1 N N N 24.218 12.461 6.693 2.740 1.170 -1.387 H5 3UW 33 3UW H6 H6 H 0 1 N N N 20.392 11.432 7.616 5.051 0.524 1.766 H6 3UW 34 3UW H7 H7 H 0 1 N N N 21.361 10.897 9.031 5.794 -0.664 0.669 H7 3UW 35 3UW H8 H8 H 0 1 N N N 22.211 10.890 6.084 6.242 1.681 -0.057 H8 3UW 36 3UW H9 H9 H 0 1 N N N 21.920 9.465 7.138 5.291 0.787 -1.269 H9 3UW 37 3UW H10 H10 H 0 1 N N N 23.865 10.027 8.531 4.295 3.031 -0.919 H10 3UW 38 3UW H11 H11 H 0 1 N N N 24.383 10.009 6.811 4.175 2.724 0.832 H11 3UW 39 3UW H12 H12 H 0 1 N N N 29.192 20.329 11.114 -7.107 -0.675 0.274 H12 3UW 40 3UW H13 H13 H 0 1 N N N 30.086 19.241 9.063 -6.519 1.316 1.592 H13 3UW 41 3UW H14 H14 H 0 1 N N N 29.139 17.026 8.322 -4.195 2.187 1.517 H14 3UW 42 3UW H15 H15 H 0 1 N N N 21.119 17.726 8.150 1.064 -4.501 -0.632 H15 3UW 43 3UW H16 H16 H 0 1 N N N 22.551 17.840 7.071 0.534 -3.540 -2.034 H16 3UW 44 3UW H17 H17 H 0 1 N N N 21.191 16.745 6.647 2.270 -3.734 -1.692 H17 3UW 45 3UW H18 H18 H 0 1 N N N 21.268 16.251 11.270 0.539 -3.480 2.619 H18 3UW 46 3UW H19 H19 H 0 1 N N N 20.898 17.262 9.913 0.707 -4.414 1.233 H19 3UW 47 # 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 3UW O26 C25 DOUB N N 1 3UW C13 C14 SING N N 2 3UW C13 C12 SING N N 3 3UW C27 N24 SING N N 4 3UW C14 C9 SING N N 5 3UW C9 O10 SING N N 6 3UW C9 C8 SING N N 7 3UW C25 N24 SING N N 8 3UW C25 C7 SING N N 9 3UW C12 O11 SING N N 10 3UW O11 C8 SING N N 11 3UW O10 C2 SING N N 12 3UW N24 C23 SING N N 13 3UW C8 C7 SING N N 14 3UW C2 C3 DOUB Y N 15 3UW C2 C1 SING Y N 16 3UW C3 C4 SING Y N 17 3UW C7 C1 SING N N 18 3UW C7 N22 SING N N 19 3UW C1 C6 DOUB Y N 20 3UW C20 C19 DOUB Y N 21 3UW C20 C15 SING Y N 22 3UW C4 C5 DOUB Y N 23 3UW C6 C5 SING Y N 24 3UW C23 N22 DOUB N N 25 3UW C23 N28 SING N N 26 3UW C5 C15 SING N N 27 3UW C19 C18 SING Y N 28 3UW C15 C16 DOUB Y N 29 3UW C18 N17 DOUB Y N 30 3UW C16 N17 SING Y N 31 3UW C16 F21 SING N N 32 3UW C3 H1 SING N N 33 3UW C4 H2 SING N N 34 3UW C6 H3 SING N N 35 3UW C8 H4 SING N N 36 3UW C9 H5 SING N N 37 3UW C12 H6 SING N N 38 3UW C12 H7 SING N N 39 3UW C13 H8 SING N N 40 3UW C13 H9 SING N N 41 3UW C14 H10 SING N N 42 3UW C14 H11 SING N N 43 3UW C18 H12 SING N N 44 3UW C19 H13 SING N N 45 3UW C20 H14 SING N N 46 3UW C27 H15 SING N N 47 3UW C27 H16 SING N N 48 3UW C27 H17 SING N N 49 3UW N28 H18 SING N N 50 3UW N28 H19 SING N N 51 # 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 3UW SMILES ACDLabs 12.01 "Fc1ncccc1c5cc3c(OC4CCCOC4C32N=C(N)N(C2=O)C)cc5" 3UW InChI InChI 1.03 "InChI=1S/C20H19FN4O3/c1-25-18(26)20(24-19(25)22)13-10-11(12-4-2-8-23-17(12)21)6-7-14(13)28-15-5-3-9-27-16(15)20/h2,4,6-8,10,15-16H,3,5,9H2,1H3,(H2,22,24)/t15-,16-,20-/m0/s1" 3UW InChIKey InChI 1.03 GZRDWAATBYKNGI-FTRWYGJKSA-N 3UW SMILES_CANONICAL CACTVS 3.385 "CN1C(=N[C@@]2([C@H]3OCCC[C@@H]3Oc4ccc(cc24)c5cccnc5F)C1=O)N" 3UW SMILES CACTVS 3.385 "CN1C(=N[C]2([CH]3OCCC[CH]3Oc4ccc(cc24)c5cccnc5F)C1=O)N" 3UW SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CN1C(=O)[C@@]2(c3cc(ccc3O[C@@H]4[C@@H]2OCCC4)c5cccnc5F)N=C1N" 3UW SMILES "OpenEye OEToolkits" 1.7.6 "CN1C(=O)C2(c3cc(ccc3OC4C2OCCC4)c5cccnc5F)N=C1N" # 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 3UW "SYSTEMATIC NAME" ACDLabs 12.01 "(4S,4a'S,10a'R)-2-amino-8'-(2-fluoropyridin-3-yl)-1-methyl-3',4',4a',10a'-tetrahydro-2'H-spiro[imidazole-4,10'-pyrano[3,2-b]chromen]-5(1H)-one" 3UW "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(4aS,10S,10aR)-2'-azanyl-8-(2-fluoranylpyridin-3-yl)-3'-methyl-spiro[3,4,4a,10a-tetrahydro-2H-pyrano[3,2-b]chromene-10,5'-imidazole]-4'-one" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 3UW "Create component" 2014-11-07 RCSB 3UW "Initial release" 2014-12-03 RCSB #