data_ZYN # _chem_comp.id ZYN _chem_comp.name "6-(3-chloro-4-fluorobenzyl)-4-hydroxy-N,N-dimethyl-2-(1-methylethyl)-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H23 Cl F N3 O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2010-10-04 _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 435.876 _chem_comp.one_letter_code ? _chem_comp.three_letter_code ZYN _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 3OYH _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 ZYN CAA CAA C 0 1 N N N -37.837 27.032 -18.450 5.808 1.268 0.365 CAA ZYN 1 ZYN CAB CAB C 0 1 N N N -35.394 26.924 -19.068 4.706 1.241 2.607 CAB ZYN 2 ZYN CAC CAC C 0 1 N N N -36.628 27.494 -23.878 4.891 -3.575 -0.251 CAC ZYN 3 ZYN CAD CAD C 0 1 N N N -34.832 28.710 -22.491 4.295 -1.678 -1.828 CAD ZYN 4 ZYN OAE OAE O 0 1 N N N -38.422 28.485 -22.012 3.238 -2.349 1.495 OAE ZYN 5 ZYN OAF OAF O 0 1 N N N -36.126 33.972 -18.916 -0.894 1.913 -1.609 OAF ZYN 6 ZYN OAG OAG O 0 1 N N N -36.115 29.304 -17.247 3.524 2.908 0.696 OAG ZYN 7 ZYN OAH OAH O 0 1 N N N -35.889 31.985 -17.366 1.015 3.221 -0.468 OAH ZYN 8 ZYN FAI FAI F 0 1 N N N -40.852 38.164 -21.414 -6.644 0.985 1.425 FAI ZYN 9 ZYN CLAJ CLAJ CL 0 0 N N N -39.925 37.713 -18.873 -6.068 -1.904 1.282 CLAJ ZYN 10 ZYN CAK CAK C 0 1 Y N N -39.204 37.032 -22.646 -4.959 1.684 -0.088 CAK ZYN 11 ZYN CAL CAL C 0 1 Y N N -38.035 36.267 -22.595 -3.914 1.370 -0.936 CAL ZYN 12 ZYN CAM CAM C 0 1 Y N N -37.968 36.391 -20.188 -4.192 -0.953 -0.422 CAM ZYN 13 ZYN CAN CAN C 0 1 N N N -36.993 31.638 -22.187 0.846 -1.662 -0.801 CAN ZYN 14 ZYN CAO CAO C 0 1 N N N -36.366 32.986 -22.369 -0.663 -1.500 -0.639 CAO ZYN 15 ZYN CAP CAP C 0 1 N N N -36.132 35.180 -21.343 -2.391 -0.289 -2.028 CAP ZYN 16 ZYN CAQ CAQ C 0 1 N N N -37.213 28.768 -21.897 3.409 -1.768 0.440 CAQ ZYN 17 ZYN CAR CAR C 0 1 N N N -36.276 33.216 -19.887 -0.428 0.871 -1.192 CAR ZYN 18 ZYN CAS CAS C 0 1 Y N N -39.735 37.437 -21.449 -5.622 0.679 0.595 CAS ZYN 19 ZYN CAT CAT C 0 1 Y N N -37.437 35.940 -21.383 -3.531 0.052 -1.103 CAT ZYN 20 ZYN CAU CAU C 0 1 Y N N -39.127 37.128 -20.257 -5.238 -0.641 0.427 CAU ZYN 21 ZYN CAV CAV C 0 1 N N N -36.186 31.218 -18.475 1.579 2.012 -0.240 CAV ZYN 22 ZYN CAW CAW C 0 1 N N N -36.717 31.032 -20.839 1.551 -0.401 -0.370 CAW ZYN 23 ZYN CAX CAX C 0 1 N N N -36.384 31.821 -19.729 0.918 0.845 -0.583 CAX ZYN 24 ZYN CAY CAY C 0 1 N N N -36.816 29.644 -20.699 2.778 -0.456 0.210 CAY ZYN 25 ZYN CAZ CAZ C 0 1 N N N -36.301 29.823 -18.348 2.910 1.905 0.378 CAZ ZYN 26 ZYN CBA CBA C 0 1 N N N -36.751 27.529 -19.412 4.755 0.574 1.231 CBA ZYN 27 ZYN NBB NBB N 0 1 N N N -36.243 28.351 -22.736 4.176 -2.324 -0.519 NBB ZYN 28 ZYN NBC NBC N 0 1 N N N -36.316 33.778 -21.163 -1.133 -0.274 -1.279 NBC ZYN 29 ZYN NBD NBD N 0 1 N N N -36.629 29.017 -19.467 3.443 0.685 0.588 NBD ZYN 30 ZYN HAA HAA H 0 1 N N N -38.803 27.484 -18.721 6.773 1.237 0.871 HAA ZYN 31 ZYN HAAA HAAA H 0 0 N N N -37.913 25.937 -18.517 5.885 0.755 -0.594 HAAA ZYN 32 ZYN HAAB HAAB H 0 0 N N N -37.574 27.319 -17.421 5.517 2.305 0.200 HAAB ZYN 33 ZYN HAB HAB H 0 1 N N N -34.636 27.297 -19.773 4.446 2.293 2.492 HAB ZYN 34 ZYN HABA HABA H 0 0 N N N -35.114 27.210 -18.043 3.956 0.747 3.224 HABA ZYN 35 ZYN HABB HABB H 0 0 N N N -35.453 25.828 -19.140 5.682 1.159 3.086 HABB ZYN 36 ZYN HAC HAC H 0 1 N N N -37.719 27.350 -23.878 5.878 -3.350 0.153 HAC ZYN 37 ZYN HACA HACA H 0 0 N N N -36.322 27.977 -24.818 4.329 -4.167 0.471 HACA ZYN 38 ZYN HACB HACB H 0 0 N N N -36.130 26.518 -23.788 4.997 -4.138 -1.179 HACB ZYN 39 ZYN HAD HAD H 0 1 N N N -34.765 29.349 -21.598 3.461 -1.983 -2.461 HAD ZYN 40 ZYN HADA HADA H 0 0 N N N -34.243 27.795 -22.331 4.279 -0.596 -1.702 HADA ZYN 41 ZYN HADB HADB H 0 0 N N N -34.436 29.254 -23.361 5.234 -1.975 -2.296 HADB ZYN 42 ZYN HOAH HOAH H 0 0 N N N -35.890 32.904 -17.606 1.562 3.969 -0.191 HOAH ZYN 43 ZYN HAK HAK H 0 1 N N N -39.668 37.292 -23.586 -5.256 2.714 0.045 HAK ZYN 44 ZYN HAL HAL H 0 1 N N N -37.587 35.923 -23.516 -3.397 2.154 -1.469 HAL ZYN 45 ZYN HAM HAM H 0 1 N N N -37.493 36.174 -19.243 -3.892 -1.982 -0.554 HAM ZYN 46 ZYN HAN HAN H 0 1 N N N -38.082 31.747 -22.299 1.189 -2.495 -0.187 HAN ZYN 47 ZYN HANA HANA H 0 0 N N N -36.589 30.964 -22.957 1.078 -1.867 -1.846 HANA ZYN 48 ZYN HAO HAO H 0 1 N N N -35.334 32.836 -22.720 -1.165 -2.355 -1.092 HAO ZYN 49 ZYN HAOA HAOA H 0 0 N N N -36.958 33.538 -23.114 -0.907 -1.465 0.423 HAOA ZYN 50 ZYN HAP HAP H 0 1 N N N -35.607 35.342 -22.296 -2.551 -1.281 -2.451 HAP ZYN 51 ZYN HAPA HAPA H 0 0 N N N -35.533 35.562 -20.503 -2.344 0.445 -2.833 HAPA ZYN 52 ZYN HBA HBA H 0 1 N N N -37.073 27.193 -20.409 5.015 -0.478 1.346 HBA ZYN 53 # 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 ZYN CAA CBA SING N N 1 ZYN CAB CBA SING N N 2 ZYN CAC NBB SING N N 3 ZYN CAD NBB SING N N 4 ZYN OAE CAQ DOUB N N 5 ZYN OAF CAR DOUB N N 6 ZYN OAG CAZ DOUB N N 7 ZYN OAH CAV SING N N 8 ZYN FAI CAS SING N N 9 ZYN CLAJ CAU SING N N 10 ZYN CAK CAL DOUB Y N 11 ZYN CAK CAS SING Y N 12 ZYN CAL CAT SING Y N 13 ZYN CAM CAT DOUB Y N 14 ZYN CAM CAU SING Y N 15 ZYN CAN CAO SING N N 16 ZYN CAN CAW SING N N 17 ZYN CAO NBC SING N N 18 ZYN CAP CAT SING N N 19 ZYN CAP NBC SING N N 20 ZYN CAQ CAY SING N N 21 ZYN CAQ NBB SING N N 22 ZYN CAR CAX SING N N 23 ZYN CAR NBC SING N N 24 ZYN CAS CAU DOUB Y N 25 ZYN CAV CAX DOUB N N 26 ZYN CAV CAZ SING N N 27 ZYN CAW CAX SING N N 28 ZYN CAW CAY DOUB N N 29 ZYN CAY NBD SING N N 30 ZYN CAZ NBD SING N N 31 ZYN CBA NBD SING N N 32 ZYN CAA HAA SING N N 33 ZYN CAA HAAA SING N N 34 ZYN CAA HAAB SING N N 35 ZYN CAB HAB SING N N 36 ZYN CAB HABA SING N N 37 ZYN CAB HABB SING N N 38 ZYN CAC HAC SING N N 39 ZYN CAC HACA SING N N 40 ZYN CAC HACB SING N N 41 ZYN CAD HAD SING N N 42 ZYN CAD HADA SING N N 43 ZYN CAD HADB SING N N 44 ZYN OAH HOAH SING N N 45 ZYN CAK HAK SING N N 46 ZYN CAL HAL SING N N 47 ZYN CAM HAM SING N N 48 ZYN CAN HAN SING N N 49 ZYN CAN HANA SING N N 50 ZYN CAO HAO SING N N 51 ZYN CAO HAOA SING N N 52 ZYN CAP HAP SING N N 53 ZYN CAP HAPA SING N N 54 ZYN CBA HBA SING N N 55 # 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 ZYN SMILES ACDLabs 12.01 "Fc1ccc(cc1Cl)CN3C(=O)C2=C(O)C(=O)N(C(=C2CC3)C(=O)N(C)C)C(C)C" ZYN SMILES_CANONICAL CACTVS 3.370 "CC(C)N1C(=O)C(=C2C(=O)N(CCC2=C1C(=O)N(C)C)Cc3ccc(F)c(Cl)c3)O" ZYN SMILES CACTVS 3.370 "CC(C)N1C(=O)C(=C2C(=O)N(CCC2=C1C(=O)N(C)C)Cc3ccc(F)c(Cl)c3)O" ZYN SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "CC(C)N1C(=C2CCN(C(=O)C2=C(C1=O)O)Cc3ccc(c(c3)Cl)F)C(=O)N(C)C" ZYN SMILES "OpenEye OEToolkits" 1.7.0 "CC(C)N1C(=C2CCN(C(=O)C2=C(C1=O)O)Cc3ccc(c(c3)Cl)F)C(=O)N(C)C" ZYN InChI InChI 1.03 "InChI=1S/C21H23ClFN3O4/c1-11(2)26-17(20(29)24(3)4)13-7-8-25(19(28)16(13)18(27)21(26)30)10-12-5-6-15(23)14(22)9-12/h5-6,9,11,27H,7-8,10H2,1-4H3" ZYN InChIKey InChI 1.03 HFCJYZIWLQSWGP-UHFFFAOYSA-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 ZYN "SYSTEMATIC NAME" ACDLabs 12.01 "6-(3-chloro-4-fluorobenzyl)-4-hydroxy-N,N-dimethyl-3,5-dioxo-2-(propan-2-yl)-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide" ZYN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.0 "6-[(3-chloro-4-fluoro-phenyl)methyl]-4-hydroxy-N,N-dimethyl-3,5-dioxo-2-propan-2-yl-7,8-dihydro-2,6-naphthyridine-1-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 ZYN "Create component" 2010-10-04 RCSB ZYN "Modify aromatic_flag" 2011-06-04 RCSB ZYN "Modify descriptor" 2011-06-04 RCSB #