data_B66 # _chem_comp.id B66 _chem_comp.name "4-{[(1R,2S)-1,2-dihydroxy-2-methyl-3-(4-nitrophenoxy)propyl]amino}-2-(trifluoromethyl)benzonitrile" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C18 H16 F3 N3 O5" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2007-11-28 _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 411.332 _chem_comp.one_letter_code ? _chem_comp.three_letter_code B66 _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 3B66 _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 B66 C17 C17 C 0 1 Y N N 28.997 2.025 8.078 -5.512 -1.375 -0.761 C17 B66 1 B66 C18 C18 C 0 1 Y N N 28.769 1.874 9.442 -6.801 -0.879 -0.724 C18 B66 2 B66 C21 C21 C 0 1 Y N N 29.431 0.879 10.156 -7.047 0.370 -0.185 C21 B66 3 B66 N19 N19 N 1 1 N N N 29.191 0.714 11.454 -8.428 0.900 -0.147 N19 B66 4 B66 O20 O20 O -1 1 N N N 29.906 -0.264 12.196 -9.347 0.235 -0.590 O20 B66 5 B66 O19 O19 O 0 1 N N N 28.245 1.541 12.120 -8.646 2.000 0.328 O19 B66 6 B66 C20 C20 C 0 1 Y N N 30.322 0.036 9.496 -6.004 1.126 0.319 C20 B66 7 B66 C19 C19 C 0 1 Y N N 30.548 0.187 8.131 -4.713 0.634 0.284 C19 B66 8 B66 C16 C16 C 0 1 Y N N 29.886 1.182 7.416 -4.464 -0.619 -0.257 C16 B66 9 B66 O14 O14 O 0 1 N N N 30.126 1.392 6.093 -3.196 -1.106 -0.292 O14 B66 10 B66 C13 C13 C 0 1 N N N 30.139 0.190 5.306 -2.167 -0.273 0.246 C13 B66 11 B66 C11 C11 C 0 1 N N S 29.761 0.566 3.883 -0.817 -0.983 0.120 C11 B66 12 B66 O11 O11 O 0 1 N N N 30.779 1.406 3.333 -0.859 -2.215 0.842 O11 B66 13 B66 C12 C12 C 0 1 N N N 29.601 -0.701 3.040 -0.526 -1.267 -1.355 C12 B66 14 B66 C10 C10 C 0 1 N N R 28.445 1.345 3.924 0.285 -0.091 0.695 C10 B66 15 B66 O10 O10 O 0 1 N N N 27.380 0.785 4.181 0.013 0.174 2.072 O10 B66 16 B66 N9 N9 N 0 1 N N N 28.594 2.650 3.708 1.576 -0.772 0.574 N9 B66 17 B66 C6 C6 C 0 1 Y N N 27.625 3.565 3.692 2.729 -0.036 0.317 C6 B66 18 B66 C5 C5 C 0 1 Y N N 26.282 3.266 3.912 3.955 -0.684 0.203 C5 B66 19 B66 C1 C1 C 0 1 Y N N 27.994 4.883 3.450 2.652 1.346 0.169 C1 B66 20 B66 C2 C2 C 0 1 Y N N 27.023 5.877 3.431 3.790 2.077 -0.086 C2 B66 21 B66 C3 C3 C 0 1 Y N N 25.685 5.565 3.654 5.025 1.430 -0.196 C3 B66 22 B66 C8 C8 C 0 1 N N N 24.765 6.662 3.625 6.211 2.187 -0.461 C8 B66 23 B66 N8 N8 N 0 1 N N N 24.039 7.538 3.594 7.152 2.788 -0.671 N8 B66 24 B66 C4 C4 C 0 1 Y N N 25.289 4.247 3.899 5.098 0.041 -0.052 C4 B66 25 B66 C7 C7 C 0 1 N N N 23.830 3.849 4.195 6.425 -0.661 -0.175 C7 B66 26 B66 F2 F2 F 0 1 N N N 23.559 4.057 5.480 6.244 -2.037 0.006 F2 B66 27 B66 F3 F3 F 0 1 N N N 22.944 4.527 3.471 6.962 -0.425 -1.445 F3 B66 28 B66 F1 F1 F 0 1 N N N 23.591 2.565 3.940 7.303 -0.175 0.800 F1 B66 29 B66 H17 H17 H 0 1 N N N 28.482 2.800 7.530 -5.322 -2.353 -1.178 H17 B66 30 B66 H18 H18 H 0 1 N N N 28.077 2.530 9.948 -7.617 -1.467 -1.117 H18 B66 31 B66 H20 H20 H 0 1 N N N 30.839 -0.737 10.045 -6.198 2.101 0.739 H20 B66 32 B66 H19 H19 H 0 1 N N N 31.239 -0.470 7.624 -3.899 1.224 0.677 H19 B66 33 B66 H13 H13 H 0 1 N N N 31.142 -0.262 5.323 -2.135 0.667 -0.306 H13 B66 34 B66 H13A H13A H 0 0 N N N 29.427 -0.543 5.712 -2.374 -0.071 1.296 H13A B66 35 B66 HO11 HO11 H 0 0 N N N 30.579 1.592 2.423 -1.039 -2.111 1.787 HO11 B66 36 B66 H12 H12 H 0 1 N N N 29.563 -0.431 1.974 -0.495 -0.327 -1.907 H12 B66 37 B66 H12A H12A H 0 0 N N N 30.456 -1.370 3.218 0.435 -1.773 -1.445 H12A B66 38 B66 H12B H12B H 0 0 N N N 28.669 -1.213 3.322 -1.311 -1.903 -1.765 H12B B66 39 B66 HN9 HN9 H 0 1 N N N 29.203 2.952 4.441 1.628 -1.735 0.674 HN9 B66 40 B66 H5 H5 H 0 1 N N N 26.000 2.240 4.099 4.011 -1.757 0.313 H5 B66 41 B66 H1 H1 H 0 1 N N N 29.030 5.133 3.278 1.699 1.845 0.254 H1 B66 42 B66 H2 H2 H 0 1 N N N 27.309 6.901 3.241 3.730 3.149 -0.202 H2 B66 43 B66 H15 H15 H 0 1 N N N 27.375 1.184 3.725 0.316 0.848 0.143 H15 B66 44 B66 H16 H16 H 0 1 N N N 27.316 0.641 5.118 -0.030 -0.619 2.624 H16 B66 45 # 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 B66 C17 C18 DOUB Y N 1 B66 C17 C16 SING Y N 2 B66 C17 H17 SING N N 3 B66 C18 C21 SING Y N 4 B66 C18 H18 SING N N 5 B66 C21 N19 SING N N 6 B66 C21 C20 DOUB Y N 7 B66 N19 O20 SING N N 8 B66 N19 O19 DOUB N N 9 B66 C20 C19 SING Y N 10 B66 C20 H20 SING N N 11 B66 C19 C16 DOUB Y N 12 B66 C19 H19 SING N N 13 B66 C16 O14 SING N N 14 B66 O14 C13 SING N N 15 B66 C13 C11 SING N N 16 B66 C13 H13 SING N N 17 B66 C13 H13A SING N N 18 B66 C11 O11 SING N N 19 B66 C11 C12 SING N N 20 B66 C11 C10 SING N N 21 B66 O11 HO11 SING N N 22 B66 C12 H12 SING N N 23 B66 C12 H12A SING N N 24 B66 C12 H12B SING N N 25 B66 C10 O10 SING N N 26 B66 C10 N9 SING N N 27 B66 N9 C6 SING N N 28 B66 N9 HN9 SING N N 29 B66 C6 C5 DOUB Y N 30 B66 C6 C1 SING Y N 31 B66 C5 C4 SING Y N 32 B66 C5 H5 SING N N 33 B66 C1 C2 DOUB Y N 34 B66 C1 H1 SING N N 35 B66 C2 C3 SING Y N 36 B66 C2 H2 SING N N 37 B66 C3 C8 SING N N 38 B66 C3 C4 DOUB Y N 39 B66 C8 N8 TRIP N N 40 B66 C4 C7 SING N N 41 B66 C7 F2 SING N N 42 B66 C7 F3 SING N N 43 B66 C7 F1 SING N N 44 B66 C10 H15 SING N N 45 B66 O10 H16 SING N N 46 # 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 B66 SMILES ACDLabs 10.04 "FC(F)(F)c1cc(ccc1C#N)NC(O)C(O)(COc2ccc(cc2)[N+]([O-])=O)C" B66 SMILES_CANONICAL CACTVS 3.341 "C[C@](O)(COc1ccc(cc1)[N+]([O-])=O)[C@@H](O)Nc2ccc(C#N)c(c2)C(F)(F)F" B66 SMILES CACTVS 3.341 "C[C](O)(COc1ccc(cc1)[N+]([O-])=O)[CH](O)Nc2ccc(C#N)c(c2)C(F)(F)F" B66 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@](COc1ccc(cc1)[N+](=O)[O-])(C(Nc2ccc(c(c2)C(F)(F)F)C#N)O)O" B66 SMILES "OpenEye OEToolkits" 1.5.0 "CC(COc1ccc(cc1)[N+](=O)[O-])(C(Nc2ccc(c(c2)C(F)(F)F)C#N)O)O" B66 InChI InChI 1.03 "InChI=1S/C18H16F3N3O5/c1-17(26,10-29-14-6-4-13(5-7-14)24(27)28)16(25)23-12-3-2-11(9-22)15(8-12)18(19,20)21/h2-8,16,23,25-26H,10H2,1H3/t16-,17+/m1/s1" B66 InChIKey InChI 1.03 INVUBEGZQHQAMY-SJORKVTESA-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 B66 "SYSTEMATIC NAME" ACDLabs 10.04 "4-{[(1R,2S)-1,2-dihydroxy-2-methyl-3-(4-nitrophenoxy)propyl]amino}-2-(trifluoromethyl)benzonitrile" B66 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "4-[[(2S)-1,2-dihydroxy-2-methyl-3-(4-nitrophenoxy)propyl]amino]-2-(trifluoromethyl)benzonitrile" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site B66 "Create component" 2007-11-28 RCSB B66 "Modify aromatic_flag" 2011-06-04 RCSB B66 "Modify descriptor" 2011-06-04 RCSB #