data_22Y # _chem_comp.id 22Y _chem_comp.name "3-(5-amino-6-{[(1R)-1-phenylethyl]amino}pyrazin-2-yl)-4-chlorobenzoic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C19 H17 Cl N4 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-08-26 _chem_comp.pdbx_modified_date 2013-08-30 _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 368.817 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 22Y _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 4M49 _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 22Y C1 C1 C 0 1 N N N 13.878 -5.927 -0.630 2.604 0.745 -1.920 C1 22Y 1 22Y C2 C2 C 0 1 N N R 14.482 -7.260 -0.178 2.736 0.362 -0.444 C2 22Y 2 22Y C4 C4 C 0 1 Y N N 13.464 -8.358 -0.351 4.144 0.628 0.020 C4 22Y 3 22Y C5 C5 C 0 1 Y N N 12.689 -8.745 0.727 4.431 1.776 0.734 C5 22Y 4 22Y C6 C6 C 0 1 Y N N 11.757 -9.752 0.574 5.723 2.021 1.160 C6 22Y 5 22Y C7 C7 C 0 1 Y N N 11.600 -10.375 -0.654 6.729 1.117 0.871 C7 22Y 6 22Y C8 C8 C 0 1 Y N N 12.374 -9.985 -1.732 6.442 -0.031 0.156 C8 22Y 7 22Y C9 C9 C 0 1 Y N N 13.310 -8.977 -1.580 5.149 -0.278 -0.264 C9 22Y 8 22Y N10 N10 N 0 1 N N N 14.851 -7.187 1.237 2.428 -1.061 -0.280 N10 22Y 9 22Y C11 C11 C 0 1 Y N N 15.646 -8.193 1.777 1.108 -1.475 -0.132 C11 22Y 10 22Y C12 C12 C 0 1 Y N N 15.823 -8.297 3.171 0.812 -2.837 0.026 C12 22Y 11 22Y N13 N13 N 0 1 Y N N 16.573 -9.267 3.673 -0.446 -3.228 0.167 N13 22Y 12 22Y C14 C14 C 0 1 Y N N 17.155 -10.132 2.853 -1.423 -2.336 0.159 C14 22Y 13 22Y C15 C15 C 0 1 Y N N 16.967 -10.050 1.474 -1.134 -0.985 0.003 C15 22Y 14 22Y N16 N16 N 0 1 Y N N 16.221 -9.069 0.965 0.130 -0.585 -0.133 N16 22Y 15 22Y C17 C17 C 0 1 Y N N 17.650 -11.019 0.583 -2.232 0.011 -0.005 C17 22Y 16 22Y C18 C18 C 0 1 Y N N 18.987 -11.294 0.870 -3.551 -0.405 0.143 C18 22Y 17 22Y C19 C19 C 0 1 Y N N 19.696 -12.186 0.070 -4.578 0.538 0.134 C19 22Y 18 22Y C20 C20 C 0 1 Y N N 19.068 -12.788 -1.025 -4.277 1.894 -0.023 C20 22Y 19 22Y C21 C21 C 0 1 Y N N 17.750 -12.514 -1.310 -2.967 2.299 -0.169 C21 22Y 20 22Y C22 C22 C 0 1 Y N N 17.028 -11.632 -0.524 -1.944 1.369 -0.156 C22 22Y 21 22Y CL1 CL23 CL 0 0 N N N 15.368 -11.343 -0.970 -0.298 1.889 -0.340 CL23 22Y 22 22Y C24 C24 C 0 1 N N N 21.112 -12.490 0.339 -5.982 0.105 0.290 C24 22Y 23 22Y O25 O25 O 0 1 N N N 21.718 -11.885 1.204 -6.973 1.017 0.282 O25 22Y 24 22Y O26 O26 O 0 1 N N N 21.744 -13.418 -0.408 -6.242 -1.074 0.426 O26 22Y 25 22Y N27 N27 N 0 1 N N N 15.219 -7.386 4.025 1.838 -3.776 0.034 N27 22Y 26 22Y H1 H1 H 0 1 N N N 14.621 -5.126 -0.504 3.300 0.152 -2.513 H1 22Y 27 22Y H2 H2 H 0 1 N N N 13.589 -5.996 -1.689 1.585 0.552 -2.256 H2 22Y 28 22Y H3 H3 H 0 1 N N N 12.989 -5.702 -0.022 2.833 1.803 -2.042 H3 22Y 29 22Y H4 H4 H 0 1 N N N 15.369 -7.481 -0.790 2.039 0.955 0.149 H4 22Y 30 22Y H5 H5 H 0 1 N N N 12.812 -8.261 1.685 3.646 2.482 0.960 H5 22Y 31 22Y H6 H6 H 0 1 N N N 11.149 -10.055 1.413 5.948 2.918 1.718 H6 22Y 32 22Y H7 H7 H 0 1 N N N 10.873 -11.165 -0.769 7.739 1.309 1.203 H7 22Y 33 22Y H8 H8 H 0 1 N N N 12.248 -10.466 -2.691 7.227 -0.739 -0.065 H8 22Y 34 22Y H9 H9 H 0 1 N N N 13.919 -8.674 -2.419 4.925 -1.175 -0.822 H9 22Y 35 22Y H10 H10 H 0 1 N N N 15.339 -6.324 1.369 3.145 -1.715 -0.274 H10 22Y 36 22Y H11 H11 H 0 1 N N N 17.783 -10.911 3.259 -2.447 -2.659 0.274 H11 22Y 37 22Y H12 H12 H 0 1 N N N 19.470 -10.817 1.710 -3.779 -1.454 0.263 H12 22Y 38 22Y H13 H13 H 0 1 N N N 19.621 -13.472 -1.651 -5.072 2.625 -0.030 H13 22Y 39 22Y H14 H14 H 0 1 N N N 17.275 -12.991 -2.154 -2.739 3.348 -0.290 H14 22Y 40 22Y H15 H15 H 0 1 N N N 22.620 -12.181 1.225 -7.876 0.686 0.387 H15 22Y 41 22Y H16 H16 H 0 1 N N N 15.454 -7.609 4.971 2.759 -3.490 -0.070 H16 22Y 42 22Y H17 H17 H 0 1 N N N 15.541 -6.464 3.810 1.633 -4.718 0.143 H17 22Y 43 # 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 22Y C8 C9 DOUB Y N 1 22Y C8 C7 SING Y N 2 22Y C9 C4 SING Y N 3 22Y C21 C20 DOUB Y N 4 22Y C21 C22 SING Y N 5 22Y C20 C19 SING Y N 6 22Y CL1 C22 SING N N 7 22Y C7 C6 DOUB Y N 8 22Y C1 C2 SING N N 9 22Y C22 C17 DOUB Y N 10 22Y O26 C24 DOUB N N 11 22Y C4 C2 SING N N 12 22Y C4 C5 DOUB Y N 13 22Y C2 N10 SING N N 14 22Y C19 C24 SING N N 15 22Y C19 C18 DOUB Y N 16 22Y C24 O25 SING N N 17 22Y C6 C5 SING Y N 18 22Y C17 C18 SING Y N 19 22Y C17 C15 SING N N 20 22Y N16 C15 DOUB Y N 21 22Y N16 C11 SING Y N 22 22Y N10 C11 SING N N 23 22Y C15 C14 SING Y N 24 22Y C11 C12 DOUB Y N 25 22Y C14 N13 DOUB Y N 26 22Y C12 N13 SING Y N 27 22Y C12 N27 SING N N 28 22Y C1 H1 SING N N 29 22Y C1 H2 SING N N 30 22Y C1 H3 SING N N 31 22Y C2 H4 SING N N 32 22Y C5 H5 SING N N 33 22Y C6 H6 SING N N 34 22Y C7 H7 SING N N 35 22Y C8 H8 SING N N 36 22Y C9 H9 SING N N 37 22Y N10 H10 SING N N 38 22Y C14 H11 SING N N 39 22Y C18 H12 SING N N 40 22Y C20 H13 SING N N 41 22Y C21 H14 SING N N 42 22Y O25 H15 SING N N 43 22Y N27 H16 SING N N 44 22Y N27 H17 SING N N 45 # 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 22Y SMILES ACDLabs 12.01 "O=C(O)c3cc(c2nc(NC(c1ccccc1)C)c(nc2)N)c(Cl)cc3" 22Y InChI InChI 1.03 "InChI=1S/C19H17ClN4O2/c1-11(12-5-3-2-4-6-12)23-18-17(21)22-10-16(24-18)14-9-13(19(25)26)7-8-15(14)20/h2-11H,1H3,(H2,21,22)(H,23,24)(H,25,26)/t11-/m1/s1" 22Y InChIKey InChI 1.03 NKUNTWSMUIPKSU-LLVKDONJSA-N 22Y SMILES_CANONICAL CACTVS 3.385 "C[C@@H](Nc1nc(cnc1N)c2cc(ccc2Cl)C(O)=O)c3ccccc3" 22Y SMILES CACTVS 3.385 "C[CH](Nc1nc(cnc1N)c2cc(ccc2Cl)C(O)=O)c3ccccc3" 22Y SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "C[C@H](c1ccccc1)Nc2c(ncc(n2)c3cc(ccc3Cl)C(=O)O)N" 22Y SMILES "OpenEye OEToolkits" 1.7.6 "CC(c1ccccc1)Nc2c(ncc(n2)c3cc(ccc3Cl)C(=O)O)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 22Y "SYSTEMATIC NAME" ACDLabs 12.01 "3-(5-amino-6-{[(1R)-1-phenylethyl]amino}pyrazin-2-yl)-4-chlorobenzoic acid" 22Y "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "3-[5-azanyl-6-[[(1R)-1-phenylethyl]amino]pyrazin-2-yl]-4-chloranyl-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 22Y "Create component" 2013-08-26 RCSB 22Y "Initial release" 2013-09-04 RCSB #