data_552 # _chem_comp.id 552 _chem_comp.name "(6S)-1-chloro-3-[(4-fluorobenzyl)oxy]-6-(pyrrolidin-1-ylcarbonyl)pyrrolo[1,2-a]pyrazin-4(6H)-one" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C19 H17 Cl F N3 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2008-07-01 _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 389.808 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 552 _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 3DDU _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 552 CL11 CL11 CL 0 0 N N N -4.810 11.378 34.503 -0.401 -4.409 0.323 CL11 552 1 552 C10 C10 C 0 1 N N N -5.462 11.749 32.934 -0.411 -2.694 0.051 C10 552 2 552 N09 N09 N 0 1 N N N -6.801 11.535 32.803 0.736 -2.023 0.044 N09 552 3 552 C12 C12 C 0 1 N N N -4.687 12.182 31.942 -1.613 -2.042 -0.163 C12 552 4 552 N23 N23 N 0 1 N N N -5.231 12.451 30.740 -1.610 -0.686 -0.378 N23 552 5 552 C15 C15 C 0 1 N N S -4.293 12.919 29.759 -3.002 -0.271 -0.572 C15 552 6 552 C16 C16 C 0 1 N N N -4.197 11.814 28.749 -3.402 0.720 0.491 C16 552 7 552 N18 N18 N 0 1 N N N -3.761 12.216 27.524 -4.378 1.616 0.244 N18 552 8 552 C22 C22 C 0 1 N N N -3.657 11.279 26.454 -5.204 1.670 -0.971 C22 552 9 552 C21 C21 C 0 1 N N N -3.179 12.102 25.278 -6.163 2.870 -0.820 C21 552 10 552 C20 C20 C 0 1 N N N -2.481 13.293 25.912 -5.440 3.764 0.221 C20 552 11 552 C19 C19 C 0 1 N N N -3.198 13.500 27.220 -4.799 2.700 1.150 C19 552 12 552 O17 O17 O 0 1 N N N -4.458 10.669 29.004 -2.845 0.711 1.568 O17 552 13 552 C14 C14 C 0 1 N N N -2.998 13.093 30.555 -3.829 -1.529 -0.448 C14 552 14 552 C13 C13 C 0 1 N N N -3.229 12.459 31.923 -2.993 -2.535 -0.212 C13 552 15 552 C24 C24 C 0 1 N N N -6.548 12.260 30.468 -0.444 -0.012 -0.378 C24 552 16 552 O25 O25 O 0 1 N N N -7.114 12.461 29.417 -0.426 1.193 -0.567 O25 552 17 552 C08 C08 C 0 1 N N N -7.328 11.759 31.647 0.765 -0.725 -0.160 C08 552 18 552 O07 O07 O 0 1 N N N -8.638 11.627 31.282 1.950 -0.064 -0.155 O07 552 19 552 C06 C06 C 0 1 N N N -9.534 11.523 32.377 3.127 -0.844 0.070 C06 552 20 552 C05 C05 C 0 1 Y N N -9.939 12.831 32.929 4.337 0.053 0.040 C05 552 21 552 C04 C04 C 0 1 Y N N -9.996 13.952 32.143 4.994 0.287 -1.154 C04 552 22 552 C03 C03 C 0 1 Y N N -10.384 15.153 32.686 6.104 1.110 -1.183 C03 552 23 552 C26 C26 C 0 1 Y N N -10.275 12.899 34.255 4.786 0.647 1.205 C26 552 24 552 C27 C27 C 0 1 Y N N -10.672 14.095 34.799 5.896 1.470 1.179 C27 552 25 552 C02 C02 C 0 1 Y N N -10.717 15.216 34.017 6.558 1.700 -0.015 C02 552 26 552 F01 F01 F 0 1 N N N -11.102 16.403 34.516 7.643 2.504 -0.042 F01 552 27 552 H15 H15 H 0 1 N N N -4.546 13.853 29.237 -3.130 0.167 -1.562 H15 552 28 552 H22 H22 H 0 1 N N N -2.943 10.478 26.695 -4.568 1.812 -1.845 H22 552 29 552 H22A H22A H 0 0 N N N -4.612 10.773 26.248 -5.774 0.747 -1.074 H22A 552 30 552 H21 H21 H 0 1 N N N -2.488 11.527 24.644 -6.276 3.395 -1.768 H21 552 31 552 H21A H21A H 0 0 N N N -4.004 12.405 24.617 -7.132 2.543 -0.441 H21A 552 32 552 H20 H20 H 0 1 N N N -1.413 13.087 26.074 -4.678 4.381 -0.255 H20 552 33 552 H20A H20A H 0 0 N N N -2.519 14.186 25.271 -6.153 4.380 0.770 H20A 552 34 552 H19 H19 H 0 1 N N N -3.982 14.266 27.127 -5.530 2.336 1.872 H19 552 35 552 H19A H19A H 0 0 N N N -2.525 13.859 28.013 -3.933 3.117 1.664 H19A 552 36 552 H14 H14 H 0 1 N N N -2.093 13.573 30.213 -4.904 -1.598 -0.535 H14 552 37 552 H13 H13 H 0 1 N N N -2.502 12.259 32.696 -3.288 -3.565 -0.076 H13 552 38 552 H06 H06 H 0 1 N N N -10.439 11.001 32.032 3.059 -1.330 1.043 H06 552 39 552 H06A H06A H 0 0 N N N -9.011 10.978 33.177 3.216 -1.601 -0.709 H06A 552 40 552 H04 H04 H 0 1 N N N -9.736 13.891 31.097 4.640 -0.174 -2.064 H04 552 41 552 H03 H03 H 0 1 N N N -10.427 16.040 32.071 6.618 1.291 -2.115 H03 552 42 552 H26 H26 H 0 1 N N N -10.228 12.013 34.871 4.270 0.467 2.136 H26 552 43 552 H27 H27 H 0 1 N N N -10.948 14.151 35.842 6.247 1.934 2.089 H27 552 44 # 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 552 C10 CL11 SING N N 1 552 C12 C10 DOUB N N 2 552 N09 C10 SING N N 3 552 C08 N09 DOUB N N 4 552 N23 C12 SING N N 5 552 C13 C12 SING N N 6 552 C15 N23 SING N N 7 552 C24 N23 SING N N 8 552 C16 C15 SING N N 9 552 C15 C14 SING N N 10 552 C15 H15 SING N N 11 552 N18 C16 SING N N 12 552 C16 O17 DOUB N N 13 552 C22 N18 SING N N 14 552 C19 N18 SING N N 15 552 C21 C22 SING N N 16 552 C22 H22 SING N N 17 552 C22 H22A SING N N 18 552 C21 C20 SING N N 19 552 C21 H21 SING N N 20 552 C21 H21A SING N N 21 552 C20 C19 SING N N 22 552 C20 H20 SING N N 23 552 C20 H20A SING N N 24 552 C19 H19 SING N N 25 552 C19 H19A SING N N 26 552 C14 C13 DOUB N N 27 552 C14 H14 SING N N 28 552 C13 H13 SING N N 29 552 O25 C24 DOUB N N 30 552 C24 C08 SING N N 31 552 O07 C08 SING N N 32 552 O07 C06 SING N N 33 552 C06 C05 SING N N 34 552 C06 H06 SING N N 35 552 C06 H06A SING N N 36 552 C04 C05 DOUB Y N 37 552 C05 C26 SING Y N 38 552 C04 C03 SING Y N 39 552 C04 H04 SING N N 40 552 C03 C02 DOUB Y N 41 552 C03 H03 SING N N 42 552 C26 C27 DOUB Y N 43 552 C26 H26 SING N N 44 552 C02 C27 SING Y N 45 552 C27 H27 SING N N 46 552 C02 F01 SING N N 47 # 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 552 SMILES ACDLabs 10.04 "Fc1ccc(cc1)COC3=NC(Cl)=C2C=CC(N2C3=O)C(=O)N4CCCC4" 552 SMILES_CANONICAL CACTVS 3.341 "Fc1ccc(COC2=NC(=C3C=C[C@H](N3C2=O)C(=O)N4CCCC4)Cl)cc1" 552 SMILES CACTVS 3.341 "Fc1ccc(COC2=NC(=C3C=C[CH](N3C2=O)C(=O)N4CCCC4)Cl)cc1" 552 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc(ccc1COC2=NC(=C3C=C[C@H](N3C2=O)C(=O)N4CCCC4)Cl)F" 552 SMILES "OpenEye OEToolkits" 1.5.0 "c1cc(ccc1COC2=NC(=C3C=CC(N3C2=O)C(=O)N4CCCC4)Cl)F" 552 InChI InChI 1.03 "InChI=1S/C19H17ClFN3O3/c20-16-14-7-8-15(18(25)23-9-1-2-10-23)24(14)19(26)17(22-16)27-11-12-3-5-13(21)6-4-12/h3-8,15H,1-2,9-11H2/t15-/m0/s1" 552 InChIKey InChI 1.03 HPAFVLDARQIHPU-HNNXBMFYSA-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 552 "SYSTEMATIC NAME" ACDLabs 10.04 "(6S)-1-chloro-3-[(4-fluorobenzyl)oxy]-6-(pyrrolidin-1-ylcarbonyl)pyrrolo[1,2-a]pyrazin-4(6H)-one" 552 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(6S)-1-chloro-3-[(4-fluorophenyl)methoxy]-6-pyrrolidin-1-ylcarbonyl-6H-pyrrolo[5,1-f]pyrazin-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 552 "Create component" 2008-07-01 RCSB 552 "Modify aromatic_flag" 2011-06-04 RCSB 552 "Modify descriptor" 2011-06-04 RCSB #