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                    2008-10-14 
_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 N N 45 
552 C27 H27  SING Y 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 InChI            InChI                1.02b InChI=1/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                1.02b HPAFVLDARQIHPU-HNNXBMFYBZ                                                                                                                 
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                                                                                         
# 
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 
# 
