data_4VF
# 
_chem_comp.id                                    4VF 
_chem_comp.name                                  "2-[(1S)-1-(3-chlorophenyl)-2-hydroxyethyl]-7-[2-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H26 Cl N5 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2015-06-05 
_chem_comp.pdbx_modified_date                    2015-09-04 
_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                        467.948 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     4VF 
_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        5BVD 
_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 
4VF C2  C1  C  0 1 Y N N 12.294 -2.720 14.912 -0.828 1.184  -0.166 C2   4VF 1  
4VF C3  C2  C  0 1 N N N 12.417 -3.685 17.122 -1.687 -0.842 1.002  C3   4VF 2  
4VF C12 C3  C  0 1 Y N N 18.038 -1.276 14.479 4.979  0.243  0.059  C12  4VF 3  
4VF C15 C4  C  0 1 Y N N 13.075 -2.084 14.011 0.358  1.722  -0.526 C15  4VF 4  
4VF C16 C5  C  0 1 Y N N 14.405 -2.109 14.647 1.365  0.850  -0.052 C16  4VF 5  
4VF C17 C6  C  0 1 Y N N 14.271 -2.742 15.821 0.733  -0.200 0.584  C17  4VF 6  
4VF C18 C7  C  0 1 N N S 8.959  -4.312 15.661 -4.577 1.279  -0.055 C18  4VF 7  
4VF C19 C8  C  0 1 Y N N 8.714  -5.383 14.587 -5.261 -0.015 -0.416 C19  4VF 8  
4VF C20 C9  C  0 1 Y N N 7.395  -5.725 14.261 -6.598 -0.197 -0.116 C20  4VF 9  
4VF C21 C10 C  0 1 Y N N 7.135  -6.709 13.306 -7.225 -1.385 -0.447 C21  4VF 10 
4VF C22 C11 C  0 1 Y N N 8.192  -7.339 12.645 -6.513 -2.389 -1.078 C22  4VF 11 
4VF C23 C12 C  0 1 Y N N 9.519  -6.995 12.948 -5.176 -2.206 -1.377 C23  4VF 12 
4VF C24 C13 C  0 1 Y N N 9.772  -6.019 13.924 -4.552 -1.017 -1.051 C24  4VF 13 
4VF C25 C14 C  0 1 N N N 19.237 -2.655 16.162 7.279  -0.603 0.347  C25  4VF 14 
4VF C26 C15 C  0 1 N N N 20.691 -3.173 16.350 7.995  -1.462 1.394  C26  4VF 15 
4VF C27 C16 C  0 1 N N N 20.764 -4.173 17.528 9.507  -1.354 1.184  C27  4VF 16 
4VF C29 C17 C  0 1 N N N 18.862 -3.217 18.589 9.230  -0.969 -1.166 C29  4VF 17 
4VF C30 C18 C  0 1 N N N 18.776 -2.094 17.533 7.707  -1.061 -1.051 C30  4VF 18 
4VF CL1 CL1 CL 0 0 N N N 5.472  -7.165 12.987 -8.904 -1.614 -0.071 CL33 4VF 19 
4VF O28 O1  O  0 1 N N N 20.248 -3.600 18.743 9.833  -1.765 -0.145 O28  4VF 20 
4VF O32 O2  O  0 1 N N N 8.537  -3.913 18.008 -5.337 0.977  2.219  O32  4VF 21 
4VF N5  N1  N  0 1 N N N 10.385 -3.982 15.718 -3.179 1.013  0.292  N5   4VF 22 
4VF C31 C19 C  0 1 N N N 8.342  -4.880 16.972 -5.287 1.915  1.142  C31  4VF 23 
4VF C8  C20 C  0 1 Y N N 15.700 -1.478 14.187 2.828  1.030  -0.209 C8   4VF 24 
4VF C6  C21 C  0 1 N N N 10.866 -3.045 14.857 -2.200 1.671  -0.373 C6   4VF 25 
4VF N13 N2  N  0 1 Y N N 16.851 -1.827 14.820 3.672  0.084  0.198  N13  4VF 26 
4VF N14 N3  N  0 1 N N N 19.173 -1.609 15.138 5.830  -0.759 0.492  N14  4VF 27 
4VF C4  C22 C  0 1 N N N 11.307 -4.649 16.651 -2.881 0.047  1.343  C4   4VF 28 
4VF C10 C23 C  0 1 Y N N 16.987 -0.003 12.817 4.713  2.313  -0.922 C10  4VF 29 
4VF O7  O3  O  0 1 N N N 10.176 -2.472 14.018 -2.443 2.614  -1.102 O7   4VF 30 
4VF C9  C24 C  0 1 Y N N 15.742 -0.556 13.141 3.342  2.195  -0.786 C9   4VF 31 
4VF N1  N4  N  0 1 Y N N 13.010 -3.064 15.939 -0.588 -0.006 0.508  N1   4VF 32 
4VF N11 N5  N  0 1 Y N N 18.092 -0.366 13.497 5.493  1.334  -0.490 N11  4VF 33 
4VF H1  H1  H  0 1 N N N 13.186 -4.244 17.675 -1.364 -1.377 1.896  H1   4VF 34 
4VF H2  H2  H  0 1 N N N 11.987 -2.910 17.774 -1.973 -1.559 0.233  H2   4VF 35 
4VF H3  H3  H  0 1 N N N 12.794 -1.661 13.058 0.508  2.641  -1.073 H3   4VF 36 
4VF H4  H4  H  0 1 N N N 15.056 -2.947 16.534 1.222  -1.036 1.061  H4   4VF 37 
4VF H5  H5  H  0 1 N N N 8.392  -3.411 15.383 -4.617 1.961  -0.905 H5   4VF 38 
4VF H6  H6  H  0 1 N N N 6.574  -5.224 14.752 -7.153 0.588  0.377  H6   4VF 39 
4VF H7  H7  H  0 1 N N N 7.988  -8.093 11.899 -7.001 -3.319 -1.333 H7   4VF 40 
4VF H8  H8  H  0 1 N N N 10.338 -7.477 12.435 -4.621 -2.990 -1.870 H8   4VF 41 
4VF H9  H9  H  0 1 N N N 10.791 -5.756 14.166 -3.507 -0.874 -1.285 H9   4VF 42 
4VF H10 H10 H  0 1 N N N 18.589 -3.499 15.884 7.550  0.444  0.486  H10  4VF 43 
4VF H11 H11 H  0 1 N N N 21.018 -3.676 15.428 7.739  -1.106 2.392  H11  4VF 44 
4VF H12 H12 H  0 1 N N N 21.355 -2.321 16.558 7.685  -2.501 1.286  H12  4VF 45 
4VF H13 H13 H  0 1 N N N 20.173 -5.066 17.275 9.822  -0.321 1.332  H13  4VF 46 
4VF H14 H14 H  0 1 N N N 21.814 -4.461 17.687 10.020 -1.996 1.900  H14  4VF 47 
4VF H15 H15 H  0 1 N N N 18.469 -2.853 19.550 9.544  -1.334 -2.144 H15  4VF 48 
4VF H16 H16 H  0 1 N N N 18.273 -4.084 18.257 9.542  0.069  -1.049 H16  4VF 49 
4VF H17 H17 H  0 1 N N N 19.428 -1.259 17.828 7.391  -2.093 -1.209 H17  4VF 50 
4VF H18 H18 H  0 1 N N N 17.738 -1.739 17.456 7.245  -0.420 -1.802 H18  4VF 51 
4VF H19 H19 H  0 1 N N N 8.167  -4.239 18.820 -5.775 1.313  3.013  H19  4VF 52 
4VF H20 H20 H  0 1 N N N 7.267  -5.063 16.830 -4.741 2.803  1.459  H20  4VF 53 
4VF H21 H21 H  0 1 N N N 8.842  -5.822 17.242 -6.302 2.194  0.856  H21  4VF 54 
4VF H22 H22 H  0 1 N N N 19.830 -1.876 14.433 5.467  -1.565 0.892  H22  4VF 55 
4VF H23 H23 H  0 1 N N N 10.741 -4.999 17.526 -3.757 -0.583 1.500  H23  4VF 56 
4VF H24 H24 H  0 1 N N N 11.770 -5.509 16.145 -2.668 0.586  2.266  H24  4VF 57 
4VF H25 H25 H  0 1 N N N 17.062 0.719  12.017 5.143  3.199  -1.364 H25  4VF 58 
4VF H26 H26 H  0 1 N N N 14.848 -0.279 12.602 2.683  2.979  -1.130 H26  4VF 59 
# 
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 
4VF C22 C23 DOUB Y N 1  
4VF C22 C21 SING Y N 2  
4VF C10 C9  DOUB Y N 3  
4VF C10 N11 SING Y N 4  
4VF C23 C24 SING Y N 5  
4VF CL1 C21 SING N N 6  
4VF C9  C8  SING Y N 7  
4VF C21 C20 DOUB Y N 8  
4VF N11 C12 DOUB Y N 9  
4VF C24 C19 DOUB Y N 10 
4VF C15 C16 SING Y N 11 
4VF C15 C2  DOUB Y N 12 
4VF O7  C6  DOUB N N 13 
4VF C8  C16 SING N N 14 
4VF C8  N13 DOUB Y N 15 
4VF C20 C19 SING Y N 16 
4VF C12 N13 SING Y N 17 
4VF C12 N14 SING N N 18 
4VF C19 C18 SING N N 19 
4VF C16 C17 DOUB Y N 20 
4VF C6  C2  SING N N 21 
4VF C6  N5  SING N N 22 
4VF C2  N1  SING Y N 23 
4VF N14 C25 SING N N 24 
4VF C18 N5  SING N N 25 
4VF C18 C31 SING N N 26 
4VF N5  C4  SING N N 27 
4VF C17 N1  SING Y N 28 
4VF N1  C3  SING N N 29 
4VF C25 C26 SING N N 30 
4VF C25 C30 SING N N 31 
4VF C26 C27 SING N N 32 
4VF C4  C3  SING N N 33 
4VF C31 O32 SING N N 34 
4VF C27 O28 SING N N 35 
4VF C30 C29 SING N N 36 
4VF C29 O28 SING N N 37 
4VF C3  H1  SING N N 38 
4VF C3  H2  SING N N 39 
4VF C15 H3  SING N N 40 
4VF C17 H4  SING N N 41 
4VF C18 H5  SING N N 42 
4VF C20 H6  SING N N 43 
4VF C22 H7  SING N N 44 
4VF C23 H8  SING N N 45 
4VF C24 H9  SING N N 46 
4VF C25 H10 SING N N 47 
4VF C26 H11 SING N N 48 
4VF C26 H12 SING N N 49 
4VF C27 H13 SING N N 50 
4VF C27 H14 SING N N 51 
4VF C29 H15 SING N N 52 
4VF C29 H16 SING N N 53 
4VF C30 H17 SING N N 54 
4VF C30 H18 SING N N 55 
4VF O32 H19 SING N N 56 
4VF C31 H20 SING N N 57 
4VF C31 H21 SING N N 58 
4VF N14 H22 SING N N 59 
4VF C4  H23 SING N N 60 
4VF C4  H24 SING N N 61 
4VF C10 H25 SING N N 62 
4VF C9  H26 SING N N 63 
# 
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 
4VF SMILES           ACDLabs              12.01 "c32n(CCN(C(CO)c1cc(ccc1)Cl)C2=O)cc(c3)c5nc(NC4CCOCC4)ncc5"                                                                                                                                    
4VF InChI            InChI                1.03  "InChI=1S/C24H26ClN5O3/c25-18-3-1-2-16(12-18)22(15-31)30-9-8-29-14-17(13-21(29)23(30)32)20-4-7-26-24(28-20)27-19-5-10-33-11-6-19/h1-4,7,12-14,19,22,31H,5-6,8-11,15H2,(H,26,27,28)/t22-/m1/s1" 
4VF InChIKey         InChI                1.03  PJPXAFCTLKCTJP-JOCHJYFZSA-N                                                                                                                                                                    
4VF SMILES_CANONICAL CACTVS               3.385 "OC[C@@H](N1CCn2cc(cc2C1=O)c3ccnc(NC4CCOCC4)n3)c5cccc(Cl)c5"                                                                                                                                   
4VF SMILES           CACTVS               3.385 "OC[CH](N1CCn2cc(cc2C1=O)c3ccnc(NC4CCOCC4)n3)c5cccc(Cl)c5"                                                                                                                                     
4VF SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1cc(cc(c1)Cl)[C@@H](CO)N2CCn3cc(cc3C2=O)c4ccnc(n4)NC5CCOCC5"                                                                                                                                 
4VF SMILES           "OpenEye OEToolkits" 1.9.2 "c1cc(cc(c1)Cl)C(CO)N2CCn3cc(cc3C2=O)c4ccnc(n4)NC5CCOCC5"                                                                                                                                      
# 
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 
4VF "SYSTEMATIC NAME" ACDLabs              12.01 "2-[(1S)-1-(3-chlorophenyl)-2-hydroxyethyl]-7-[2-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one" 
4VF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "2-[(1S)-1-(3-chlorophenyl)-2-oxidanyl-ethyl]-7-[2-(oxan-4-ylamino)pyrimidin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-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 
4VF "Create component" 2015-06-05 RCSB 
4VF "Initial release"  2015-09-09 RCSB 
# 
