data_VSF
# 
_chem_comp.id                                    VSF 
_chem_comp.name                                  "5-(4-phenoxyphenyl)-7-(tetrahydro-2H-pyran-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H22 N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2012-05-28 
_chem_comp.pdbx_modified_date                    2013-04-26 
_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                        386.446 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     VSF 
_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        3VS4 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
VSF NAK NAK N 0 1 N N N 3.377  -7.639  12.631 0.712  2.731  -0.123 NAK VSF 1  
VSF C6  C6  C 0 1 Y N N 4.264  -8.571  12.212 -0.668 2.668  -0.054 C6  VSF 2  
VSF N1  N1  N 0 1 Y N N 5.398  -8.184  11.581 -1.399 3.778  0.002  N1  VSF 3  
VSF C2  C2  C 0 1 Y N N 6.292  -9.087  11.158 -2.718 3.721  0.063  C2  VSF 4  
VSF N3  N3  N 0 1 Y N N 6.090  -10.390 11.346 -3.380 2.585  0.073  N3  VSF 5  
VSF C4  C4  C 0 1 Y N N 4.975  -10.837 11.978 -2.735 1.420  0.021  C4  VSF 6  
VSF C5  C5  C 0 1 Y N N 4.030  -9.923  12.429 -1.331 1.433  -0.045 C5  VSF 7  
VSF NAG NAG N 0 1 Y N N 4.551  -12.077 12.298 -3.133 0.111  0.016  NAG VSF 8  
VSF CAQ CAQ C 0 1 N N N 5.258  -13.351 11.998 -4.525 -0.342 0.073  CAQ VSF 9  
VSF CAV CAV C 0 1 N N N 4.436  -14.192 11.026 -4.728 -1.219 1.313  CAV VSF 10 
VSF CAU CAU C 0 1 N N N 4.330  -15.624 11.541 -6.163 -1.751 1.322  CAU VSF 11 
VSF OAT OAT O 0 1 N N N 5.646  -16.079 11.871 -6.408 -2.479 0.117  OAT VSF 12 
VSF CAS CAS C 0 1 N N N 6.134  -15.462 13.075 -6.279 -1.698 -1.073 CAS VSF 13 
VSF CAR CAR C 0 1 N N N 5.444  -14.116 13.304 -4.848 -1.164 -1.178 CAR VSF 14 
VSF CAH CAH C 0 1 Y N N 3.366  -11.988 12.919 -2.043 -0.716 -0.051 CAH VSF 15 
VSF CAI CAI C 0 1 Y N N 3.009  -10.651 13.037 -0.910 0.027  -0.096 CAI VSF 16 
VSF CAJ CAJ C 0 1 Y N N 1.736  -10.167 13.659 0.480  -0.480 -0.177 CAJ VSF 17 
VSF CAL CAL C 0 1 Y N N 1.309  -10.567 14.925 0.917  -1.466 0.706  CAL VSF 18 
VSF CAM CAM C 0 1 Y N N 0.089  -10.110 15.433 2.211  -1.936 0.627  CAM VSF 19 
VSF CAN CAN C 0 1 Y N N -0.723 -9.272  14.671 3.079  -1.427 -0.330 CAN VSF 20 
VSF CAO CAO C 0 1 Y N N -0.300 -8.892  13.410 2.648  -0.444 -1.210 CAO VSF 21 
VSF CAP CAP C 0 1 Y N N 0.909  -9.350  12.899 1.353  0.025  -1.141 CAP VSF 22 
VSF OBD OBD O 0 1 N N N -1.928 -8.794  15.123 4.354  -1.892 -0.405 OBD VSF 23 
VSF CBE CBE C 0 1 Y N N -2.143 -8.352  16.402 5.363  -1.043 -0.079 CBE VSF 24 
VSF CBJ CBJ C 0 1 Y N N -1.255 -7.474  17.007 5.075  0.213  0.437  CBJ VSF 25 
VSF CBI CBI C 0 1 Y N N -1.479 -7.035  18.306 6.103  1.075  0.767  CBI VSF 26 
VSF CBH CBH C 0 1 Y N N -2.597 -7.481  19.000 7.418  0.687  0.585  CBH VSF 27 
VSF CBG CBG C 0 1 Y N N -3.488 -8.364  18.395 7.707  -0.563 0.072  CBG VSF 28 
VSF CBF CBF C 0 1 Y N N -3.261 -8.802  17.097 6.683  -1.431 -0.255 CBF VSF 29 
VSF H1  H1  H 0 1 N N N 3.714  -6.728  12.395 1.233  1.914  -0.167 H1  VSF 30 
VSF H2  H2  H 0 1 N N N 2.495  -7.794  12.185 1.158  3.592  -0.132 H2  VSF 31 
VSF H3  H3  H 0 1 N N N 7.189  -8.754  10.657 -3.274 4.646  0.106  H3  VSF 32 
VSF H4  H4  H 0 1 N N N 6.242  -13.138 11.555 -5.187 0.522  0.123  H4  VSF 33 
VSF H5  H5  H 0 1 N N N 4.925  -14.194 10.041 -4.029 -2.055 1.286  H5  VSF 34 
VSF H6  H6  H 0 1 N N N 3.428  -13.762 10.934 -4.553 -0.626 2.211  H6  VSF 35 
VSF H7  H7  H 0 1 N N N 3.691  -15.651 12.436 -6.301 -2.410 2.179  H7  VSF 36 
VSF H8  H8  H 0 1 N N N 3.898  -16.269 10.762 -6.860 -0.916 1.390  H8  VSF 37 
VSF H9  H9  H 0 1 N N N 5.930  -16.124 13.930 -6.500 -2.319 -1.941 H9  VSF 38 
VSF H10 H10 H 0 1 N N N 7.219  -15.302 12.986 -6.977 -0.862 -1.036 H10 VSF 39 
VSF H11 H11 H 0 1 N N N 6.059  -13.512 13.987 -4.760 -0.532 -2.062 H11 VSF 40 
VSF H12 H12 H 0 1 N N N 4.458  -14.293 13.758 -4.152 -1.999 -1.256 H12 VSF 41 
VSF H13 H13 H 0 1 N N N 2.781  -12.824 13.272 -2.081 -1.795 -0.069 H13 VSF 42 
VSF H14 H14 H 0 1 N N N 1.923  -11.232 15.515 0.243  -1.862 1.450  H14 VSF 43 
VSF H15 H15 H 0 1 N N N -0.226 -10.408 16.422 2.550  -2.700 1.311  H15 VSF 44 
VSF H16 H16 H 0 1 N N N -0.916 -8.233  12.816 3.325  -0.051 -1.953 H16 VSF 45 
VSF H17 H17 H 0 1 N N N 1.208  -9.068  11.900 1.018  0.790  -1.826 H17 VSF 46 
VSF H18 H18 H 0 1 N N N -0.386 -7.130  16.466 4.048  0.517  0.578  H18 VSF 47 
VSF H19 H19 H 0 1 N N N -0.787 -6.350  18.774 5.879  2.053  1.168  H19 VSF 48 
VSF H20 H20 H 0 1 N N N -2.775 -7.142  20.010 8.219  1.363  0.844  H20 VSF 49 
VSF H21 H21 H 0 1 N N N -4.357 -8.709  18.936 8.735  -0.864 -0.070 H21 VSF 50 
VSF H22 H22 H 0 1 N N N -3.950 -9.489  16.629 6.910  -2.410 -0.652 H22 VSF 51 
# 
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 
VSF CAV CAU SING N N 1  
VSF CAV CAQ SING N N 2  
VSF C2  N3  DOUB Y N 3  
VSF C2  N1  SING Y N 4  
VSF N3  C4  SING Y N 5  
VSF CAU OAT SING N N 6  
VSF N1  C6  DOUB Y N 7  
VSF OAT CAS SING N N 8  
VSF C4  NAG SING Y N 9  
VSF C4  C5  DOUB Y N 10 
VSF CAQ NAG SING N N 11 
VSF CAQ CAR SING N N 12 
VSF C6  C5  SING Y N 13 
VSF C6  NAK SING N N 14 
VSF NAG CAH SING Y N 15 
VSF C5  CAI SING Y N 16 
VSF CAP CAO DOUB Y N 17 
VSF CAP CAJ SING Y N 18 
VSF CAH CAI DOUB Y N 19 
VSF CAI CAJ SING N N 20 
VSF CAS CAR SING N N 21 
VSF CAO CAN SING Y N 22 
VSF CAJ CAL DOUB Y N 23 
VSF CAN OBD SING N N 24 
VSF CAN CAM DOUB Y N 25 
VSF CAL CAM SING Y N 26 
VSF OBD CBE SING N N 27 
VSF CBE CBJ DOUB Y N 28 
VSF CBE CBF SING Y N 29 
VSF CBJ CBI SING Y N 30 
VSF CBF CBG DOUB Y N 31 
VSF CBI CBH DOUB Y N 32 
VSF CBG CBH SING Y N 33 
VSF NAK H1  SING N N 34 
VSF NAK H2  SING N N 35 
VSF C2  H3  SING N N 36 
VSF CAQ H4  SING N N 37 
VSF CAV H5  SING N N 38 
VSF CAV H6  SING N N 39 
VSF CAU H7  SING N N 40 
VSF CAU H8  SING N N 41 
VSF CAS H9  SING N N 42 
VSF CAS H10 SING N N 43 
VSF CAR H11 SING N N 44 
VSF CAR H12 SING N N 45 
VSF CAH H13 SING N N 46 
VSF CAL H14 SING N N 47 
VSF CAM H15 SING N N 48 
VSF CAO H16 SING N N 49 
VSF CAP H17 SING N N 50 
VSF CBJ H18 SING N N 51 
VSF CBI H19 SING N N 52 
VSF CBH H20 SING N N 53 
VSF CBG H21 SING N N 54 
VSF CBF H22 SING N N 55 
# 
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 
VSF SMILES           ACDLabs              12.01 "O(c1ccccc1)c5ccc(c2cn(c3ncnc(N)c23)C4CCOCC4)cc5"                                                                                                        
VSF InChI            InChI                1.03  "InChI=1S/C23H22N4O2/c24-22-21-20(14-27(23(21)26-15-25-22)17-10-12-28-13-11-17)16-6-8-19(9-7-16)29-18-4-2-1-3-5-18/h1-9,14-15,17H,10-13H2,(H2,24,25,26)" 
VSF InChIKey         InChI                1.03  BCWVVERKADMJGG-UHFFFAOYSA-N                                                                                                                              
VSF SMILES_CANONICAL CACTVS               3.370 "Nc1ncnc2n(cc(c3ccc(Oc4ccccc4)cc3)c12)C5CCOCC5"                                                                                                          
VSF SMILES           CACTVS               3.370 "Nc1ncnc2n(cc(c3ccc(Oc4ccccc4)cc3)c12)C5CCOCC5"                                                                                                          
VSF SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1ccc(cc1)Oc2ccc(cc2)c3cn(c4c3c(ncn4)N)C5CCOCC5"                                                                                                        
VSF SMILES           "OpenEye OEToolkits" 1.7.6 "c1ccc(cc1)Oc2ccc(cc2)c3cn(c4c3c(ncn4)N)C5CCOCC5"                                                                                                        
# 
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 
VSF "SYSTEMATIC NAME" ACDLabs              12.01 "5-(4-phenoxyphenyl)-7-(tetrahydro-2H-pyran-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine" 
VSF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "7-(oxan-4-yl)-5-(4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-4-amine"                    
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
VSF "Create component" 2012-05-28 PDBJ 
VSF "Initial release"  2013-05-01 RCSB 
# 
