data_3FQ
# 
_chem_comp.id                                    3FQ 
_chem_comp.name                                  (2S)-1-(DIMETHYLAMINO)-3-{4-[(6-{[2-FLUORO-5-(TRIFLUOROMETHYL)PHENYL]AMINO}PYRIMIDIN-4-YL)AMINO]PHENOXY}PROPAN-2-OL 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H25 F4 N5 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         1-(DIMETHYLAMINO)-3-{4-[(6-{[2-FLUORO-5-(TRIFLUOROMETHYL)PHENYL]AMINO}PYRIMIDIN-4-YL)AMINO]PHENOXY}PROPAN-2-OL 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-06-11 
_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                        483.459 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     3FQ 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
3FQ C1   C1   C 0 1 N N N 13.511 -8.428  13.575 -2.752 -0.674 -0.751 C1   3FQ 1  
3FQ N1   N1   N 0 1 N N N 11.841 -10.454 14.542 -0.256 0.325  -0.007 N1   3FQ 2  
3FQ C2   C2   C 0 1 N N N 12.467 -8.987  12.728 -1.475 -1.428 -0.991 C2   3FQ 3  
3FQ C7   C7   C 0 1 Y N N 14.299 -5.451  9.280  -7.587 -0.208 0.669  C7   3FQ 4  
3FQ C6   C6   C 0 1 Y N N 13.283 -5.240  10.205 -7.278 -1.542 0.856  C6   3FQ 5  
3FQ C5   C5   C 0 1 Y N N 13.308 -5.879  11.434 -6.013 -2.009 0.551  C5   3FQ 6  
3FQ C4   C4   C 0 1 Y N N 14.395 -6.713  11.752 -5.048 -1.132 0.068  C4   3FQ 7  
3FQ C3   C3   C 0 1 N N N 11.638 -10.031 13.277 -0.302 -0.920 -0.630 C3   3FQ 8  
3FQ C11  C11  C 0 1 Y N N 9.948  -9.216  10.494 2.143  -0.534 0.870  C11  3FQ 9  
3FQ C10  C10  C 0 1 Y N N 10.026 -10.493 11.133 2.090  -1.149 -0.374 C10  3FQ 10 
3FQ C9   C9   C 0 1 Y N N 15.420 -6.875  10.770 -5.363 0.207  -0.118 C9   3FQ 11 
3FQ C8   C8   C 0 1 Y N N 15.413 -6.393  9.372  -6.631 0.665  0.183  C8   3FQ 12 
3FQ C12  C12  C 0 1 Y N N 9.442  -9.087  9.192  3.346  -0.061 1.355  C12  3FQ 13 
3FQ C16  C16  C 0 1 N N N 8.852  -10.608 5.890  6.674  -0.020 0.087  C16  3FQ 14 
3FQ C14  C14  C 0 1 Y N N 9.057  -11.518 9.078  4.449  -0.809 -0.645 C14  3FQ 15 
3FQ C13  C13  C 0 1 Y N N 8.993  -10.220 8.470  4.502  -0.200 0.600  C13  3FQ 16 
3FQ C15  C15  C 0 1 Y N N 9.574  -11.652 10.409 3.247  -1.288 -1.129 C15  3FQ 17 
3FQ C    C    C 0 1 N N N 12.830 -9.880  15.256 -1.398 0.852  0.534  C    3FQ 18 
3FQ N    N    N 0 1 N N N 13.662 -8.897  14.841 -2.559 0.404  0.211  N    3FQ 19 
3FQ N2   N2   N 0 1 N N N 14.403 -7.350  13.073 -3.765 -1.599 -0.236 N2   3FQ 20 
3FQ F1   F1   F 0 1 N N N 12.296 -5.649  12.335 -5.711 -3.314 0.733  F1   3FQ 21 
3FQ N3   N3   N 0 1 N N N 10.554 -10.662 12.503 0.871  -1.629 -0.867 N3   3FQ 22 
3FQ O    O    O 0 1 N N N 8.474  -10.026 7.179  5.686  0.267  1.078  O    3FQ 23 
3FQ C21  C21  C 0 1 N N N 16.618 -6.146  8.413  -6.973 2.119  -0.018 C21  3FQ 24 
3FQ F2   F2   F 0 1 N N N 17.693 -6.531  9.017  -7.466 2.307  -1.314 F2   3FQ 25 
3FQ F3   F3   F 0 1 N N N 16.542 -6.876  7.219  -7.946 2.502  0.911  F3   3FQ 26 
3FQ F4   F4   F 0 1 N N N 16.947 -4.820  8.234  -5.825 2.898  0.161  F4   3FQ 27 
3FQ C17  C17  C 0 1 N N S 8.112  -9.835  4.753  8.038  0.482  0.565  C17  3FQ 28 
3FQ C18  C18  C 0 1 N N N 8.016  -8.317  5.090  9.071  0.288  -0.547 C18  3FQ 29 
3FQ C19  C19  C 0 1 N N N 6.746  -7.492  3.072  11.364 0.338  -1.089 C19  3FQ 30 
3FQ C20  C20  C 0 1 N N N 6.976  -6.045  5.026  10.334 2.237  -0.146 C20  3FQ 31 
3FQ N4   N4   N 0 1 N N N 6.874  -7.466  4.558  10.381 0.770  -0.087 N4   3FQ 32 
3FQ O1   O1   O 0 1 N N N 6.807  -10.384 4.546  8.438  -0.255 1.722  O1   3FQ 33 
3FQ O1L  O1L  O 0 1 N Y N ?      ?       ?      -3.209 -0.121 -1.987 O1L  3FQ 34 
3FQ HN1  HN1  H 0 1 N N N 11.978 -11.465 14.537 0.578  0.818  0.037  HN1  3FQ 35 
3FQ H2   H2   H 0 1 N N N 12.315 -8.623  11.698 -1.512 -2.398 -1.465 H2   3FQ 36 
3FQ H7   H7   H 0 1 N N N 14.260 -4.833  8.367  -8.578 0.154  0.903  H7   3FQ 37 
3FQ H6   H6   H 0 1 N N N 12.451 -4.559  9.959  -8.027 -2.222 1.236  H6   3FQ 38 
3FQ H11  H11  H 0 1 N N N 10.291 -8.318  11.034 1.243  -0.426 1.458  H11  3FQ 39 
3FQ H9   H9   H 0 1 N N N 16.321 -7.423  11.092 -4.618 0.890  -0.497 H9   3FQ 40 
3FQ H12  H12  H 0 1 N N N 9.393  -8.089  8.724  3.388  0.417  2.322  H12  3FQ 41 
3FQ H161 1H16 H 0 0 N N N 8.667  -11.707 5.848  6.409  0.479  -0.845 H161 3FQ 42 
3FQ H162 2H16 H 0 0 N N N 9.957  -10.631 5.740  6.721  -1.097 -0.079 H162 3FQ 43 
3FQ H14  H14  H 0 1 N N N 8.711  -12.407 8.525  5.349  -0.917 -1.232 H14  3FQ 44 
3FQ H15  H15  H 0 1 N N N 9.625  -12.648 10.880 3.207  -1.767 -2.096 H15  3FQ 45 
3FQ H    H    H 0 1 N N N 12.976 -10.250 16.285 -1.322 1.658  1.248  H    3FQ 46 
3FQ HA   HA   H 0 1 N N N 15.108 -7.011  13.728 -3.546 -2.535 -0.106 HA   3FQ 47 
3FQ H3   H3   H 0 1 N N N 10.056 -11.377 13.033 0.844  -2.456 -1.373 H3   3FQ 48 
3FQ H17  H17  H 0 1 N N N 8.696  -9.950  3.810  7.968  1.541  0.815  H17  3FQ 49 
3FQ H181 1H18 H 0 0 N N N 8.976  -7.835  4.790  8.766  0.850  -1.429 H181 3FQ 50 
3FQ H182 2H18 H 0 0 N N N 8.042  -8.207  6.199  9.141  -0.771 -0.796 H182 3FQ 51 
3FQ H191 1H19 H 0 0 N N N 5.909  -6.868  2.682  12.358 0.674  -0.791 H191 3FQ 52 
3FQ H192 2H19 H 0 0 N N N 6.659  -8.541  2.703  11.355 -0.749 -1.162 H192 3FQ 53 
3FQ H193 3H19 H 0 0 N N N 7.709  -7.203  2.590  11.110 0.770  -2.057 H193 3FQ 54 
3FQ H201 1H20 H 0 0 N N N 6.139  -5.421  4.636  9.614  2.607  0.584  H201 3FQ 55 
3FQ H202 2H20 H 0 0 N N N 7.967  -5.602  4.769  11.321 2.641  0.081  H202 3FQ 56 
3FQ H203 3H20 H 0 0 N N N 7.043  -5.987  6.137  10.033 2.552  -1.145 H203 3FQ 57 
3FQ H1   H1   H 0 1 N N N 6.357  -9.914  3.854  8.487  -1.184 1.458  H1   3FQ 58 
3FQ H1L  H1L  H 0 1 N N N 14.343 -8.532  15.394 -2.512 0.470  -2.303 H1L  3FQ 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 
3FQ C1  C2   SING N N 1  
3FQ C1  N    SING N N 2  
3FQ C1  N2   SING N N 3  
3FQ C1  O1L  SING N N 4  
3FQ N1  C3   SING N N 5  
3FQ N1  C    SING N N 6  
3FQ N1  HN1  SING N N 7  
3FQ C2  C3   DOUB N N 8  
3FQ C2  H2   SING N N 9  
3FQ C7  C6   DOUB Y N 10 
3FQ C7  C8   SING Y N 11 
3FQ C7  H7   SING N N 12 
3FQ C6  C5   SING Y N 13 
3FQ C6  H6   SING N N 14 
3FQ C5  C4   DOUB Y N 15 
3FQ C5  F1   SING N N 16 
3FQ C4  C9   SING Y N 17 
3FQ C4  N2   SING N N 18 
3FQ C3  N3   SING N N 19 
3FQ C11 C10  DOUB Y N 20 
3FQ C11 C12  SING Y N 21 
3FQ C11 H11  SING N N 22 
3FQ C10 C15  SING Y N 23 
3FQ C10 N3   SING N N 24 
3FQ C9  C8   DOUB Y N 25 
3FQ C9  H9   SING N N 26 
3FQ C8  C21  SING N N 27 
3FQ C12 C13  DOUB Y N 28 
3FQ C12 H12  SING N N 29 
3FQ C16 O    SING N N 30 
3FQ C16 C17  SING N N 31 
3FQ C16 H161 SING N N 32 
3FQ C16 H162 SING N N 33 
3FQ C14 C13  SING Y N 34 
3FQ C14 C15  DOUB Y N 35 
3FQ C14 H14  SING N N 36 
3FQ C13 O    SING N N 37 
3FQ C15 H15  SING N N 38 
3FQ C   N    DOUB N N 39 
3FQ C   H    SING N N 40 
3FQ N2  HA   SING N N 41 
3FQ N3  H3   SING N N 42 
3FQ C21 F2   SING N N 43 
3FQ C21 F3   SING N N 44 
3FQ C21 F4   SING N N 45 
3FQ C17 C18  SING N N 46 
3FQ C17 O1   SING N N 47 
3FQ C17 H17  SING N N 48 
3FQ C18 N4   SING N N 49 
3FQ C18 H181 SING N N 50 
3FQ C18 H182 SING N N 51 
3FQ C19 N4   SING N N 52 
3FQ C19 H191 SING N N 53 
3FQ C19 H192 SING N N 54 
3FQ C19 H193 SING N N 55 
3FQ C20 N4   SING N N 56 
3FQ C20 H201 SING N N 57 
3FQ C20 H202 SING N N 58 
3FQ C20 H203 SING N N 59 
3FQ O1  H1   SING N N 60 
3FQ O1L H1L  SING N N 61 
# 
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 
3FQ SMILES           ACDLabs              10.04 FC(F)(F)c1cc(c(F)cc1)NC3(O)N=CNC(Nc2ccc(OCC(O)CN(C)C)cc2)=C3                                                                                                                                       
3FQ InChI            InChI                1.02b InChI=1/C22H25F4N5O3/c1-31(2)11-16(32)12-34-17-6-4-15(5-7-17)29-20-10-21(33,28-13-27-20)30-19-9-14(22(24,25)26)3-8-18(19)23/h3-10,13,16,29-30,32-33H,11-12H2,1-2H3,(H,27,28)/t16-,21+/m0/s1/f/h27H 
3FQ InChIKey         InChI                1.02b NCMGCAICQSAQFF-LSGMMQLQDH                                                                                                                                                                          
3FQ SMILES_CANONICAL CACTVS               3.341 CN(C)C[C@H](O)COc1ccc(NC2=C[C@](O)(Nc3cc(ccc3F)C(F)(F)F)N=CN2)cc1                                                                                                                                  
3FQ SMILES           CACTVS               3.341 CN(C)C[CH](O)COc1ccc(NC2=C[C](O)(Nc3cc(ccc3F)C(F)(F)F)N=CN2)cc1                                                                                                                                    
3FQ SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CN(C)C[C@@H](COc1ccc(cc1)NC2=CC(N=CN2)(Nc3cc(ccc3F)C(F)(F)F)O)O                                                                                                                                    
3FQ SMILES           "OpenEye OEToolkits" 1.5.0 CN(C)CC(COc1ccc(cc1)NC2=CC(N=CN2)(Nc3cc(ccc3F)C(F)(F)F)O)O                                                                                                                                         
# 
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 
3FQ "SYSTEMATIC NAME" ACDLabs              10.04 (4S)-6-[(4-{[(2S)-3-(dimethylamino)-2-hydroxypropyl]oxy}phenyl)amino]-4-{[2-fluoro-5-(trifluoromethyl)phenyl]amino}-1,4-dihydropyrimidin-4-ol 
3FQ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 6-[[4-[(2S)-3-dimethylamino-2-hydroxy-propoxy]phenyl]amino]-4-[[2-fluoro-5-(trifluoromethyl)phenyl]amino]-1H-pyrimidin-4-ol                   
# 
