data_11F
# 
_chem_comp.id                                    11F 
_chem_comp.name                                  5-[(3S)-3-(2-methoxybiphenyl-4-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H22 N4 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         2,4-Diamino-5-[3S-(3-methoxy-4-phenylphenyl)but-1-ynyl]-6-methylpyrimidine 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2009-01-13 
_chem_comp.pdbx_modified_date                    2009-03-20 
_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                        358.436 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     11F 
_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        3FQV 
_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 
11F C1K  C1K  C 0 1 Y N N -32.598 -12.819 48.325 -5.020 0.951  1.447  C1K  11F 1  
11F C1I  C1I  C 0 1 Y N N -33.347 -12.867 49.501 -6.168 1.717  1.412  C1I  11F 2  
11F C1H  C1H  C 0 1 Y N N -34.092 -14.006 49.811 -6.573 2.305  0.228  C1H  11F 3  
11F C1J  C1J  C 0 1 Y N N -34.084 -15.102 48.949 -5.832 2.131  -0.927 C1J  11F 4  
11F C1L  C1L  C 0 1 Y N N -33.335 -15.051 47.773 -4.682 1.367  -0.903 C1L  11F 5  
11F C1V  C1V  C 0 1 Y N N -32.588 -13.911 47.457 -4.266 0.777  0.289  C1V  11F 6  
11F C1Z  C1Z  C 0 1 Y N N -31.853 -13.893 46.271 -3.031 -0.045 0.320  C1Z  11F 7  
11F C1Y  C1Y  C 0 1 Y N N -32.151 -12.990 45.238 -2.832 -1.050 -0.630 C1Y  11F 8  
11F C1O  C1O  C 0 1 Y N N -31.390 -13.010 44.060 -1.675 -1.812 -0.593 C1O  11F 9  
11F O1R  O1R  O 0 1 N N N -33.162 -12.081 45.394 -3.768 -1.279 -1.587 O1R  11F 10 
11F C1A  C1A  C 0 1 N N N -33.650 -11.490 44.168 -3.496 -2.322 -2.525 C1A  11F 11 
11F C1N  C1N  C 0 1 Y N N -30.815 -14.812 46.109 -2.062 0.186  1.295  C1N  11F 12 
11F C1M  C1M  C 0 1 Y N N -30.075 -14.824 44.930 -0.915 -0.581 1.320  C1M  11F 13 
11F C1W  C1W  C 0 1 Y N N -30.347 -13.920 43.903 -0.723 -1.579 0.381  C1W  11F 14 
11F C2A  C2A  C 0 1 N N R -29.534 -13.952 42.590 0.533  -2.411 0.417  C2A  11F 15 
11F C1C  C1C  C 0 1 N N N -28.323 -14.853 42.727 0.619  -3.146 1.757  C1C  11F 16 
11F C1G  C1G  C 0 1 N N N -29.048 -12.640 42.162 1.706  -1.536 0.261  C1G  11F 17 
11F C1F  C1F  C 0 1 N N N -28.609 -11.582 41.770 2.642  -0.839 0.137  C1F  11F 18 
11F C5   C5   C 0 1 Y N N -28.079 -10.342 41.295 3.784  0.012  -0.015 C5   11F 19 
11F C6   C6   C 0 1 Y N N -28.546 -9.134  41.802 5.076  -0.515 -0.015 C6   11F 20 
11F C1B  C1B  C 0 1 N N N -29.627 -9.100  42.878 5.295  -1.997 0.144  C1B  11F 21 
11F N1   N1   N 0 1 Y N N -28.031 -7.984  41.342 6.105  0.304  -0.158 N1   11F 22 
11F C2   C2   C 0 1 Y N N -27.079 -7.980  40.394 5.926  1.610  -0.300 C2   11F 23 
11F N1D  N1D  N 0 1 N N N -26.595 -6.822  39.952 7.032  2.426  -0.446 N1D  11F 24 
11F N3   N3   N 0 1 Y N N -26.619 -9.134  39.883 4.719  2.156  -0.306 N3   11F 25 
11F C4   C4   C 0 1 Y N N -27.091 -10.316 40.310 3.632  1.404  -0.174 C4   11F 26 
11F N1E  N1E  N 0 1 N N N -26.607 -11.442 39.789 2.375  1.979  -0.181 N1E  11F 27 
11F H1K  H1K  H 0 1 N N N -32.025 -11.935 48.086 -4.704 0.492  2.372  H1K  11F 28 
11F H1I  H1I  H 0 1 N N N -33.350 -12.021 50.173 -6.750 1.856  2.310  H1I  11F 29 
11F H1H  H1H  H 0 1 N N N -34.675 -14.038 50.719 -7.472 2.904  0.204  H1H  11F 30 
11F H1J  H1J  H 0 1 N N N -34.655 -15.986 49.191 -6.153 2.592  -1.849 H1J  11F 31 
11F H1L  H1L  H 0 1 N N N -33.332 -15.897 47.102 -4.104 1.231  -1.806 H1L  11F 32 
11F H1O  H1O  H 0 1 N N N -31.615 -12.313 43.267 -1.517 -2.590 -1.326 H1O  11F 33 
11F H1A  H1A  H 0 1 N N N -33.774 -10.406 44.307 -2.577 -2.095 -3.064 H1A  11F 34 
11F H1AA H1AA H 0 0 N N N -32.928 -11.676 43.359 -3.383 -3.267 -1.994 H1AA 11F 35 
11F H1AB H1AB H 0 0 N N N -34.619 -11.939 43.905 -4.322 -2.400 -3.232 H1AB 11F 36 
11F H1N  H1N  H 0 1 N N N -30.586 -15.513 46.898 -2.209 0.964  2.029  H1N  11F 37 
11F H1M  H1M  H 0 1 N N N -29.279 -15.544 44.809 -0.164 -0.401 2.076  H1M  11F 38 
11F H2A  H2A  H 0 1 N N N -30.239 -14.329 41.835 0.511  -3.138 -0.395 H2A  11F 39 
11F H1C  H1C  H 0 1 N N N -27.913 -15.071 41.730 1.527  -3.748 1.783  H1C  11F 40 
11F H1CA H1CA H 0 0 N N N -27.558 -14.349 43.335 0.641  -2.420 2.569  H1CA 11F 41 
11F H1CB H1CB H 0 0 N N N -28.619 -15.793 43.215 -0.250 -3.794 1.872  H1CB 11F 42 
11F H1B  H1B  H 0 1 N N N -29.156 -9.092  43.872 5.300  -2.471 -0.837 H1B  11F 43 
11F H1BA H1BA H 0 0 N N N -30.238 -8.194  42.755 6.252  -2.172 0.637  H1BA 11F 44 
11F H1BB H1BB H 0 0 N N N -30.267 -9.990  42.783 4.493  -2.421 0.748  H1BB 11F 45 
11F HN1D HN1D H 0 0 N N N -26.474 -6.195  40.722 7.923  2.041  -0.444 HN1D 11F 46 
11F HN1A HN1A H 0 0 N N N -25.713 -6.978  39.507 6.918  3.384  -0.551 HN1A 11F 47 
11F HN1E HN1E H 0 0 N N N -26.486 -11.328 38.803 2.280  2.939  -0.282 HN1E 11F 48 
11F HN1B HN1B H 0 0 N N N -25.725 -11.652 40.211 1.586  1.422  -0.084 HN1B 11F 49 
# 
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 
11F C1V C1K  DOUB Y N 1  
11F C1K C1I  SING N N 2  
11F C1K H1K  SING Y N 3  
11F C1I C1H  DOUB N N 4  
11F C1I H1I  SING N N 5  
11F C1J C1H  SING Y N 6  
11F C1H H1H  SING N N 7  
11F C1L C1J  DOUB Y N 8  
11F C1J H1J  SING N N 9  
11F C1V C1L  SING Y N 10 
11F C1L H1L  SING Y N 11 
11F C1Z C1V  SING N N 12 
11F C1Y C1Z  DOUB Y N 13 
11F C1N C1Z  SING N N 14 
11F C1O C1Y  SING Y N 15 
11F C1Y O1R  SING N N 16 
11F C1W C1O  DOUB N N 17 
11F C1O H1O  SING N N 18 
11F C1A O1R  SING N N 19 
11F C1A H1A  SING N N 20 
11F C1A H1AA SING Y N 21 
11F C1A H1AB SING N N 22 
11F C1M C1N  DOUB Y N 23 
11F C1N H1N  SING N N 24 
11F C1W C1M  SING Y N 25 
11F C1M H1M  SING Y N 26 
11F C2A C1W  SING N N 27 
11F C1G C2A  SING N N 28 
11F C2A C1C  SING N N 29 
11F C2A H2A  SING N N 30 
11F C1C H1C  SING N N 31 
11F C1C H1CA SING N N 32 
11F C1C H1CB SING N N 33 
11F C1F C1G  TRIP N N 34 
11F C5  C1F  SING N N 35 
11F C4  C5   DOUB Y N 36 
11F C5  C6   SING N N 37 
11F N1  C6   DOUB N N 38 
11F C6  C1B  SING N N 39 
11F C1B H1B  SING N N 40 
11F C1B H1BA SING Y N 41 
11F C1B H1BB SING Y N 42 
11F C2  N1   SING N N 43 
11F N3  C2   DOUB N N 44 
11F N1D C2   SING N N 45 
11F N1D HN1D SING Y N 46 
11F N1D HN1A SING Y N 47 
11F N3  C4   SING Y N 48 
11F N1E C4   SING N N 49 
11F N1E HN1E SING N N 50 
11F N1E HN1B SING N N 51 
# 
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 
11F SMILES           ACDLabs              10.04 C(#CC(c2ccc(c1ccccc1)c(OC)c2)C)c3c(nc(nc3C)N)N                                                                                                                  
11F InChI            InChI                1.02b InChI=1/C22H22N4O/c1-14(9-11-18-15(2)25-22(24)26-21(18)23)17-10-12-19(20(13-17)27-3)16-7-5-4-6-8-16/h4-8,10,12-14H,1-3H3,(H4,23,24,25,26)/t14-/m1/s1/f/h23-24H2 
11F InChIKey         InChI                1.02b YYCPXVRHQUEVAW-YEEWCJOLDE                                                                                                                                       
11F SMILES_CANONICAL CACTVS               3.341 COc1cc(ccc1c2ccccc2)[C@H](C)C#Cc3c(C)nc(N)nc3N                                                                                                                  
11F SMILES           CACTVS               3.341 COc1cc(ccc1c2ccccc2)[CH](C)C#Cc3c(C)nc(N)nc3N                                                                                                                   
11F SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c(c(nc(n1)N)N)C#C[C@@H](C)c2ccc(c(c2)OC)c3ccccc3                                                                                                             
11F SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c(c(nc(n1)N)N)C#CC(C)c2ccc(c(c2)OC)c3ccccc3                                                                                                                  
# 
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 
11F "SYSTEMATIC NAME" ACDLabs              10.04 5-[(3S)-3-(2-methoxybiphenyl-4-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine  
11F "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 5-[(3S)-3-(3-methoxy-4-phenyl-phenyl)but-1-ynyl]-6-methyl-pyrimidine-2,4-diamine 
# 
