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                   2020-06-17
_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  Y  N   2  
11F  C1K  H1K   SING  N  N   3  
11F  C1I  C1H   DOUB  Y  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  N  N  11  
11F  C1Z  C1V   SING  Y  N  12  
11F  C1Y  C1Z   DOUB  Y  N  13  
11F  C1N  C1Z   SING  Y  N  14  
11F  C1O  C1Y   SING  Y  N  15  
11F  C1Y  O1R   SING  N  N  16  
11F  C1W  C1O   DOUB  Y  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  N  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  N  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  Y  N  37  
11F  N1   C6    DOUB  Y  N  38  
11F  C6   C1B   SING  N  N  39  
11F  C1B  H1B   SING  N  N  40  
11F  C1B  H1BA  SING  N  N  41  
11F  C1B  H1BB  SING  N  N  42  
11F  C2   N1    SING  Y  N  43  
11F  N3   C2    DOUB  Y  N  44  
11F  N1D  C2    SING  N  N  45  
11F  N1D  HN1D  SING  N  N  46  
11F  N1D  HN1A  SING  N  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  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"  
11F  InChI             InChI                 1.03   "InChI=1S/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"  
11F  InChIKey          InChI                 1.03   YYCPXVRHQUEVAW-CQSZACIVSA-N  
#   #
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"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
11F  "Create component"      2009-01-13  RCSB  
11F  "Modify aromatic_flag"  2011-06-04  RCSB  
11F  "Modify descriptor"     2011-06-04  RCSB  
11F  "Modify synonyms"       2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     11F
_pdbx_chem_comp_synonyms.name        "2,4-Diamino-5-[3S-(3-methoxy-4-phenylphenyl)but-1-ynyl]-6-methylpyrimidine"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
