data_03P
#

_chem_comp.id                                   03P
_chem_comp.name                                 "N-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-3-hydroxy-3-methylbutanamide"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C26 H25 Cl F3 N5 O3"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        TAK-285
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2010-11-30
_chem_comp.pdbx_modified_date                   2021-03-01
_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                       547.957
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    03P
_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       3POZ
_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
03P  N1    N1    N   0  1  Y  N  N  14.734  33.559  13.161   1.440  -3.600   0.328  N1    03P   1  
03P  N3    N3    N   0  1  N  N  N  20.225  35.775  15.395   4.131   1.591  -1.208  N3    03P   2  
03P  C4    C4    C   0  1  Y  N  N  15.890  35.034  17.235   5.418  -2.868  -1.694  C4    03P   3  
03P  C5    C5    C   0  1  Y  N  N  14.518  34.854  17.058   5.264  -4.092  -1.155  C5    03P   4  
03P  C6    C6    C   0  1  N  N  N  18.073  34.788  16.054   4.102  -0.743  -1.936  C6    03P   5  
03P  C7    C7    C   0  1  N  N  N  18.783  36.032  15.531   4.322   0.210  -0.760  C7    03P   6  
03P  C8    C8    C   0  1  N  N  N  20.715  35.001  14.407   4.275   2.609  -0.336  C8    03P   7  
03P  C10   C10   C   0  1  Y  N  N  17.224  33.527  11.835   0.220  -1.128   0.066  C10   03P   8  
03P  C13   C13   C   0  1  Y  N  N  17.550  32.921   9.098  -2.232  -0.590   1.236  C13   03P   9  
03P  C15   C15   C   0  1  Y  N  N  18.135  32.543  11.422  -0.703  -0.324  -0.591  C15   03P  10  
03P  C17   C17   C   0  1  Y  N  N  18.404  30.743   6.486  -4.400   1.838   1.593  C17   03P  11  
03P  C20   C20   C   0  1  Y  N  N  16.048  29.394   7.164  -5.872   0.944  -0.575  C20   03P  12  
03P  C21   C21   C   0  1  Y  N  N  16.266  30.695   7.625  -5.017   0.078   0.079  C21   03P  13  
03P  C22   C22   C   0  1  N  N  N  14.802  28.623   7.500  -6.682   0.458  -1.749  C22   03P  14  
03P  C24   C24   C   0  1  N  N  N  24.121  33.228  14.043   5.900   4.734   0.761  C24   03P  15  
03P  F2    F2    F   0  1  N  N  N  13.867  29.356   8.056  -7.909  -0.038  -1.295  F2    03P  16  
03P  F     F     F   0  1  N  N  N  14.283  28.118   6.395  -6.907   1.520  -2.632  F     03P  17  
03P  F1    F1    F   0  1  N  N  N  15.102  27.632   8.330  -5.984  -0.558  -2.410  F1    03P  18  
03P  C19   C19   C   0  1  Y  N  N  17.012  28.782   6.348  -5.984   2.256  -0.154  C19   03P  19  
03P  C18   C18   C   0  1  Y  N  N  18.188  29.452   6.017  -5.253   2.701   0.932  C18   03P  20  
03P  C16   C16   C   0  1  Y  N  N  17.456  31.366   7.300  -4.278   0.523   1.166  C16   03P  21  
03P  O1    O1    O   0  1  N  N  N  17.688  32.640   7.745  -3.436  -0.326   1.810  O1    03P  22  
03P  C12   C12   C   0  1  Y  N  N  16.654  33.895   9.521  -1.314  -1.400   1.890  C12   03P  23  
03P  CL    CL    CL  0  0  N  N  N  15.676  34.766   8.319  -1.700  -2.069   3.445  CL    03P  24  
03P  C11   C11   C   0  1  Y  N  N  16.476  34.203  10.862  -0.090  -1.668   1.307  C11   03P  25  
03P  C14   C14   C   0  1  Y  N  N  18.317  32.250  10.052  -1.925  -0.056  -0.007  C14   03P  26  
03P  N4    N4    N   0  1  N  N  N  17.081  33.810  13.180   1.459  -1.400  -0.526  N4    03P  27  
03P  C1    C1    C   0  1  Y  N  N  15.875  33.886  13.812   2.070  -2.627  -0.322  C1    03P  28  
03P  C     C     C   0  1  Y  N  N  13.519  33.645  13.738   2.011  -4.774   0.530  C     03P  29  
03P  C3    C3    C   0  1  Y  N  N  15.733  34.309  15.146   3.365  -2.867  -0.796  C3    03P  30  
03P  C2    C2    C   0  1  Y  N  N  14.475  34.412  15.705   3.933  -4.131  -0.558  C2    03P  31  
03P  N     N     N   0  1  Y  N  N  13.371  34.064  15.005   3.224  -5.049   0.105  N     03P  32  
03P  N2    N2    N   0  1  Y  N  N  16.593  34.740  16.100   4.293  -2.125  -1.487  N2    03P  33  
03P  O     O     O   0  1  N  N  N  20.014  34.442  13.583   4.563   2.381   0.820  O     03P  34  
03P  C9    C9    C   0  1  N  N  N  22.220  34.825  14.324   4.078   4.030  -0.798  C9    03P  35  
03P  C23   C23   C   0  1  N  N  N  22.607  33.386  13.956   4.453   4.990   0.333  C23   03P  36  
03P  O2    O2    O   0  1  N  N  N  22.020  32.500  14.919   3.582   4.778   1.447  O2    03P  37  
03P  C25   C25   C   0  1  N  N  N  22.147  32.956  12.561   4.313   6.433  -0.155  C25   03P  38  
03P  HN3   HN3   H   0  1  N  N  N  20.857  36.185  16.052   3.900   1.774  -2.132  HN3   03P  39  
03P  H4    H4    H   0  1  N  N  N  16.342  35.366  18.158   6.301  -2.525  -2.212  H4    03P  40  
03P  H5    H5    H   0  1  N  N  N  13.709  35.008  17.757   5.988  -4.893  -1.164  H5    03P  41  
03P  H6    H6    H   0  1  N  N  N  18.384  33.962  15.398   3.088  -0.622  -2.317  H6    03P  42  
03P  H6A   H6A   H   0  1  N  N  N  18.414  34.657  17.092   4.817  -0.516  -2.727  H6A   03P  43  
03P  H7    H7    H   0  1  N  N  N  18.628  36.861  16.237   5.336   0.089  -0.379  H7    03P  44  
03P  H7A   H7A   H   0  1  N  N  N  18.368  36.299  14.548   3.607  -0.018   0.031  H7A   03P  45  
03P  H15   H15   H   0  1  N  N  N  18.705  32.002  12.162  -0.464   0.093  -1.558  H15   03P  46  
03P  H17   H17   H   0  1  N  N  N  19.310  31.267   6.219  -3.826   2.187   2.438  H17   03P  47  
03P  H21   H21   H   0  1  N  N  N  15.519  31.185   8.232  -4.930  -0.947  -0.250  H21   03P  48  
03P  H24   H24   H   0  1  N  N  N  24.398  32.197  13.779   6.563   4.896  -0.088  H24   03P  49  
03P  H24A  H24A  H   0  0  N  N  N  24.603  33.927  13.344   6.167   5.418   1.567  H24A  03P  50  
03P  H24B  H24B  H   0  0  N  N  N  24.454  33.446  15.068   5.999   3.706   1.109  H24B  03P  51  
03P  H19   H19   H   0  1  N  N  N  16.841  27.784   5.974  -6.652   2.932  -0.667  H19   03P  52  
03P  H18   H18   H   0  1  N  N  N  18.930  28.970   5.398  -5.348   3.724   1.265  H18   03P  53  
03P  H11   H11   H   0  1  N  N  N  15.764  34.961  11.155   0.624  -2.298   1.816  H11   03P  54  
03P  H14   H14   H   0  1  N  N  N  19.044  31.513   9.745  -2.640   0.574  -0.515  H14   03P  55  
03P  HN4   HN4   H   0  1  N  N  N  17.908  33.968  13.720   1.889  -0.729  -1.079  HN4   03P  56  
03P  H     H     H   0  1  N  N  N  12.644  33.370  13.168   1.461  -5.535   1.064  H     03P  57  
03P  H9    H9    H   0  1  N  N  N  22.612  35.504  13.552   4.713   4.222  -1.663  H9    03P  58  
03P  H9A   H9A   H   0  1  N  N  N  22.658  35.068  15.303   3.034   4.182  -1.072  H9A   03P  59  
03P  HO2   HO2   H   0  1  N  N  N  21.074  32.578  14.886   3.619   3.882   1.809  HO2   03P  60  
03P  H25   H25   H   0  1  N  N  N  21.055  33.065  12.485   4.912   6.571  -1.056  H25   03P  61  
03P  H25A  H25A  H   0  0  N  N  N  22.633  33.589  11.804   3.267   6.641  -0.379  H25A  03P  62  
03P  H25B  H25B  H   0  0  N  N  N  22.423  31.905  12.392   4.662   7.115   0.621  H25B  03P  63  
#   #
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
03P  N1   C     DOUB  Y  N   1  
03P  N1   C1    SING  Y  N   2  
03P  C8   N3    SING  N  N   3  
03P  N3   C7    SING  N  N   4  
03P  N3   HN3   SING  N  N   5  
03P  N2   C4    SING  Y  N   6  
03P  C5   C4    DOUB  Y  N   7  
03P  C4   H4    SING  N  N   8  
03P  C2   C5    SING  Y  N   9  
03P  C5   H5    SING  N  N  10  
03P  C7   C6    SING  N  N  11  
03P  C6   N2    SING  N  N  12  
03P  C6   H6    SING  N  N  13  
03P  C6   H6A   SING  N  N  14  
03P  C7   H7    SING  N  N  15  
03P  C7   H7A   SING  N  N  16  
03P  O    C8    DOUB  N  N  17  
03P  C9   C8    SING  N  N  18  
03P  C11  C10   DOUB  Y  N  19  
03P  C15  C10   SING  Y  N  20  
03P  C10  N4    SING  N  N  21  
03P  O1   C13   SING  N  N  22  
03P  C13  C12   DOUB  Y  N  23  
03P  C13  C14   SING  Y  N  24  
03P  C14  C15   DOUB  Y  N  25  
03P  C15  H15   SING  N  N  26  
03P  C18  C17   DOUB  Y  N  27  
03P  C17  C16   SING  Y  N  28  
03P  C17  H17   SING  N  N  29  
03P  C19  C20   DOUB  Y  N  30  
03P  C20  C22   SING  N  N  31  
03P  C20  C21   SING  Y  N  32  
03P  C16  C21   DOUB  Y  N  33  
03P  C21  H21   SING  N  N  34  
03P  F    C22   SING  N  N  35  
03P  C22  F2    SING  N  N  36  
03P  C22  F1    SING  N  N  37  
03P  C23  C24   SING  N  N  38  
03P  C24  H24   SING  N  N  39  
03P  C24  H24A  SING  N  N  40  
03P  C24  H24B  SING  N  N  41  
03P  C18  C19   SING  Y  N  42  
03P  C19  H19   SING  N  N  43  
03P  C18  H18   SING  N  N  44  
03P  C16  O1    SING  N  N  45  
03P  CL   C12   SING  N  N  46  
03P  C12  C11   SING  Y  N  47  
03P  C11  H11   SING  N  N  48  
03P  C14  H14   SING  N  N  49  
03P  N4   C1    SING  N  N  50  
03P  N4   HN4   SING  N  N  51  
03P  C1   C3    DOUB  Y  N  52  
03P  C    N     SING  Y  N  53  
03P  C    H     SING  N  N  54  
03P  C3   C2    SING  Y  N  55  
03P  C3   N2    SING  Y  N  56  
03P  N    C2    DOUB  Y  N  57  
03P  C23  C9    SING  N  N  58  
03P  C9   H9    SING  N  N  59  
03P  C9   H9A   SING  N  N  60  
03P  C25  C23   SING  N  N  61  
03P  C23  O2    SING  N  N  62  
03P  O2   HO2   SING  N  N  63  
03P  C25  H25   SING  N  N  64  
03P  C25  H25A  SING  N  N  65  
03P  C25  H25B  SING  N  N  66  
#   #
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
03P  SMILES            ACDLabs               12.01  "FC(F)(F)c4cc(Oc1ccc(cc1Cl)Nc2ncnc3c2n(cc3)CCNC(=O)CC(O)(C)C)ccc4"  
03P  InChI             InChI                 1.03   "InChI=1S/C26H25ClF3N5O3/c1-25(2,37)14-22(36)31-9-11-35-10-8-20-23(35)24(33-15-32-20)34-17-6-7-21(19(27)13-17)38-18-5-3-4-16(12-18)26(28,29)30/h3-8,10,12-13,15,37H,9,11,14H2,1-2H3,(H,31,36)(H,32,33,34)"  
03P  InChIKey          InChI                 1.03   ZYQXEVJIFYIBHZ-UHFFFAOYSA-N  
03P  SMILES_CANONICAL  CACTVS                3.370  "CC(C)(O)CC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(c4)C(F)(F)F)c(Cl)c3)c12"  
03P  SMILES            CACTVS                3.370  "CC(C)(O)CC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(c4)C(F)(F)F)c(Cl)c3)c12"  
03P  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.2  "CC(C)(CC(=O)NCCn1ccc2c1c(ncn2)Nc3ccc(c(c3)Cl)Oc4cccc(c4)C(F)(F)F)O"  
03P  SMILES            "OpenEye OEToolkits"  1.7.2  "CC(C)(CC(=O)NCCn1ccc2c1c(ncn2)Nc3ccc(c(c3)Cl)Oc4cccc(c4)C(F)(F)F)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
03P  "SYSTEMATIC NAME"  ACDLabs               12.01  "N-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-3-hydroxy-3-methylbutanamide"  
03P  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.7.2  "N-[2-[4-[[3-chloranyl-4-[3-(trifluoromethyl)phenoxy]phenyl]amino]pyrrolo[3,2-d]pyrimidin-5-yl]ethyl]-3-methyl-3-oxidanyl-butanamide"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
03P  "Create component"      2010-11-30  RCSB  
03P  "Modify aromatic_flag"  2011-06-04  RCSB  
03P  "Modify descriptor"     2011-06-04  RCSB  
03P  "Modify synonyms"       2011-07-31  RCSB  
03P  "Modify synonyms"       2021-03-01  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     03P
_pdbx_chem_comp_synonyms.name        TAK-285
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
