data_T22
#

_chem_comp.id                                   T22
_chem_comp.name                                 "2-({6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl}methyl)benzonitrile"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C18 H21 N5 O2"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        Alogliptin
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2009-02-03
_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                       339.392
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    T22
_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       3G0B
_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
T22  O26   O26   O  0  1  N  N  N  41.263  33.852  11.770  -2.675  -0.987   1.174  O26   T22   1  
T22  C25   C25   C  0  1  N  N  N  42.084  33.401  12.602  -1.694  -1.348   0.553  C25   T22   2  
T22  N2    N2    N  0  1  N  N  N  42.564  32.142  12.429  -1.741  -2.493  -0.151  N2    T22   3  
T22  C1    C1    C  0  1  N  N  N  42.092  31.354  11.271  -2.970  -3.291  -0.161  C1    T22   4  
T22  N15   N15   N  0  1  N  N  N  42.467  34.161  13.653  -0.581  -0.593   0.575  N15   T22   5  
T22  C16   C16   C  0  1  N  N  N  41.910  35.534  13.785  -0.561   0.653   1.346  C16   T22   6  
T22  C17   C17   C  0  1  Y  N  N  40.389  35.600  13.945  -0.809   1.819   0.423  C17   T22   7  
T22  C22   C22   C  0  1  Y  N  N  39.662  34.805  14.864  -2.115   2.169   0.074  C22   T22   8  
T22  C23   C23   C  0  1  N  N  N  40.228  33.929  15.651  -3.223   1.423   0.591  C23   T22   9  
T22  N24   N24   N  0  1  N  N  N  40.724  33.151  16.376  -4.101   0.831   1.002  N24   T22  10  
T22  C21   C21   C  0  1  Y  N  N  38.265  34.948  14.932  -2.336   3.250  -0.781  C21   T22  11  
T22  C20   C20   C  0  1  Y  N  N  37.593  35.873  14.115  -1.264   3.965  -1.276  C20   T22  12  
T22  C19   C19   C  0  1  Y  N  N  38.318  36.680  13.231   0.027   3.612  -0.926  C19   T22  13  
T22  C18   C18   C  0  1  Y  N  N  39.705  36.526  13.154   0.253   2.545  -0.074  C18   T22  14  
T22  C6    C6    C  0  1  N  N  N  43.372  33.658  14.552   0.538  -0.984  -0.120  C6    T22  15  
T22  C5    C5    C  0  1  N  N  N  43.872  32.359  14.396   0.510  -2.148  -0.837  C5    T22  16  
T22  C3    C3    C  0  1  N  N  N  43.446  31.620  13.311  -0.666  -2.913  -0.848  C3    T22  17  
T22  O4    O4    O  0  1  N  N  N  43.910  30.473  13.181  -0.716  -3.952  -1.484  O4    T22  18  
T22  N7    N7    N  0  1  N  N  N  43.991  34.411  15.581   1.672  -0.213  -0.096  N7    T22  19  
T22  C14   C14   C  0  1  N  N  N  44.077  33.892  16.969   2.465  -0.086   1.134  C14   T22  20  
T22  C11   C11   C  0  1  N  N  R  44.045  34.972  18.063   3.919  -0.452   0.823  C11   T22  21  
T22  N13   N13   N  0  1  N  N  N  42.672  35.500  18.280   4.751  -0.207   2.009  N13   T22  22  
T22  C10   C10   C  0  1  N  N  N  45.000  36.108  17.730   4.421   0.407  -0.339  C10   T22  23  
T22  C9    C9    C  0  1  N  N  N  44.753  36.657  16.331   3.576   0.128  -1.584  C9    T22  24  
T22  C8    C8    C  0  1  N  N  N  44.820  35.582  15.268   2.120   0.497  -1.302  C8    T22  25  
T22  H1    H1    H  0  1  N  N  N  41.975  32.015  10.400  -3.605  -2.970  -0.986  H1    T22  26  
T22  H1A   H1A   H  0  1  N  N  N  42.826  30.569  11.038  -2.718  -4.344  -0.284  H1A   T22  27  
T22  H1B   H1B   H  0  1  N  N  N  41.124  30.891  11.513  -3.500  -3.152   0.782  H1B   T22  28  
T22  H16   H16   H  0  1  N  N  N  42.360  35.993  14.677  -1.339   0.621   2.108  H16   T22  29  
T22  H16A  H16A  H  0  0  N  N  N  42.148  36.058  12.848   0.412   0.769   1.824  H16A  T22  30  
T22  H21   H21   H  0  1  N  N  N  37.700  34.338  15.622  -3.343   3.526  -1.056  H21   T22  31  
T22  H20   H20   H  0  1  N  N  N  36.518  35.961  14.169  -1.434   4.801  -1.938  H20   T22  32  
T22  H19   H19   H  0  1  N  N  N  37.813  37.411  12.617   0.862   4.174  -1.316  H19   T22  33  
T22  H18   H18   H  0  1  N  N  N  40.264  37.140  12.463   1.263   2.278   0.199  H18   T22  34  
T22  H5    H5    H  0  1  N  N  N  44.573  31.946  15.106   1.379  -2.471  -1.390  H5    T22  35  
T22  H14   H14   H  0  1  N  N  N  43.218  33.225  17.131   2.416   0.942   1.496  H14   T22  36  
T22  H14A  H14A  H  0  0  N  N  N  45.051  33.388  17.055   2.072  -0.762   1.894  H14A  T22  37  
T22  H11   H11   H  0  1  N  N  N  44.373  34.495  18.999   3.978  -1.506   0.550  H11   T22  38  
T22  HN13  HN13  H  0  0  N  N  N  42.511  35.619  19.260   5.715  -0.441   1.829  HN13  T22  39  
T22  HN1A  HN1A  H  0  0  N  N  N  42.577  36.382  17.818   4.663   0.749   2.321  HN1A  T22  40  
T22  H10   H10   H  0  1  N  N  N  44.853  36.919  18.459   4.338   1.461  -0.073  H10   T22  41  
T22  H10A  H10A  H  0  0  N  N  N  46.028  35.718  17.771   5.463   0.165  -0.546  H10A  T22  42  
T22  H9    H9    H  0  1  N  N  N  43.751  37.110  16.306   3.948   0.723  -2.418  H9    T22  43  
T22  H9A   H9A   H  0  1  N  N  N  45.541  37.394  16.115   3.638  -0.931  -1.836  H9A   T22  44  
T22  H8    H8    H  0  1  N  N  N  45.865  35.251  15.177   1.500   0.205  -2.150  H8    T22  45  
T22  H8A   H8A   H  0  1  N  N  N  44.437  36.017  14.333   2.043   1.572  -1.143  H8A   T22  46  
#   #
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
T22  O26  C25   DOUB  N  N   1  
T22  N2   C25   SING  N  N   2  
T22  C25  N15   SING  N  N   3  
T22  C1   N2    SING  N  N   4  
T22  N2   C3    SING  N  N   5  
T22  C1   H1    SING  N  N   6  
T22  C1   H1A   SING  N  N   7  
T22  C1   H1B   SING  N  N   8  
T22  N15  C16   SING  N  N   9  
T22  N15  C6    SING  N  N  10  
T22  C16  C17   SING  N  N  11  
T22  C16  H16   SING  N  N  12  
T22  C16  H16A  SING  N  N  13  
T22  C18  C17   DOUB  Y  N  14  
T22  C17  C22   SING  Y  N  15  
T22  C22  C21   DOUB  Y  N  16  
T22  C22  C23   SING  N  N  17  
T22  C23  N24   TRIP  N  N  18  
T22  C20  C21   SING  Y  N  19  
T22  C21  H21   SING  N  N  20  
T22  C19  C20   DOUB  Y  N  21  
T22  C20  H20   SING  N  N  22  
T22  C18  C19   SING  Y  N  23  
T22  C19  H19   SING  N  N  24  
T22  C18  H18   SING  N  N  25  
T22  C5   C6    DOUB  N  N  26  
T22  C6   N7    SING  N  N  27  
T22  C3   C5    SING  N  N  28  
T22  C5   H5    SING  N  N  29  
T22  O4   C3    DOUB  N  N  30  
T22  C8   N7    SING  N  N  31  
T22  N7   C14   SING  N  N  32  
T22  C14  C11   SING  N  N  33  
T22  C14  H14   SING  N  N  34  
T22  C14  H14A  SING  N  N  35  
T22  C10  C11   SING  N  N  36  
T22  C11  N13   SING  N  N  37  
T22  C11  H11   SING  N  N  38  
T22  N13  HN13  SING  N  N  39  
T22  N13  HN1A  SING  N  N  40  
T22  C9   C10   SING  N  N  41  
T22  C10  H10   SING  N  N  42  
T22  C10  H10A  SING  N  N  43  
T22  C8   C9    SING  N  N  44  
T22  C9   H9    SING  N  N  45  
T22  C9   H9A   SING  N  N  46  
T22  C8   H8    SING  N  N  47  
T22  C8   H8A   SING  N  N  48  
#   #
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
T22  SMILES            ACDLabs               10.04  "N#Cc1ccccc1CN2C(=O)N(C(=O)C=C2N3CCCC(N)C3)C"  
T22  SMILES_CANONICAL  CACTVS                3.341  "CN1C(=O)C=C(N2CCC[C@@H](N)C2)N(Cc3ccccc3C#N)C1=O"  
T22  SMILES            CACTVS                3.341  "CN1C(=O)C=C(N2CCC[CH](N)C2)N(Cc3ccccc3C#N)C1=O"  
T22  SMILES_CANONICAL  "OpenEye OEToolkits"  1.5.0  "CN1C(=O)C=C(N(C1=O)Cc2ccccc2C#N)N3CCC[C@H](C3)N"  
T22  SMILES            "OpenEye OEToolkits"  1.5.0  "CN1C(=O)C=C(N(C1=O)Cc2ccccc2C#N)N3CCCC(C3)N"  
T22  InChI             InChI                 1.03   "InChI=1S/C18H21N5O2/c1-21-17(24)9-16(22-8-4-7-15(20)12-22)23(18(21)25)11-14-6-3-2-5-13(14)10-19/h2-3,5-6,9,15H,4,7-8,11-12,20H2,1H3/t15-/m1/s1"  
T22  InChIKey          InChI                 1.03   ZSBOMTDTBDDKMP-OAHLLOKOSA-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
T22  "SYSTEMATIC NAME"  ACDLabs               10.04  "2-({6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl}methyl)benzonitrile"  
T22  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.5.0  "2-[[6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-pyrimidin-1-yl]methyl]benzonitrile"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
T22  "Create component"      2009-02-03  RCSB  
T22  "Modify aromatic_flag"  2011-06-04  RCSB  
T22  "Modify descriptor"     2011-06-04  RCSB  
T22  "Modify synonyms"       2016-03-28  RCSB  
T22  "Modify synonyms"       2021-03-01  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     T22
_pdbx_chem_comp_synonyms.name        Alogliptin
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
