data_F89
#

_chem_comp.id                                   F89
_chem_comp.name                                 "S)-2-(5(((1,2-DIHYDRO-3-METHYL-1-OXOBENZO(F)QUINAZOLIN-9-YL)METHYL)AMINO)1-OXO-2-ISOINDOLINYL)GLUTARIC ACID"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C27 H24 N4 O6"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "FOLATE ANALOG 1843U89"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    1999-07-08
_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                        U18
_chem_comp.formula_weight                       500.503
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    F89
_chem_comp.pdbx_model_coordinates_details       ?
_chem_comp.pdbx_model_coordinates_missing_flag  N
_chem_comp.pdbx_ideal_coordinates_details       ?
_chem_comp.pdbx_ideal_coordinates_missing_flag  N
_chem_comp.pdbx_model_coordinates_db_code       1SYN
_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
F89  C1    C1    C  0  1  Y  N  N  46.857  37.044  24.079   1.766  -0.399   5.729  C1    F89   1  
F89  O1A   O1A   O  0  1  N  N  N  46.039  37.671  24.746   1.966  -0.832   4.608  O1A   F89   2  
F89  N2    N2    N  0  1  Y  N  N  47.946  36.568  24.713   2.774  -0.276   6.625  N2    F89   3  
F89  C3    C3    C  0  1  Y  N  N  48.750  35.643  24.158   2.528   0.203   7.871  C3    F89   4  
F89  C3M   C3M   C  0  1  N  N  N  49.908  35.097  24.911   3.681   0.314   8.835  C3M   F89   5  
F89  N4    N4    N  0  1  Y  N  N  48.497  35.198  22.919   1.350   0.576   8.272  N4    F89   6  
F89  C4A   C4A   C  0  1  Y  N  N  47.488  35.708  22.193   0.270   0.506   7.466  C4A   F89   7  
F89  C5    C5    C  0  1  Y  N  N  47.225  35.191  20.921  -1.001   0.913   7.908  C5    F89   8  
F89  C6    C6    C  0  1  Y  N  N  46.690  36.076  19.988  -2.084   0.843   7.100  C6    F89   9  
F89  C6A   C6A   C  0  1  Y  N  N  45.718  36.960  20.455  -1.985   0.359   5.779  C6A   F89  10  
F89  C7    C7    C  0  1  Y  N  N  44.734  37.412  19.574  -3.111   0.288   4.945  C7    F89  11  
F89  C8    C8    C  0  1  Y  N  N  43.770  38.317  20.014  -2.983  -0.184   3.673  C8    F89  12  
F89  C9    C9    C  0  1  Y  N  N  43.834  38.845  21.312  -1.748  -0.599   3.186  C9    F89  13  
F89  C10   C10   C  0  1  Y  N  N  44.841  38.404  22.201  -0.632  -0.543   3.969  C10   F89  14  
F89  C1B   C1B   C  0  1  Y  N  N  45.750  37.388  21.814  -0.728  -0.063   5.279  C1B   F89  15  
F89  C1A   C1A   C  0  1  Y  N  N  46.674  36.752  22.705   0.431   0.015   6.157  C1A   F89  16  
F89  C11   C11   C  0  1  N  N  N  42.854  39.874  21.718  -1.641  -1.117   1.775  C11   F89  17  
F89  N12   N12   N  0  1  N  N  N  42.669  40.916  20.714  -1.354  -0.004   0.866  N12   F89  18  
F89  C13   C13   C  0  1  Y  N  N  43.552  42.069  20.638  -1.210  -0.238  -0.496  C13   F89  19  
F89  C14   C14   C  0  1  Y  N  N  44.883  41.973  21.079  -0.943   0.820  -1.360  C14   F89  20  
F89  C15   C15   C  0  1  Y  N  N  45.696  43.108  21.037  -0.797   0.586  -2.705  C15   F89  21  
F89  C16   C16   C  0  1  Y  N  N  45.235  44.320  20.542  -0.926  -0.709  -3.216  C16   F89  22  
F89  C17   C17   C  0  1  Y  N  N  43.919  44.438  20.068  -1.199  -1.768  -2.345  C17   F89  23  
F89  C18   C18   C  0  1  Y  N  N  43.080  43.296  20.123  -1.340  -1.531  -0.997  C18   F89  24  
F89  C19   C19   C  0  1  N  N  N  47.071  43.318  21.460  -0.508   1.482  -3.883  C19   F89  25  
F89  C     C     C  0  1  N  N  N  46.304  45.310  20.650  -0.727  -0.651  -4.674  C     F89  26  
F89  O     O     O  0  1  N  N  N  46.227  46.505  20.318  -0.774  -1.611  -5.419  O     F89  27  
F89  N     N     N  0  1  N  N  N  47.367  44.714  21.211  -0.485   0.611  -5.064  N     F89  28  
F89  CA    CA    C  0  1  N  N  S  48.748  45.182  21.235  -0.240   1.047  -6.441  CA    F89  29  
F89  CT    CT    C  0  1  N  N  N  48.946  46.303  22.275  -1.434   0.708  -7.295  CT    F89  30  
F89  O1    O1    O  0  1  N  N  N  49.669  47.273  22.051  -1.709   1.396  -8.250  O1    F89  31  
F89  O2    O2    O  0  1  N  N  N  48.386  46.202  23.362  -2.193  -0.357  -6.996  O2    F89  32  
F89  CB    CB    C  0  1  N  N  N  49.151  45.624  19.800   0.997   0.333  -6.988  CB    F89  33  
F89  CG    CG    C  0  1  N  N  N  49.181  44.502  18.760   2.209   0.677  -6.121  CG    F89  34  
F89  CD    CD    C  0  1  N  N  N  50.334  43.506  18.820   3.428  -0.025  -6.661  CD    F89  35  
F89  OE1   OE1   O  0  1  N  N  N  50.629  42.933  19.867   3.337  -0.728  -7.639  OE1   F89  36  
F89  OE2   OE2   O  0  1  N  N  N  50.910  43.239  17.767   4.616   0.130  -6.055  OE2   F89  37  
F89  HN2   HN2   H  0  1  N  N  N  48.169  36.919  25.644   3.674  -0.540   6.379  HN2   F89  38  
F89  H3M1  1H3M  H  0  0  N  N  N  50.574  34.330  24.451   3.324   0.717   9.783  H3M1  F89  39  
F89  H3M2  2H3M  H  0  0  N  N  N  50.540  35.952  25.246   4.113  -0.672   9.000  H3M2  F89  40  
F89  H3M3  3H3M  H  0  0  N  N  N  49.534  34.696  25.882   4.439   0.978   8.420  H3M3  F89  41  
F89  H5    H5    H  0  1  N  N  N  47.429  34.137  20.666  -1.115   1.289   8.914  H5    F89  42  
F89  H6    H6    H  0  1  N  N  N  47.018  36.076  18.935  -3.045   1.164   7.474  H6    F89  43  
F89  H7    H7    H  0  1  N  N  N  44.718  37.054  18.530  -4.077   0.606   5.310  H7    F89  44  
F89  H8    H8    H  0  1  N  N  N  42.954  38.615  19.333  -3.852  -0.237   3.035  H8    F89  45  
F89  H10   H10   H  0  1  N  N  N  44.918  38.856  23.204   0.320  -0.868   3.579  H10   F89  46  
F89  H111  1H11  H  0  0  N  N  N  41.878  39.407  21.991  -0.837  -1.850   1.717  H111  F89  47  
F89  H112  2H11  H  0  0  N  N  N  43.127  40.316  22.704  -2.582  -1.587   1.488  H112  F89  48  
F89  HN12  2HN1  H  0  0  N  N  N  41.711  41.259  20.792  -1.264   0.895   1.216  HN12  F89  49  
F89  H14   H14   H  0  1  N  N  N  45.285  41.016  21.454  -0.842   1.823  -0.972  H14   F89  50  
F89  H17   H17   H  0  1  N  N  N  43.555  45.398  19.664  -1.300  -2.772  -2.730  H17   F89  51  
F89  H18   H18   H  0  1  N  N  N  42.041  43.363  19.758  -1.551  -2.350  -0.326  H18   F89  52  
F89  H191  1H19  H  0  0  N  N  N  47.261  43.006  22.513  -1.293   2.232  -3.986  H191  F89  53  
F89  H192  2H19  H  0  0  N  N  N  47.793  42.619  20.976   0.459   1.967  -3.757  H192  F89  54  
F89  HA    HA    H  0  1  N  N  N  49.420  44.351  21.553  -0.075   2.124  -6.457  HA    F89  55  
F89  HO2   HO2   H  0  1  N  N  N  48.508  46.892  24.002  -2.959  -0.575  -7.544  HO2   F89  56  
F89  HB1   1HB   H  0  1  N  N  N  48.489  46.452  19.453   0.832  -0.743  -6.972  HB1   F89  57  
F89  HB2   2HB   H  0  1  N  N  N  50.131  46.153  19.822   1.179   0.657  -8.013  HB2   F89  58  
F89  HG1   1HG   H  0  1  N  N  N  48.214  43.946  18.792   2.374   1.755  -6.138  HG1   F89  59  
F89  HG2   2HG   H  0  1  N  N  N  49.134  44.947  17.738   2.027   0.353  -5.097  HG2   F89  60  
F89  HOE2  2HOE  H  0  0  N  N  N  51.628  42.618  17.804   5.398  -0.320  -6.401  HOE2  F89  61  
#   #
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
F89  C1   O1A   DOUB  N  N   1  
F89  C1   N2    SING  Y  N   2  
F89  C1   C1A   SING  Y  N   3  
F89  N2   C3    SING  Y  N   4  
F89  N2   HN2   SING  N  N   5  
F89  C3   C3M   SING  N  N   6  
F89  C3   N4    DOUB  Y  N   7  
F89  C3M  H3M1  SING  N  N   8  
F89  C3M  H3M2  SING  N  N   9  
F89  C3M  H3M3  SING  N  N  10  
F89  N4   C4A   SING  Y  N  11  
F89  C4A  C5    DOUB  Y  N  12  
F89  C4A  C1A   SING  Y  N  13  
F89  C5   C6    SING  Y  N  14  
F89  C5   H5    SING  N  N  15  
F89  C6   C6A   DOUB  Y  N  16  
F89  C6   H6    SING  N  N  17  
F89  C6A  C7    SING  Y  N  18  
F89  C6A  C1B   SING  Y  N  19  
F89  C7   C8    DOUB  Y  N  20  
F89  C7   H7    SING  N  N  21  
F89  C8   C9    SING  Y  N  22  
F89  C8   H8    SING  N  N  23  
F89  C9   C10   DOUB  Y  N  24  
F89  C9   C11   SING  N  N  25  
F89  C10  C1B   SING  Y  N  26  
F89  C10  H10   SING  N  N  27  
F89  C1B  C1A   DOUB  Y  N  28  
F89  C11  N12   SING  N  N  29  
F89  C11  H111  SING  N  N  30  
F89  C11  H112  SING  N  N  31  
F89  N12  C13   SING  N  N  32  
F89  N12  HN12  SING  N  N  33  
F89  C13  C14   DOUB  Y  N  34  
F89  C13  C18   SING  Y  N  35  
F89  C14  C15   SING  Y  N  36  
F89  C14  H14   SING  N  N  37  
F89  C15  C16   DOUB  Y  N  38  
F89  C15  C19   SING  N  N  39  
F89  C16  C17   SING  Y  N  40  
F89  C16  C     SING  N  N  41  
F89  C17  C18   DOUB  Y  N  42  
F89  C17  H17   SING  N  N  43  
F89  C18  H18   SING  N  N  44  
F89  C19  N     SING  N  N  45  
F89  C19  H191  SING  N  N  46  
F89  C19  H192  SING  N  N  47  
F89  C    O     DOUB  N  N  48  
F89  C    N     SING  N  N  49  
F89  N    CA    SING  N  N  50  
F89  CA   CT    SING  N  N  51  
F89  CA   CB    SING  N  N  52  
F89  CA   HA    SING  N  N  53  
F89  CT   O1    DOUB  N  N  54  
F89  CT   O2    SING  N  N  55  
F89  O2   HO2   SING  N  N  56  
F89  CB   CG    SING  N  N  57  
F89  CB   HB1   SING  N  N  58  
F89  CB   HB2   SING  N  N  59  
F89  CG   CD    SING  N  N  60  
F89  CG   HG1   SING  N  N  61  
F89  CG   HG2   SING  N  N  62  
F89  CD   OE1   DOUB  N  N  63  
F89  CD   OE2   SING  N  N  64  
F89  OE2  HOE2  SING  N  N  65  
#   #
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
F89  SMILES            ACDLabs               10.04  "O=C(O)C(N5C(=O)c1c(cc(cc1)NCc4cc3c(ccc2N=C(NC(=O)c23)C)cc4)C5)CCC(=O)O"  
F89  SMILES_CANONICAL  CACTVS                3.341  "CC1=Nc2ccc3ccc(CNc4ccc5c(CN([C@@H](CCC(O)=O)C(O)=O)C5=O)c4)cc3c2C(=O)N1"  
F89  SMILES            CACTVS                3.341  "CC1=Nc2ccc3ccc(CNc4ccc5c(CN([CH](CCC(O)=O)C(O)=O)C5=O)c4)cc3c2C(=O)N1"  
F89  SMILES_CANONICAL  "OpenEye OEToolkits"  1.5.0  "CC1=Nc2ccc3ccc(cc3c2C(=O)N1)CNc4ccc5c(c4)CN(C5=O)[C@@H](CCC(=O)O)C(=O)O"  
F89  SMILES            "OpenEye OEToolkits"  1.5.0  "CC1=Nc2ccc3ccc(cc3c2C(=O)N1)CNc4ccc5c(c4)CN(C5=O)C(CCC(=O)O)C(=O)O"  
F89  InChI             InChI                 1.03   "InChI=1S/C27H24N4O6/c1-14-29-21-7-4-16-3-2-15(10-20(16)24(21)25(34)30-14)12-28-18-5-6-19-17(11-18)13-31(26(19)35)22(27(36)37)8-9-23(32)33/h2-7,10-11,22,28H,8-9,12-13H2,1H3,(H,32,33)(H,36,37)(H,29,30,34)/t22-/m0/s1"  
F89  InChIKey          InChI                 1.03   BRVFNEZMTRVUGW-QFIPXVFZSA-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
F89  "SYSTEMATIC NAME"  ACDLabs               10.04  "(2S)-2-(5-{[(3-methyl-1-oxo-1,2-dihydrobenzo[f]quinazolin-9-yl)methyl]amino}-1-oxo-1,3-dihydro-2H-isoindol-2-yl)pentanedioic acid"  
F89  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.5.0  "(2S)-2-[6-[(3-methyl-1-oxo-2H-benzo[f]quinazolin-9-yl)methylamino]-3-oxo-1H-isoindol-2-yl]pentanedioic acid"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
F89  "Create component"   1999-07-08  RCSB  
F89  "Modify descriptor"  2011-06-04  RCSB  
F89  "Modify synonyms"    2021-03-01  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     F89
_pdbx_chem_comp_synonyms.name        "FOLATE ANALOG 1843U89"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
