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                    2008-10-14 
_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 InChI            InChI                1.02b 
InChI=1/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/f/h30,32,36H 
F89 InChIKey         InChI                1.02b BRVFNEZMTRVUGW-NNSDDZCYDQ 
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 
# 
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"                       
# 
