data_F20
# 
_chem_comp.id                                    F20 
_chem_comp.name                                  N-BENZOYL-L-PHENYLALANYL-4-[(5S)-1,1-DIOXIDO-3-OXOISOTHIAZOLIDIN-5-YL]-L-PHENYLALANINAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C28 H28 N4 O6 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "ISOTHIAZOLIDINONE ANALOG" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-05-04 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        548.610 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     F20 
_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        2CMA 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
F20 C1   C1   C 0 1 N N S 16.779 -1.193  -0.446  -4.549 -1.560 0.923  C1   F20 1  
F20 C2   C2   C 0 1 N N N 17.550 -1.689  0.740   -4.378 -2.587 -0.227 C2   F20 2  
F20 C3   C3   C 0 1 N N N 16.993 -1.062  1.988   -5.542 -2.456 -1.163 C3   F20 3  
F20 N4   N4   N 0 1 N N N 15.728 -0.642  1.878   -6.655 -1.852 -0.719 N4   F20 4  
F20 S5   S5   S 0 1 N N N 15.141 -1.013  0.198   -6.375 -1.346 0.854  S5   F20 5  
F20 O6   O6   O 0 1 N N N 14.336 0.151   -0.656  -7.057 -2.315 1.637  O6   F20 6  
F20 O7   O7   O 0 1 N N N 14.466 -2.567  0.163   -6.752 0.024  0.830  O7   F20 7  
F20 O9   O9   O 0 1 N N N 17.616 -0.928  3.046   -5.480 -2.888 -2.295 O9   F20 8  
F20 C11  C11  C 0 1 Y N N 16.813 -2.072  -1.690  -3.831 -0.270 0.623  C11  F20 9  
F20 C12  C12  C 0 1 Y N N 16.963 -3.522  -1.567  -2.894 0.223  1.512  C12  F20 10 
F20 C13  C13  C 0 1 Y N N 16.993 -4.351  -2.773  -2.235 1.406  1.236  C13  F20 11 
F20 C14  C14  C 0 1 Y N N 16.875 -3.721  -4.098  -2.511 2.096  0.070  C14  F20 12 
F20 C15  C15  C 0 1 Y N N 16.736 -2.279  -4.214  -3.451 1.605  -0.817 C15  F20 13 
F20 C16  C16  C 0 1 Y N N 16.705 -1.451  -3.014  -4.107 0.420  -0.543 C16  F20 14 
F20 C21  C21  C 0 1 N N N 16.898 -4.575  -5.347  -1.791 3.385  -0.231 C21  F20 15 
F20 C22  C22  C 0 1 N N S 18.177 -4.405  -6.164  -0.512 3.085  -1.014 C22  F20 16 
F20 C25  C25  C 0 1 N N N 19.362 -4.987  -5.422  0.144  4.379  -1.421 C25  F20 17 
F20 O26  O26  O 0 1 N N N 20.170 -4.283  -4.859  1.268  4.634  -1.044 O26  F20 18 
F20 N27  N27  N 0 1 N N N 19.502 -6.310  -5.416  -0.519 5.253  -2.204 N27  F20 19 
F20 N45  N45  N 0 1 N N N 18.011 -5.128  -7.427  0.407  2.316  -0.171 N45  F20 20 
F20 C47  C47  C 0 1 N N N 18.581 -4.583  -8.490  1.334  1.518  -0.738 C47  F20 21 
F20 C48  C48  C 0 1 N N S 18.416 -5.301  -9.815  2.280  0.728  0.129  C48  F20 22 
F20 O49  O49  O 0 1 N N N 19.193 -3.528  -8.389  1.407  1.437  -1.945 O49  F20 23 
F20 N51  N51  N 0 1 N N N 18.671 -4.401  -10.947 3.183  -0.054 -0.719 N51  F20 24 
F20 C4   C4   C 0 1 N N N 19.387 -6.471  -9.904  3.098  1.686  0.998  C4   F20 25 
F20 C5   C5   C 0 1 Y N N 19.054 -7.434  -11.012 3.954  0.893  1.951  C5   F20 26 
F20 C30  C30  C 0 1 Y N N 18.255 -8.633  -10.722 5.229  0.509  1.579  C30  F20 27 
F20 C31  C31  C 0 1 Y N N 17.933 -9.576  -11.798 6.014  -0.218 2.454  C31  F20 28 
F20 C6   C6   C 0 1 Y N N 18.414 -9.320  -13.160 5.525  -0.562 3.700  C6   F20 29 
F20 C33  C33  C 0 1 Y N N 19.208 -8.114  -13.454 4.251  -0.177 4.072  C33  F20 30 
F20 C34  C34  C 0 1 Y N N 19.529 -7.175  -12.380 3.467  0.554  3.200  C34  F20 31 
F20 C67  C67  C 0 1 N N N 17.520 -4.150  -11.567 3.752  -1.178 -0.241 C67  F20 32 
F20 O70  O70  O 0 1 N N N 16.473 -4.644  -11.139 3.516  -1.544 0.894  O70  F20 33 
F20 C71  C71  C 0 1 Y N N 17.492 -3.257  -12.797 4.663  -1.967 -1.098 C71  F20 34 
F20 C74  C74  C 0 1 Y N N 16.328 -2.394  -13.048 5.254  -3.132 -0.606 C74  F20 35 
F20 C75  C75  C 0 1 Y N N 16.323 -1.488  -14.204 6.103  -3.864 -1.410 C75  F20 36 
F20 C76  C76  C 0 1 Y N N 17.478 -1.453  -15.113 6.369  -3.445 -2.702 C76  F20 37 
F20 C77  C77  C 0 1 Y N N 18.625 -2.345  -14.885 5.787  -2.291 -3.195 C77  F20 38 
F20 C78  C78  C 0 1 Y N N 18.627 -3.255  -13.732 4.931  -1.553 -2.403 C78  F20 39 
F20 H1   H1   H 0 1 N N N 17.226 -0.267  -0.835  -4.232 -1.976 1.880  H1   F20 40 
F20 H2C1 1H2C H 0 0 N N N 18.610 -1.418  0.631   -3.452 -2.385 -0.765 H2C1 F20 41 
F20 H2C2 2H2C H 0 0 N N N 17.461 -2.783  0.806   -4.349 -3.596 0.183  H2C2 F20 42 
F20 H4   H4   H 0 1 N N N 15.195 -0.199  2.599   -7.476 -1.730 -1.220 H4   F20 43 
F20 H12  H12  H 0 1 N N N 17.051 -3.978  -0.592  -2.678 -0.316 2.423  H12  F20 44 
F20 H13  H13  H 0 1 N N N 17.101 -5.422  -2.691  -1.503 1.792  1.931  H13  F20 45 
F20 H15  H15  H 0 1 N N N 16.656 -1.821  -5.189  -3.667 2.144  -1.727 H15  F20 46 
F20 H16  H16  H 0 1 N N N 16.602 -0.379  -3.100  -4.838 0.035  -1.238 H16  F20 47 
F20 H211 1H21 H 0 0 N N N 16.057 -4.257  -5.980  -1.537 3.886  0.703  H211 F20 48 
F20 H212 2H21 H 0 0 N N N 16.818 -5.630  -5.046  -2.437 4.032  -0.825 H212 F20 49 
F20 H22  H22  H 0 1 N N N 18.359 -3.335  -6.340  -0.758 2.506  -1.904 H22  F20 50 
F20 H271 1H27 H 0 0 N N N 20.245 -6.804  -4.964  -0.097 6.086  -2.466 H271 F20 51 
F20 H272 2H27 H 0 0 N N N 18.758 -6.740  -5.927  -1.417 5.047  -2.509 H272 F20 52 
F20 H45  H45  H 0 1 N N N 17.497 -5.984  -7.483  0.349  2.381  0.795  H45  F20 53 
F20 H48  H48  H 0 1 N N N 17.378 -5.660  -9.865  1.709  0.055  0.769  H48  F20 54 
F20 H51  H51  H 0 1 N N N 19.564 -4.036  -11.210 3.371  0.238  -1.625 H51  F20 55 
F20 H4C1 1H4C H 0 0 N N N 19.323 -7.025  -8.956  3.735  2.299  0.361  H4C1 F20 56 
F20 H4C2 2H4C H 0 0 N N N 20.395 -6.069  -10.088 2.423  2.328  1.564  H4C2 F20 57 
F20 H30  H30  H 0 1 N N N 17.905 -8.819  -9.717  5.611  0.777  0.606  H30  F20 58 
F20 H31  H31  H 0 1 N N N 17.344 -10.456 -11.588 7.010  -0.519 2.163  H31  F20 59 
F20 H6   H6   H 0 1 N N N 18.185 -10.019 -13.951 6.139  -1.131 4.383  H6   F20 60 
F20 H33  H33  H 0 1 N N N 19.552 -7.924  -14.460 3.868  -0.446 5.046  H33  F20 61 
F20 H34  H34  H 0 1 N N N 20.114 -6.292  -12.591 2.471  0.854  3.490  H34  F20 62 
F20 H74  H74  H 0 1 N N N 15.478 -2.426  -12.383 5.047  -3.460 0.402  H74  F20 63 
F20 H75  H75  H 0 1 N N N 15.472 -0.848  -14.386 6.561  -4.765 -1.031 H75  F20 64 
F20 H76  H76  H 0 1 N N N 17.484 -0.771  -15.950 7.035  -4.021 -3.327 H76  F20 65 
F20 H77  H77  H 0 1 N N N 19.464 -2.331  -15.564 5.999  -1.969 -4.204 H77  F20 66 
F20 H78  H78  H 0 1 N N N 19.461 -3.922  -13.571 4.477  -0.653 -2.790 H78  F20 67 
# 
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 
F20 C1  C2   SING N N 1  
F20 C1  S5   SING N N 2  
F20 C1  C11  SING N N 3  
F20 C1  H1   SING N N 4  
F20 C2  C3   SING N N 5  
F20 C2  H2C1 SING N N 6  
F20 C2  H2C2 SING N N 7  
F20 C3  N4   SING N N 8  
F20 C3  O9   DOUB N N 9  
F20 N4  S5   SING N N 10 
F20 N4  H4   SING N N 11 
F20 S5  O6   DOUB N N 12 
F20 S5  O7   DOUB N N 13 
F20 C11 C12  DOUB Y N 14 
F20 C11 C16  SING Y N 15 
F20 C12 C13  SING Y N 16 
F20 C12 H12  SING N N 17 
F20 C13 C14  DOUB Y N 18 
F20 C13 H13  SING N N 19 
F20 C14 C15  SING Y N 20 
F20 C14 C21  SING N N 21 
F20 C15 C16  DOUB Y N 22 
F20 C15 H15  SING N N 23 
F20 C16 H16  SING N N 24 
F20 C21 C22  SING N N 25 
F20 C21 H211 SING N N 26 
F20 C21 H212 SING N N 27 
F20 C22 C25  SING N N 28 
F20 C22 N45  SING N N 29 
F20 C22 H22  SING N N 30 
F20 C25 O26  DOUB N N 31 
F20 C25 N27  SING N N 32 
F20 N27 H271 SING N N 33 
F20 N27 H272 SING N N 34 
F20 N45 C47  SING N N 35 
F20 N45 H45  SING N N 36 
F20 C47 C48  SING N N 37 
F20 C47 O49  DOUB N N 38 
F20 C48 N51  SING N N 39 
F20 C48 C4   SING N N 40 
F20 C48 H48  SING N N 41 
F20 N51 C67  SING N N 42 
F20 N51 H51  SING N N 43 
F20 C4  C5   SING N N 44 
F20 C4  H4C1 SING N N 45 
F20 C4  H4C2 SING N N 46 
F20 C5  C30  DOUB Y N 47 
F20 C5  C34  SING Y N 48 
F20 C30 C31  SING Y N 49 
F20 C30 H30  SING N N 50 
F20 C31 C6   DOUB Y N 51 
F20 C31 H31  SING N N 52 
F20 C6  C33  SING Y N 53 
F20 C6  H6   SING N N 54 
F20 C33 C34  DOUB Y N 55 
F20 C33 H33  SING N N 56 
F20 C34 H34  SING N N 57 
F20 C67 O70  DOUB N N 58 
F20 C67 C71  SING N N 59 
F20 C71 C74  DOUB Y N 60 
F20 C71 C78  SING Y N 61 
F20 C74 C75  SING Y N 62 
F20 C74 H74  SING N N 63 
F20 C75 C76  DOUB Y N 64 
F20 C75 H75  SING N N 65 
F20 C76 C77  SING Y N 66 
F20 C76 H76  SING N N 67 
F20 C77 C78  DOUB Y N 68 
F20 C77 H77  SING N N 69 
F20 C78 H78  SING N N 70 
# 
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 
F20 SMILES           ACDLabs              10.04 O=C4NS(=O)(=O)C(c1ccc(cc1)CC(C(=O)N)NC(=O)C(NC(=O)c2ccccc2)Cc3ccccc3)C4 
F20 InChI            InChI                1.02b 
InChI=1/C28H28N4O6S/c29-26(34)22(15-19-11-13-20(14-12-19)24-17-25(33)32-39(24,37)38)30-28(36)23(16-18-7-3-1-4-8-18)31-27(35)21-9-5-2-6-10-21/h1-14,22-24H,15-17H2,(H2,29,34)(H,30,36)(H,31,35)(H,32,33)/t22-,23-,24-/m0/s1/f/h30-32H,29H2 
F20 InChIKey         InChI                1.02b ZSFPNCCMRAHJSA-XZELGKBUDP 
F20 SMILES_CANONICAL CACTVS               3.341 NC(=O)[C@H](Cc1ccc(cc1)[C@@H]2CC(=O)N[S]2(=O)=O)NC(=O)[C@H](Cc3ccccc3)NC(=O)c4ccccc4 
F20 SMILES           CACTVS               3.341 NC(=O)[CH](Cc1ccc(cc1)[CH]2CC(=O)N[S]2(=O)=O)NC(=O)[CH](Cc3ccccc3)NC(=O)c4ccccc4 
F20 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)C[C@@H](C(=O)N[C@@H](Cc2ccc(cc2)[C@@H]3CC(=O)NS3(=O)=O)C(=O)N)NC(=O)c4ccccc4 
F20 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CC(C(=O)NC(Cc2ccc(cc2)C3CC(=O)NS3(=O)=O)C(=O)N)NC(=O)c4ccccc4 
# 
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 
F20 "SYSTEMATIC NAME" ACDLabs              10.04 N-(phenylcarbonyl)-L-phenylalanyl-4-[(5S)-1,1-dioxido-3-oxoisothiazolidin-5-yl]-L-phenylalaninamide                                        
F20 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-[4-[(5S)-1,1,3-trioxo-1,2-thiazolidin-5-yl]phenyl]propan-2-yl]amino]-1-oxo-3-phenyl-propan-2-yl]benzamide 
# 
