data_CYF
# 
_chem_comp.id                                    CYF 
_chem_comp.name                                  "5-[2-(2-AMINO-2-CARBAMOYL-ETHYLSULFANYL)-ACETYLAMINO]-2-(3,6-DIHYDROXY-9,9A-DIHYDRO-3H-XANTHEN-9-YL)-BENZOIC ACID" 
_chem_comp.type                                  "L-PEPTIDE LINKING" 
_chem_comp.pdbx_type                             ATOMP 
_chem_comp.formula                               "C25 H23 N3 O7 S" 
_chem_comp.mon_nstd_parent_comp_id               CYS 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_chem_comp.pdbx_modified_date                    2024-09-27 
_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                        509.531 
_chem_comp.one_letter_code                       C 
_chem_comp.three_letter_code                     CYF 
_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        1MPA 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
_chem_comp.pdbx_pcm                              N 
# 
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.pdbx_backbone_atom_flag 
_chem_comp_atom.pdbx_n_terminal_atom_flag 
_chem_comp_atom.pdbx_c_terminal_atom_flag 
_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 
CYF C1   C1   C 0 1 Y N N N N N -2.256  5.863  52.204 3.064  0.703  -5.956 C1   CYF 1  
CYF O1   O1   O 0 1 N N N N N N -1.623  6.699  52.855 4.024  1.166  -6.799 O1   CYF 2  
CYF C2   C2   C 0 1 Y N N N N N -1.564  4.811  51.647 1.842  1.346  -5.881 C2   CYF 3  
CYF C3   C3   C 0 1 Y N N N N N -2.227  3.874  50.867 0.849  0.880  -5.019 C3   CYF 4  
CYF O2   O2   O 0 1 N N N N N N -1.382  2.827  50.341 -0.311 1.556  -4.970 O2   CYF 5  
CYF C4   C4   C 0 1 Y N N N N N -2.130  1.935  49.574 -1.381 0.811  -4.641 C4   CYF 6  
CYF C5   C5   C 0 1 Y N N N N N -1.350  0.919  49.081 -2.631 1.218  -5.110 C5   CYF 7  
CYF C6   C6   C 0 1 Y N N N N N -1.935  -0.074 48.316 -3.771 0.513  -4.770 C6   CYF 8  
CYF O3   O3   O 0 1 N N N N N N -1.256  -1.035 47.919 -4.983 0.919  -5.232 O3   CYF 9  
CYF C7   C7   C 0 1 Y N N N N N -3.297  -0.022 48.040 -3.678 -0.607 -3.958 C7   CYF 10 
CYF C8   C8   C 0 1 Y N N N N N -4.068  1.010  48.539 -2.443 -1.017 -3.497 C8   CYF 11 
CYF C9   C9   C 0 1 Y N N N N N -3.497  1.988  49.310 -1.302 -0.315 -3.842 C9   CYF 12 
CYF C10  C10  C 0 1 N N R N N N -4.244  3.001  49.871 0.036  -0.793 -3.340 C10  CYF 13 
CYF C11  C11  C 0 1 Y N N N N N -3.604  3.980  50.646 1.104  -0.244 -4.254 C11  CYF 14 
CYF C12  C12  C 0 1 Y N N N N N -4.299  5.056  51.219 2.327  -0.884 -4.324 C12  CYF 15 
CYF C13  C13  C 0 1 Y N N N N N -3.625  5.988  51.990 3.311  -0.414 -5.171 C13  CYF 16 
CYF C14  C14  C 0 1 Y N N N N N -5.656  2.998  49.806 0.261  -0.291 -1.937 C14  CYF 17 
CYF C15  C15  C 0 1 Y N N N N N -6.371  2.905  50.999 0.381  1.062  -1.698 C15  CYF 18 
CYF C16  C16  C 0 1 Y N N N N N -7.754  2.983  51.002 0.587  1.526  -0.413 C16  CYF 19 
CYF C17  C17  C 0 1 Y N N N N N -8.480  3.140  49.831 0.676  0.633  0.647  C17  CYF 20 
CYF C18  C18  C 0 1 Y N N N N N -7.784  3.213  48.626 0.563  -0.728 0.418  C18  CYF 21 
CYF C19  C19  C 0 1 Y N N N N N -6.375  3.157  48.571 0.349  -1.197 -0.878 C19  CYF 22 
CYF C20  C20  C 0 1 N N N N N N -5.787  3.424  47.337 0.221  -2.647 -1.130 C20  CYF 23 
CYF O4   O4   O 0 1 N N N N N N -4.635  3.902  47.276 -0.616 -3.057 -1.907 O4   CYF 24 
CYF O5   O5   O 0 1 N N N N N N -6.408  3.214  46.261 1.035  -3.515 -0.497 O5   CYF 25 
CYF NL   NL   N 0 1 N N N N N N -9.809  3.179  49.849 0.886  1.109  1.947  NL   CYF 26 
CYF CL   CL   C 0 1 N N N N N N -10.886 3.889  49.530 0.352  0.457  2.998  CL   CYF 27 
CYF OL   OL   O 0 1 N N N N N N -10.930 4.980  48.967 -0.387 -0.486 2.814  OL   CYF 28 
CYF CAL  CAL  C 0 1 N N N N N N -12.172 3.228  49.878 0.674  0.899  4.402  CAL  CYF 29 
CYF SG   SG   S 0 1 N N N N N N -12.847 2.495  48.413 -0.190 -0.169 5.586  SG   CYF 30 
CYF CB   CB   C 0 1 N N N N N N -13.029 3.939  47.394 0.364  0.573  7.145  CB   CYF 31 
CYF CA   CA   C 0 1 N N R N N N -14.380 4.618  47.484 -0.255 -0.185 8.320  CA   CYF 32 
CYF N    N    N 0 1 N N N N N N -14.552 5.429  46.304 -1.719 -0.107 8.235  N    CYF 33 
CYF O    O    O 0 1 N N N N N N -13.665 6.422  48.886 -0.432 1.329  10.121 O    CYF 34 
CYF C    C    C 0 1 N N N N N N -14.439 5.471  48.746 0.206  0.431  9.615  C    CYF 35 
CYF NT   NT   N 0 1 N N N N N N -15.327 5.113  49.688 1.329  -0.015 10.212 NT   CYF 36 
CYF HO1  HO1  H 0 1 N N N N N N -2.100  7.424  53.239 4.550  1.806  -6.299 HO1  CYF 37 
CYF HC2  H2   H 0 1 N N N N N N -0.479  4.719  51.825 1.655  2.215  -6.495 HC2  CYF 38 
CYF H5   H5   H 0 1 N N N N N N -0.268  0.900  49.296 -2.708 2.089  -5.744 H5   CYF 39 
CYF HO3  HO3  H 0 1 N N N N N N -1.657  -1.717 47.393 -5.338 1.536  -4.579 HO3  CYF 40 
CYF H7   H7   H 0 1 N N N N N N -3.768  -0.804 47.421 -4.568 -1.156 -3.687 H7   CYF 41 
CYF H8   H8   H 0 1 N N N N N N -5.148  1.053  48.320 -2.366 -1.890 -2.866 H8   CYF 42 
CYF H10  H10  H 0 1 N N N N N N -4.236  3.413  48.835 0.066  -1.882 -3.351 H10  CYF 43 
CYF H12  H12  H 0 1 N N N N N N -5.384  5.170  51.062 2.513  -1.757 -3.715 H12  CYF 44 
CYF H13  H13  H 0 1 N N N N N N -4.179  6.831  52.434 4.268  -0.912 -5.222 H13  CYF 45 
CYF H15  H15  H 0 1 N N N N N N -5.835  2.767  51.953 0.313  1.761  -2.519 H15  CYF 46 
CYF H16  H16  H 0 1 N N N N N N -8.291  2.918  51.962 0.679  2.587  -0.233 H16  CYF 47 
CYF H18  H18  H 0 1 N N N N N N -8.362  3.317  47.692 0.633  -1.423 1.242  H18  CYF 48 
CYF HO5  HO5  H 0 1 N N N N N N -6.006  3.396  45.419 0.952  -4.464 -0.662 HO5  CYF 49 
CYF HNL  HNL  H 0 1 N N N N N N -10.110 2.341  50.273 1.416  1.909  2.091  HNL  CYF 50 
CYF HAL3 1HAL H 0 0 N N N N N N -12.063 2.494  50.711 0.351  1.931  4.541  HAL3 CYF 51 
CYF HAL2 2HAL H 0 0 N N N N N N -12.887 3.922  50.376 1.749  0.829  4.568  HAL2 CYF 52 
CYF HB3  1HB  H 0 1 N N N N N N -12.215 4.669  47.612 0.053  1.617  7.181  HB3  CYF 53 
CYF HB2  2HB  H 0 1 N N N N N N -12.790 3.694  46.332 1.451  0.515  7.208  HB2  CYF 54 
CYF HA   HA   H 0 1 N N N N N N -15.200 3.865  47.539 0.056  -1.229 8.284  HA   CYF 55 
CYF H    1HN  H 0 1 N N N N N N -14.210 6.351  46.280 -1.960 0.871  8.273  H    CYF 56 
CYF H2   2HN  H 0 1 N Y N N N N -14.433 4.898  45.440 -1.974 -0.433 7.315  H2   CYF 57 
CYF HNT1 1HNT H 0 0 N N N N N N -15.894 4.331  49.537 1.626  0.381  11.046 HNT1 CYF 58 
CYF HNT2 2HNT H 0 0 N N N N N N -15.393 5.643  50.510 1.840  -0.733 9.808  HNT2 CYF 59 
# 
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 
CYF C1  O1   SING N N 1  
CYF C1  C2   DOUB Y N 2  
CYF C1  C13  SING Y N 3  
CYF O1  HO1  SING N N 4  
CYF C2  C3   SING Y N 5  
CYF C2  HC2  SING N N 6  
CYF C3  O2   SING N N 7  
CYF C3  C11  DOUB Y N 8  
CYF O2  C4   SING N N 9  
CYF C4  C5   DOUB Y N 10 
CYF C4  C9   SING Y N 11 
CYF C5  C6   SING Y N 12 
CYF C5  H5   SING N N 13 
CYF C6  O3   SING N N 14 
CYF C6  C7   DOUB Y N 15 
CYF O3  HO3  SING N N 16 
CYF C7  C8   SING Y N 17 
CYF C7  H7   SING N N 18 
CYF C8  C9   DOUB Y N 19 
CYF C8  H8   SING N N 20 
CYF C9  C10  SING N N 21 
CYF C10 C11  SING N N 22 
CYF C10 C14  SING N N 23 
CYF C10 H10  SING N N 24 
CYF C11 C12  SING Y N 25 
CYF C12 C13  DOUB Y N 26 
CYF C12 H12  SING N N 27 
CYF C13 H13  SING N N 28 
CYF C14 C15  DOUB Y N 29 
CYF C14 C19  SING Y N 30 
CYF C15 C16  SING Y N 31 
CYF C15 H15  SING N N 32 
CYF C16 C17  DOUB Y N 33 
CYF C16 H16  SING N N 34 
CYF C17 C18  SING Y N 35 
CYF C17 NL   SING N N 36 
CYF C18 C19  DOUB Y N 37 
CYF C18 H18  SING N N 38 
CYF C19 C20  SING N N 39 
CYF C20 O4   DOUB N N 40 
CYF C20 O5   SING N N 41 
CYF O5  HO5  SING N N 42 
CYF NL  CL   SING N N 43 
CYF NL  HNL  SING N N 44 
CYF CL  OL   DOUB N N 45 
CYF CL  CAL  SING N N 46 
CYF CAL SG   SING N N 47 
CYF CAL HAL3 SING N N 48 
CYF CAL HAL2 SING N N 49 
CYF SG  CB   SING N N 50 
CYF CB  CA   SING N N 51 
CYF CB  HB3  SING N N 52 
CYF CB  HB2  SING N N 53 
CYF CA  N    SING N N 54 
CYF CA  C    SING N N 55 
CYF CA  HA   SING N N 56 
CYF N   H    SING N N 57 
CYF N   H2   SING N N 58 
CYF O   C    DOUB N N 59 
CYF C   NT   SING N N 60 
CYF NT  HNT1 SING N N 61 
CYF NT  HNT2 SING N N 62 
# 
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 
CYF SMILES           ACDLabs              10.04 "O=C(N)C(N)CSCC(=O)Nc1ccc(c(C(=O)O)c1)C3c4c(Oc2c3ccc(O)c2)cc(O)cc4"                                                                                                                                         
CYF SMILES_CANONICAL CACTVS               3.341 "N[C@@H](CSCC(=O)Nc1ccc([C@H]2c3ccc(O)cc3Oc4cc(O)ccc24)c(c1)C(O)=O)C(N)=O"                                                                                                                                  
CYF SMILES           CACTVS               3.341 "N[CH](CSCC(=O)Nc1ccc([CH]2c3ccc(O)cc3Oc4cc(O)ccc24)c(c1)C(O)=O)C(N)=O"                                                                                                                                     
CYF SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc(c(cc1NC(=O)CSC[C@@H](C(=O)N)N)C(=O)O)C2c3ccc(cc3Oc4c2ccc(c4)O)O"                                                                                                                                      
CYF SMILES           "OpenEye OEToolkits" 1.5.0 "c1cc(c(cc1NC(=O)CSCC(C(=O)N)N)C(=O)O)C2c3ccc(cc3Oc4c2ccc(c4)O)O"                                                                                                                                           
CYF InChI            InChI                1.03  "InChI=1S/C25H23N3O7S/c26-19(24(27)32)10-36-11-22(31)28-12-1-4-15(18(7-12)25(33)34)23-16-5-2-13(29)8-20(16)35-21-9-14(30)3-6-17(21)23/h1-9,19,23,29-30H,10-11,26H2,(H2,27,32)(H,28,31)(H,33,34)/t19-/m0/s1" 
CYF InChIKey         InChI                1.03  YQXANHSECNNVJK-IBGZPJMESA-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 
CYF "SYSTEMATIC NAME" ACDLabs              10.04 "5-[({[(2R)-2,3-diamino-3-oxopropyl]sulfanyl}acetyl)amino]-2-(3,6-dihydroxy-9H-xanthen-9-yl)benzoic acid"  
CYF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "5-[2-[(2R)-2,3-diamino-3-oxo-propyl]sulfanylethanoylamino]-2-(3,6-dihydroxy-9H-xanthen-9-yl)benzoic 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 
CYF "Create component"  1999-07-08 RCSB 
CYF "Modify descriptor" 2011-06-04 RCSB 
CYF "Modify PCM"        2024-09-27 PDBE 
# 
