data_4F3
# 
_chem_comp.id                                    4F3 
_chem_comp.name                                  "[2-(1-AMINO-2-HYDROXY-PROPYL)-4-(4-FLUORO-1H-INDOL-3-YLMETHYL)-5-HYDROXY-IMIDAZOL-1-YL]-ACETIC ACID" 
_chem_comp.type                                  "L-PEPTIDE LINKING" 
_chem_comp.pdbx_type                             ATOMP 
_chem_comp.formula                               "C17 H19 F N4 O4" 
_chem_comp.mon_nstd_parent_comp_id               "GLY, TYR, GLY" 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-12-16 
_chem_comp.pdbx_modified_date                    2009-01-07 
_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                        362.356 
_chem_comp.one_letter_code                       GYG 
_chem_comp.three_letter_code                     4F3 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1RM9 
_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 
4F3 C1   C1   C 0 1 Y N N 29.600 29.514 37.946 -4.724 1.778 1.995  C1   4F3 1  
4F3 C2   C2   C 0 1 Y N N 30.284 30.044 39.040 -3.729 1.006 1.364  C2   4F3 2  
4F3 C3   C3   C 0 1 Y N N 31.554 30.706 38.885 -3.750 0.871 -0.029 C3   4F3 3  
4F3 C4   C4   C 0 1 Y N N 32.147 30.841 37.625 -4.740 1.489 -0.790 C4   4F3 4  
4F3 C5   C5   C 0 1 Y N N 31.476 30.319 36.502 -5.738 2.260 -0.186 C5   4F3 5  
4F3 C6   C6   C 0 1 Y N N 30.232 29.674 36.671 -5.704 2.386 1.207  C6   4F3 6  
4F3 C7   C7   C 0 1 Y N N 28.394 28.829 37.671 -5.004 2.122 3.348  C7   4F3 7  
4F3 C8   C8   C 0 1 Y N N 28.387 28.638 36.288 -6.127 2.917 3.354  C8   4F3 8  
4F3 N9   N9   N 0 1 Y N N 29.479 29.141 35.731 -6.542 3.070 2.058  N9   4F3 9  
4F3 F10  F10  F 0 1 N N N 29.702 29.910 40.212 -2.767 0.404 2.077  F10  4F3 10 
4F3 C11  C11  C 0 1 N N N 27.385 28.422 38.551 -4.235 1.707 4.539  C11  4F3 11 
4F3 C12  C12  C 0 1 Y N N 26.187 27.787 38.225 -3.110 2.657 4.924  C12  4F3 12 
4F3 N13  N13  N 0 1 Y N N 25.749 27.440 37.042 -1.886 2.456 4.396  N13  4F3 13 
4F3 C14  C14  C 0 1 Y N N 24.599 26.907 37.072 -1.175 3.427 4.924  C14  4F3 14 
4F3 N15  N15  N 0 1 Y N N 24.150 26.855 38.378 -1.925 4.211 5.756  N15  4F3 15 
4F3 C16  C16  C 0 1 Y N N 25.154 27.401 39.134 -3.196 3.708 5.757  C16  4F3 16 
4F3 O17  O17  O 0 1 N N N 25.145 27.548 40.380 -4.173 4.247 6.471  O17  4F3 17 
4F3 C18  C18  C 0 1 N N N 22.860 26.339 38.902 -1.463 5.361 6.499  C18  4F3 18 
4F3 C    C    C 0 1 N N N 22.840 24.976 39.458 -1.607 6.640 5.722  C    4F3 19 
4F3 O    O    O 0 1 N N N 21.757 24.881 40.351 -2.056 6.755 4.591  O    4F3 20 
4F3 C22  C22  C 0 1 N N R 23.898 26.444 35.797 0.259  3.683 4.681  C22  4F3 21 
4F3 C23  C23  C 0 1 N N S 24.886 26.051 34.694 0.717  3.274 3.241  C23  4F3 22 
4F3 O24  O24  O 0 1 N N N 25.686 24.928 35.134 -0.098 3.974 2.295  O24  4F3 23 
4F3 C25  C25  C 0 1 N N N 24.224 25.605 33.385 2.173  3.588 2.904  C25  4F3 24 
4F3 N    N    N 0 1 N N N 22.726 27.430 35.664 1.118  3.024 5.695  N    4F3 25 
4F3 OXT  OXT  O 0 1 N Y N ?      ?      ?      -1.156 7.685 6.463  OXT  4F3 26 
4F3 H3   H3   H 0 1 N N N 32.087 31.121 39.756 -2.984 0.278 -0.521 H3   4F3 27 
4F3 H4   H4   H 0 1 N N N 33.121 31.347 37.519 -4.737 1.371 -1.871 H4   4F3 28 
4F3 H5   H5   H 0 1 N N N 31.921 30.414 35.497 -6.508 2.741 -0.780 H5   4F3 29 
4F3 H8   H8   H 0 1 N N N 27.599 28.140 35.696 -6.668 3.388 4.163  H8   4F3 30 
4F3 H9   H9   H 0 1 N N N 29.704 29.121 34.736 -7.347 3.608 1.768  H9   4F3 31 
4F3 H111 1H11 H 0 0 N N N 27.881 27.770 39.307 -4.897 1.580 5.419  H111 4F3 32 
4F3 H112 2H11 H 0 0 N N N 27.102 29.328 39.135 -3.802 0.695 4.404  H112 4F3 33 
4F3 H17  H17  H 0 1 N N N 24.458 27.291 40.984 -4.571 5.030 6.027  H17  4F3 34 
4F3 H181 1H18 H 0 0 N N N 22.462 27.050 39.662 -0.410 5.197 6.750  H181 4F3 35 
4F3 H182 2H18 H 0 0 N N N 22.082 26.422 38.107 -2.048 5.420 7.423  H182 4F3 36 
4F3 H22  H22  H 0 1 N N N 23.402 25.446 35.755 0.476  4.771 4.773  H22  4F3 37 
4F3 H23  H23  H 0 1 N N N 25.482 26.973 34.500 0.545  2.203 3.079  H23  4F3 38 
4F3 HO42 2HO4 H 0 0 N N N 26.298 24.684 34.450 0.498  4.263 1.588  HO42 4F3 39 
4F3 H251 1H25 H 0 0 N N N 24.943 25.319 32.582 2.868  2.983 3.493  H251 4F3 40 
4F3 H252 2H25 H 0 0 N N N 23.502 24.776 33.575 2.395  4.647 3.074  H252 4F3 41 
4F3 H253 3H25 H 0 0 N N N 23.520 26.388 33.017 2.368  3.394 1.843  H253 4F3 42 
4F3 H    H    H 0 1 N N N 22.257 27.120 34.812 2.047  3.347 5.770  H    4F3 43 
4F3 HN2  HN2  H 0 1 N N N 22.996 28.413 35.666 0.783  2.182 6.084  HN2  4F3 44 
4F3 HXT  HXT  H 0 1 N Y N -0.012 -0.879 0.358  -1.236 8.536 5.981  HXT  4F3 45 
# 
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 
4F3 C1  C2   DOUB Y N 1  
4F3 C1  C6   SING Y N 2  
4F3 C1  C7   SING Y N 3  
4F3 C2  C3   SING Y N 4  
4F3 C2  F10  SING N N 5  
4F3 C3  C4   DOUB Y N 6  
4F3 C3  H3   SING N N 7  
4F3 C4  C5   SING Y N 8  
4F3 C4  H4   SING N N 9  
4F3 C5  C6   DOUB Y N 10 
4F3 C5  H5   SING N N 11 
4F3 C6  N9   SING Y N 12 
4F3 C7  C8   DOUB Y N 13 
4F3 C7  C11  SING N N 14 
4F3 C8  N9   SING Y N 15 
4F3 C8  H8   SING N N 16 
4F3 N9  H9   SING N N 17 
4F3 C11 C12  SING N N 18 
4F3 C11 H111 SING N N 19 
4F3 C11 H112 SING N N 20 
4F3 C12 N13  SING Y N 21 
4F3 C12 C16  DOUB Y N 22 
4F3 N13 C14  DOUB Y N 23 
4F3 C14 N15  SING Y N 24 
4F3 C14 C22  SING N N 25 
4F3 N15 C16  SING Y N 26 
4F3 N15 C18  SING N N 27 
4F3 C16 O17  SING N N 28 
4F3 O17 H17  SING N N 29 
4F3 C18 C    SING N N 30 
4F3 C18 H181 SING N N 31 
4F3 C18 H182 SING N N 32 
4F3 C   O    DOUB N N 33 
4F3 C   OXT  SING N N 34 
4F3 C22 C23  SING N N 35 
4F3 C22 N    SING N N 36 
4F3 C22 H22  SING N N 37 
4F3 C23 O24  SING N N 38 
4F3 C23 C25  SING N N 39 
4F3 C23 H23  SING N N 40 
4F3 O24 HO42 SING N N 41 
4F3 C25 H251 SING N N 42 
4F3 C25 H252 SING N N 43 
4F3 C25 H253 SING N N 44 
4F3 N   H    SING N N 45 
4F3 N   HN2  SING N N 46 
4F3 OXT HXT  SING N N 47 
# 
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 
4F3 SMILES           ACDLabs              10.04 "O=C(O)Cn1c(O)c(nc1C(N)C(O)C)Cc3c2c(F)cccc2nc3"                                                                                                                       
4F3 InChI            InChI                1.02b "InChI=1/C17H19FN4O4/c1-8(23)15(19)16-21-12(17(26)22(16)7-13(24)25)5-9-6-20-11-4-2-3-10(18)14(9)11/h2-4,6,8,15,20,23,26H,5,7,19H2,1H3,(H,24,25)/t8-,15-/m0/s1/f/h24H" 
4F3 InChIKey         InChI                1.02b AYMRQIHECFEMIQ-BBOGANOKDU                                                                                                                                             
4F3 SMILES_CANONICAL CACTVS               3.341 "C[C@H](O)[C@H](N)c1nc(Cc2c[nH]c3cccc(F)c23)c(O)n1CC(O)=O"                                                                                                            
4F3 SMILES           CACTVS               3.341 "C[CH](O)[CH](N)c1nc(Cc2c[nH]c3cccc(F)c23)c(O)n1CC(O)=O"                                                                                                              
4F3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@@H]([C@@H](c1nc(c(n1CC(=O)O)O)Cc2c[nH]c3c2c(ccc3)F)N)O"                                                                                                          
4F3 SMILES           "OpenEye OEToolkits" 1.5.0 "CC(C(c1nc(c(n1CC(=O)O)O)Cc2c[nH]c3c2c(ccc3)F)N)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 
4F3 "SYSTEMATIC NAME" ACDLabs              10.04 "{2-[(1R,2S)-1-amino-2-hydroxypropyl]-4-[(4-fluoro-1H-indol-3-yl)methyl]-5-hydroxy-1H-imidazol-1-yl}acetic acid"   
4F3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[2-[(1R,2S)-1-amino-2-hydroxy-propyl]-4-[(4-fluoro-1H-indol-3-yl)methyl]-5-hydroxy-imidazol-1-yl]ethanoic acid" 
# 
