data_FR6
# 
_chem_comp.id                                    FR6 
_chem_comp.name                                  1-{(1R,2S)-2-HYDROXY-1-[2-(1-NAPHTHYL)ETHYL]PROPYL}-1H-IMIDAZOLE-4-CARBOXAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H21 N3 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         FR233623 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-12-16 
_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                         ? 
_chem_comp.formula_weight                        323.389 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FR6 
_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        1V78,2E1W 
_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 
FR6 C1   C1   C 0 1 Y N N 51.527 54.519 20.979 2.774  -0.028 -0.739 C1   FR6 1  
FR6 N2   N2   N 0 1 Y N N 51.464 55.544 22.034 1.945  -0.602 0.164  N2   FR6 2  
FR6 C3   C3   C 0 1 Y N N 51.338 54.918 23.205 1.951  0.172  1.281  C3   FR6 3  
FR6 N4   N4   N 0 1 Y N N 51.481 53.584 23.065 2.741  1.189  1.087  N4   FR6 4  
FR6 C5   C5   C 0 1 Y N N 51.536 53.332 21.609 3.270  1.103  -0.160 C5   FR6 5  
FR6 C8   C8   C 0 1 N N N 51.570 51.965 21.007 4.213  2.054  -0.773 C8   FR6 6  
FR6 O9   O9   O 0 1 N N N 52.065 51.694 19.923 4.616  1.866  -1.905 O9   FR6 7  
FR6 N10  N10  N 0 1 N N N 51.120 50.980 21.751 4.627  3.133  -0.081 N10  FR6 8  
FR6 C13  C13  C 0 1 N N R 51.552 56.991 21.856 1.185  -1.840 -0.025 C13  FR6 9  
FR6 C14  C14  C 0 1 N N S 53.051 57.533 21.827 1.609  -2.866 1.028  C14  FR6 10 
FR6 O15  O15  O 0 1 N N N 53.969 57.211 22.931 0.854  -4.066 0.855  O15  FR6 11 
FR6 C18  C18  C 0 1 N N N 50.671 57.460 20.678 -0.310 -1.547 0.122  C18  FR6 12 
FR6 C19  C19  C 0 1 N N N 49.130 57.358 20.884 -0.763 -0.626 -1.013 C19  FR6 13 
FR6 C22  C22  C 0 1 Y N N 48.417 57.836 19.626 -2.257 -0.440 -0.943 C22  FR6 14 
FR6 C25  C25  C 0 1 Y N N 48.022 59.182 19.517 -3.080 -1.226 -1.690 C25  FR6 15 
FR6 C26  C26  C 0 1 Y N N 47.518 59.700 18.322 -4.464 -1.068 -1.638 C26  FR6 16 
FR6 C27  C27  C 0 1 Y N N 47.504 58.903 17.176 -5.032 -0.124 -0.839 C27  FR6 17 
FR6 C28  C28  C 0 1 Y N N 47.903 57.559 17.259 -4.214 0.706  -0.053 C28  FR6 18 
FR6 C29  C29  C 0 1 Y N N 48.388 57.027 18.465 -2.807 0.542  -0.102 C29  FR6 19 
FR6 C2   C2   C 0 1 Y N N 47.762 56.765 16.108 -4.764 1.692  0.783  C2   FR6 20 
FR6 C4   C4   C 0 1 Y N N 48.678 55.642 18.524 -1.989 1.376  0.679  C4   FR6 21 
FR6 C6   C6   C 0 1 Y N N 48.098 55.413 16.171 -3.941 2.478  1.529  C6   FR6 22 
FR6 C7   C7   C 0 1 Y N N 48.520 54.842 17.377 -2.557 2.320  1.477  C7   FR6 23 
FR6 C9   C9   C 0 1 N N N 53.814 57.318 20.492 3.099  -3.173 0.869  C9   FR6 24 
FR6 H1   H1   H 0 1 N N N 51.562 54.625 19.882 2.994  -0.392 -1.732 H1   FR6 25 
FR6 H3   H3   H 0 1 N N N 51.142 55.434 24.160 1.390  -0.024 2.183  H3   FR6 26 
FR6 H101 1H10 H 0 0 N N N 51.143 50.047 21.340 4.305  3.283  0.822  H101 FR6 27 
FR6 H102 2H10 H 0 0 N N N 50.707 51.206 22.656 5.248  3.760  -0.485 H102 FR6 28 
FR6 H13  H13  H 0 1 N N N 51.124 57.471 22.767 1.381  -2.238 -1.020 H13  FR6 29 
FR6 H14  H14  H 0 1 N N N 52.782 58.606 21.968 1.425  -2.461 2.024  H14  FR6 30 
FR6 HO   HO   H 0 1 N N N 54.862 57.534 22.914 1.044  -4.390 -0.036 HO   FR6 31 
FR6 H181 1H18 H 0 0 N N N 50.963 56.916 19.750 -0.869 -2.481 0.077  H181 FR6 32 
FR6 H182 2H18 H 0 0 N N N 50.945 58.503 20.396 -0.493 -1.060 1.079  H182 FR6 33 
FR6 H191 1H19 H 0 0 N N N 48.790 57.904 21.795 -0.271 0.341  -0.915 H191 FR6 34 
FR6 H192 2H19 H 0 0 N N N 48.812 56.333 21.185 -0.497 -1.073 -1.971 H192 FR6 35 
FR6 H25  H25  H 0 1 N N N 48.110 59.849 20.391 -2.655 -1.983 -2.332 H25  FR6 36 
FR6 H26  H26  H 0 1 N N N 47.133 60.733 18.284 -5.095 -1.704 -2.241 H26  FR6 37 
FR6 H27  H27  H 0 1 N N N 47.180 59.332 16.213 -6.106 -0.013 -0.809 H27  FR6 38 
FR6 H2   H2   H 0 1 N N N 47.391 57.199 15.164 -5.835 1.826  0.833  H2   FR6 39 
FR6 H4   H4   H 0 1 N N N 49.028 55.185 19.465 -0.915 1.266  0.648  H4   FR6 40 
FR6 H6   H6   H 0 1 N N N 48.030 54.792 15.262 -4.366 3.235  2.171  H6   FR6 41 
FR6 H7   H7   H 0 1 N N N 48.728 53.760 17.424 -1.926 2.957  2.079  H7   FR6 42 
FR6 H91  1H9  H 0 1 N N N 53.234 57.755 19.646 3.283  -3.577 -0.126 H91  FR6 43 
FR6 H92  2H9  H 0 1 N N N 54.862 57.697 20.472 3.675  -2.257 1.001  H92  FR6 44 
FR6 H93  3H9  H 0 1 N N N 53.793 56.240 20.210 3.401  -3.904 1.619  H93  FR6 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 
FR6 C1  N2   SING Y N 1  
FR6 C1  C5   DOUB Y N 2  
FR6 C1  H1   SING N N 3  
FR6 N2  C3   SING Y N 4  
FR6 N2  C13  SING N N 5  
FR6 C3  N4   DOUB Y N 6  
FR6 C3  H3   SING N N 7  
FR6 N4  C5   SING Y N 8  
FR6 C5  C8   SING N N 9  
FR6 C8  O9   DOUB N N 10 
FR6 C8  N10  SING N N 11 
FR6 N10 H101 SING N N 12 
FR6 N10 H102 SING N N 13 
FR6 C13 C14  SING N N 14 
FR6 C13 C18  SING N N 15 
FR6 C13 H13  SING N N 16 
FR6 C14 O15  SING N N 17 
FR6 C14 C9   SING N N 18 
FR6 C14 H14  SING N N 19 
FR6 O15 HO   SING N N 20 
FR6 C18 C19  SING N N 21 
FR6 C18 H181 SING N N 22 
FR6 C18 H182 SING N N 23 
FR6 C19 C22  SING N N 24 
FR6 C19 H191 SING N N 25 
FR6 C19 H192 SING N N 26 
FR6 C22 C25  DOUB Y N 27 
FR6 C22 C29  SING Y N 28 
FR6 C25 C26  SING Y N 29 
FR6 C25 H25  SING N N 30 
FR6 C26 C27  DOUB Y N 31 
FR6 C26 H26  SING N N 32 
FR6 C27 C28  SING Y N 33 
FR6 C27 H27  SING N N 34 
FR6 C28 C29  DOUB Y N 35 
FR6 C28 C2   SING Y N 36 
FR6 C29 C4   SING Y N 37 
FR6 C2  C6   DOUB Y N 38 
FR6 C2  H2   SING N N 39 
FR6 C4  C7   DOUB Y N 40 
FR6 C4  H4   SING N N 41 
FR6 C6  C7   SING Y N 42 
FR6 C6  H6   SING N N 43 
FR6 C7  H7   SING N N 44 
FR6 C9  H91  SING N N 45 
FR6 C9  H92  SING N N 46 
FR6 C9  H93  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 
FR6 SMILES           ACDLabs              10.04 O=C(c1ncn(c1)C(C(O)C)CCc3c2ccccc2ccc3)N                                                                                                                    
FR6 InChI            InChI                1.02b InChI=1/C19H21N3O2/c1-13(23)18(22-11-17(19(20)24)21-12-22)10-9-15-7-4-6-14-5-2-3-8-16(14)15/h2-8,11-13,18,23H,9-10H2,1H3,(H2,20,24)/t13-,18+/m0/s1/f/h20H2 
FR6 InChIKey         InChI                1.02b OODDZQQDDOVCFD-WFKWMPGYDS                                                                                                                                  
FR6 SMILES_CANONICAL CACTVS               3.341 C[C@H](O)[C@@H](CCc1cccc2ccccc12)n3cnc(c3)C(N)=O                                                                                                           
FR6 SMILES           CACTVS               3.341 C[CH](O)[CH](CCc1cccc2ccccc12)n3cnc(c3)C(N)=O                                                                                                              
FR6 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@@H]([C@@H](CCc1cccc2c1cccc2)n3cc(nc3)C(=O)N)O                                                                                                          
FR6 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C(CCc1cccc2c1cccc2)n3cc(nc3)C(=O)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 
FR6 "SYSTEMATIC NAME" ACDLabs              10.04 1-[(1R,2S)-2-hydroxy-1-(2-naphthalen-1-ylethyl)propyl]-1H-imidazole-4-carboxamide 
FR6 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 1-[(3R,4S)-4-hydroxy-1-naphthalen-1-yl-pentan-3-yl]imidazole-4-carboxamide        
# 
