data_1FR
# 
_chem_comp.id                                    1FR 
_chem_comp.name                                  3-[3-chloro-5-(5-{[(1S)-1-phenylethyl]amino}isoxazolo[5,4-c]pyridin-3-yl)phenyl]propan-1-ol 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H22 Cl N3 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         3-{3-Chloro-5-[5-(1-phenyl-ethylamino)-isoxazolo[5,4-c]pyridin-3-yl]-phenyl}-propan-1-ol 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-06-16 
_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                        407.893 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     1FR 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        3DB8 
_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 
1FR C28  C28  C  0 1 Y N N 118.734 57.066 42.634 -4.669 -2.141 -1.146 C28  1FR 1  
1FR C27  C27  C  0 1 Y N N 119.073 58.336 43.106 -5.812 -2.722 -1.662 C27  1FR 2  
1FR C26  C26  C  0 1 Y N N 119.818 58.483 44.276 -7.053 -2.199 -1.351 C26  1FR 3  
1FR C24  C24  C  0 1 Y N N 119.876 56.090 44.514 -6.008 -0.515 -0.008 C24  1FR 4  
1FR C23  C23  C  0 1 Y N N 119.134 55.926 43.338 -4.767 -1.038 -0.319 C23  1FR 5  
1FR C22  C22  C  0 1 N N S 118.800 54.541 42.886 -3.520 -0.405 0.244  C22  1FR 6  
1FR C17  C17  C  0 1 N N N 117.701 58.754 47.149 5.092  -1.025 -1.365 C17  1FR 7  
1FR C15  C15  C  0 1 Y N N 115.790 57.722 45.832 3.176  0.389  -0.604 C15  1FR 8  
1FR C12  C12  C  0 1 Y N N 114.206 57.608 48.115 2.100  -1.723 0.836  C12  1FR 9  
1FR C13  C13  C  0 1 Y N N 115.499 58.124 48.188 3.275  -1.890 0.124  C13  1FR 10 
1FR C14  C14  C  0 1 Y N N 116.298 58.187 47.047 3.811  -0.835 -0.593 C14  1FR 11 
1FR C11  C11  C  0 1 Y N N 113.697 57.151 46.902 1.455  -0.501 0.832  C11  1FR 12 
1FR C10  C10  C  0 1 Y N N 114.493 57.201 45.758 1.991  0.564  0.110  C10  1FR 13 
1FR C8   C8   C  0 1 Y N N 113.950 56.711 44.457 1.304  1.878  0.102  C8   1FR 14 
1FR C4   C4   C  0 1 Y N N 114.716 55.971 43.404 -0.148 2.104  0.129  C4   1FR 15 
1FR C5   C5   C  0 1 Y N N 113.830 55.725 42.392 -0.336 3.497  0.109  C5   1FR 16 
1FR C6   C6   C  0 1 Y N N 114.210 55.047 41.238 -1.630 3.997  0.128  C6   1FR 17 
1FR C3   C3   C  0 1 Y N N 116.027 55.540 43.305 -1.270 1.276  0.167  C3   1FR 18 
1FR C2   C2   C  0 1 Y N N 116.401 54.860 42.139 -2.526 1.862  0.184  C2   1FR 19 
1FR CL   CL   CL 0 0 N N N 113.197 57.535 49.595 1.434  -3.052 1.733  CL   1FR 20 
1FR C18  C18  C  0 1 N N N 117.789 60.128 46.483 6.283  -0.685 -0.467 C18  1FR 21 
1FR C19  C19  C  0 1 N N N 117.325 61.249 47.405 7.583  -0.877 -1.251 C19  1FR 22 
1FR O20  O20  O  0 1 N N N 116.184 61.904 46.831 8.696  -0.560 -0.412 O20  1FR 23 
1FR O21  O21  O  0 1 Y N N 112.567 56.249 42.724 0.887  4.062  0.073  O21  1FR 24 
1FR N9   N9   N  0 1 Y N N 112.662 56.865 44.023 1.876  3.052  0.075  N9   1FR 25 
1FR N1   N1   N  0 1 Y N N 115.489 54.632 41.147 -2.664 3.181  0.163  N1   1FR 26 
1FR N7   N7   N  0 1 N N N 117.675 54.416 41.954 -3.661 1.054  0.222  N7   1FR 27 
1FR C29  C29  C  0 1 N N N 120.012 53.916 42.200 -3.316 -0.876 1.686  C29  1FR 28 
1FR C25  C25  C  0 1 Y N N 120.221 57.357 44.988 -7.152 -1.096 -0.524 C25  1FR 29 
1FR H28  H28  H  0 1 N N N 118.162 56.964 41.724 -3.699 -2.552 -1.385 H28  1FR 30 
1FR H27  H27  H  0 1 N N N 118.755 59.212 42.560 -5.735 -3.583 -2.309 H27  1FR 31 
1FR H26  H26  H  0 1 N N N 120.082 59.469 44.629 -7.946 -2.653 -1.755 H26  1FR 32 
1FR H24  H24  H  0 1 N N N 120.189 55.217 45.067 -6.085 0.346  0.639  H24  1FR 33 
1FR H22  H22  H  0 1 N N N 118.504 54.029 43.813 -2.661 -0.696 -0.359 H22  1FR 34 
1FR H17  H17  H  0 1 N N N 117.969 58.854 48.211 5.168  -2.061 -1.693 H17  1FR 35 
1FR H17A H17A H  0 0 N N N 118.393 58.071 46.635 5.093  -0.367 -2.234 H17A 1FR 36 
1FR H15  H15  H  0 1 N N N 116.402 57.765 44.943 3.597  1.213  -1.161 H15  1FR 37 
1FR H13  H13  H  0 1 N N N 115.884 58.477 49.133 3.776  -2.846 0.130  H13  1FR 38 
1FR H11  H11  H  0 1 N N N 112.692 56.760 46.848 0.538  -0.372 1.387  H11  1FR 39 
1FR H6   H6   H  0 1 N N N 113.504 54.860 40.442 -1.792 5.065  0.113  H6   1FR 40 
1FR H3   H3   H  0 1 N N N 116.737 55.721 44.099 -1.162 0.202  0.183  H3   1FR 41 
1FR H18  H18  H  0 1 N N N 118.837 60.315 46.205 6.207  0.352  -0.139 H18  1FR 42 
1FR H18A H18A H  0 0 N N N 117.129 60.120 45.603 6.282  -1.343 0.402  H18A 1FR 43 
1FR H19  H19  H  0 1 N N N 117.051 60.828 48.384 7.660  -1.914 -1.579 H19  1FR 44 
1FR H19A H19A H  0 0 N N N 118.139 61.978 47.532 7.584  -0.220 -2.120 H19A 1FR 45 
1FR HO20 HO20 H  0 0 N N N 115.529 62.049 47.504 9.555  -0.660 -0.845 HO20 1FR 46 
1FR HN7  HN7  H  0 1 N N N 117.984 54.902 41.137 -4.543 1.456  0.234  HN7  1FR 47 
1FR H29  H29  H  0 1 N N N 119.793 53.766 41.133 -3.212 -1.960 1.702  H29  1FR 48 
1FR H29A H29A H  0 0 N N N 120.878 54.585 42.305 -2.414 -0.418 2.093  H29A 1FR 49 
1FR H29B H29B H  0 0 N N N 120.238 52.946 42.668 -4.176 -0.584 2.289  H29B 1FR 50 
1FR H25  H25  H  0 1 N N N 120.794 57.462 45.897 -8.122 -0.688 -0.282 H25  1FR 51 
# 
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 
1FR C28 C27  DOUB Y N 1  
1FR C28 C23  SING Y N 2  
1FR C27 C26  SING N N 3  
1FR C26 C25  DOUB Y N 4  
1FR C24 C23  DOUB N N 5  
1FR C24 C25  SING Y N 6  
1FR C23 C22  SING N N 7  
1FR C22 N7   SING Y N 8  
1FR C22 C29  SING Y N 9  
1FR C17 C14  SING N N 10 
1FR C17 C18  SING N N 11 
1FR C15 C14  DOUB N N 12 
1FR C15 C10  SING N N 13 
1FR C12 C13  DOUB N N 14 
1FR C12 C11  SING N N 15 
1FR C12 CL   SING N N 16 
1FR C13 C14  SING N N 17 
1FR C11 C10  DOUB N N 18 
1FR C10 C8   SING Y N 19 
1FR C8  C4   SING Y N 20 
1FR C8  N9   DOUB N N 21 
1FR C4  C5   DOUB Y N 22 
1FR C4  C3   SING Y N 23 
1FR C5  C6   SING N N 24 
1FR C5  O21  SING Y N 25 
1FR C6  N1   DOUB N N 26 
1FR C3  C2   DOUB Y N 27 
1FR C2  N1   SING N N 28 
1FR C2  N7   SING N N 29 
1FR C18 C19  SING Y N 30 
1FR C19 O20  SING Y N 31 
1FR O21 N9   SING Y N 32 
1FR C28 H28  SING Y N 33 
1FR C27 H27  SING Y N 34 
1FR C26 H26  SING Y N 35 
1FR C24 H24  SING Y N 36 
1FR C22 H22  SING N N 37 
1FR C17 H17  SING Y N 38 
1FR C17 H17A SING N N 39 
1FR C15 H15  SING Y N 40 
1FR C13 H13  SING N N 41 
1FR C11 H11  SING N N 42 
1FR C6  H6   SING N N 43 
1FR C3  H3   SING N N 44 
1FR C18 H18  SING N N 45 
1FR C18 H18A SING N N 46 
1FR C19 H19  SING N N 47 
1FR C19 H19A SING N N 48 
1FR O20 HO20 SING Y N 49 
1FR N7  HN7  SING N N 50 
1FR C29 H29  SING N N 51 
1FR C29 H29A SING N N 52 
1FR C29 H29B SING N N 53 
1FR C25 H25  SING N N 54 
# 
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 
1FR SMILES           ACDLabs              10.04 Clc4cc(cc(c2noc1cnc(cc12)NC(c3ccccc3)C)c4)CCCO                                                                                                                             
1FR InChI            InChI                1.02b InChI=1/C23H22ClN3O2/c1-15(17-7-3-2-4-8-17)26-22-13-20-21(14-25-22)29-27-23(20)18-10-16(6-5-9-28)11-19(24)12-18/h2-4,7-8,10-15,28H,5-6,9H2,1H3,(H,25,26)/t15-/m0/s1/f/h26H 
1FR InChIKey         InChI                1.02b MMGKIHLBFPJYJL-XMFOCRCDDM                                                                                                                                                  
1FR SMILES_CANONICAL CACTVS               3.341 C[C@H](Nc1cc2c(onc2c3cc(Cl)cc(CCCO)c3)cn1)c4ccccc4                                                                                                                         
1FR SMILES           CACTVS               3.341 C[CH](Nc1cc2c(onc2c3cc(Cl)cc(CCCO)c3)cn1)c4ccccc4                                                                                                                          
1FR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@@H](c1ccccc1)Nc2cc3c(cn2)onc3c4cc(cc(c4)Cl)CCCO                                                                                                                        
1FR SMILES           "OpenEye OEToolkits" 1.5.0 CC(c1ccccc1)Nc2cc3c(cn2)onc3c4cc(cc(c4)Cl)CCCO                                                                                                                             
# 
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 
1FR "SYSTEMATIC NAME" ACDLabs              10.04 3-[3-chloro-5-(5-{[(1S)-1-phenylethyl]amino}isoxazolo[5,4-c]pyridin-3-yl)phenyl]propan-1-ol     
1FR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 3-[3-chloro-5-[5-[[(1S)-1-phenylethyl]amino]-[1,2]oxazolo[4,5-d]pyridin-3-yl]phenyl]propan-1-ol 
# 
