data_395
# 
_chem_comp.id                                    395 
_chem_comp.name                                  "S-3-FLUORO-4-[2-HYDROXY-2-(5,5,8,8-TETRAMETHYL-5,6,7,8,-TETRAHYDRO-NAPHTALEN-2-YL)-ACETYLAMINO]-BENZOIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H26 F N O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         BMS270395 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-05-10 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   OBS 
_chem_comp.pdbx_replaced_by                      961 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        399.455 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     395 
_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        1EXX 
_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 
395 C1   C1   C 0 1 Y N N 36.924 15.209 87.680 0.348  -1.343 3.506  C1   395 1  
395 C2   C2   C 0 1 Y N N 35.977 16.063 88.225 0.841  -0.790 4.668  C2   395 2  
395 C3   C3   C 0 1 Y N N 35.816 17.326 87.658 0.600  0.556  4.955  C3   395 3  
395 C4   C4   C 0 1 Y N N 36.595 17.690 86.566 -0.135 1.338  4.060  C4   395 4  
395 C5   C5   C 0 1 Y N N 37.541 16.801 86.044 -0.620 0.781  2.898  C5   395 5  
395 C6   C6   C 0 1 Y N N 37.734 15.550 86.620 -0.379 -0.558 2.614  C6   395 6  
395 C7   C7   C 0 1 N N N 34.801 18.225 88.184 1.121  1.151  6.200  C7   395 7  
395 C8   C8   C 0 1 Y N N 42.440 14.137 83.698 -1.218 0.231  -2.254 C8   395 8  
395 C9   C9   C 0 1 Y N N 41.249 13.471 83.962 -1.301 -0.929 -1.513 C9   395 9  
395 C10  C10  C 0 1 Y N N 40.662 12.769 82.923 -0.366 -1.930 -1.700 C10  395 10 
395 C11  C11  C 0 1 Y N N 41.211 12.805 81.656 0.643  -1.761 -2.623 C11  395 11 
395 C12  C12  C 0 1 Y N N 42.442 13.420 81.403 0.729  -0.592 -3.370 C12  395 12 
395 C13  C13  C 0 1 N N N 43.010 13.274 80.002 1.863  -0.472 -4.354 C13  395 13 
395 C14  C14  C 0 1 N N N 44.465 13.744 79.951 1.577  0.634  -5.368 C14  395 14 
395 C15  C15  C 0 1 N N N 44.628 15.060 80.715 1.197  1.906  -4.601 C15  395 15 
395 C16  C16  C 0 1 N N N 44.333 14.886 82.214 -0.174 1.692  -3.964 C16  395 16 
395 C17  C17  C 0 1 Y N N 43.081 14.076 82.436 -0.202 0.403  -3.186 C17  395 17 
395 C18  C18  C 0 1 N N N 45.484 14.107 82.884 -0.479 2.857  -3.020 C18  395 18 
395 C19  C19  C 0 1 N N N 44.245 16.272 82.850 -1.238 1.641  -5.063 C19  395 19 
395 C20  C20  C 0 1 N N N 42.996 11.787 79.629 2.033  -1.801 -5.093 C20  395 20 
395 C21  C21  C 0 1 N N N 42.103 14.047 79.055 3.153  -0.144 -3.600 C21  395 21 
395 C22  C22  C 0 1 N N S 40.634 13.517 85.340 -2.406 -1.104 -0.504 C22  395 22 
395 C23  C23  C 0 1 N N N 39.872 14.838 85.637 -1.952 -0.581 0.833  C23  395 23 
395 N6   N6   N 0 1 N N N 38.618 14.639 86.058 -0.873 -1.119 1.436  N6   395 24 
395 F1   F1   F 0 1 N N N 37.073 14.010 88.232 0.579  -2.644 3.227  F1   395 25 
395 O22  O22  O 0 1 N N N 39.855 12.369 85.696 -3.561 -0.378 -0.932 O22  395 26 
395 O23  O23  O 0 1 N N N 40.461 15.913 85.551 -2.557 0.322  1.369  O23  395 27 
395 O71  O71  O 0 1 N N N 34.163 17.829 89.172 0.911  2.322  6.448  O71  395 28 
395 O72  O72  O 0 1 N N N 34.495 19.296 87.620 1.830  0.396  7.062  O72  395 29 
395 H2   H2   H 0 1 N N N 35.367 15.745 89.087 1.408  -1.396 5.358  H2   395 30 
395 H4   H4   H 0 1 N N N 36.462 18.686 86.112 -0.322 2.379  4.279  H4   395 31 
395 H5   H5   H 0 1 N N N 38.143 17.090 85.166 -1.188 1.385  2.207  H5   395 32 
395 H8   H8   H 0 1 N N N 42.888 14.730 84.512 -1.948 1.013  -2.108 H8   395 33 
395 H10  H10  H 0 1 N N N 39.749 12.176 83.106 -0.427 -2.842 -1.124 H10  395 34 
395 H11  H11  H 0 1 N N N 40.654 12.332 80.828 1.374  -2.544 -2.767 H11  395 35 
395 H141 1H14 H 0 0 N N N 45.167 12.960 80.319 2.467  0.820  -5.969 H141 395 36 
395 H142 2H14 H 0 0 N N N 44.839 13.822 78.903 0.753  0.335  -6.015 H142 395 37 
395 H151 1H15 H 0 0 N N N 45.636 15.505 80.547 1.936  2.101  -3.824 H151 395 38 
395 H152 2H15 H 0 0 N N N 44.004 15.869 80.268 1.155  2.751  -5.288 H152 395 39 
395 H181 1H18 H 0 0 N N N 45.270 13.980 83.971 -1.458 2.708  -2.564 H181 395 40 
395 H182 2H18 H 0 0 N N N 45.681 13.132 82.379 0.281  2.903  -2.241 H182 395 41 
395 H183 3H18 H 0 0 N N N 46.475 14.585 82.703 -0.479 3.791  -3.583 H183 395 42 
395 H191 1H19 H 0 0 N N N 44.031 16.145 83.937 -2.218 1.489  -4.612 H191 395 43 
395 H192 2H19 H 0 0 N N N 45.153 16.889 82.660 -1.234 2.580  -5.616 H192 395 44 
395 H193 3H19 H 0 0 N N N 43.504 16.931 82.340 -1.018 0.818  -5.743 H193 395 45 
395 H201 1H20 H 0 0 N N N 43.413 11.679 78.600 2.247  -2.591 -4.373 H201 395 46 
395 H202 2H20 H 0 0 N N N 43.527 11.152 80.375 1.116  -2.037 -5.631 H202 395 47 
395 H203 3H20 H 0 0 N N N 41.985 11.328 79.732 2.859  -1.720 -5.800 H203 395 48 
395 H211 1H21 H 0 0 N N N 42.520 13.939 78.026 3.365  -0.936 -2.882 H211 395 49 
395 H212 2H21 H 0 0 N N N 41.035 13.734 79.125 3.978  -0.065 -4.309 H212 395 50 
395 H213 3H21 H 0 0 N N N 41.964 15.110 79.358 3.036  0.801  -3.073 H213 395 51 
395 H22  H22  H 0 1 N N N 41.523 13.491 86.011 -2.654 -2.162 -0.416 H22  395 52 
395 HN6  HN6  H 0 1 N N N 38.297 13.678 85.936 -0.439 -1.897 1.050  HN6  395 53 
395 HO22 2HO2 H 0 0 N N N 39.468 12.397 86.563 -3.299 0.549  -0.996 HO22 395 54 
395 HO27 7HO2 H 0 0 N N N 33.832 19.883 87.963 2.172  0.786  7.879  HO27 395 55 
# 
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 
395 C1  C2   DOUB Y N 1  
395 C1  C6   SING Y N 2  
395 C1  F1   SING N N 3  
395 C2  C3   SING Y N 4  
395 C2  H2   SING N N 5  
395 C3  C4   DOUB Y N 6  
395 C3  C7   SING N N 7  
395 C4  C5   SING Y N 8  
395 C4  H4   SING N N 9  
395 C5  C6   DOUB Y N 10 
395 C5  H5   SING N N 11 
395 C6  N6   SING N N 12 
395 C7  O71  DOUB N N 13 
395 C7  O72  SING N N 14 
395 C8  C9   DOUB Y N 15 
395 C8  C17  SING Y N 16 
395 C8  H8   SING N N 17 
395 C9  C10  SING Y N 18 
395 C9  C22  SING N N 19 
395 C10 C11  DOUB Y N 20 
395 C10 H10  SING N N 21 
395 C11 C12  SING Y N 22 
395 C11 H11  SING N N 23 
395 C12 C13  SING N N 24 
395 C12 C17  DOUB Y N 25 
395 C13 C14  SING N N 26 
395 C13 C20  SING N N 27 
395 C13 C21  SING N N 28 
395 C14 C15  SING N N 29 
395 C14 H141 SING N N 30 
395 C14 H142 SING N N 31 
395 C15 C16  SING N N 32 
395 C15 H151 SING N N 33 
395 C15 H152 SING N N 34 
395 C16 C17  SING N N 35 
395 C16 C18  SING N N 36 
395 C16 C19  SING N N 37 
395 C18 H181 SING N N 38 
395 C18 H182 SING N N 39 
395 C18 H183 SING N N 40 
395 C19 H191 SING N N 41 
395 C19 H192 SING N N 42 
395 C19 H193 SING N N 43 
395 C20 H201 SING N N 44 
395 C20 H202 SING N N 45 
395 C20 H203 SING N N 46 
395 C21 H211 SING N N 47 
395 C21 H212 SING N N 48 
395 C21 H213 SING N N 49 
395 C22 C23  SING N N 50 
395 C22 O22  SING N N 51 
395 C22 H22  SING N N 52 
395 C23 N6   SING N N 53 
395 C23 O23  DOUB N N 54 
395 N6  HN6  SING N N 55 
395 O22 HO22 SING N N 56 
395 O72 HO27 SING N N 57 
# 
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 
395 SMILES           ACDLabs              10.04 O=C(O)c1ccc(c(F)c1)NC(=O)C(O)c2ccc3c(c2)C(CCC3(C)C)(C)C                                                                                                                           
395 InChI            InChI                1.02b InChI=1/C23H26FNO4/c1-22(2)9-10-23(3,4)16-11-13(5-7-15(16)22)19(26)20(27)25-18-8-6-14(21(28)29)12-17(18)24/h5-8,11-12,19,26H,9-10H2,1-4H3,(H,25,27)(H,28,29)/t19-/m0/s1/f/h25,28H 
395 InChIKey         InChI                1.02b AANFHDFOMFRLLR-YYAIOWFZDI                                                                                                                                                         
395 SMILES_CANONICAL CACTVS               3.341 CC1(C)CCC(C)(C)c2cc(ccc12)[C@H](O)C(=O)Nc3ccc(cc3F)C(O)=O                                                                                                                         
395 SMILES           CACTVS               3.341 CC1(C)CCC(C)(C)c2cc(ccc12)[CH](O)C(=O)Nc3ccc(cc3F)C(O)=O                                                                                                                          
395 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC1(CCC(c2c1ccc(c2)[C@@H](C(=O)Nc3ccc(cc3F)C(=O)O)O)(C)C)C                                                                                                                        
395 SMILES           "OpenEye OEToolkits" 1.5.0 CC1(CCC(c2c1ccc(c2)C(C(=O)Nc3ccc(cc3F)C(=O)O)O)(C)C)C                                                                                                                             
# 
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 
395 "SYSTEMATIC NAME" ACDLabs              10.04 "3-fluoro-4-{[(2S)-2-hydroxy-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)acetyl]amino}benzoic acid" 
395 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "3-fluoro-4-[[(2S)-2-hydroxy-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)ethanoyl]amino]benzoic acid"      
# 
