data_394
# 
_chem_comp.id                                    394 
_chem_comp.name                                  "R-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                         BMS270394 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-05-08 
_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                        399.455 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     394 
_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        1EXA 
_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 
394 C1   C1   C 0 1 Y N N 37.411 16.573 86.233 -1.039 -0.238 2.780  C1   394 1  
394 C2   C2   C 0 1 Y N N 36.528 17.547 86.716 -1.484 0.072  4.047  C2   394 2  
394 C3   C3   C 0 1 Y N N 35.619 17.156 87.714 -0.566 0.218  5.091  C3   394 3  
394 C4   C4   C 0 1 Y N N 35.625 15.809 88.273 0.798  0.044  4.847  C4   394 4  
394 C5   C5   C 0 1 Y N N 36.569 14.884 87.722 1.236  -0.270 3.580  C5   394 5  
394 C6   C6   C 0 1 Y N N 37.441 15.237 86.683 0.321  -0.416 2.543  C6   394 6  
394 C7   C7   C 0 1 N N N 34.617 18.093 88.194 -1.037 0.555  6.447  C7   394 7  
394 C8   C8   C 0 1 Y N N 41.093 13.098 82.565 0.596  -1.012 -2.000 C8   394 8  
394 C9   C9   C 0 1 Y N N 40.634 13.524 83.814 1.696  -0.314 -1.547 C9   394 9  
394 C10  C10  C 0 1 Y N N 41.321 14.600 84.477 2.009  0.911  -2.105 C10  394 10 
394 C11  C11  C 0 1 Y N N 42.424 15.168 83.894 1.218  1.428  -3.111 C11  394 11 
394 C12  C12  C 0 1 Y N N 42.901 14.744 82.651 0.110  0.726  -3.568 C12  394 12 
394 C13  C13  C 0 1 N N N 44.184 15.401 82.145 -0.713 1.353  -4.662 C13  394 13 
394 C14  C14  C 0 1 N N N 44.392 15.058 80.662 -1.601 0.306  -5.332 C14  394 14 
394 C15  C15  C 0 1 N N N 44.105 13.629 80.244 -2.371 -0.444 -4.240 C15  394 15 
394 C16  C16  C 0 1 N N N 42.690 13.192 80.646 -1.382 -1.312 -3.464 C16  394 16 
394 C17  C17  C 0 1 Y N N 42.222 13.698 81.969 -0.200 -0.494 -3.014 C17  394 17 
394 C18  C18  C 0 1 N N N 41.749 13.695 79.535 -2.082 -1.903 -2.239 C18  394 18 
394 C19  C19  C 0 1 N N N 42.716 11.646 80.676 -0.894 -2.449 -4.364 C19  394 19 
394 C20  C20  C 0 1 N N N 44.193 16.898 82.194 0.220  1.967  -5.708 C20  394 20 
394 C21  C21  C 0 1 N N N 45.447 15.030 82.915 -1.593 2.453  -4.064 C21  394 21 
394 C22  C22  C 0 1 N N R 39.426 12.895 84.466 2.552  -0.884 -0.446 C22  394 22 
394 C23  C23  C 0 1 N N N 38.383 14.000 84.853 2.026  -0.425 0.888  C23  394 23 
394 N6   N6   N 0 1 N N N 38.332 14.256 86.178 0.769  -0.735 1.260  N6   394 24 
394 F1   F1   F 0 1 N N N 38.380 16.909 85.356 -1.925 -0.379 1.769  F1   394 25 
394 O22  O22  O 0 1 N N N 39.804 12.148 85.670 3.899  -0.433 -0.608 O22  394 26 
394 O23  O23  O 0 1 N N N 37.687 14.538 83.994 2.734  0.224  1.628  O23  394 27 
394 O71  O71  O 0 1 N N N 34.430 19.146 87.524 -0.238 0.682  7.354  O71  394 28 
394 O72  O72  O 0 1 N N N 33.909 17.753 89.175 -2.354 0.723  6.681  O72  394 29 
394 H2   H2   H 0 1 N N N 36.547 18.578 86.326 -2.540 0.206  4.232  H2   394 30 
394 H4   H4   H 0 1 N N N 34.941 15.501 89.082 1.510  0.156  5.652  H4   394 31 
394 H5   H5   H 0 1 N N N 36.627 13.855 88.114 2.291  -0.405 3.392  H5   394 32 
394 H8   H8   H 0 1 N N N 40.560 12.283 82.046 0.352  -1.969 -1.563 H8   394 33 
394 H10  H10  H 0 1 N N N 40.995 14.997 85.452 2.870  1.462  -1.756 H10  394 34 
394 H11  H11  H 0 1 N N N 42.937 15.981 84.434 1.463  2.385  -3.546 H11  394 35 
394 H141 1H14 H 0 0 N N N 43.797 15.758 80.030 -2.304 0.798  -6.005 H141 394 36 
394 H142 2H14 H 0 0 N N N 45.427 15.335 80.356 -0.983 -0.393 -5.894 H142 394 37 
394 H151 1H15 H 0 0 N N N 44.281 13.481 79.152 -2.841 0.269  -3.565 H151 394 38 
394 H152 2H15 H 0 0 N N N 44.875 12.927 80.641 -3.133 -1.076 -4.696 H152 394 39 
394 H181 1H18 H 0 0 N N N 40.720 13.377 79.827 -1.380 -2.523 -1.682 H181 394 40 
394 H182 2H18 H 0 0 N N N 41.836 14.789 79.343 -2.440 -1.095 -1.600 H182 394 41 
394 H183 3H18 H 0 0 N N N 42.045 13.352 78.515 -2.927 -2.511 -2.562 H183 394 42 
394 H191 1H19 H 0 0 N N N 41.687 11.328 80.968 -0.188 -3.071 -3.813 H191 394 43 
394 H192 2H19 H 0 0 N N N 43.069 11.187 79.723 -1.745 -3.055 -4.676 H192 394 44 
394 H193 3H19 H 0 0 N N N 43.514 11.226 81.331 -0.403 -2.032 -5.243 H193 394 45 
394 H201 1H20 H 0 0 N N N 45.129 17.377 81.824 0.849  2.721  -5.235 H201 394 46 
394 H202 2H20 H 0 0 N N N 43.311 17.305 81.647 0.848  1.186  -6.136 H202 394 47 
394 H203 3H20 H 0 0 N N N 43.962 17.250 83.226 -0.372 2.430  -6.497 H203 394 48 
394 H211 1H21 H 0 0 N N N 46.383 15.509 82.545 -0.962 3.207  -3.593 H211 394 49 
394 H212 2H21 H 0 0 N N N 45.310 15.239 84.001 -2.184 2.915  -4.855 H212 394 50 
394 H213 3H21 H 0 0 N N N 45.568 13.922 82.944 -2.260 2.019  -3.319 H213 394 51 
394 H22  H22  H 0 1 N N N 38.972 12.188 83.731 2.526  -1.973 -0.492 H22  394 52 
394 HN6  HN6  H 0 1 N N N 38.953 13.720 86.784 0.174  -1.181 0.636  HN6  394 53 
394 HO22 2HO2 H 0 0 N N N 39.044 11.752 86.080 3.878  0.531  -0.561 HO22 394 54 
394 HO27 7HO2 H 0 0 N N N 33.254 18.365 89.488 -2.663 0.944  7.570  HO27 394 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 
394 C1  C2   DOUB Y N 1  
394 C1  C6   SING Y N 2  
394 C1  F1   SING N N 3  
394 C2  C3   SING Y N 4  
394 C2  H2   SING N N 5  
394 C3  C4   DOUB Y N 6  
394 C3  C7   SING N N 7  
394 C4  C5   SING Y N 8  
394 C4  H4   SING N N 9  
394 C5  C6   DOUB Y N 10 
394 C5  H5   SING N N 11 
394 C6  N6   SING N N 12 
394 C7  O71  DOUB N N 13 
394 C7  O72  SING N N 14 
394 C8  C9   DOUB Y N 15 
394 C8  C17  SING Y N 16 
394 C8  H8   SING N N 17 
394 C9  C10  SING Y N 18 
394 C9  C22  SING N N 19 
394 C10 C11  DOUB Y N 20 
394 C10 H10  SING N N 21 
394 C11 C12  SING Y N 22 
394 C11 H11  SING N N 23 
394 C12 C13  SING N N 24 
394 C12 C17  DOUB Y N 25 
394 C13 C14  SING N N 26 
394 C13 C20  SING N N 27 
394 C13 C21  SING N N 28 
394 C14 C15  SING N N 29 
394 C14 H141 SING N N 30 
394 C14 H142 SING N N 31 
394 C15 C16  SING N N 32 
394 C15 H151 SING N N 33 
394 C15 H152 SING N N 34 
394 C16 C17  SING N N 35 
394 C16 C18  SING N N 36 
394 C16 C19  SING N N 37 
394 C18 H181 SING N N 38 
394 C18 H182 SING N N 39 
394 C18 H183 SING N N 40 
394 C19 H191 SING N N 41 
394 C19 H192 SING N N 42 
394 C19 H193 SING N N 43 
394 C20 H201 SING N N 44 
394 C20 H202 SING N N 45 
394 C20 H203 SING N N 46 
394 C21 H211 SING N N 47 
394 C21 H212 SING N N 48 
394 C21 H213 SING N N 49 
394 C22 C23  SING N N 50 
394 C22 O22  SING N N 51 
394 C22 H22  SING N N 52 
394 C23 N6   SING N N 53 
394 C23 O23  DOUB N N 54 
394 N6  HN6  SING N N 55 
394 O22 HO22 SING N N 56 
394 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 
394 SMILES           ACDLabs              10.04 O=C(O)c1ccc(c(F)c1)NC(=O)C(O)c2ccc3c(c2)C(CCC3(C)C)(C)C                                                                                                                           
394 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-/m1/s1/f/h25,28H 
394 InChIKey         InChI                1.02b AANFHDFOMFRLLR-BINADRATDP                                                                                                                                                         
394 SMILES_CANONICAL CACTVS               3.341 CC1(C)CCC(C)(C)c2cc(ccc12)[C@@H](O)C(=O)Nc3ccc(cc3F)C(O)=O                                                                                                                        
394 SMILES           CACTVS               3.341 CC1(C)CCC(C)(C)c2cc(ccc12)[CH](O)C(=O)Nc3ccc(cc3F)C(O)=O                                                                                                                          
394 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC1(CCC(c2c1ccc(c2)[C@H](C(=O)Nc3ccc(cc3F)C(=O)O)O)(C)C)C                                                                                                                         
394 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 
394 "SYSTEMATIC NAME" ACDLabs              10.04 "3-fluoro-4-{[(2R)-2-hydroxy-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)acetyl]amino}benzoic acid" 
394 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "3-fluoro-4-[[(2R)-2-hydroxy-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)ethanoyl]amino]benzoic acid"      
# 
