data_FBI
# 
_chem_comp.id                                    FBI 
_chem_comp.name                                  "7-[4-(4-FLUORO-PHENYL)-6-ISOPROPYL-2-(METHANESULFONYL-METHYL-AMINO)-PYRIMIDIN-5-YL] -3,5-DIHYDROXY-HEPTANOIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H30 F N3 O6 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ROSUVASTATIN 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-01-17 
_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                        483.554 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FBI 
_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        1HWL 
_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 
FBI O1S  O1S  O 0 1 N N N 23.230 -31.609 31.958 -0.250 1.881  -6.464 O1S  FBI 1  
FBI O2S  O2S  O 0 1 N N N 25.535 -32.629 32.417 1.151  1.389  -4.470 O2S  FBI 2  
FBI N3   N3   N 0 1 N N N 24.469 -32.989 29.915 -1.081 0.505  -4.668 N3   FBI 3  
FBI C12  C12  C 0 1 N N N 25.886 -33.103 29.473 -2.394 0.550  -5.316 C12  FBI 4  
FBI S1   S1   S 0 1 N N N 24.179 -32.855 31.623 0.270  0.972  -5.504 S1   FBI 5  
FBI C13  C13  C 0 1 N N N 23.379 -34.327 32.241 0.830  -0.569 -6.278 C13  FBI 6  
FBI C8   C8   C 0 1 Y N N 22.609 -32.718 26.827 0.365  -0.371 -1.531 C8   FBI 7  
FBI C10  C10  C 0 1 Y N N 21.276 -33.046 27.247 -0.770 -0.761 -0.816 C10  FBI 8  
FBI C9   C9   C 0 1 Y N N 21.102 -33.324 28.646 -1.997 -0.715 -1.451 C9   FBI 9  
FBI N2   N2   N 0 1 Y N N 22.155 -33.290 29.465 -2.062 -0.295 -2.705 N2   FBI 10 
FBI C11  C11  C 0 1 Y N N 23.333 -33.001 28.996 -0.969 0.073  -3.358 C11  FBI 11 
FBI N1   N1   N 0 1 Y N N 23.590 -32.715 27.748 0.225  0.039  -2.790 N1   FBI 12 
FBI C83  C83  C 0 1 Y N N 24.193 -32.640 23.436 3.373  -1.583 0.367  C83  FBI 13 
FBI C82  C82  C 0 1 Y N N 23.882 -33.091 24.738 2.126  -1.552 -0.221 C82  FBI 14 
FBI C81  C81  C 0 1 Y N N 22.961 -32.373 25.534 1.704  -0.408 -0.896 C81  FBI 15 
FBI C86  C86  C 0 1 Y N N 22.387 -31.210 24.976 2.548  0.698  -0.978 C86  FBI 16 
FBI C85  C85  C 0 1 Y N N 22.695 -30.772 23.701 3.791  0.661  -0.382 C85  FBI 17 
FBI C84  C84  C 0 1 Y N N 23.588 -31.474 22.934 4.207  -0.478 0.287  C84  FBI 18 
FBI F1   F1   F 0 1 N N N 23.880 -31.020 21.685 5.427  -0.512 0.865  F1   FBI 19 
FBI O1B  O1B  O 0 1 N N N 19.244 -27.796 21.786 -0.957 1.811  8.771  O1B  FBI 20 
FBI O1A  O1A  O 0 1 N N N 20.255 -27.598 23.814 -0.435 -0.191 7.995  O1A  FBI 21 
FBI O3   O3   O 0 1 N N N 18.827 -30.861 22.813 0.616  -0.220 5.546  O3   FBI 22 
FBI C1   C1   C 0 1 N N N 19.263 -28.012 22.987 -0.778 0.943  7.762  C1   FBI 23 
FBI C2   C2   C 0 1 N N N 18.201 -28.769 23.716 -1.006 1.384  6.339  C2   FBI 24 
FBI C3   C3   C 0 1 N N R 18.600 -30.194 24.048 -0.736 0.213  5.393  C3   FBI 25 
FBI C4   C4   C 0 1 N N N 17.489 -30.915 24.802 -0.967 0.661  3.948  C4   FBI 26 
FBI C5   C5   C 0 1 N N R 17.885 -32.316 25.288 -0.697 -0.509 3.002  C5   FBI 27 
FBI C6   C6   C 0 1 N N N 19.070 -32.238 26.236 -0.928 -0.061 1.557  C6   FBI 28 
FBI C7   C7   C 0 1 N N N 20.073 -33.094 26.263 -0.658 -1.233 0.610  C7   FBI 29 
FBI C91  C91  C 0 1 N N N 19.716 -33.666 29.280 -3.248 -1.131 -0.722 C91  FBI 30 
FBI C92  C92  C 0 1 N N N 19.758 -34.856 30.252 -4.220 0.048  -0.662 C92  FBI 31 
FBI C93  C93  C 0 1 N N N 19.125 -32.431 30.026 -3.906 -2.297 -1.463 C93  FBI 32 
FBI O5   O5   O 0 1 N N N 16.757 -32.869 25.954 0.655  -0.943 3.155  O5   FBI 33 
FBI H121 1H12 H 0 0 N N N 26.072 -33.189 28.377 -3.156 0.209  -4.616 H121 FBI 34 
FBI H122 2H12 H 0 0 N N N 26.472 -32.247 29.882 -2.614 1.573  -5.622 H122 FBI 35 
FBI H123 3H12 H 0 0 N N N 26.371 -33.957 29.999 -2.389 -0.097 -6.192 H123 FBI 36 
FBI H131 1H13 H 0 0 N N N 24.039 -35.194 32.007 1.729  -0.376 -6.863 H131 FBI 37 
FBI H132 2H13 H 0 0 N N N 23.120 -34.257 33.323 1.051  -1.305 -5.505 H132 FBI 38 
FBI H133 3H13 H 0 0 N N N 22.342 -34.453 31.849 0.047  -0.952 -6.932 H133 FBI 39 
FBI H83  H83  H 0 1 N N N 24.909 -33.199 22.810 3.701  -2.468 0.890  H83  FBI 40 
FBI H82  H82  H 0 1 N N N 24.358 -34.004 25.133 1.478  -2.413 -0.158 H82  FBI 41 
FBI H86  H86  H 0 1 N N N 21.665 -30.616 25.562 2.225  1.587  -1.501 H86  FBI 42 
FBI H85  H85  H 0 1 N N N 22.226 -29.859 23.294 4.444  1.519  -0.442 H85  FBI 43 
FBI H1B  H1B  H 0 1 N N N 18.549 -28.086 21.206 -0.811 1.527  9.684  H1B  FBI 44 
FBI HO3  HO3  H 0 1 N N N 19.076 -31.753 23.021 1.179  0.534  5.327  HO3  FBI 45 
FBI H21  1H2  H 0 1 N N N 17.884 -28.222 24.634 -0.331 2.207  6.102  H21  FBI 46 
FBI H22  2H2  H 0 1 N N N 17.240 -28.748 23.149 -2.038 1.715  6.222  H22  FBI 47 
FBI H3   H3   H 0 1 N N N 19.508 -30.191 24.694 -1.410 -0.609 5.631  H3   FBI 48 
FBI H41  1H4  H 0 1 N N N 17.120 -30.292 25.650 -0.292 1.483  3.711  H41  FBI 49 
FBI H42  2H4  H 0 1 N N N 16.559 -30.959 24.187 -1.999 0.992  3.831  H42  FBI 50 
FBI H5   H5   H 0 1 N N N 18.186 -32.955 24.425 -1.371 -1.332 3.239  H5   FBI 51 
FBI H61  1H6  H 0 1 N N N 19.516 -31.224 26.110 -0.253 0.760  1.319  H61  FBI 52 
FBI H62  2H6  H 0 1 N N N 18.652 -32.198 27.269 -1.960 0.269  1.440  H62  FBI 53 
FBI H71  1H7  H 0 1 N N N 20.504 -33.110 25.234 -1.388 -2.021 0.791  H71  FBI 54 
FBI H72  2H7  H 0 1 N N N 19.621 -34.108 26.362 0.345  -1.619 0.788  H72  FBI 55 
FBI H91  H91  H 0 1 N N N 19.064 -33.954 28.422 -2.992 -1.443 0.290  H91  FBI 56 
FBI H921 1H92 H 0 0 N N N 18.768 -35.100 30.704 -3.752 0.878  -0.135 H921 FBI 57 
FBI H922 2H92 H 0 0 N N N 20.196 -35.753 29.756 -4.477 0.359  -1.675 H922 FBI 58 
FBI H923 3H92 H 0 0 N N N 20.523 -34.688 31.045 -5.126 -0.252 -0.135 H923 FBI 59 
FBI H931 1H93 H 0 0 N N N 18.135 -32.675 30.478 -3.214 -3.138 -1.506 H931 FBI 60 
FBI H932 2H93 H 0 0 N N N 19.836 -32.028 30.784 -4.812 -2.598 -0.936 H932 FBI 61 
FBI H933 3H93 H 0 0 N N N 19.064 -31.538 29.360 -4.163 -1.986 -2.476 H933 FBI 62 
FBI HO5  HO5  H 0 1 N N N 17.002 -33.736 26.254 1.218  -0.188 2.936  HO5  FBI 63 
# 
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 
FBI O1S S1   DOUB N N 1  
FBI O2S S1   DOUB N N 2  
FBI N3  C12  SING N N 3  
FBI N3  S1   SING N N 4  
FBI N3  C11  SING N N 5  
FBI C12 H121 SING N N 6  
FBI C12 H122 SING N N 7  
FBI C12 H123 SING N N 8  
FBI S1  C13  SING N N 9  
FBI C13 H131 SING N N 10 
FBI C13 H132 SING N N 11 
FBI C13 H133 SING N N 12 
FBI C8  C10  DOUB Y N 13 
FBI C8  N1   SING Y N 14 
FBI C8  C81  SING N N 15 
FBI C10 C9   SING Y N 16 
FBI C10 C7   SING N N 17 
FBI C9  N2   DOUB Y N 18 
FBI C9  C91  SING N N 19 
FBI N2  C11  SING Y N 20 
FBI C11 N1   DOUB Y N 21 
FBI C83 C82  DOUB Y N 22 
FBI C83 C84  SING Y N 23 
FBI C83 H83  SING N N 24 
FBI C82 C81  SING Y N 25 
FBI C82 H82  SING N N 26 
FBI C81 C86  DOUB Y N 27 
FBI C86 C85  SING Y N 28 
FBI C86 H86  SING N N 29 
FBI C85 C84  DOUB Y N 30 
FBI C85 H85  SING N N 31 
FBI C84 F1   SING N N 32 
FBI O1B C1   SING N N 33 
FBI O1B H1B  SING N N 34 
FBI O1A C1   DOUB N N 35 
FBI O3  C3   SING N N 36 
FBI O3  HO3  SING N N 37 
FBI C1  C2   SING N N 38 
FBI C2  C3   SING N N 39 
FBI C2  H21  SING N N 40 
FBI C2  H22  SING N N 41 
FBI C3  C4   SING N N 42 
FBI C3  H3   SING N N 43 
FBI C4  C5   SING N N 44 
FBI C4  H41  SING N N 45 
FBI C4  H42  SING N N 46 
FBI C5  C6   SING N N 47 
FBI C5  O5   SING N N 48 
FBI C5  H5   SING N N 49 
FBI C6  C7   SING N N 50 
FBI C6  H61  SING N N 51 
FBI C6  H62  SING N N 52 
FBI C7  H71  SING N N 53 
FBI C7  H72  SING N N 54 
FBI C91 C92  SING N N 55 
FBI C91 C93  SING N N 56 
FBI C91 H91  SING N N 57 
FBI C92 H921 SING N N 58 
FBI C92 H922 SING N N 59 
FBI C92 H923 SING N N 60 
FBI C93 H931 SING N N 61 
FBI C93 H932 SING N N 62 
FBI C93 H933 SING N N 63 
FBI O5  HO5  SING N N 64 
# 
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 
FBI SMILES           ACDLabs              10.04 O=S(=O)(N(c1nc(c(c(n1)C(C)C)CCC(O)CC(O)CC(=O)O)c2ccc(F)cc2)C)C                                                                                                                          
FBI InChI            InChI                1.02b InChI=1/C22H30FN3O6S/c1-13(2)20-18(10-9-16(27)11-17(28)12-19(29)30)21(14-5-7-15(23)8-6-14)25-22(24-20)26(3)33(4,31)32/h5-8,13,16-17,27-28H,9-12H2,1-4H3,(H,29,30)/t16-,17-/m1/s1/f/h29H 
FBI InChIKey         InChI                1.02b ZVPAUNJUMAQCNK-JSUUWLAWDG                                                                                                                                                               
FBI SMILES_CANONICAL CACTVS               3.341 CC(C)c1nc(nc(c2ccc(F)cc2)c1CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C)[S](C)(=O)=O                                                                                                                
FBI SMILES           CACTVS               3.341 CC(C)c1nc(nc(c2ccc(F)cc2)c1CC[CH](O)C[CH](O)CC(O)=O)N(C)[S](C)(=O)=O                                                                                                                    
FBI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)c1c(c(nc(n1)N(C)S(=O)(=O)C)c2ccc(cc2)F)CC[C@H](C[C@H](CC(=O)O)O)O                                                                                                                  
FBI SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)c1c(c(nc(n1)N(C)S(=O)(=O)C)c2ccc(cc2)F)CCC(CC(CC(=O)O)O)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 
FBI "SYSTEMATIC NAME" ACDLabs              10.04 "(3R,5R)-7-{4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl}-3,5-dihydroxyheptanoic acid" 
FBI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(3R,5R)-7-[4-(4-fluorophenyl)-2-(methyl-methylsulfonyl-amino)-6-propan-2-yl-pyrimidin-5-yl]-3,5-dihydroxy-heptanoic acid"   
# 
