data_SIM
# 
_chem_comp.id                                    SIM 
_chem_comp.name                                  SIMVASTATIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H40 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         DIMETHYL-COMPACTIN 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-01-16 
_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                        436.582 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     SIM 
_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        1HW9 
_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 
SIM O1A  O1A  O 0 1 N N N 2.991  -12.141 -6.414  0.575  0.396  6.849  O1A  SIM 1  
SIM O1B  O1B  O 0 1 N N N 4.955  -13.041 -5.805  -0.867 -0.571 8.213  O1B  SIM 2  
SIM O3   O3   O 0 1 N N N 6.553  -11.097 -7.874  -0.439 1.226  4.528  O3   SIM 3  
SIM O5   O5   O 0 1 N N N 6.880  -7.026  -8.799  -0.526 1.269  2.031  O5   SIM 4  
SIM O14  O14  O 0 1 N N N 3.944  -9.727  -13.854 1.000  0.086  -1.916 O14  SIM 5  
SIM O18  O18  O 0 1 N N N 6.039  -10.733 -13.906 2.846  1.153  -2.498 O18  SIM 6  
SIM C1   C1   C 0 1 N N N 4.302  -12.070 -6.107  -0.436 -0.250 6.984  C1   SIM 7  
SIM C2   C2   C 0 1 N N N 4.867  -10.654 -6.170  -1.213 -0.695 5.772  C2   SIM 8  
SIM C3   C3   C 0 1 N N R 5.461  -10.255 -7.537  -0.511 -0.200 4.506  C3   SIM 9  
SIM C4   C4   C 0 1 N N N 5.999  -8.839  -7.534  -1.300 -0.652 3.275  C4   SIM 10 
SIM C5   C5   C 0 1 N N R 6.170  -8.246  -8.929  -0.598 -0.157 2.009  C5   SIM 11 
SIM C6   C6   C 0 1 N N N 4.803  -7.974  -9.584  -1.387 -0.609 0.779  C6   SIM 12 
SIM C7   C7   C 0 1 N N N 4.850  -7.731  -11.118 -0.690 -0.106 -0.486 C7   SIM 13 
SIM C8   C8   C 0 1 N N S 3.446  -7.695  -11.818 -1.537 -0.462 -1.710 C8   SIM 14 
SIM C9   C9   C 0 1 N N S 2.431  -6.686  -11.149 -3.019 -0.281 -1.379 C9   SIM 15 
SIM C10  C10  C 0 1 N N N 1.088  -6.742  -11.908 -3.876 -0.370 -2.604 C10  SIM 16 
SIM C11  C11  C 0 1 N N N 0.977  -7.080  -13.224 -3.428 -0.213 -3.838 C11  SIM 17 
SIM C12  C12  C 0 1 N N N 2.063  -7.402  -13.991 -1.989 0.052  -4.066 C12  SIM 18 
SIM C17  C17  C 0 1 N N N 1.887  -7.732  -15.307 -1.490 -0.082 -5.281 C17  SIM 19 
SIM C16  C16  C 0 1 N N R 3.023  -8.113  -16.289 -0.019 0.121  -5.539 C16  SIM 20 
SIM C15  C15  C 0 1 N N N 4.452  -8.063  -15.648 0.741  -0.341 -4.289 C15  SIM 21 
SIM C14  C14  C 0 1 N N S 4.443  -8.380  -14.123 0.309  0.532  -3.112 C14  SIM 22 
SIM C13  C13  C 0 1 N N R 3.505  -7.394  -13.370 -1.178 0.462  -2.874 C13  SIM 23 
SIM C9A  C9A  C 0 1 N N N 2.889  -5.213  -11.176 -3.220 1.088  -0.728 C9A  SIM 24 
SIM C18  C18  C 0 1 N N N 4.809  -10.804 -13.766 2.289  0.409  -1.726 C18  SIM 25 
SIM C19  C19  C 0 1 N N N 4.032  -12.146 -13.455 3.042  -0.155 -0.549 C19  SIM 26 
SIM C20  C20  C 0 1 N N N 4.502  -12.755 -12.087 4.527  0.192  -0.678 C20  SIM 27 
SIM C21  C21  C 0 1 N N N 4.141  -11.999 -10.783 5.291  -0.381 0.515  C21  SIM 28 
SIM C22  C22  C 0 1 N N N 4.245  -13.194 -14.595 2.876  -1.676 -0.520 C22  SIM 29 
SIM C23  C23  C 0 1 N N N 2.488  -11.938 -13.385 2.489  0.442  0.745  C23  SIM 30 
SIM C24  C24  C 0 1 N N N 2.720  -9.518  -16.846 0.416  -0.707 -6.749 C24  SIM 31 
SIM H1B  H1B  H 0 1 N N N 5.878  -12.991 -5.588  -0.369 -0.286 8.991  H1B  SIM 32 
SIM HO3  HO3  H 0 1 N N N 6.918  -10.851 -8.715  -1.349 1.551  4.565  HO3  SIM 33 
SIM HO5  HO5  H 0 1 N N N 6.986  -6.656  -9.667  -1.436 1.594  2.068  HO5  SIM 34 
SIM H21  1H2  H 0 1 N N N 4.093  -9.915  -5.854  -2.220 -0.281 5.814  H21  SIM 35 
SIM H22  2H2  H 0 1 N N N 5.620  -10.502 -5.362  -1.268 -1.783 5.755  H22  SIM 36 
SIM H3   H3   H 0 1 N N N 4.626  -10.348 -8.270  0.496  -0.614 4.464  H3   SIM 37 
SIM H41  1H4  H 0 1 N N N 5.363  -8.177  -6.900  -2.307 -0.238 3.318  H41  SIM 38 
SIM H42  2H4  H 0 1 N N N 6.954  -8.782  -6.962  -1.355 -1.740 3.259  H42  SIM 39 
SIM H5   H5   H 0 1 N N N 6.724  -8.966  -9.574  0.409  -0.571 1.967  H5   SIM 40 
SIM H61  1H6  H 0 1 N N N 4.090  -8.797  -9.345  -2.396 -0.201 0.824  H61  SIM 41 
SIM H62  2H6  H 0 1 N N N 4.293  -7.123  -9.074  -1.436 -1.698 0.758  H62  SIM 42 
SIM H71  1H7  H 0 1 N N N 5.420  -6.800  -11.345 0.289  -0.576 -0.573 H71  SIM 43 
SIM H72  2H7  H 0 1 N N N 5.508  -8.484  -11.609 -0.570 0.975  -0.429 H72  SIM 44 
SIM H8   H8   H 0 1 N N N 3.072  -8.735  -11.674 -1.349 -1.497 -1.996 H8   SIM 45 
SIM H9   H9   H 0 1 N N N 2.351  -7.005  -10.083 -3.323 -1.056 -0.675 H9   SIM 46 
SIM H10  H10  H 0 1 N N N 0.104  -6.516  -11.463 -4.928 -0.576 -2.471 H10  SIM 47 
SIM H11  H11  H 0 1 N N N -0.025 -7.093  -13.683 -4.107 -0.278 -4.675 H11  SIM 48 
SIM H17  H17  H 0 1 N N N 0.818  -7.690  -15.578 -2.144 -0.343 -6.100 H17  SIM 49 
SIM H16  H16  H 0 1 N N N 3.044  -7.354  -17.105 0.179  1.177  -5.724 H16  SIM 50 
SIM H151 1H15 H 0 0 N N N 5.156  -8.735  -16.191 1.813  -0.234 -4.451 H151 SIM 51 
SIM H152 2H15 H 0 0 N N N 4.945  -7.083  -15.848 0.503  -1.383 -4.079 H152 SIM 52 
SIM H14  H14  H 0 1 N N N 5.497  -8.285  -13.773 0.587  1.565  -3.318 H14  SIM 53 
SIM H13  H13  H 0 1 N N N 3.938  -6.374  -13.494 -1.501 1.466  -2.597 H13  SIM 54 
SIM H9A1 1H9A H 0 0 N N N 2.172  -4.500  -10.703 -4.228 1.152  -0.318 H9A1 SIM 55 
SIM H9A2 2H9A H 0 0 N N N 3.899  -5.110  -10.716 -2.493 1.220  0.072  H9A2 SIM 56 
SIM H9A3 3H9A H 0 0 N N N 3.121  -4.896  -12.219 -3.082 1.869  -1.476 H9A3 SIM 57 
SIM H201 1H20 H 0 0 N N N 4.135  -13.805 -12.011 4.645  1.275  -0.699 H201 SIM 58 
SIM H202 2H20 H 0 0 N N N 5.604  -12.915 -12.120 4.921  -0.234 -1.601 H202 SIM 59 
SIM H211 1H21 H 0 0 N N N 4.474  -12.431 -9.811  6.348  -0.133 0.423  H211 SIM 60 
SIM H212 2H21 H 0 0 N N N 4.507  -10.948 -10.858 4.897  0.044  1.438  H212 SIM 61 
SIM H213 3H21 H 0 0 N N N 3.038  -11.838 -10.749 5.172  -1.465 0.536  H213 SIM 62 
SIM H221 1H22 H 0 0 N N N 3.697  -14.140 -14.375 3.270  -2.102 -1.442 H221 SIM 63 
SIM H222 2H22 H 0 0 N N N 3.966  -12.779 -15.591 3.420  -2.085 0.330  H222 SIM 64 
SIM H223 3H22 H 0 0 N N N 5.327  -13.380 -14.785 1.818  -1.924 -0.428 H223 SIM 65 
SIM H231 1H23 H 0 0 N N N 1.940  -12.884 -13.165 2.684  1.514  0.762  H231 SIM 66 
SIM H232 2H23 H 0 0 N N N 2.223  -11.141 -12.651 1.414  0.268  0.795  H232 SIM 67 
SIM H233 3H23 H 0 0 N N N 2.104  -11.458 -14.315 2.974  -0.029 1.599  H233 SIM 68 
SIM H241 1H24 H 0 0 N N N 3.537  -9.792  -17.552 -0.127 -0.374 -7.633 H241 SIM 69 
SIM H242 2H24 H 0 0 N N N 2.571  -10.277 -16.043 1.486  -0.579 -6.910 H242 SIM 70 
SIM H243 3H24 H 0 0 N N N 1.708  -9.589  -17.308 0.200  -1.759 -6.565 H243 SIM 71 
# 
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 
SIM O1A C1   DOUB N N 1  
SIM O1B C1   SING N N 2  
SIM O1B H1B  SING N N 3  
SIM O3  C3   SING N N 4  
SIM O3  HO3  SING N N 5  
SIM O5  C5   SING N N 6  
SIM O5  HO5  SING N N 7  
SIM O14 C14  SING N N 8  
SIM O14 C18  SING N N 9  
SIM O18 C18  DOUB N N 10 
SIM C1  C2   SING N N 11 
SIM C2  C3   SING N N 12 
SIM C2  H21  SING N N 13 
SIM C2  H22  SING N N 14 
SIM C3  C4   SING N N 15 
SIM C3  H3   SING N N 16 
SIM C4  C5   SING N N 17 
SIM C4  H41  SING N N 18 
SIM C4  H42  SING N N 19 
SIM C5  C6   SING N N 20 
SIM C5  H5   SING N N 21 
SIM C6  C7   SING N N 22 
SIM C6  H61  SING N N 23 
SIM C6  H62  SING N N 24 
SIM C7  C8   SING N N 25 
SIM C7  H71  SING N N 26 
SIM C7  H72  SING N N 27 
SIM C8  C9   SING N N 28 
SIM C8  C13  SING N N 29 
SIM C8  H8   SING N N 30 
SIM C9  C10  SING N N 31 
SIM C9  C9A  SING N N 32 
SIM C9  H9   SING N N 33 
SIM C10 C11  DOUB N N 34 
SIM C10 H10  SING N N 35 
SIM C11 C12  SING N N 36 
SIM C11 H11  SING N N 37 
SIM C12 C17  DOUB N N 38 
SIM C12 C13  SING N N 39 
SIM C17 C16  SING N N 40 
SIM C17 H17  SING N N 41 
SIM C16 C15  SING N N 42 
SIM C16 C24  SING N N 43 
SIM C16 H16  SING N N 44 
SIM C15 C14  SING N N 45 
SIM C15 H151 SING N N 46 
SIM C15 H152 SING N N 47 
SIM C14 C13  SING N N 48 
SIM C14 H14  SING N N 49 
SIM C13 H13  SING N N 50 
SIM C9A H9A1 SING N N 51 
SIM C9A H9A2 SING N N 52 
SIM C9A H9A3 SING N N 53 
SIM C18 C19  SING N N 54 
SIM C19 C20  SING N N 55 
SIM C19 C22  SING N N 56 
SIM C19 C23  SING N N 57 
SIM C20 C21  SING N N 58 
SIM C20 H201 SING N N 59 
SIM C20 H202 SING N N 60 
SIM C21 H211 SING N N 61 
SIM C21 H212 SING N N 62 
SIM C21 H213 SING N N 63 
SIM C22 H221 SING N N 64 
SIM C22 H222 SING N N 65 
SIM C22 H223 SING N N 66 
SIM C23 H231 SING N N 67 
SIM C23 H232 SING N N 68 
SIM C23 H233 SING N N 69 
SIM C24 H241 SING N N 70 
SIM C24 H242 SING N N 71 
SIM C24 H243 SING N N 72 
# 
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 
SIM SMILES           ACDLabs              10.04 O=C(O)CC(O)CC(O)CCC2C(C=CC1=CC(CC(OC(=O)C(C)(C)CC)C12)C)C 
SIM InChI            InChI                1.02b 
InChI=1/C25H40O6/c1-6-25(4,5)24(30)31-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-18(26)13-19(27)14-22(28)29/h7-8,11,15-16,18-21,23,26-27H,6,9-10,12-14H2,1-5H3,(H,28,29)/t15-,16-,18+,19+,20-,21-,23-/m0/s1/f/h28H 
SIM InChIKey         InChI                1.02b XWLXKKNPFMNSFA-XQFOCRQSDD 
SIM SMILES_CANONICAL CACTVS               3.341 CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@@H]12 
SIM SMILES           CACTVS               3.341 CCC(C)(C)C(=O)O[CH]1C[CH](C)C=C2C=C[CH](C)[CH](CC[CH](O)C[CH](O)CC(O)=O)[CH]12 
SIM SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCC(C)(C)C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@H](C[C@H](CC(=O)O)O)O)C 
SIM SMILES           "OpenEye OEToolkits" 1.5.0 CCC(C)(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC(CC(CC(=O)O)O)O)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 
SIM "SYSTEMATIC NAME" ACDLabs              10.04 "(3R,5R)-7-{(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl}-3,5-dihydroxyheptanoic acid" 
SIM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-(2,2-dimethylbutanoyloxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxy-heptanoic acid"  
# 
