data_803
# 
_chem_comp.id                                    803 
_chem_comp.name                                  LOVASTATIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H36 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "MK-803; LOVALIP; MEVACOR" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-08-11 
_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                        404.540 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     803 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "not provided" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   Y 
_chem_comp.pdbx_model_coordinates_db_code        1CQP 
_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 
803 C1   C1   C 0 1 N N S 52.497 19.025 23.052 ? ? ? C1   803 1  
803 C2   C2   C 0 1 N N N 52.393 17.482 22.971 ? ? ? C2   803 2  
803 C3   C3   C 0 1 N N R 52.359 16.834 24.377 ? ? ? C3   803 3  
803 C21  C21  C 0 1 N N N 53.777 16.458 24.857 ? ? ? C21  803 4  
803 C4   C4   C 0 1 N N N 51.698 17.697 25.428 ? ? ? C4   803 5  
803 C24  C24  C 0 1 N N N 51.206 18.918 25.189 ? ? ? C24  803 6  
803 C5   C5   C 0 1 N N N 50.582 19.686 26.274 ? ? ? C5   803 7  
803 C6   C6   C 0 1 N N N 50.106 20.922 26.085 ? ? ? C6   803 8  
803 C7   C7   C 0 1 N N S 50.176 21.632 24.761 ? ? ? C7   803 9  
803 C20  C20  C 0 1 N N N 48.868 21.542 23.949 ? ? ? C20  803 10 
803 C8   C8   C 0 1 N N S 51.364 21.058 23.971 ? ? ? C8   803 11 
803 C9   C9   C 0 1 N N R 51.266 19.532 23.823 ? ? ? C9   803 12 
803 C10  C10  C 0 1 N N N 51.447 21.694 22.580 ? ? ? C10  803 13 
803 C11  C11  C 0 1 N N N 51.671 23.209 22.727 ? ? ? C11  803 14 
803 C12  C12  C 0 1 N N R 52.177 23.696 21.366 ? ? ? C12  803 15 
803 C13  C13  C 0 1 N N N 52.436 25.218 21.438 ? ? ? C13  803 16 
803 C14  C14  C 0 1 N N R 51.599 25.984 20.409 ? ? ? C14  803 17 
803 O3   O3   O 0 1 N N N 52.158 25.821 19.102 ? ? ? O3   803 18 
803 C15  C15  C 0 1 N N N 50.196 25.374 20.521 ? ? ? C15  803 19 
803 C22  C22  C 0 1 N N N 50.282 23.978 19.974 ? ? ? C22  803 20 
803 O2   O2   O 0 1 N N N 49.463 23.585 19.156 ? ? ? O2   803 21 
803 O1   O1   O 0 1 N N N 51.261 23.169 20.389 ? ? ? O1   803 22 
803 O4   O4   O 0 1 N N N 53.678 19.407 23.772 ? ? ? O4   803 23 
803 C23  C23  C 0 1 N N N 54.765 19.395 22.995 ? ? ? C23  803 24 
803 O5   O5   O 0 1 N N N 54.734 19.102 21.809 ? ? ? O5   803 25 
803 C16  C16  C 0 1 N N S 56.030 19.778 23.712 ? ? ? C16  803 26 
803 C19  C19  C 0 1 N N N 57.059 18.637 23.609 ? ? ? C19  803 27 
803 C17  C17  C 0 1 N N N 56.607 21.070 23.116 ? ? ? C17  803 28 
803 C18  C18  C 0 1 N N N 55.592 22.202 23.360 ? ? ? C18  803 29 
803 H1   H1   H 0 1 N N N 52.544 19.457 22.025 ? ? ? H1   803 30 
803 H21  1H2  H 0 1 N N N 51.517 17.165 22.356 ? ? ? H21  803 31 
803 H22  2H2  H 0 1 N N N 53.209 17.052 22.345 ? ? ? H22  803 32 
803 H3   H3   H 0 1 N N N 51.738 15.915 24.256 ? ? ? H3   803 33 
803 H211 1H21 H 0 0 N N N 53.752 15.991 25.869 ? ? ? H211 803 34 
803 H212 2H21 H 0 0 N N N 54.299 15.805 24.118 ? ? ? H212 803 35 
803 H213 3H21 H 0 0 N N N 54.464 17.335 24.827 ? ? ? H213 803 36 
803 H4   H4   H 0 1 N N N 51.559 17.404 26.482 ? ? ? H4   803 37 
803 H5   H5   H 0 1 N N N 50.462 19.307 27.303 ? ? ? H5   803 38 
803 H6   H6   H 0 1 N N N 49.664 21.347 27.002 ? ? ? H6   803 39 
803 H7   H7   H 0 1 N N N 50.323 22.720 24.953 ? ? ? H7   803 40 
803 H201 1H20 H 0 0 N N N 48.919 22.068 22.967 ? ? ? H201 803 41 
803 H202 2H20 H 0 0 N N N 48.559 20.479 23.812 ? ? ? H202 803 42 
803 H203 3H20 H 0 0 N N N 48.003 21.909 24.549 ? ? ? H203 803 43 
803 H8   H8   H 0 1 N N N 52.286 21.299 24.549 ? ? ? H8   803 44 
803 H9   H9   H 0 1 N N N 50.347 19.248 23.258 ? ? ? H9   803 45 
803 H101 1H10 H 0 0 N N N 52.222 21.212 21.940 ? ? ? H101 803 46 
803 H102 2H10 H 0 0 N N N 50.555 21.457 21.953 ? ? ? H102 803 47 
803 H111 1H11 H 0 0 N N N 50.770 23.758 23.089 ? ? ? H111 803 48 
803 H112 2H11 H 0 0 N N N 52.344 23.478 23.574 ? ? ? H112 803 49 
803 H12  H12  H 0 1 N N N 53.176 23.320 21.045 ? ? ? H12  803 50 
803 H131 1H13 H 0 0 N N N 52.271 25.610 22.468 ? ? ? H131 803 51 
803 H132 2H13 H 0 0 N N N 53.521 25.451 21.334 ? ? ? H132 803 52 
803 H14  H14  H 0 1 N N N 51.574 27.083 20.592 ? ? ? H14  803 53 
803 HO3  HO3  H 0 1 N N N 51.638 26.296 18.463 ? ? ? HO3  803 54 
803 H151 1H15 H 0 0 N N N 49.780 25.415 21.555 ? ? ? H151 803 55 
803 H152 2H15 H 0 0 N N N 49.408 25.990 20.027 ? ? ? H152 803 56 
803 H16  H16  H 0 1 N N N 55.796 19.955 24.787 ? ? ? H16  803 57 
803 H191 1H19 H 0 0 N N N 57.997 18.921 24.140 ? ? ? H191 803 58 
803 H192 2H19 H 0 0 N N N 56.647 17.668 23.976 ? ? ? H192 803 59 
803 H193 3H19 H 0 0 N N N 57.251 18.341 22.551 ? ? ? H193 803 60 
803 H171 1H17 H 0 0 N N N 57.622 21.309 23.508 ? ? ? H171 803 61 
803 H172 2H17 H 0 0 N N N 56.883 20.963 22.041 ? ? ? H172 803 62 
803 H181 1H18 H 0 0 N N N 56.011 23.140 22.927 ? ? ? H181 803 63 
803 H182 2H18 H 0 0 N N N 54.576 21.962 22.967 ? ? ? H182 803 64 
803 H183 3H18 H 0 0 N N N 55.315 22.308 24.434 ? ? ? H183 803 65 
# 
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 
803 C1  C2   SING N N 1  
803 C1  C9   SING N N 2  
803 C1  O4   SING N N 3  
803 C1  H1   SING N N 4  
803 C2  C3   SING N N 5  
803 C2  H21  SING N N 6  
803 C2  H22  SING N N 7  
803 C3  C21  SING N N 8  
803 C3  C4   SING N N 9  
803 C3  H3   SING N N 10 
803 C21 H211 SING N N 11 
803 C21 H212 SING N N 12 
803 C21 H213 SING N N 13 
803 C4  C24  DOUB N N 14 
803 C4  H4   SING N N 15 
803 C24 C5   SING N N 16 
803 C24 C9   SING N N 17 
803 C5  C6   DOUB N N 18 
803 C5  H5   SING N N 19 
803 C6  C7   SING N N 20 
803 C6  H6   SING N N 21 
803 C7  C20  SING N N 22 
803 C7  C8   SING N N 23 
803 C7  H7   SING N N 24 
803 C20 H201 SING N N 25 
803 C20 H202 SING N N 26 
803 C20 H203 SING N N 27 
803 C8  C9   SING N N 28 
803 C8  C10  SING N N 29 
803 C8  H8   SING N N 30 
803 C9  H9   SING N N 31 
803 C10 C11  SING N N 32 
803 C10 H101 SING N N 33 
803 C10 H102 SING N N 34 
803 C11 C12  SING N N 35 
803 C11 H111 SING N N 36 
803 C11 H112 SING N N 37 
803 C12 C13  SING N N 38 
803 C12 O1   SING N N 39 
803 C12 H12  SING N N 40 
803 C13 C14  SING N N 41 
803 C13 H131 SING N N 42 
803 C13 H132 SING N N 43 
803 C14 O3   SING N N 44 
803 C14 C15  SING N N 45 
803 C14 H14  SING N N 46 
803 O3  HO3  SING N N 47 
803 C15 C22  SING N N 48 
803 C15 H151 SING N N 49 
803 C15 H152 SING N N 50 
803 C22 O2   DOUB N N 51 
803 C22 O1   SING N N 52 
803 O4  C23  SING N N 53 
803 C23 O5   DOUB N N 54 
803 C23 C16  SING N N 55 
803 C16 C19  SING N N 56 
803 C16 C17  SING N N 57 
803 C16 H16  SING N N 58 
803 C19 H191 SING N N 59 
803 C19 H192 SING N N 60 
803 C19 H193 SING N N 61 
803 C17 C18  SING N N 62 
803 C17 H171 SING N N 63 
803 C17 H172 SING N N 64 
803 C18 H181 SING N N 65 
803 C18 H182 SING N N 66 
803 C18 H183 SING N N 67 
# 
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 
803 SMILES           ACDLabs              10.04 O=C(OC1C3C(=CC(C)C1)C=CC(C3CCC2OC(=O)CC(O)C2)C)C(C)CC                                                                                                                                          
803 InChI            InChI                1.02b InChI=1/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1 
803 InChIKey         InChI                1.02b PCZOHLXUXFIOCF-BXMDZJJMBQ                                                                                                                                                                      
803 SMILES_CANONICAL CACTVS               3.341 CC[C@H](C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@@H]12                                                                                                      
803 SMILES           CACTVS               3.341 CC[CH](C)C(=O)O[CH]1C[CH](C)C=C2C=C[CH](C)[CH](CC[CH]3C[CH](O)CC(=O)O3)[CH]12                                                                                                                  
803 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@H](C)C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O)C                                                                                                         
803 SMILES           "OpenEye OEToolkits" 1.5.0 CCC(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)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 
803 "SYSTEMATIC NAME" ACDLabs              10.04 "(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate" 
803 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxo-oxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate"             
# 
