Compound: lovastatin
SMILES: O=C1O[C@@H](C[C@H](C1)O)CC[C@@H]2[C@@H]3C(C=C[C@@H]2C)=C[C@H](C)C[C@@H]3OC(=O)[C@H](CC)C
InChIKey: PCZOHLXUXFIOCF-BXMDZJJMSA-N
Synonyms: lovastatin, 75330-75-5, mevinolin, Mevacor, Altoprev, Mevlor, Sivlor, Altocor, MK-803, Monacolin K, Lovastatine, 6alpha-Methylcompactin, Lovastatina, Mevinacor, Lovastatinum [Latin], 6-alpha-Methylcompactin, Lovastatinum, MK 803, DTXSID5020784, 9LHU78OQFD, NSC-758662, (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate, L-154803, C10AA02, 2beta,6alpha-Dimethyl-8alpha-(2-methyl-1-oxobutoxy)-mevinic acid lactone, [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate, DTXCID50784, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-(2-(2R,4R)-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl (S)-2-methyl-butyrate, CHEBI:40303, 6-Methylcompactin, NSC633781, Lovastatinum (Latin), (1S-(1alpha(R*),3alpha,7beta,8beta(2S*,4S*),8abeta))-2-Methylbutanoic acid 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (S)-2-Methylbutyric acid, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one, 1,2,6,7,8,8a-Hexahydro-beta,delta-dihydroxy-2,6-dimethyl-8-(2-methyl-1-oxobutyoxy)-1-naphthaleneheptanoic acid delta-lactone, Butanoic acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (1S-(1alpha(R*),3alpha,7beta,8beta(2S*,4S*),8abeta))-, 1 alpha-Isomer Lovastatin, 6 Methylcompactin, (1S,3R,7S,8S,8aR)-8-(2-((2R,4R)-4-Hydroxy-6-oxooxan-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate, MK803, alpha-Isomer Lovastatin, 1, ML-530B, Mevinacor 10, Mevinacor 40, ((1S,3R,7S,8S,8aR)-8-(2-((2R,4R)-4-hydroxy-6-oxooxan-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl) (2S)-2-methylbutanoate, (S)-2-Methylbutyric acid, 8-ester with (4R,6R)-6-[2-[(1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl]ethyl]tetrahydro-4-hydroxy-2H-pyran-2-one, Lovastatin, 1 alpha, RefChem:5964, (2S)-2-Methylbutanoic Acid, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl Ester, (8-(2-(4-hydroxy-6-oxooxan-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl) 2-methylbutanoate, 616-212-7, ((1S,3R,7S,8S,8aR)-8-(2-((2R,4R)-4-hydroxy-6-oxooxan-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl) (2R)-2-methylbutanoate, Lovalord, Nergadan, Artein, Lovastatine [French], Lovastatina [Spanish], Lovalip, Hipovastin, Lovasterol, Cholestra, Closterol, Colevix, Hipolip, Lestatin, Lipivas, Lipofren, Lovastin, Lozutin, Paschol, Rodatin, Rovacor, Tecnolip, Teroltrat, Belvas, Lipdip, Taucor, butanoic acid, 2-methyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester, (2S)-, Lovastatin [USAN], MLS000069585, Lovastatin (Standard), 6.alpha.-Methylcompactin, MSD 803, MFCD00072164, SMR000058779, (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, C24H36O5, (S)-(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 2-methylbutanoate, HSDB 6534, NCGC00023509-03, Liposcler, 6 alpha-Methylcompactin, Rextat, Monakolin K, Lovastatin (Mevacor), (+)-mevinolin, (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 (S)-2-methylbutanoate, [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxo-tetrahydropyran-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate, Mevacor (TN), CHEMBL503, Lovastatin & Primycin, Lovastatin (USP/INN), SR-05000001880, UNII-9LHU78OQFD, Simvastatin EP Impurity E, BRN 3631989, Tancor, Mevinolin from Aspergillus sp., CCRIS 8092, Mevinacor;, Lipofren;, Nergadan;, Mevacor;, Lovastatin CRS, Monacolin K;, 1cqp, Lovastatin [USAN:USP:INN:BAN], (2S)-2-METHYLBUTANOIC ACID (1S,3R,7S,8S,8AR)-1,2,3,7,8,8A-HEXAHYDRO-3,7-DIMETHYL-8-(2-((2R,4R)-TETRAHYDRO-4-HYDROXY-6-OXO-2H-PYRAN-2-YL)ETHYL)-1-NAPHTHALENYL ESTER, (2S)-2-Methylbutanoic acid (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester, Butanoic acid, 2-methyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (2S)-, Prestwick_819, CAS-75330-75-5, Mevinolin (lovastatin), LOVASTATIN [MI], LOVASTATIN [INN], Opera_ID_1578, Prestwick0_000516, Prestwick1_000516, Prestwick2_000516, Prestwick3_000516, Spectrum3_001873, Spectrum5_001294, Lovastatin (MK-803), LOVASTATIN [HSDB], LOVASTATIN [VANDF], EC 616-212-7, LOVASTATIN [MART.], SCHEMBL3136, LOVASTATIN [USP-RS], LOVASTATIN [WHO-DD], US9115116, lovastatin, BIDD:PXR0113, BSPBio_000471, BSPBio_001265, BSPBio_003346, cid_53232, MLS001055358, MLS006011867, US9353061, Lovastatina, BIDD:GT0749, DivK1c_001032, SPECTRUM1503977, SPBio_002392, BPBio1_000519, GTPL2739, Lovastatin - Bio-X trade mark, MEGxm0_000398, orb1309414, orb3139800, LOVASTATIN [ORANGE BOOK], ACon0_000534, ACon1_000390, BDBM34168, HMS503O05, HY-N0504R, KBio1_001032, KBio3_002848, LOVASTATIN [EP MONOGRAPH], Simvastatin impurity, lovastatin-, Lovastatin for peak identification, NINDS_001032, GLXC-06458, HMS1569H13, HMS1792O07, HMS1923O13, HMS1990O07, HMS2089M06, HMS2093O03, HMS2096H13, HMS2236F07, HMS3039N16, HMS3259F10, HMS3268C03, HMS3403O07, HMS3412H19, HMS3676H19, HMS3713H13, HMS3884B03, LOVASTATIN [USP MONOGRAPH], Pharmakon1600-01503977, ADVICOR COMPONENT LOVASTATIN, ALBB-027272, HY-N0504, MK-803; LOVALIP; MEVACOR, MSK10235, Tox21_110888, Tox21_201475, Tox21_300268, BBL024473, CCG-39627, EBC-02080, NSC758662, NSC779704, s2061, SBB080686, STK801953, AKOS005267139, Lovastatin for peak identification CRS, Lovastatin; Simvastatin EP Impurity E, Tox21_110888_1, CS-1990, DB00227, FH24950, KS-1082, Mevinolin from Aspergillus sp., powder, NC00713, NSC 758662, NSC-633781, NSC-779704, IDI1_001032, NCGC00023509-04, NCGC00023509-05, NCGC00023509-06, NCGC00023509-07, NCGC00023509-08, NCGC00023509-09, NCGC00023509-10, NCGC00023509-11, NCGC00023509-13, NCGC00023509-14, NCGC00023509-16, NCGC00254157-01, NCGC00259026-01, AC-13961, BL164644, Butanoic acid, 2-methyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (2S)-, G226, SMR000673570, SBI-0051881.P002, CS-0694830, L0214, NS00000544, SIMVASTATIN IMPURITY E [EP IMPURITY], EN300-52515, C07074, D00359, M02056, AB00052400-17, AB00052400_18, AB00052400_19, Mevinolin from Aspergillus sp., >=98% (HPLC), Q417740, SR-01000000123, SR-01000000123-3, SR-05000001880-1, SR-05000001880-2, BRD-K09416995-001-06-8, BRD-K09416995-001-21-7, BRD-K09416995-001-38-1, BRD-K09416995-001-39-9, BRD-K09416995-001-40-7, Mevacor;Monacolin K;mevinolin;6-alpha-Methylcompactin, SIMVASTATIN IMPURITY, LOVASTATIN- [USP IMPURITY], Z754931258, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-8-(2-((4R,6R)-4-hydroxy-2-oxo-2H-pyran-6-yl)ethyl)-3,7-dimethylnaphtyl(S)-2-methylbutyrat, (S)-2-Methyl-butyric acid (1S,3R,7S,8S,8aR)-8-[2-((3R,5R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl ester, 1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl 2-methylbutanoate, 1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate, 8-[2-((2R,4R)-4-hydroxy-6-oxo(2H-3,4,5-trihydropyran-2-yl))ethyl](1S,7S,8S,3R, 8aR)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthyl (2S)-2-methylbutanoate, Butanoic acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-- oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (1S-(1alpha(R*),3alpha,7beta,8beta(2S*,4S*),8abeta))-, BUTANOIC ACID, 2-METHYL-, 1,2,3,7,8,8A-HEXAHYDRO-3,7-DIMETHYL-8-(2-(TETRAHYDRO-4-HYDROXY-6-OXO-2H-PYRAN-2-YL)ETHYL)-1-NAPHTHALENYL ESTER, (1S-(1.ALPHA.(R*),3.ALPHA.,7.BETA.,8.BETA.(2S*,4S*),8.ALPHA..BETA.))-
Theoretical properties:
molecular_formula: C24H36O5
molecular_weight: 404.5 g/mol
exact_mass: 404.25627424 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 7
heavy_atom_count: 29
topological_polar_surface_area: 72.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White crystals
color: White crystals
Descriptions:
pubchem: Lovastatin can cause developmental toxicity according to state or federal government labeling requirements.
chebi: A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as <em>Aspergillus terreus</em> and <em>Pleurotus ostreatus</em> (oyster mushroom).
chembl: LOVASTATIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Lovastatin, sold under the brand name Mevacor among others, is a statin medication, to treat high blood cholesterol and reduce the risk of cardiovascular disease. Its use is recommended together with lifestyle changes. It is taken by mouth.
Common side effects include diarrhea, constipation, headache, muscles pains, rash, and trouble sleeping. Serious side effects may include liver problems, muscle breakdown, and kidney failure. Use during pregnancy may harm the baby and use during breastfeeding is not recommended. It works by decreasing the liver's ability to produce cholesterol by blocking the enzyme HMG-CoA reductase.
Lovastatin was patented in 1979 and approved for medical use in 1987. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2023, it was the 132nd most commonly prescribed medication in the United States, with more than 4 million prescriptions.