GtoPdb Ligand ID: 2739

Synonyms: (+)-mevinolin | 6α-methylcompactin | Mevacor®
lovastatin is an approved drug (FDA (1987))
Comment: Lovastatin is a 3-hydroxy-3-methylglutaryl-CoA reductase (HMG-CoA) inhibitor; a statin drug used for the prevention of cardiovascular diseases.
NB: there may be ambiguity in the chiral specification in the reported literature, compared to the structure represented here.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 72.83
Molecular weight 404.26
XLogP 4.57
No. Lipinski's rules broken 0
Isomeric SMILES CC[C@@H](C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)C
InChI InChI=1S/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
1. Alberts AW, Chen J, Kuron G, Hunt V, Huff J, Hoffman C, Rothrock J, Lopez M, Joshua H, Harris E et al.. (1980)
Mevinolin: a highly potent competitive inhibitor of hydroxymethylglutaryl-coenzyme A reductase and a cholesterol-lowering agent.
Proc. Natl. Acad. Sci. U.S.A., 77 (7): 3957-61. [PMID:6933445]
2. Bone EA, Cunningham EM, Davidson AH, Galloway WA, Lewis CN, Morrice EM, Reeve M, Todd RS, White IM. (1992)
The design and biological evaluation of a series of 3-hydroxy-3-methylglutaryl coenzyme a (HMG-CoA) reductase inhibitors related to dihydromevinolin.
Bioorg. Med. Chem. Lett., 2 (3): 223-228. DOI: 10.1016/S0960-894X(01)81069-6
3. Choi HW, Shin PG, Lee JH, Choi WS, Kang MJ, Kong WS, Oh MJ, Seo YB, Kim GD. (2018)
Anti-inflammatory effect of lovastatin is mediated via the modulation of NF-κB and inhibition of HDAC1 and the PI3K/Akt/mTOR pathway in RAW264.7 macrophages.
Int. J. Mol. Med., 41 (2): 1103-1109. [PMID:29207042]
4. Coppola GM, Damon RE, Yu H, Engstrom RG, Scallen TJ. (1997)
Design and biological evaluation of a series of thiophene-based 3-hydroxy-3-methylglutaryl coenzyme a reductase inhibitors.
Bioorg. Med. Chem. Lett., 7 (4): 549-554.
5. Jendralla H, Baader E, Bartmann W, Beck G, Bergmann A, Granzer E, von Kerekjarto B, Kesseler K, Krause R, Schubert W. (1990)
Synthesis and biological activity of new HMG-CoA reductase inhibitors. 2. Derivatives of 7-(1H-pyrrol-3-yl)-substituted-3,5-dihydroxyhept-6(E)-enoic (-heptanoic) acids.
J. Med. Chem., 33 (1): 61-70. [PMID:2153213]
6. Jendralla H, Granzer E, von Kerekjarto B, Krause R, Schacht U, Baader E, Bartmann W, Beck G, Bergmann A, Kesseler K. (1991)
Synthesis and biological activity of new HMG-CoA reductase inhibitors. 3. Lactones of 6-phenoxy-3,5-dihydroxyhexanoic acids.
J. Med. Chem., 34 (10): 2962-83. [PMID:1656041]
7. Lehmann JM, McKee DD, Watson MA, Willson TM, Moore JT, Kliewer SA. (1998)
The human orphan nuclear receptor PXR is activated by compounds that regulate CYP3A4 gene expression and cause drug interactions.
J. Clin. Invest., 102 (5): 1016-23. [PMID:9727070]
8. Procopiou PA, Draper CD, Hutson JL, Inglis GG, Ross BC, Watson NS. (1993)
Inhibitors of cholesterol biosynthesis. 2. 3,5-Dihydroxy-7-(N-pyrrolyl)-6-heptenoates, a novel series of HMG-CoA reductase inhibitors.
J. Med. Chem., 36 (23): 3658-62. [PMID:8246234]
9. Sliskovic DR, Blankley CJ, Krause BR, Newton RS, Picard JA, Roark WH, Roth BD, Sekerke C, Shaw MK, Stanfield RL. (1992)
Inhibitors of cholesterol biosynthesis. 6. trans-6-[2-(2-N-heteroaryl-3,5-disubstituted- pyrazol-4-yl)ethyl/ethenyl]tetrahydro-4-hydroxy-2H-pyran-2-ones.
J. Med. Chem., 35 (11): 2095-103. [PMID:1597859]
10. Sliskovic DR, Picard JA, Roark WH, Roth BD, Ferguson E, Krause BR, Newton RS, Sekerke C, Shaw MK. (1991)
Inhibitors of cholesterol biosynthesis. 4. trans-6-[2-(substituted-quinolinyl)ethenyl/ethyl]tetrahydro-4-hydroxy-2 H-pyran-2-ones, a novel series of HMG-CoA reductase inhibitors.
J. Med. Chem., 34 (1): 367-73. [PMID:1992138]