lovastatin   

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
SMILES / InChI / InChIKey
Canonical SMILES CCC(C(=O)OC1CC(C)C=C2C1C(CCC1CC(O)CC(=O)O1)C(C=C2)C)C
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
InChI Key PCZOHLXUXFIOCF-BXMDZJJMSA-N
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Pregnane X receptor Hs Agonist Full agonist 5.3 – 6.0 pEC50 - 7
pEC50 5.3 – 6.0 (EC50 5x10-6 – 1x10-6 M) [7]
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
hydroxymethylglutaryl-CoA reductase Hs Inhibitor Competitive 9.2 pKi - 1
pKi 9.2 (Ki 6x10-10 M) [1]
Description: Inhibition of HMG-CoA reductase
Conditions: Substrate concentrations: 200µM NADPH, HMG-CoA concentration varied- 17.5µM, 34.8µM or 52.1µM
hydroxymethylglutaryl-CoA reductase Mm Inhibitor Competitive 7.6 pIC50 - 2
pIC50 7.6 (IC50 2.7x10-8 M) [2]
Description: In vitro inhibition of HMG-CoA reductase
Conditions: Isolated enzyme HMG-CoA reductase
hydroxymethylglutaryl-CoA reductase Hs Inhibitor Competitive 7.3 – 7.7 pIC50 - 5,9
pIC50 7.7 (IC50 2x10-8 M) [9]
Description: in vitro inhition of HMG-CoA reductase
Conditions: Inhibitory activity assay used partially purified microsomal preparations.
pIC50 7.3 (IC50 5x10-8 M) [5]
Description: in vitro inhibition of HMG-CoA reductase
Conditions: Substrate concentrations: NADP 50mM, 0.91 mM HMG-CoA. Inhibition of cellular HMG-CoA reductase in cultures of hepatic cells (HEP G2, a human hepatoma cell line)
hydroxymethylglutaryl-CoA reductase Rn Inhibitor Competitive 6.3 – 8.5 pIC50 - 2,4-6,8,10
pIC50 8.5 (IC50 3x10-9 M) [8]
Description: in vitro inhition of HMG-CoA reductase
Conditions: Inhibition of rat liver microsomal HMG-CoA reductase. Sodium salt preparation used.
pIC50 8.1 (IC50 8x10-9 M) [6]
Description: in vitro inhibition of HMG-CoA reductase
Conditions: Substrate concentrations: 0.91mM HMG-CoA, 50mM NADP. Inhibition of HMG-CoA reductase in solubilized rat liver.
pIC50 8.1 (IC50 8x10-9 M) [5]
Description: in vitro inhibition of HMG-CoA reductase
Conditions: In vitro inhibition of HMG-CoA reductase in solubilized rat liver.
pIC50 8.0 (IC50 1.1x10-8 M) [2]
Description: in vitro inhibition of HMG-CoA reductase
Conditions: Inhibition of microsomal rat liver HMG-CoA reductase
pIC50 7.6 (IC50 2.7x10-8 M) [10]
Description: in vitro inhition of HMG-CoA reductase
Conditions: Substrate concentrations: 0.45 µM HMG-CoA, 4mM NADPH. Compound was evaluated for the inhibition of HMG-CoA reductase (COR) in rats.
pIC50 6.8 (IC50 1.6x10-7 M) [4]
Description: in vitro inhition of HMG-CoA reductase
Conditions: The Na+ salt of mevinoline was tested for HMG-CoA reductase inhibitory activity in a microsomal preparation
pIC50 6.3 (IC50 5.3x10-7 M) [4]
Description: in vitro inhition of HMG-CoA reductase
Conditions: The lactone form of lovastatin was tested for HMG-CoA reductase inhibitory activity in a microsomal preparation