(3R,5R)-7-[(1S,2S,8S,8aR)-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

• ChemBase ID: 4431
• Molecular Formular: C23H36O6
• Molecular Mass: 408.52834
• Monoisotopic Mass: 408.25118887
• SMILES: O=C(O)C[C@H](O)C[C@H](O)CC[C@H]1[C@H](C=CC2=CCC[C@H](OC(=O)[C@H](CC)C)[C@H]12)C
• Canonical SMILES: CC[C@@H](C(=O)O[C@H]1CCC=C2[C@H]1[C@@H](CC[C@H](C[C@H](CC(=O)O)O)O)[C@H](C=C2)C)C
• InChI: InChI=1S/C23H36O6/c1-4-14(2)23(28)29-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-17(24)12-18(25)13-21(26)27/h6,8-9,14-15,17-20,22,24-25H,4-5,7,10-13H2,1-3H3,(H,26,27)/t14-,15-,17+,18+,19-,20-,22-/m0/s1
• InChIKey: BOZILQFLQYBIIY-INTXDZFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,5R)-7-[(1S,2S,8S,8aR)-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
• IUPAC Traditional name: (3R,5R)-7-[(1S,2S,8S,8aR)-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
• Synonyms: Compactin; Mevastatin

Database IDs

• CAS Number: 73573-88-3
• PubChem SID: 160967863; 99443247
• PubChem CID: 446154

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.212299
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.643644
• LogD (pH = 7.4): -0.07435383
• Log P: 2.9506967
• Molar Refractivity: 112.126 cm^3
• Polarizability: 43.689632 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.03
• LOG S: -3.71
• Solubility (Water): 7.98e-02 g/l

DETAILS

DrugBank - DB06693

• Drug Groups: experimental
• Description: Mevastatin or compactin is a cholesterol-lowering agent isolated from Penicillium citinium. It was the first discovered agent belonging to the class of cholesterol-lowering medications known as statins. During a search for antibiotic compounds produced by fungi in 1971, Akira Endo at Sankyo Co. (Japan) discovered a class of compounds that appeared to lower plasma cholesterol levels. Two years later, the research group isolated a compound structurally similar to hydroxymethylglutarate (HMG) that inhibited the incorporation of acetate. The compound was proposed to bind to the reductase enzyme and was named compactin. Mevastatin is a competitive inhibitor of HMG-Coenzyme A (HMG-CoA) reductase with a binding affinity 10,000 times greater than the HMG-CoA substrate itself. Mevastatin is a pro-drug that is activated by in vivo hydrolysis of the lactone ring. It has served as one of the lead compounds for the development of the synthetic compounds used today.
• Indication: Not used therapeutically due to its many side effects.
• Pharmacology: The primary cause of cardiovascular disease is atherosclerotic plaque formation. Sustained elevations of cholesterol in the blood increase the risk of cardiovascular disease. Mevastatin lowers hepatic production of cholesterol by competitively inhibiting HMG-CoA reductase, the enzyme that catalyzes the rate-limiting step in the cholesterol biosynthesis pathway via the mevalonic acid pathway. Decreased hepatic cholesterol levels causes increased uptake of low density lipoprotein (LDL) cholesterol and reduces cholesterol levels in the circulation.
• Toxicity: Side effects include those of other statins, such as myalgias, abdominal pain, nausea. It also has a higher chance of giving more severe side effects related to myotoxicity (myopathy, myositis, rhabdomyolysis), and hepatotoxicity, than other statins. Due to these major side effects and their enhanced rate of occurance, Mevastatin is not given therapeutically.
• Affected Organisms: Humans and other mammals
• References: [Chemspider]
• External Links: Wikipedia

REFERENCES

• Pubchem
• Chemspider
• Chemspider