mevastatin

Also known as compactin, ML-236B, antibiotic ML 236B, CS 500, ML 236 B, Mévastatine, mevastatinum, Mevastatina

Mevastatin (compactin, ML-236B) is a hypolipidemic agent that belongs to the statins class.

Chemical data

Formula: C23H34O5
Molecular weight: 390.5 g/mol
IUPAC name: [(1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
SMILES: CC[C@H](C)C(=O)O[C@H]1CCC=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O
InChIKey: AJLFOPYRIVGYMJ-INTXDZFKSA-N
XLogP: 3.9
Polar surface area: 72.8 Å²
H-bond donors: 1
H-bond acceptors: 5
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule

via ChEMBL · EBI

Research

629 papers

Mevastatin promotes healing by targeting caveolin-1 to restore EGFR signaling.JCI insight · 2019
Effects of Mycotoxin Fumagillin, Mevastatin, Radicicol, and Wortmannin on Photosynthesis of Chlamydomonas reinhardtii.Plants (Basel, Switzerland) · 2023
Mevastatin promotes neuronal survival against Aβ-induced neurotoxicity through AMPK activation.Metabolic brain disease · 2017
Mevastatin-Induced HO-1 Expression in Cardiac Fibroblasts: A Strategy to Combat Cardiovascular Inflammation and Fibrosis.Environmental toxicology · 2025
Mevastatin in colon cancer by spectroscopic and microscopic methods - Raman imaging and AFM studies.Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy · 2022

via PubMed

Wikidata facts

Mass: 390.240624

Show 7 more facts

chemical formula: C₂₃H₃₄O₅
canonical SMILES: CCC(C)C(=O)OC1CCC=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O
isomeric SMILES: CC[C@H](C)C(=O)O[C@H]1CCC=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O
World Health Organisation international non-proprietary name: mevastatin
subject has role: antifungal
physically interacts with: 3-hydroxy-3-methylglutaryl-CoA reductase
Commons category: Mevastatin

Sources (2)

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Encyclopedic overview

4 sections

Contents

Biosynthesis
Pharmacology
See also
References

{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 462252043 | IUPAC_name = (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate | image = Mevastatin.svg | image_class = skin-invert-image | width = 215

| tradename = | pregnancy_category = | legal_status = | routes_of_administration =

Excerpted from Wikipedia’s “mevastatin” article, available under the CC BY-SA 4.0 licence.

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