لانوسترول

Also known as (3β)-lanosta-8,24-dien-3-ol, (3β,20R)-lanosta-8,24-dien-3-ol, lanosterin, (3beta,5alpha)-4,4,14-trimethylcholesta-8,24-dien-3-ol, (3beta)-lanosta-8,24-dien-3-ol, (2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol, (3 beta)-lanosta-8,24-dien-3-ol, (3beta,5alpha)-4,4,14-trimethyl-cholesta-8,24-dien-3-ol

Lanosterol is a tetracyclic triterpenoid and is the compound from which all animal and fungal steroids are derived. By contrast, plant steroids are produced via cycloartenol. In the eyes of vertebrates, lanosterol is a natural constituent, having a role in maintaining health of the lens. Lanosterol is the precursor to cholesterol.

Chemical data

Formula: C30H50O
Molecular weight: 426.7 g/mol
IUPAC name: (3S,5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
SMILES: C[C@H](CCC=C(C)C)[C@H]1CC[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C
InChIKey: CAHGCLMLTWQZNJ-BQNIITSRSA-N
XLogP: 8.9
Polar surface area: 20.2 Å²
H-bond donors: 1
H-bond acceptors: 1
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

2,896 papers

Lanosterol reverses protein aggregation in cataracts.Nature · 2015
Ergosterol and Lanosterol Derivatives: Synthesis and Possible Biomedical Applications.ChemMedChem · 2025
Post-lanosterol biosynthesis of cholesterol and cancer.Current opinion in pharmacology · 2012
Lanosterol analogs: dual-action inhibitors of cholesterol biosynthesis.Critical reviews in biochemistry and molecular biology · 1999
Lanosterol Disrupts the Aggregation of Amyloid-β Peptides.ACS chemical neuroscience · 2019

via PubMed

Wikidata facts

Has part: carbon
Mass: 426.386

Show 6 more facts

found in taxon: Lingulodinium polyedra
chemical formula: C₃₀H₅₀O
Commons category: Lanosterol
canonical SMILES: CC(CCC=C(C)C)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)O)C)C)C
isomeric SMILES: C[C@H](CCC=C(C)C)[C@H]1CC[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C
subject has role: primary metabolite

Sources (5)

via Wikidata · CC0