lanosterol
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 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
2,896 papersArticle
4 sectionsContents
- Biosynthesis
- Research as an eye drop supplement
- See also
- References
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.
==Biosynthesis== The biosynthesis of lanosterol has been intensively investigated. {| class="wikitable" ! Description !! Illustration !! Enzyme |- | Two molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalene || 400px || squalene synthase |- | Squalene is oxidized to 2,3-oxidosqualene (squalene epoxide) || 400x400px || squalene monooxygenase |- | 2,3-Oxidosqualene is converted to a protosterol cation and finally to lanosterol || 400px || lanosterol synthase |- | (step 2) || 400px || (step 2) |}