LIPID MAPS

Lanosterol is a naturally-occurring sterol and biosynthetic precursor of several animal, fungal, and protozoan steroids, including cholesterol and ergosterol.^1,2,3 Defects in the processing of lanosterol contribute to a wide variety of disorders, including the formation of cataracts.^2,4 Similarly, certain fungicides act by blocking lanosterol processing by fungi.^5,6

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References

1. Espenshade, P.J., and Hughes, A.L. Regulation of sterol synthesis in eukaryotes. Annu. Rev. Genet. 41, 401-427 (2007).

2. Saag, M.S., and Dismukes, W.E. Azole antifungal agents: Emphasis on new triazoles. Antimicrob. Agents Chemother. 32(1), 1-8 (1988).

3. Warrilow, A.G., Melo, N., Martel, C.M., et al. Expression, purification, and characterization of Aspergillus fumigatus sterol 14-a demethylase (CYP51) isoenzymes A and B. Antimicrob. Agents Chemother. 54(10), 4225-4234 (2010).

4. Clayton, P.T. Disorders of cholesterol biosynthesis. Arch. Dis. Child. 78(2), 185-189 (1998).

5. Asami, T., Mizutani, M., Shimada, U., et al. Triadimefon, a fungicidal triazole-type P450 inhibitor, induces brassinosteroid deficiency-like phenotypes in plants and binds to DWF4 protein in the brassinosteroid biosynthesis pathway. Biochem. J. 369 (Pt 1), 71-76 (2003).

6. Zhao, L., Chen, X.J., Zhu, J., et al. Lanosterol reverses protein aggregation in cataracts. Nature 523(7562), 607-611 (2015).

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Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

CAHGCLMLTWQZNJ-BQNIITSRSA-N

InChi (Click to copy)

InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1

SMILES (Click to copy)

C12CC[C@@]3([H])C(C)(C)[C@@H](O)CC[C@]3(C)C=1CC[C@]1(C)[C@@]([H])([C@@](C)([H])CC/C=C(\C)/C)CC[C@@]21C