Structure via PubChem · Public domain (PubChem)
ergosterol
Sign in to saveAlso known as (22E,24S)-24-methylcholesta-5,7,22-trien-3beta-ol, Ergosta-5,7,22-trien-3beta-ol, 24alpha-Methyl-22E-dehydrocholesterol, Ergosterin, Ergosta-5,7,22-trien-3-ol, (3beta,22E)-, 24R-Methylcholesta-5,7,2E-trien-3beta-ol, (3S,9S,10R,13R,14R,17R)-10,13-dimethyl-17-[(E,1R,4R)-1,4,5-trimethylhex-2-enyl]-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol, (3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Ergosterol (ergosta-5,7,22-trien-3β-ol) is a mycosterol found in cell membranes of fungi and protozoa, serving many of the same functions that cholesterol serves in animal cells. Because many fungi and protozoa cannot survive without ergosterol, the enzymes that synthesize it have become important targets for drug discovery. In human nutrition, ergosterol is a provitamin form of vitamin D2; exposure to ultraviolet (UV) light causes a chemical reaction that produces vitamin D2.
Chemical data
- Formula
- C28H44O
- Molecular weight
- 396.6 g/mol
- IUPAC name
- (3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
- SMILES
- C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3C2=CC=C4[C@@]3(CC[C@@H](C4)O)C)C
- InChIKey
- DNVPQKQSNYMLRS-APGDWVJJSA-N
- XLogP
- 7.4
- Polar surface area
- 20.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
8,088 papers- Regulation of Ergosterol Biosynthesis in Saccharomyces cerevisiae.Genes · 2020
- Ergosterol and Lanosterol Derivatives: Synthesis and Possible Biomedical Applications.ChemMedChem · 2025
- Outline of the biosynthesis and regulation of ergosterol in yeast.World journal of microbiology & biotechnology · 2019
- Ergosterol Peroxide: A Mushroom-Derived Compound with Promising Biological Activities-A Review.International journal of medicinal mushrooms · 2017
- Ergosterol-loaded brain-targeted liposomes attenuate stroke via gut microbiota-metabolite-brain axis modulation.Journal of nanobiotechnology · 2025
via PubMed
Wikidata facts
- Mass
- 396.339
Show 4 more facts
- chemical formula
- C₂₈H₄₄O
- isomeric SMILES
- C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3C2=CC=C4[C@@]3(CC[C@@H](C4)O)C)C
- canonical SMILES
- CC(C)C(C)C=CC(C)C1CCC2C1(CCC3C2=CC=C4C3(CCC(C4)O)C)C
- Commons category
- Ergosterol
Sources (7)
via Wikidata · CC0
~6 min read
Article
10 sectionsContents
- Role in fungi
- Biosynthesis
- As a vitamin D<sub>2</sub> precursor
- Target for antifungal drugs
- Target for antiprotozoal drugs
- Safety
- Toxicity
- Metabolism
- See also
- References
Ergosterol (ergosta-5,7,22-trien-3β-ol) is a mycosterol found in cell membranes of fungi and protozoa, serving many of the same functions that cholesterol serves in animal cells. Because many fungi and protozoa cannot survive without ergosterol, the enzymes that synthesize it have become important targets for drug discovery. In human nutrition, ergosterol is a provitamin form of vitamin D2; exposure to ultraviolet (UV) light causes a chemical reaction that produces vitamin D2.
==Role in fungi== Ergosterol (ergosta-5,7,22-trien-3β-ol) is a sterol found in fungi, and named after ergot, the common name of members of the fungal genus Claviceps from which ergosterol was first isolated. Ergosterol is a component of yeast and other fungal cell membranes, serving many of the same functions that cholesterol serves in animal cells. Its specificity in higher fungi is thought to be related to the climatic instabilities (highly varying humidity and moisture conditions) encountered by these organisms in their typical ecological niches (plant and animal surfaces, soil). Thus, despite the added energy requirements of ergosterol synthesis (if compared to cholesterol), ergosterol is thought to have evolved as a nearly ubiquitous, evolutionarily advantageous fungal alternative to cholesterol. This advantage could be linked to the presence of two conjugated double bonds in the structure (B-ring) of ergosterol giving it antioxidant properties. Additionally, the structure of ergosterol appears to have been finely tuned towards optimal interaction with saturated lipids.