Structure via PubChem · Public domain (PubChem)
エルゴステロール
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.
OverviewAI-generated
Ergosterol is a chemical compound with the formula C₂₈H₄₄O. Its mass is listed as 396.339, while its weight is recorded as 396.6. The substance has a charge of 0 and an xlogp value of 7.4. It features one hydrogen bond donor and one hydrogen bond acceptor, with a topological polar surface area of 20.2.
The compound is associated with a PubMed query count of 8088. It is referenced by 468 other encyclopedia articles.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
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 6 more facts
- found in taxon
- Saccharomyces cerevisiae
- 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
- subject has role
- provitamin
- Commons category
- Ergosterol
Sources (7)
via Wikidata · CC0
Article · 日本語
エルゴステロール (ergosterol) は、分子式 C28H44O、分子量 396.65 のステロールの一種。骨格を持つ脂溶性物質である。カビなどの菌類においてラノステロールから生合成される。紫外線を受けてとなり、これを経てエルゴカルシフェロール（ビタミンD2）となる。 菌類の細胞膜を構成する物質であり、動物の細胞におけるコレステロールと同様な働きをする。菌類には存在するが動物には見られないという性質は抗真菌薬の開発に応用されている。トリパノソーマのような原生生物の細胞膜の流動化剤 (fluidizer) としても作用し、これは東アフリカでみられるアフリカ睡眠病に対して用いられる。
Abstract from DBpedia / Wikipedia · CC BY-SA