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ergosterol

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EntityQ143263· pop 36· linked from 468 articles

ergosterol

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Also 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

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)

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Article

10 sections
Contents
  • 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.

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