Structure via PubChem · Public domain (PubChem)
alternariol
Sign in to saveAlso known as AOH, 3,4',5-trihydroxy-6'-methyldibenzo-alpha-pyrone, 3,4,4'-trihydroxy-6'-methyl-2-biphenylcarboxylic acid gamma-lactone
Alternariol (commonly abbreviated as AOH) is a toxic metabolite of Alternaria fungi. It is an important contaminant in cereals and fruits. Alternariol exhibits antifungal and phytotoxic activity. It is reported to inhibit cholinesterase enzymes. It is also a mycoestrogen.
Chemical data
- Formula
- C14H10O5
- Molecular weight
- 258.23 g/mol
- IUPAC name
- 3,7,9-trihydroxy-1-methylbenzo[c]chromen-6-one
- SMILES
- CC1=CC(=CC2=C1C3=C(C(=CC(=C3)O)O)C(=O)O2)O
- InChIKey
- CEBXXEKPIIDJHL-UHFFFAOYSA-N
- XLogP
- 2.9
- Polar surface area
- 87 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
708 papers- Natural resorcylic lactones derived from alternariol.Beilstein journal of organic chemistry · 2024
- The characteristics, occurrence, and toxicological effects of alternariol: a mycotoxin.Archives of toxicology · 2024
- Alternariol.Acta crystallographica. Section E, Structure reports online · 2010
- Alternariol disturbs oocyte maturation and preimplantation development.Mycotoxin research · 2020
- Alternariol Monomethyl-Ether Induces Toxicity via Cell Death and Oxidative Stress in Swine Intestinal Epithelial Cells.Toxins · 2024
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- oxygen
- Mass
- 258.052823
Show 5 more facts
- found in taxon
- Gymnosporia acuminata
- canonical SMILES
- CC1=CC(=CC2=C1C3=CC(=CC(=C3C(=O)O2)O)O)O
- chemical formula
- C₁₄H₁₀O₅
- subject has role
- acetylcholinesterase inhibitor
- Commons category
- Alternariol
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Alternariol (commonly abbreviated as AOH) is a toxic metabolite of Alternaria fungi. It is an important contaminant in cereals and fruits. Alternariol exhibits antifungal and phytotoxic activity. It is reported to inhibit cholinesterase enzymes. It is also a mycoestrogen.
A 2017 in vitro assay study reported alternariol to be a full androgen agonist.
Excerpted from Wikipedia’s “alternariol” article, available under the CC BY-SA 4.0 licence.
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via Wikidata sitelinks · CC0