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Details

Stereochemistry ACHIRAL
Molecular Formula C14H10O5
Molecular Weight 258.2262
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALTERNARIOL

SMILES

CC1=C2C(OC(=O)C3=C2C=C(O)C=C3O)=CC(O)=C1

InChI

InChIKey=CEBXXEKPIIDJHL-UHFFFAOYSA-N
InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3

HIDE SMILES / InChI

Molecular Formula C14H10O5
Molecular Weight 258.2262
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Alternariol is the mycotoxin produced by Alternaria fungi. It occurs naturally in foodstuffs and is frequently found as contaminant in fruit and grain products. It forms reactive oxygen species and interacts with DNA topoisomerase, thereby generating both single- and double-strand DNA beaks. Alternariol demonstrated dual inhibition of acetylcholinesterase (AChE) and monoamine oxidase (MAO-A) enzymes extracted from whole and five different parts of male albino rat brains; namely: frontal cortex, basal ganglia, cerebellum, pons, medulla oblongata. In vitro studies have suggested that Alternariol may be linked to reduced immune response in case of infections and/or a disturbed balance of the adaptive immune system. Although the absorption appears to be relative low, it is nevertheless important to further clarify the mode of genotoxicity.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.8 mM [Ki]
2.4 mM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Logarithmic growth phase NIH/3T3 cells were treated at the dose of 10 uM/L and 50 uM/L altemariol. The inhibition rates of 10 uM/L and 50 uM/L altemariol were 19.88% and 32.47% respectively.
Substance Class Chemical
Record UNII
KN9L4260JW
Record Status Validated (UNII)
Record Version