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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H20O6
Molecular Weight 296.3157
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEOXYNIVALENOL

SMILES

[H][C@@]12O[C@]3([H])C=C(C)C(=O)[C@@H](O)[C@]3(CO)[C@@](C)(C[C@H]1O)[C@]24CO4

InChI

InChIKey=LINOMUASTDIRTM-QGRHZQQGSA-N
InChI=1S/C15H20O6/c1-7-3-9-14(5-16,11(19)10(7)18)13(2)4-8(17)12(21-9)15(13)6-20-15/h3,8-9,11-12,16-17,19H,4-6H2,1-2H3/t8-,9-,11-,12-,13-,14-,15+/m1/s1

HIDE SMILES / InChI

Molecular Formula C15H20O6
Molecular Weight 296.3157
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Deoxynivalenol (DON) is one of several mycotoxins produced by certain Fusarium species that frequently infect corn, wheat, oats, barley, rice, and other grains in the field or during storage. DON-induced activation of the p44/42 ERK signaling pathway inhibits the expression of claudin-4 protein, which leads to impaired intestinal barrier function. Given the high levels of DON in cereal grains, these observations of impaired barrier function have implications for human and animal health.

CNS Activity

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
in animals: Acute toxicity: Male B6C3F1 mice were orally administered deoxynivalenol (DON) (25 mg/kg [84 µmol/kg]) to assess the kinetics of DON distribution and clearance. DON was detectable in the plasma, liver, spleen, and brain from 5 minutes up to 24 hours post administration chronic toxicity: Female B6C7F1 mice (7 weeks old) were fed experimental diets for 16 weeks that contained DON (20 mg/kg [67 µmol/kg]). DON reduced the mean daily food consumption (2.94 ± 0.66 g vs. 3.6 ± 0.48 g), the mean body weight gain (2.76 ± 0.84 g vs.12.94 ± 1.68 g), and total body weight, and increased serum immunoglobulin A (IgA) levels in treated vs. control mice starting 8 weeks after diet initiation.
Route of Administration: Oral
In Vitro Use Guide
Porcine circovirus type 2 (PCV2) is the main causative agent of several syndromes in weaning piglets collectively known as porcine circovirus-associated disease (PCVAD). The objectives of this study were to investigate the impact of deoxynivalenol (DON) on PCV2 replication in NPTr permissive cell line. Noninfected and infected cells with PCV2 were treated with increasing concentrations of DON (0, 70, 140, 280, 560, 1200 ng/mL) and cell survival and virus titer were evaluated 72 h postinfection. In vitro results showed that low concentrations of DON could potentially increase PCV2 replication depending on virus genotype.
Substance Class Chemical
Record UNII
JT37HYP23V
Record Status Validated (UNII)
Record Version