TENUAZONIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H15NO3
Molecular Weight	197.231
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@H](C)[C@@H]1NC(=O)C(C(C)=O)=C1O

InChI

InChIKey=CEIZFXOZIQNICU-XNCJUZBTSA-N

InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,8,13H,4H2,1-3H3,(H,11,14)/t5-,8-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C10H15NO3
Molecular Weight	197.231
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12111715
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17379181

Tenuazonic acid is one of the major Alternaria mycotoxins commonly found as a natural contaminant in food. Tenuazonic acid contamination has been linked to esophageal cancer in human populations at risk of high exposure. Tenuazonic acid inhibits protein synthesis by suppression at the ribosome. Tenuazonic acid was shown to inhibit 12-O-tetradecanoyl phorbol-13-acetate (TPA) induced ornithine decarboxylase (ODC) activity in a mouse model, and in turn suppressed mouse skin tumor promotion. In addition, this compound has been shown to be a new type of Photosystem II inhibitor.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Evaluation of an enzyme immunoassay for the detection of the mycotoxin tenuazonic acid in sorghum grains and sorghum-based infant food.	2017-02	27957687
Determination of Exposure to the Alternaria Mycotoxin Tenuazonic Acid and Its Isomer allo-Tenuazonic Acid in a German Population by Stable Isotope Dilution HPLC-MS(3).	2016-08-31	27452834

Patents

Sample Use Guides

In Vivo Use Guide

in mice: (skin carcinogenesis): Female Swiss albino mice were exposed topically to 100 nmole of 7,12-dimethyl benz(a) antracene (DMBA) twice weekly for 20 weeks. Another group of animals was treated with 250 microg tenuazonic acid (TA) in acetone daily for a period of 1 week, followed by the same dose of TA prior to every application of DMBA.

Route of Administration: Topical

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:07:48 GMT 2025` Edited by `admin` on `Mon Mar 31 22:07:48 GMT 2025`
Record UNII	Y2J8Y1TO29
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TENUAZONIC ACID

Common Name

English

AAC-TOXIN

Preferred Name

English

2H-PYRROL-2-ONE, 3-ACETYL-1,5-DIHYDRO-4-HYDROXY-5-((1S)-1-METHYLPROPYL)-, (5S)-

Systematic Name

English

TENUAZONIC ACID, HYDROXY FORM

Common Name

English

2,4-PYRROLIDINEDIONE, 3-(1-HYDROXYETHYLIDENE)-5-((1S)-1-METHYLPROPYL)-, (5S)-

Systematic Name

English

2,4-PYRROLIDINEDIONE, 3-ACETYL-5-((1S)-1-METHYLPROPYL)-, (5S)-

Systematic Name

English

L-TENUAZONIC ACID

Common Name

English

(5S)-3-ACETYL-1,5-DIHYDRO-4-HYDROXY-5-((1S)-1-METHYLPROPYL)-2H-PYRROL-2-ONE

Systematic Name

English

TENUAZONIC ACID [MI]

Common Name

English

TENUAZONIC ACID, DIONE FORM

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C674