SODIUM TENUAZONATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H14NO3.Na
Molecular Weight	219.2128
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[H][C@]1(NC(=O)C(C(C)=O)=C1[O-])[C@@H](C)CC

InChI

InChIKey=GNZBHOOZDKNFTO-XMLTWROESA-M

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

HIDE SMILES / InChI

Molecular Formula	C10H14NO3
Molecular Weight	196.2231
Charge	-1
Count

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

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 2578

PubMed

Title	Date	PubMed
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 Aug 31	27452834
Evaluation of an enzyme immunoassay for the detection of the mycotoxin tenuazonic acid in sorghum grains and sorghum-based infant food.	2017 Feb	27957687

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 `Sat Dec 16 07:56:18 GMT 2023` Edited by `admin` on `Sat Dec 16 07:56:18 GMT 2023`
Record UNII	J830SJ75M3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SODIUM TENUAZONATE

Common Name

English

TENUAZONIC ACID SODIUM SALT

Common Name

English

L-TENUAZONIC ACID SODIUM SALT

Common Name

English

SODIUM L-TENUAZONATE

Common Name

English

TENUAZONIC ACID SODIUM SALT [MI]

Common Name

English

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

Systematic Name

English

NSC-525816

Code

English

Code System Code Type Description

CAS

93115-21-0