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
SMILES
[H][C@]1(NC(=O)C(C(C)=O)=C1O)[C@@H](C)CC
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
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17379181
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
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 |
|
| Evaluation of an enzyme immunoassay for the detection of the mycotoxin tenuazonic acid in sorghum grains and sorghum-based infant food. | 2017 Feb |
Patents
Sample Use Guides
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
Curator's Comment: The results of competitive replacement with [(14)C]atrazine combined with JIP-test and D1-mutant showed that Tenuazonic acid (TeA) should be considered as a new type of photosystem II inhibitor because it has a different binding behavior within Q(B)-niche from other known photosystem II inhibitors.
Unknown
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C674
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
610-88-8
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
PRIMARY | |||
|
54683011
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
PRIMARY | |||
|
128892-49-9
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
SUPERSEDED | |||
|
99152-09-7
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
ALTERNATIVE | |||
|
1446789-58-7
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
ALTERNATIVE | |||
|
75652-74-3
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
ALTERNATIVE | |||
|
Tenuazonic acid
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
PRIMARY | |||
|
16818-18-1
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
SUPERSEDED | |||
|
46286-76-4
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
NON-SPECIFIC STEREOCHEMISTRY | |||
|
27778-66-1
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
ALTERNATIVE | |||
|
Y2J8Y1TO29
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
PRIMARY | |||
|
136842
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
PRIMARY | |||
|
C858
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
PRIMARY | |||
|
9440
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
PRIMARY | |||
|
33061-01-7
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
NON-SPECIFIC STEREOCHEMISTRY | |||
|
m10562
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
PRIMARY | Merck Index | ||
|
DTXSID20926233
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
PRIMARY | |||
|
76562-67-9
Created by
admin on Sat Dec 16 08:30:35 GMT 2023 , Edited by admin on Sat Dec 16 08:30:35 GMT 2023
|
NON-SPECIFIC STEREOCHEMISTRY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
