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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H20N2.2C10H15NO3
Molecular Weight 634.8054
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZATHINE DITENUAZONATE

SMILES

[H][C@]1(NC(=O)C(C(C)=O)=C1O)[C@@H](C)CC.[H][C@]2(NC(=O)C(C(C)=O)=C2O)[C@@H](C)CC.C(CNCC3=CC=CC=C3)NCC4=CC=CC=C4

InChI

InChIKey=CRFJGWXZMWORFV-OFSDVPJRSA-N
InChI=1S/C16H20N2.2C10H15NO3/c1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16;2*1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h1-10,17-18H,11-14H2;2*5,8,13H,4H2,1-3H3,(H,11,14)/t;2*5-,8-/m.00/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

Molecular Formula C16H20N2
Molecular Weight 240.3434
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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

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
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:59:59 GMT 2023
Edited
by admin
on Sat Dec 16 18:59:59 GMT 2023
Record UNII
A77Y2XUW1C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENZATHINE DITENUAZONATE
Common Name English
2H-PYRROL-2-ONE, 3-ACETYL-1,5-DIHYDRO-4-HYDROXY-5-(1-METHYLPROPYL)-, (S-(R*,R*))-, COMPD. WITH N,N'-BIS(PHENYLMETHYL)-1,2-ETHANEDIAMINE (2:1)
Systematic Name English
1,2-ETHANEDIAMINE, N,N'-BIS(PHENYLMETHYL)-, COMPD. WITH (S-(R*,R*))-3-ACETYL-1,5-DIHYDRO-4-HYDROXY-5-(1-METHYLPROPYL)-2H-PYRROL-2-ONE (1:2)
Systematic Name English
ETHYLENEDIAMINE, N,N'-DIBENZYL-, COMPD. WITH L-3-ACETYL-5-SEC-BUTYL-4-HYDROXY-3-PYRROLIN-2-ONE (1:2)
Systematic Name English
N,N'-DIBENZYLETHYLENEDIAMINE L-TENUAZONATE
Common Name English
NSC-82260
Code English
3-PYRROLIN-2-ONE, 3-ACETYL-5-SEC-BUTYL-4-HYDROXY-, COMPD. WITH N,N'-DIBENZYLETHYLENEDIAMINE (2:1), L-
Systematic Name English
Code System Code Type Description
CAS
1476-70-6
Created by admin on Sat Dec 16 18:59:59 GMT 2023 , Edited by admin on Sat Dec 16 18:59:59 GMT 2023
SUPERSEDED
FDA UNII
A77Y2XUW1C
Created by admin on Sat Dec 16 18:59:59 GMT 2023 , Edited by admin on Sat Dec 16 18:59:59 GMT 2023
PRIMARY
CAS
105730-55-0
Created by admin on Sat Dec 16 18:59:59 GMT 2023 , Edited by admin on Sat Dec 16 18:59:59 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
CAS
18413-37-1
Created by admin on Sat Dec 16 18:59:59 GMT 2023 , Edited by admin on Sat Dec 16 18:59:59 GMT 2023
PRIMARY
PUBCHEM
123133495
Created by admin on Sat Dec 16 18:59:59 GMT 2023 , Edited by admin on Sat Dec 16 18:59:59 GMT 2023
PRIMARY
CAS
18684-25-8
Created by admin on Sat Dec 16 18:59:59 GMT 2023 , Edited by admin on Sat Dec 16 18:59:59 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
NSC
82260
Created by admin on Sat Dec 16 18:59:59 GMT 2023 , Edited by admin on Sat Dec 16 18:59:59 GMT 2023
PRIMARY
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