Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H18ClNO6 |
| Molecular Weight | 403.813 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H]1CC2=C(Cl)C=C(C(=O)N[C@@H](CC3=CC=CC=C3)C(O)=O)C(O)=C2C(=O)O1
InChI
InChIKey=RWQKHEORZBHNRI-BMIGLBTASA-N
InChI=1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15+/m1/s1
| Molecular Formula | C20H18ClNO6 |
| Molecular Weight | 403.813 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17344223 | https://www.ncbi.nlm.nih.gov/pubmed/27531992
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17344223 | https://www.ncbi.nlm.nih.gov/pubmed/27531992
Ochratoxin A—a toxin produced by Aspergillus ochraceus, Aspergillus carbonarius, and Penicillium verrucosum—is one of the most-abundant food-contaminating mycotoxins. It is also a frequent contaminant of water-damaged houses and of heating ducts. Human exposure can occur through consumption of contaminated food products, particularly contaminated grain and pork products, as well as coffee, wine grapes, and dried grapes. The toxin has been found in the tissues and organs of animals, including human blood and breast milk. Ochratoxin A, like most toxic substances, has large species- and sex-specific toxicological differences.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inhibition of CXCL12-mediated chemotaxis of Jurkat cells by direct immunotoxicants. | 2016-07 |
|
| Quercetin protects human peripheral blood mononuclear cells from OTA-induced oxidative stress, genotoxicity, and inflammation. | 2016-07 |
|
| Effect of Penicillium mycotoxins on the cytokine gene expression, reactive oxygen species production, and phagocytosis of bovine macrophage (BoMacs) function. | 2015-12-25 |
|
| Assessment of global and gene-specific DNA methylation in rat liver and kidney in response to non-genotoxic carcinogen exposure. | 2015-12-01 |
|
| Modulation of the xenobiotic transformation system and inflammatory response by ochratoxin A exposure using a co-culture system of Caco-2 and HepG2 cells. | 2015-12 |
|
| A food contaminant ochratoxin A suppresses pregnane X receptor (PXR)-mediated CYP3A4 induction in primary cultures of human hepatocytes. | 2015-11-04 |
|
| The influence of ochratoxin A on DNA adduct formation by the carcinogen aristolochic acid in rats. | 2015-11 |
|
| Ochratoxin A activates opposing c-MET/PI3K/Akt and MAPK/ERK 1-2 pathways in human proximal tubule HK-2 cells. | 2015-08 |
|
| Role of p53 in the progression from ochratoxin A-induced DNA damage to gene mutations in the kidneys of mice. | 2015-03 |
|
| Ochratoxin A induces rat renal carcinogenicity with limited induction of oxidative stress responses. | 2014-11-01 |
|
| Repeated exposure to Ochratoxin A generates a neuroinflammatory response, characterized by neurodegenerative M1 microglial phenotype. | 2014-09 |
|
| Central role of Nix in the autophagic response to ochratoxin A. | 2014-07 |
|
| Downregulation of Rad51 participates in OTA-induced DNA double-strand breaks in GES-1 cells in vitro. | 2014-04-21 |
|
| Transcriptome-based functional classifiers for direct immunotoxicity. | 2014-03 |
|
| Ochratoxin A induces karyomegaly and cell cycle aberrations in renal tubular cells without relation to induction of oxidative stress responses in rats. | 2014-01-03 |
|
| Toxicogenomics-based identification of mechanisms for direct immunotoxicity. | 2013-10 |
|
| Potential endocrine disrupting effect of ochratoxin A on human placental 3β-hydroxysteroid dehydrogenase/isomerase in JEG-3 cells at levels relevant to human exposure. | 2013-07 |
|
| Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity. | 2013-06 |
|
| Zinc protects HepG2 cells against the oxidative damage and DNA damage induced by ochratoxin A. | 2013-04-15 |
|
| Endocrine disrupting effects of ochratoxin A at the level of nuclear receptor activation and steroidogenesis. | 2013-03-13 |
|
| Ochratoxin A-induced cell proliferation and tumor promotion in mouse skin by activating the expression of cyclin-D1 and cyclooxygenase-2 through nuclear factor-kappa B and activator protein-1. | 2013-03 |
|
| Effects of p53 knockout on ochratoxin A-induced genotoxicity in p53-deficient gpt delta mice. | 2013-02-08 |
|
| Molecular mechanisms underlying ochratoxin A-induced genotoxicity: global gene expression analysis suggests induction of DNA double-strand breaks and cell cycle progression. | 2013-02 |
|
| Ochratoxin a and mitotic disruption: mode of action analysis of renal tumor formation by ochratoxin A. | 2012-06 |
|
| Transcriptomic alterations induced by Ochratoxin A in rat and human renal proximal tubular in vitro models and comparison to a rat in vivo model. | 2012-04 |
|
| ERK and p38 MAPK signaling pathways are involved in ochratoxin A-induced G2 phase arrest in human gastric epithelium cells. | 2012-03-07 |
|
| Fate of the teratogenic and carcinogenic ochratoxin A in human perfused placenta. | 2012-01-05 |
|
| Ochratoxin A induces CYP3A4, 2B6, 3A5, 2C9, 1A1, and CYP1A2 gene expression in primary cultured human hepatocytes: a possible activation of nuclear receptors. | 2012-01 |
|
| Aberrant activation of ubiquitin D at G2 phase and apoptosis by carcinogens that evoke cell proliferation after 28-day administration in rats. | 2012 |
|
| Molecular events involved in ochratoxin A induced mitochondrial pathway of apoptosis, modulation by Bcl-2 family members. | 2011-11 |
|
| Ochratoxin A at nanomolar concentration perturbs the homeostasis of neural stem cells in highly differentiated but not in immature three-dimensional brain cell cultures. | 2011-08-28 |
|
| Site-specific in vivo mutagenicity in the kidney of gpt delta rats given a carcinogenic dose of ochratoxin A. | 2011-08 |
|
| Perturbation of mitosis through inhibition of histone acetyltransferases: the key to ochratoxin a toxicity and carcinogenicity? | 2011-08 |
|
| Aristolochic acid I and ochratoxin A differentially regulate VEGF expression in porcine kidney epithelial cells--the involvement of SP-1 and HIFs transcription factors. | 2011-07-28 |
|
| Ochratoxin A inhibits adipogenesis through the extracellular signal-related kinases-peroxisome proliferator-activated receptor-γ pathway in human adipose tissue-derived mesenchymal stem cells. | 2011-03 |
|
| The food-associated fungal neurotoxin ochratoxin A inhibits the absorption of glutamate by astrocytes through a decrease in cell surface expression of the excitatory amino-acid transporters GLAST and GLT-1. | 2010-09 |
|
| Immunopathological effects of ochratoxin A and T-2 toxin combination on broilers. | 2010-06 |
|
| Characterization of ochratoxin A-induced apoptosis in primary rat hepatocytes. | 2010-06 |
|
| Ochratoxin A induces G(2) phase arrest in human gastric epithelium GES-1 cells in vitro. | 2010-03-15 |
|
| Gender-dependent differences in the incidence of ochratoxin A-induced neural tube defects in the Pdn/Pdn mouse. | 2010-03 |
|
| Evaluation of transcriptional activity of caspase-3 gene as a marker of acute neurotoxicity in rat cerebellar granular cells. | 2010-03 |
|
| Ochratoxin A induces craniofacial malformation in mice acting on Dlx5 gene expression. | 2010-01-01 |
|
| Functional characterization of mouse organic anion transporting peptide 1a4 in the uptake and efflux of drugs across the blood-brain barrier. | 2010-01 |
|
| Intracellular zinc stores protect the intestinal epithelium from Ochratoxin A toxicity. | 2009-12 |
|
| Molecular characterization of preneoplastic lesions provides insight on the development of renal tumors. | 2009-10 |
|
| Low doses of ochratoxin A upregulate the protein expression of organic anion transporters Oat1, Oat2, Oat3 and Oat5 in rat kidney cortex. | 2009-09-15 |
|
| Culture period-dependent change of function and expression of ATP-binding cassette transporters in Caco-2 cells. | 2009-09 |
|
| The mycotoxin ochratoxin A inhibits DNA topoisomerase II and induces polyploidy in cultured CHO cells. | 2009-09 |
|
| Mutagenicity and genotoxicity of the mycotoxin ochratoxin A. | 1996-02-15 |
|
| Ochratoxin A decreases the activity of phosphoenolpyruvate carboxykinase and its mRNA content in primary cultures of rat kidney proximal convoluted tubule cells. | 1989-08-15 |
Sample Use Guides
Male F344 rats had been treated with 0, 21, 70, or 210 lg/kg bw OTA for 14, 28, or 90 days. Animals were administered OTA (Ochratoxin-A) dissolved in corn oil by gavage, 5 days/week.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:51:55 GMT 2025
by
admin
on
Mon Mar 31 18:51:55 GMT 2025
|
| Record UNII |
1779SX6LUY
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C45175
Created by
admin on Mon Mar 31 18:51:55 GMT 2025 , Edited by admin on Mon Mar 31 18:51:55 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
7719
Created by
admin on Mon Mar 31 18:51:55 GMT 2025 , Edited by admin on Mon Mar 31 18:51:55 GMT 2025
|
PRIMARY | |||
|
C44427
Created by
admin on Mon Mar 31 18:51:55 GMT 2025 , Edited by admin on Mon Mar 31 18:51:55 GMT 2025
|
PRIMARY | |||
|
DTXSID7021073
Created by
admin on Mon Mar 31 18:51:55 GMT 2025 , Edited by admin on Mon Mar 31 18:51:55 GMT 2025
|
PRIMARY | |||
|
4305
Created by
admin on Mon Mar 31 18:51:55 GMT 2025 , Edited by admin on Mon Mar 31 18:51:55 GMT 2025
|
PRIMARY | |||
|
201422
Created by
admin on Mon Mar 31 18:51:55 GMT 2025 , Edited by admin on Mon Mar 31 18:51:55 GMT 2025
|
PRIMARY | |||
|
1779SX6LUY
Created by
admin on Mon Mar 31 18:51:55 GMT 2025 , Edited by admin on Mon Mar 31 18:51:55 GMT 2025
|
PRIMARY | |||
|
C025589
Created by
admin on Mon Mar 31 18:51:55 GMT 2025 , Edited by admin on Mon Mar 31 18:51:55 GMT 2025
|
PRIMARY | |||
|
206-143-7
Created by
admin on Mon Mar 31 18:51:55 GMT 2025 , Edited by admin on Mon Mar 31 18:51:55 GMT 2025
|
PRIMARY | |||
|
OCHRATOXIN A
Created by
admin on Mon Mar 31 18:51:55 GMT 2025 , Edited by admin on Mon Mar 31 18:51:55 GMT 2025
|
PRIMARY | |||
|
442530
Created by
admin on Mon Mar 31 18:51:55 GMT 2025 , Edited by admin on Mon Mar 31 18:51:55 GMT 2025
|
PRIMARY | |||
|
m8099
Created by
admin on Mon Mar 31 18:51:55 GMT 2025 , Edited by admin on Mon Mar 31 18:51:55 GMT 2025
|
PRIMARY | Merck Index | ||
|
303-47-9
Created by
admin on Mon Mar 31 18:51:55 GMT 2025 , Edited by admin on Mon Mar 31 18:51:55 GMT 2025
|
PRIMARY | |||
|
166829
Created by
admin on Mon Mar 31 18:51:55 GMT 2025 , Edited by admin on Mon Mar 31 18:51:55 GMT 2025
|
PRIMARY |