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(C(=O)O1)C(O)=C(C=C2Cl)C(=O)N[C@@H](CC3=CC=CC=C3)C(O)=O
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
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 |
|---|---|---|
| Ochratoxin A decreases the activity of phosphoenolpyruvate carboxykinase and its mRNA content in primary cultures of rat kidney proximal convoluted tubule cells. | 1989 Aug 15 |
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| Mutagenicity and genotoxicity of the mycotoxin ochratoxin A. | 1996 Feb 15 |
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| Intracellular zinc stores protect the intestinal epithelium from Ochratoxin A toxicity. | 2009 Dec |
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| Molecular characterization of preneoplastic lesions provides insight on the development of renal tumors. | 2009 Oct |
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| Culture period-dependent change of function and expression of ATP-binding cassette transporters in Caco-2 cells. | 2009 Sep |
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| Low doses of ochratoxin A upregulate the protein expression of organic anion transporters Oat1, Oat2, Oat3 and Oat5 in rat kidney cortex. | 2009 Sep 15 |
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| Functional characterization of mouse organic anion transporting peptide 1a4 in the uptake and efflux of drugs across the blood-brain barrier. | 2010 Jan |
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| Ochratoxin A induces craniofacial malformation in mice acting on Dlx5 gene expression. | 2010 Jan 1 |
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| Immunopathological effects of ochratoxin A and T-2 toxin combination on broilers. | 2010 Jun |
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| Characterization of ochratoxin A-induced apoptosis in primary rat hepatocytes. | 2010 Jun |
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| Gender-dependent differences in the incidence of ochratoxin A-induced neural tube defects in the Pdn/Pdn mouse. | 2010 Mar |
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| Evaluation of transcriptional activity of caspase-3 gene as a marker of acute neurotoxicity in rat cerebellar granular cells. | 2010 Mar |
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| Ochratoxin A induces G(2) phase arrest in human gastric epithelium GES-1 cells in vitro. | 2010 Mar 15 |
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| 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 Sep |
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| Site-specific in vivo mutagenicity in the kidney of gpt delta rats given a carcinogenic dose of ochratoxin A. | 2011 Aug |
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| Perturbation of mitosis through inhibition of histone acetyltransferases: the key to ochratoxin a toxicity and carcinogenicity? | 2011 Aug |
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| 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 Aug 28 |
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| 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 Jul 28 |
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| 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 Mar |
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| Molecular events involved in ochratoxin A induced mitochondrial pathway of apoptosis, modulation by Bcl-2 family members. | 2011 Nov |
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| Aberrant activation of ubiquitin D at G2 phase and apoptosis by carcinogens that evoke cell proliferation after 28-day administration in rats. | 2012 |
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| 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 Apr |
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| Ochratoxin A induces CYP3A4, 2B6, 3A5, 2C9, 1A1, and CYP1A2 gene expression in primary cultured human hepatocytes: a possible activation of nuclear receptors. | 2012 Jan |
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| Fate of the teratogenic and carcinogenic ochratoxin A in human perfused placenta. | 2012 Jan 5 |
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| Ochratoxin a and mitotic disruption: mode of action analysis of renal tumor formation by ochratoxin A. | 2012 Jun |
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| ERK and p38 MAPK signaling pathways are involved in ochratoxin A-induced G2 phase arrest in human gastric epithelium cells. | 2012 Mar 7 |
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| Zinc protects HepG2 cells against the oxidative damage and DNA damage induced by ochratoxin A. | 2013 Apr 15 |
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| Molecular mechanisms underlying ochratoxin A-induced genotoxicity: global gene expression analysis suggests induction of DNA double-strand breaks and cell cycle progression. | 2013 Feb |
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| Effects of p53 knockout on ochratoxin A-induced genotoxicity in p53-deficient gpt delta mice. | 2013 Feb 8 |
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| 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 Jul |
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| Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity. | 2013 Jun |
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| 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 Mar |
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| Endocrine disrupting effects of ochratoxin A at the level of nuclear receptor activation and steroidogenesis. | 2013 Mar 13 |
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| Toxicogenomics-based identification of mechanisms for direct immunotoxicity. | 2013 Oct |
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| Downregulation of Rad51 participates in OTA-induced DNA double-strand breaks in GES-1 cells in vitro. | 2014 Apr 21 |
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| Ochratoxin A induces karyomegaly and cell cycle aberrations in renal tubular cells without relation to induction of oxidative stress responses in rats. | 2014 Jan 3 |
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| Central role of Nix in the autophagic response to ochratoxin A. | 2014 Jul |
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| Transcriptome-based functional classifiers for direct immunotoxicity. | 2014 Mar |
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| Ochratoxin A induces rat renal carcinogenicity with limited induction of oxidative stress responses. | 2014 Nov 1 |
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| Repeated exposure to Ochratoxin A generates a neuroinflammatory response, characterized by neurodegenerative M1 microglial phenotype. | 2014 Sep |
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| Ochratoxin A activates opposing c-MET/PI3K/Akt and MAPK/ERK 1-2 pathways in human proximal tubule HK-2 cells. | 2015 Aug |
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| 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 Dec |
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| Assessment of global and gene-specific DNA methylation in rat liver and kidney in response to non-genotoxic carcinogen exposure. | 2015 Dec 1 |
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| Effect of Penicillium mycotoxins on the cytokine gene expression, reactive oxygen species production, and phagocytosis of bovine macrophage (BoMacs) function. | 2015 Dec 25 |
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| Role of p53 in the progression from ochratoxin A-induced DNA damage to gene mutations in the kidneys of mice. | 2015 Mar |
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| The influence of ochratoxin A on DNA adduct formation by the carcinogen aristolochic acid in rats. | 2015 Nov |
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| A food contaminant ochratoxin A suppresses pregnane X receptor (PXR)-mediated CYP3A4 induction in primary cultures of human hepatocytes. | 2015 Nov 4 |
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| Inhibition of CXCL12-mediated chemotaxis of Jurkat cells by direct immunotoxicants. | 2016 Jul |
|
| Quercetin protects human peripheral blood mononuclear cells from OTA-induced oxidative stress, genotoxicity, and inflammation. | 2016 Jul |
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
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C45175
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C44427
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OCHRATOXIN A
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m8099
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SUBSTANCE RECORD
