Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H17ClNO6.Na |
| Molecular Weight | 425.795 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].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=HXNIIXUGQQXXLM-VSLILLSYSA-M
InChI=1S/C20H18ClNO6.Na/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);/q;+1/p-1/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 |
|---|---|---|
| DNA adduct formation in mice treated with ochratoxin A. | 1991 |
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| Ochratoxin A-binding proteins in rat organs and plasma and in different cell lines of the kidney. | 1999 Jul 1 |
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| Transport of ochratoxin A by renal multispecific organic anion transporter 1. | 1999 Jun |
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| Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. | 2000 Feb 11 |
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| Aspartame prevents the karyomegaly induced by ochratoxin A in rat kidney. | 2001 May |
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| Identification of mammary carcinogens in rodent bioassays. | 2002 |
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| Functional characterization of rat organic anion transporter 5 (Slc22a19) at the apical membrane of renal proximal tubules. | 2005 Nov |
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| Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1. | 2005 Oct 1 |
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| A toxicogenomics approach to identify new plausible epigenetic mechanisms of ochratoxin a carcinogenicity in rat. | 2006 Jan |
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| In vitro gene expression data supporting a DNA non-reactive genotoxic mechanism for ochratoxin A. | 2007 Apr 15 |
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| Adult hippocampal neural stem/progenitor cells in vitro are vulnerable to the mycotoxin ochratoxin-A. | 2007 Jul |
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| Ochratoxin A: 13-week oral toxicity and cell proliferation in male F344/n rats. | 2007 Jun |
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| Reduction in antioxidant defenses may contribute to ochratoxin A toxicity and carcinogenicity. | 2007 Mar |
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| Carcinogen-specific gene expression profiles in short-term treated Eker and wild-type rats indicative of pathways involved in renal tumorigenesis. | 2007 May 1 |
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| The chloride dependence of the human organic anion transporter 1 (hOAT1) is blunted by mutation of a single amino acid. | 2007 May 4 |
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| MAPK-ERK activation in kidney of male rats chronically fed ochratoxin A at a dose causing a significant incidence of renal carcinoma. | 2007 Oct 15 |
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| Prevention of ochratoxin A-induced neural tube defects by folic acid in the genetic polydactyly/arhinencephaly mouse, Pdn/Pdn. | 2007 Sep |
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| Effect of ochratoxin A on redox-regulated transcription factors, antioxidant enzymes and glutathione-S-transferase in cultured kidney tubulus cells. | 2008 Aug |
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| Hepatocyte growth factor increases uptake of estradiol 17beta-D-glucuronide and Oatp1 protein level in rat hepatocytes. | 2008 Feb 2 |
|
| Ochratoxin A inhibits the production of tissue factor and plasminogen activator inhibitor-2 by human blood mononuclear cells: another potential mechanism of immune-suppression. | 2008 Jun 1 |
|
| Ochratoxin A impairs Nrf2-dependent gene expression in porcine kidney tubulus cells. | 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 |
|
| Ochratoxin A induces craniofacial malformation in mice acting on Dlx5 gene expression. | 2010 Jan 1 |
|
| Perturbation of mitosis through inhibition of histone acetyltransferases: the key to ochratoxin a toxicity and carcinogenicity? | 2011 Aug |
|
| 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 |
|
| 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 |
|
| 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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| 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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| 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 rat renal carcinogenicity with limited induction of oxidative stress responses. | 2014 Nov 1 |
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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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| Role of p53 in the progression from ochratoxin A-induced DNA damage to gene mutations in the kidneys of mice. | 2015 Mar |
|
| The influence of ochratoxin A on DNA adduct formation by the carcinogen aristolochic acid in rats. | 2015 Nov |
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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121596546
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DTXSID001009061
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89930-55-2
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LU2A4O8EY3
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SUBSTANCE RECORD
