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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/17195275Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17195275
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 |
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Mutagenicity and genotoxicity of the mycotoxin ochratoxin A. | 1996 Feb 15 |
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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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Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. | 1999 May 7 |
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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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Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
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Photochemically catalyzed reaction of ochratoxin A with D- and L-cysteine. | 2002 Dec |
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Ochratoxin A induces apoptosis in human lymphocytes through down regulation of Bcl-xL. | 2004 Jun |
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Relative contribution of OAT and OCT transporters to organic electrolyte transport in rabbit proximal tubule. | 2004 Nov |
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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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Differential modulation of ochratoxin A absorption across Caco-2 cells by dietary polyphenols, used at realistic intestinal concentrations. | 2005 Oct 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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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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Proteome response to ochratoxin A-induced apoptotic cell death in mouse hippocampal HT22 cells. | 2009 Jul |
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Toxicities induced in cultured human hepatocarcinoma cells exposed to ochratoxin A: oxidative stress and apoptosis status. | 2009 Mar-Apr |
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Ochratoxin A impairs Nrf2-dependent gene expression in porcine kidney tubulus cells. | 2009 Oct |
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The mycotoxin ochratoxin A inhibits DNA topoisomerase II and induces polyploidy in cultured CHO cells. | 2009 Sep |
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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 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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Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity. | 2013 Jun |
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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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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 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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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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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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17344223
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27531992
Ochratoxin-A (OTA) treatment (50–750 nM) reduced the viability of Neuro-2a cells in a dose-dependent manner. The OTA induced toxicity showed 50.75% cell survival rate at 500 nM concentration.
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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