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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
Structure of OCHRATOXIN A SODIUM

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

HIDE SMILES / InChI

Description
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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
1999 May 7
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.
2000 Feb 11
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
Identification of mammary carcinogens in rodent bioassays.
2002
Functional analysis of ABCA8, a new drug transporter.
2002 Oct 18
Ochratoxin A-induced renal cortex fibrosis and epithelial-to-mesenchymal transition: molecular mechanisms of ochratoxin A-injury and potential effects of red wine.
2005 Jan-Dec
Differential modulation of ochratoxin A absorption across Caco-2 cells by dietary polyphenols, used at realistic intestinal concentrations.
2005 Oct 15
Adult hippocampal neural stem/progenitor cells in vitro are vulnerable to the mycotoxin ochratoxin-A.
2007 Jul
Reduction in antioxidant defenses may contribute to ochratoxin A toxicity and carcinogenicity.
2007 Mar
Prevention of ochratoxin A-induced neural tube defects by folic acid in the genetic polydactyly/arhinencephaly mouse, Pdn/Pdn.
2007 Sep
Functional and immunochemical characterization of a novel organic anion transporter Oat8 (Slc22a9) in rat renal collecting duct.
2008
Both direct and indirect effects account for the pro-inflammatory activity of enteropathogenic mycotoxins on the human intestinal epithelium: stimulation of interleukin-8 secretion, potentiation of interleukin-1beta effect and increase in the transepithelial passage of commensal bacteria.
2008 Apr 1
Evaluation of putative biomarkers of nephrotoxicity after exposure to ochratoxin a in vivo and in vitro.
2008 Jun
Intracellular zinc stores protect the intestinal epithelium from Ochratoxin A toxicity.
2009 Dec
Ochratoxin A-mediated DNA and protein damage: roles of nitrosative and oxidative stresses.
2009 Jul
Culture period-dependent change of function and expression of ATP-binding cassette transporters in Caco-2 cells.
2009 Sep
Functional characterization of mouse organic anion transporting peptide 1a4 in the uptake and efflux of drugs across the blood-brain barrier.
2010 Jan
Gender-dependent differences in the incidence of ochratoxin A-induced neural tube defects in the Pdn/Pdn mouse.
2010 Mar
Evaluation of transcriptional activity of caspase-3 gene as a marker of acute neurotoxicity in rat cerebellar granular cells.
2010 Mar
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
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
Molecular events involved in ochratoxin A induced mitochondrial pathway of apoptosis, modulation by Bcl-2 family members.
2011 Nov
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
Fate of the teratogenic and carcinogenic ochratoxin A in human perfused placenta.
2012 Jan 5
ERK and p38 MAPK signaling pathways are involved in ochratoxin A-induced G2 phase arrest in human gastric epithelium cells.
2012 Mar 7
Molecular mechanisms underlying ochratoxin A-induced genotoxicity: global gene expression analysis suggests induction of DNA double-strand breaks and cell cycle progression.
2013 Feb
Effects of p53 knockout on ochratoxin A-induced genotoxicity in p53-deficient gpt delta mice.
2013 Feb 8
Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity.
2013 Jun
Endocrine disrupting effects of ochratoxin A at the level of nuclear receptor activation and steroidogenesis.
2013 Mar 13
Toxicogenomics-based identification of mechanisms for direct immunotoxicity.
2013 Oct
Downregulation of Rad51 participates in OTA-induced DNA double-strand breaks in GES-1 cells in vitro.
2014 Apr 21
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
Central role of Nix in the autophagic response to ochratoxin A.
2014 Jul
Transcriptome-based functional classifiers for direct immunotoxicity.
2014 Mar
Ochratoxin A induces rat renal carcinogenicity with limited induction of oxidative stress responses.
2014 Nov 1
Repeated exposure to Ochratoxin A generates a neuroinflammatory response, characterized by neurodegenerative M1 microglial phenotype.
2014 Sep
Ochratoxin A activates opposing c-MET/PI3K/Akt and MAPK/ERK 1-2 pathways in human proximal tubule HK-2 cells.
2015 Aug
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
A food contaminant ochratoxin A suppresses pregnane X receptor (PXR)-mediated CYP3A4 induction in primary cultures of human hepatocytes.
2015 Nov 4
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
Patents

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
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.
Name Type Language
OCHRATOXIN A SODIUM
Common Name English
OCHRATOXIN A SODIUM, (-)-
Common Name English
OCHRATOXIN A, SODIUM SALT
Common Name English
L-PHENYLALANINE, N-((5-CHLORO-3,4-DIHYDRO-8-HYDROXY-3-METHYL-1-OXO-1H-2-BENZOPYRAN-7-YL)CARBONYL)-, MONOSODIUM SALT, (R)-
Systematic Name English
Code System Code Type Description
PUBCHEM
121596546
Created by admin on Sat Dec 16 08:13:18 GMT 2023 , Edited by admin on Sat Dec 16 08:13:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID001009061
Created by admin on Sat Dec 16 08:13:18 GMT 2023 , Edited by admin on Sat Dec 16 08:13:18 GMT 2023
PRIMARY
CAS
89930-55-2
Created by admin on Sat Dec 16 08:13:18 GMT 2023 , Edited by admin on Sat Dec 16 08:13:18 GMT 2023
PRIMARY
FDA UNII
LU2A4O8EY3
Created by admin on Sat Dec 16 08:13:18 GMT 2023 , Edited by admin on Sat Dec 16 08:13:18 GMT 2023
PRIMARY