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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
Mutagenicity and genotoxicity of the mycotoxin ochratoxin A.
1996 Feb 15
Ochratoxin A-binding proteins in rat organs and plasma and in different cell lines of the kidney.
1999 Jul 1
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
Photochemically catalyzed reaction of ochratoxin A with D- and L-cysteine.
2002 Dec
Ochratoxin A induces apoptosis in human lymphocytes through down regulation of Bcl-xL.
2004 Jun
Relative contribution of OAT and OCT transporters to organic electrolyte transport in rabbit proximal tubule.
2004 Nov
Functional characterization of rat organic anion transporter 5 (Slc22a19) at the apical membrane of renal proximal tubules.
2005 Nov
Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1.
2005 Oct 1
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
Effect of ochratoxin A on redox-regulated transcription factors, antioxidant enzymes and glutathione-S-transferase in cultured kidney tubulus cells.
2008 Aug
Proteome response to ochratoxin A-induced apoptotic cell death in mouse hippocampal HT22 cells.
2009 Jul
Toxicities induced in cultured human hepatocarcinoma cells exposed to ochratoxin A: oxidative stress and apoptosis status.
2009 Mar-Apr
Ochratoxin A impairs Nrf2-dependent gene expression in porcine kidney tubulus cells.
2009 Oct
The mycotoxin ochratoxin A inhibits DNA topoisomerase II and induces polyploidy in cultured CHO cells.
2009 Sep
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
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
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
Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity.
2013 Jun
Downregulation of Rad51 participates in OTA-induced DNA double-strand breaks in GES-1 cells in vitro.
2014 Apr 21
Central role of Nix in the autophagic response to ochratoxin A.
2014 Jul
Transcriptome-based functional classifiers for direct immunotoxicity.
2014 Mar
Ochratoxin A activates opposing c-MET/PI3K/Akt and MAPK/ERK 1-2 pathways in human proximal tubule HK-2 cells.
2015 Aug
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
Effect of Penicillium mycotoxins on the cytokine gene expression, reactive oxygen species production, and phagocytosis of bovine macrophage (BoMacs) function.
2015 Dec 25
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
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