1.0 2009-11-13 22:25:18 UTC 2026-08-20 05:04:05 UTC T3D3605 Ochratoxin A SmallMolecule Ochratoxin A belongs to the ochratoxins and related substances, a class of phenylpropanoids and polyketides within the organic compounds. This exogenous compound has the formula C20H18ClNO6 and an average molecular weight of 403.81 g/mol. At room temperature, it exists as a solid. It is identified as a toxin (PMC5486318), a mycotoxin (PMC11620267, PMC12567793, PMC3153256, PMC3153288, PMC8841369, PMC8876995, PMC9146908), a nephrotoxin, a carcinogenic agent, and a teratogenic agent. Additionally, it serves as a calcium channel blocker and is a metabolite of Aspergillus and Penicillium (PMC5486318). Ochratoxin A is found in various sources, including electrical and electronic equipment such as cell phones, batteries, capacitors, printed circuit boards, and wires and cables. It is also associated with healthcare, pharmaceuticals, and veterinary products like medical devices and antibiotics; textiles, leather, and furnishings including synthetic textiles and carpets and rugs; and lubricants used in energy, oil, gas, and industrial manufacturing. It is also found in food packaging and the preparation of malt, vinegar, wort, and wine or sparkling wine. Exposure routes include oral, inhalation, and touch. The compound interacts with several protein targets. It acts as an uncompetitive inhibitor of succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial (SDHD) and succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial (SDHB). It also inhibits renal phosphoenolpyruvate carboxykinase, cytosolic [GTP] (PCK1). Furthermore, certain metabolites of ochratoxin A can form DNA adducts, and some cytochrome P-450 enzymes, such as CYP2C9, metabolize the compound into more cytotoxic compounds capable of forming these adducts. Fungal Toxin Food Toxin Natural Toxin Organic Compound Organochloride Amine Ether Amide Ester Food Toxin Mycotoxin Metabolite Fungal Toxin Natural Compound PFAS Antibiotic 9663 N-[(5-Chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl]phenylalanine, 9CI Ochratoxin a Ochratoxin a-bsa conjugate from aspergillus ochraceus Ochratoxin A OTA Phenylalanine - ochratoxin a C20H18ClNO6 403.813 403.08226502 2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid 2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid 303-47-9 CC1CC2=C(Cl)C=C(C(O)=NC(CC3=CC=CC=C3)C(O)=O)C(O)=C2C(=O)O1 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) RWQKHEORZBHNRI-UHFFFAOYSA-N Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Glutamine and derivatives Benzene and substituted derivatives Carbonyl compounds Carboxylic acid anhydrides Dicarboxylic acids and derivatives Fatty amides Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds Primary carboxylic acid amides Amine Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxamide group Carboxylic acid anhydride Dicarboxylic acid or derivatives Fatty acyl Fatty amide Glutamine or derivatives Hydrocarbon derivative Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Primary carboxylic acid amide Aromatic homomonocyclic compounds Detected and Not Quantified Exogenous Membrane Solid Crystals from xylene. Exhibits green fluorescence. (A715) melting_point 169°C logp 4.74 logp 3.66 ALOGPS logs -4.20 ALOGPS solubility 2.56e-02 g/l ALOGPS logp 5.43 ChemAxon pka_strongest_acidic 3.26 ChemAxon pka_strongest_basic 0.14 ChemAxon iupac 2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid ChemAxon average_mass 403.813 ChemAxon mono_mass 403.08226502 ChemAxon smiles CC1CC2=C(Cl)C=C(C(O)=NC(CC3=CC=CC=C3)C(O)=O)C(O)=C2C(=O)O1 ChemAxon formula C20H18ClNO6 ChemAxon inchi 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) ChemAxon inchikey RWQKHEORZBHNRI-UHFFFAOYSA-N ChemAxon polar_surface_area 116.42 ChemAxon refractivity 102.29 ChemAxon polarizability 39.19 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) Ochratoxin A has been shown to be weakly mutagenic, possibly by induction of oxidative DNA damage. The nephrotoxin ochratoxin A (OTA) causes a reduction of glomerular filtration rate (GFR) and of para-aminohippuric acid (PAH) clearance. It is a nephrotoxin which blocks plasma membrane anion conductance in Madin-Darby canine kidney (MDCK) cells. Some cytochrome P-450 enzymes, such as CYP2C9, are known to metabolize ochratoxin A into more cytotoxic compounds capable of forming DNA adducts. (A2869, A3099) Ochratoxin A is cleaved into phenylalanine and a less toxic iso-coumarin derivative (ochratoxin alpha) by the microbial flora of the colon, and by carboxypeptidase A and alpha-chymotrypsim. This is is the major metabolic pathway. 4-Hydroxyochratoxin A is the main hepatic metabolite and its formation appears to be via a polymorphic-like debrisoquine 4-hydroxylation. Some cytochrome P-450 enzymes, such as CYP2C9, and known to metabolize ochratoxin A into more cytotoxic compounds. (T35, A2870, A3099) LD50: 20 mg/kg (Oral, Rat) (A716) LD50: 12,600 ug/kg (Intraperitoneal, Rat) (A716) LD50: 12,750 ug/kg (Intravenous, Rat ) (A716) LD50: 46 mg/kg (Oral, Mouse) (A716) 2B, possibly carcinogenic to humans. (L135) Human exposure occurs mainly through consumption of improperly stored food products, particularly contaminated grain and pork products, as well as coffee, wine grapes and dried grapes. (L1939) #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72218538e8> Might cause respiratory irritation. (A704) Care is symptomatic and supportive. (A704) HMDB29399 442530 390954 C09955 7719 http://en.wikipedia.org/wiki/Ochratoxin_A 1820333 1820345 15046773 11370295 6726060 8229758 8415778 15509185 IARC (1983). Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-Present. (Multivolume work). Rumack BH POISINDEX(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010. Hall AH & Rumack BH (Eds): TOMES(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010. O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1209 Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 779 Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. : http://monographs.iarc.fr/index.php Wikipedia. Ochratoxin A. Last Updated 26 February 2010.: http://en.wikipedia.org/wiki/Ochratoxin_A BE0002793 Some cytochrome P-450 enzymes, such as CYP2C9, are known to metabolize ochratoxin A into more cytotoxic compounds capable of forming DNA adducts. (A3099) BE0004796 Certain metabolites of ochratoxin A can form DNA adducts. (A3099) BE0000906 Ochratoxin A is an inhibitor of renal phosphoenolpyruvate carboxykinase. (A2875) BE0002252 Ochratoxin A is an uncompetitive inhibitor of succinate dehydrogenase. (A2874) BE0002254 Ochratoxin A is an uncompetitive inhibitor of succinate dehydrogenase. (A2874)