Ochratoxin A

Ochratoxin A

Names
IUPAC name N-​{[(3R)-​5-​chloro-​8-​hydroxy-​3-​methyl-​1-​oxo-​3,​4-​dihydro-​1H-​isochromen-​7-​yl]​carbonyl}-​L-​phenylalanine
Other names (R)-N- [(5-Chloro- 3,4-dihydro- 8-hydroxy- 3-methyl- 1-oxo- 1H-2-benzopyran-7-yl) -carbonyl]- L- phenylalanine (−)-N- [(5-Chloro- 8-hydroxy- 3-methyl- 1-oxo- 7-isochromanyl) carbonyl]- 3-phenylalanine
Identifiers
CAS Number	303-47-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:7719 Y
ChEMBL	ChEMBL589366 Y
ChemSpider	390954 Y
ECHA InfoCard	100.005.586
IUPHAR/BPS	4672
KEGG	C09955 Y
PubChem	442530
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)/t10-,15+/m1/s1 Y Key: RWQKHEORZBHNRI-BMIGLBTASA-N Y InChI=1/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)/t10-,15+/m1/s1 Key: RWQKHEORZBHNRI-BMIGLBTABQ
SMILES O=C(O)[C@@H](NC(=O)c1c(O)c2c(c(Cl)c1)C[C@H](OC2=O)C)Cc3ccccc3
Properties
Chemical formula	C20H18ClNO6
Molar mass	403.813
Melting point	169 °C (336 °F; 442 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

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.

Ochratoxin A is potentially carcinogenic to humans (Group 2B), and has been shown to be weakly mutagenic, possibly by induction of oxidative DNA damage.

The evidence in experimental animals is sufficient to indicate carcinogenicity of ochratoxin A. It was tested for carcinogenicity by oral administration in mice and rats. It slightly increased the incidence of in mice of each sex. and produced renal adenomas and carcinomas in male mice and in rats (carcinomas in 46% of males and 5% of females). In humans, very little histology data are available, so a relationship between ochratoxin A and renal cell carcinoma has not been found. However, the incidence of transitional cell (urothelial) urinary cancers seems abnormally high in Balkan endemic nephropathy patients, especially for the upper urinary tract. The molecular mechanism of ochratoxin A carcinogenicity has been under debate due to conflicting literature, however this mycotoxin has been proposed to play a major role in reducing antioxidant defenses.