CHEBI:7719 - ochratoxin A

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ChEBI Name ochratoxin A
ChEBI ID CHEBI:7719
Definition A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin α). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information eMolecules:499362, eMolecules:26757802, ZINC000003861782
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Ochratoxin A—a toxin produced by different Aspergillus and Penicillium species — 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.
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Formula C20H18ClNO6
Net Charge 0
Average Mass 403.820
Monoisotopic Mass 403.08227
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
InChIKey RWQKHEORZBHNRI-BMIGLBTASA-N
SMILES 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
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
Penicillium metabolite
Any fungal metabolite produced during a metabolic reaction in Penicillium.
calcium channel blocker
One of a class of drugs that acts by selective inhibition of calcium influx through cell membranes or on the release and binding of calcium in intracellular pools.
mycotoxin
Poisonous substance produced by fungi.
nephrotoxin
A toxin that is produced by a biological organism such as a microbe, animal or plant which interferes with the function of the kidney in animals.
carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
teratogenic agent
A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
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ChEBI Ontology
Outgoing ochratoxin A (CHEBI:7719) has functional parent ochratoxin α (CHEBI:133917)
ochratoxin A (CHEBI:7719) has role Aspergillus metabolite (CHEBI:76956)
ochratoxin A (CHEBI:7719) has role Penicillium metabolite (CHEBI:76964)
ochratoxin A (CHEBI:7719) has role calcium channel blocker (CHEBI:38215)
ochratoxin A (CHEBI:7719) has role carcinogenic agent (CHEBI:50903)
ochratoxin A (CHEBI:7719) has role mycotoxin (CHEBI:25442)
ochratoxin A (CHEBI:7719) has role nephrotoxin (CHEBI:61015)
ochratoxin A (CHEBI:7719) has role teratogenic agent (CHEBI:50905)
ochratoxin A (CHEBI:7719) is a N-acyl-L-phenylalanine (CHEBI:77673)
ochratoxin A (CHEBI:7719) is a isochromanes (CHEBI:38762)
ochratoxin A (CHEBI:7719) is a monocarboxylic acid amide (CHEBI:29347)
ochratoxin A (CHEBI:7719) is a organochlorine compound (CHEBI:36683)
ochratoxin A (CHEBI:7719) is a phenylalanine derivative (CHEBI:25985)
ochratoxin A (CHEBI:7719) is conjugate acid of ochratoxin A(1−) (CHEBI:166829)
Incoming hapten OTAb (CHEBI:141300) has functional parent ochratoxin A (CHEBI:7719)
hapten OTAd (CHEBI:141313) has functional parent ochratoxin A (CHEBI:7719)
hapten OTAe (CHEBI:141327) has functional parent ochratoxin A (CHEBI:7719)
ochratoxin C (CHEBI:141525) has functional parent ochratoxin A (CHEBI:7719)
hapten OTAf (CHEBI:141331) has part ochratoxin A (CHEBI:7719)
ochratoxin A(1−) (CHEBI:166829) is conjugate base of ochratoxin A (CHEBI:7719)
IUPAC Name
N-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl]carbonyl}-L-phenylalanine
Synonyms Sources
(−)-N-((5-chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenylalanine ChemIDplus
(2S)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]amino}-3-phenylpropanoic acid IUPAC
(R)-N-((5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl)phenylalanine ChemIDplus
N-(((3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenyl-L-alanine ChemIDplus
N-[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]-L-phenylalanine IUPAC
N-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl]carbonyl}-L-phenylalanine IUPAC
Ochratoxin A KEGG COMPOUND
OTA ChEBI
Manual Xrefs Databases
C00003008 KNApSAcK
C09955 KEGG COMPOUND
HMDB0029399 HMDB
LSM-5521 LINCS
Ochratoxin_A Wikipedia
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Registry Numbers Types Sources
1301486 Reaxys Registry Number Reaxys
303-47-9 CAS Registry Number KEGG COMPOUND
303-47-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
18 February 2021