CHEBI:7719 - ochratoxin A

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ChEBI Name ochratoxin A
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.
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Formula C20H18ClNO6
Net Charge 0
Average Mass 403.81300
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
SMILES C[C@@H]1Cc2c(Cl)cc(C(=O)N[C@@H](Cc3ccccc3)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.
Poisonous substance produced by fungi.
A poison that interferes with the function of the kidneys.
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)
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)
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
Manual Xrefs Databases
C00003008 KNApSAcK
HMDB0029399 HMDB
Ochratoxin_A Wikipedia
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Registry Numbers Types Sources
1301486 Reaxys Registry Number Reaxys
1301486 Beilstein Registry Number Beilstein
303-47-9 CAS Registry Number ChemIDplus
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Last Modified
02 August 2018