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.
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Formula C20H18ClNO6
Net Charge 0
Average Mass 403.81300
Monoisotopic Mass 403.082
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]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.
mycotoxin
Poisonous substance produced by fungi.
nephrotoxin
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.
View more via ChEBI Ontology
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)
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
(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
Ochratoxin A KEGG COMPOUND
Database Links 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
1301486 Beilstein Registry Number Beilstein
303-47-9 CAS Registry Number ChemIDplus
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Last Modified
15 March 2017