CHEBI:7719 - ochratoxin A

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
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 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)
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
View more database links
Registry Numbers Types Sources
1301486 Reaxys Registry Number Reaxys
1301486 Beilstein Registry Number Beilstein
303-47-9 CAS Registry Number KEGG COMPOUND
303-47-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11513689 PubMed citation Europe PMC
11899122 PubMed citation Europe PMC
15056805 PubMed citation Europe PMC
16022500 PubMed citation Europe PMC
16097797 PubMed citation Europe PMC
16293235 PubMed citation Europe PMC
16332622 PubMed citation Europe PMC
16332628 PubMed citation Europe PMC
16781114 PubMed citation Europe PMC
17195275 PubMed citation Europe PMC
17218050 PubMed citation Europe PMC
17580629 PubMed citation Europe PMC
18638518 PubMed citation Europe PMC
18680942 PubMed citation Europe PMC
19919898 PubMed citation Europe PMC
20201966 PubMed citation Europe PMC
23282670 PubMed citation Europe PMC
23296271 PubMed citation Europe PMC
23358140 PubMed citation Europe PMC
23369011 PubMed citation Europe PMC
29950703 PubMed citation Europe PMC
33078253 PubMed citation Europe PMC
33138019 PubMed citation Europe PMC
33171643 PubMed citation Europe PMC
33338836 PubMed citation Europe PMC
8941986 PubMed citation Europe PMC
8956233 PubMed citation Europe PMC
9894829 PubMed citation Europe PMC
Last Modified
18 February 2021