CHEBI:141524 - ochratoxin B

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ChEBI Name ochratoxin B
Definition A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid. Ochratoxin B differs from the more naturally abundant ochratoxin A in the absence of the dihydroisocoumarin chlorine atom. It has cytotoxic effects on kidney and liver cells in vitro but only minor effects in vivo, due to its rapid metabolism and excretion. It inhibits cell proliferation of human liver HepG2 cells at doses as low as 1 μg/ ml but lacks the genotoxic activity of ochratoxin A, even at higher concentrations.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H19NO6
Net Charge 0
Average Mass 369.369
Monoisotopic Mass 369.12124
InChI InChI=1S/C20H19NO6/c1-11-9-13-7-8-14(17(22)16(13)20(26)27-11)18(23)21-15(19(24)25)10-12-5-3-2-4-6-12/h2-8,11,15,22H,9-10H2,1H3,(H,21,23)(H,24,25)/t11-,15+/m1/s1
SMILES C1=CC=CC=C1C[C@@H](C(=O)O)NC(=O)C2=CC=C3C(=C2O)C(O[C@@H](C3)C)=O
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.
Poisonous substance produced by fungi.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ochratoxin B (CHEBI:141524) has role Aspergillus metabolite (CHEBI:76956)
ochratoxin B (CHEBI:141524) has role Penicillium metabolite (CHEBI:76964)
ochratoxin B (CHEBI:141524) has role calcium channel blocker (CHEBI:38215)
ochratoxin B (CHEBI:141524) has role mycotoxin (CHEBI:25442)
ochratoxin B (CHEBI:141524) is a N-acyl-L-phenylalanine (CHEBI:77673)
ochratoxin B (CHEBI:141524) is a isochromanes (CHEBI:38762)
ochratoxin B (CHEBI:141524) is a phenylalanine derivative (CHEBI:25985)
Synonyms Sources
(2S)-2-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]amino}-3-phenylpropanoic acid IUPAC
N-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl]carbonyl}-L-phenylalanine IUPAC
Registry Numbers Types Sources
1300160 Reaxys Registry Number Reaxys
1300160 Beilstein Registry Number ChemIDplus
4825-86-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15623466 PubMed citation Europe PMC
15963343 PubMed citation Europe PMC
17161512 PubMed citation Europe PMC
22069651 PubMed citation Europe PMC
22331050 PubMed citation Europe PMC
24968897 PubMed citation Europe PMC
26133228 PubMed citation Europe PMC
28749978 PubMed citation Europe PMC
29428592 PubMed citation Europe PMC
299 PubMed citation Europe PMC
879783 PubMed citation Europe PMC
Last Modified
02 August 2018