EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:141524 - ochratoxin B

Default Structure
ChEBI IDCHEBI:141524
ChEBI Nameochratoxin B
Stars
DefinitionA 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.
Last Modified5 August 2022
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC20H19NO6
Net Charge0
Average Mass369.373
Monoisotopic Mass369.12124
SMILESC[C@@H]1Cc2ccc(C(=O)N[C@@H](Cc3ccccc3)C(=O)O)c(O)c2C(=O)O1
InChIInChI=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
InChIKeyDAEYIVCTQUFNTM-ABAIWWIYSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
mycotoxin  Poisonous substance produced by fungi.
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
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.
ChEBI Ontology
Outgoing Relation(s)
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 monocarboxylic acid (CHEBI:25384)
ochratoxin B (CHEBI:141524) is a phenylalanine derivative (CHEBI:25985)
ochratoxin B (CHEBI:141524) is conjugate acid of ochratoxin B(1−) (CHEBI:192526)
Incoming Relation(s)
ochratoxin B(1−) (CHEBI:192526) is conjugate base of ochratoxin B (CHEBI:141524)
IUPAC Name 
N-[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]-L-phenylalanine
Synonyms  Source
(2S)-2-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]amino}-3-phenylpropanoic acidIUPAC
N-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl]carbonyl}-L-phenylalanineIUPAC
OTBChEBI
Manual XrefsDatabases
C00037570KNApSAcK
HMDB0029401HMDB
Registry NumbersSources
Reaxys:1300160Reaxys
CAS:4825-86-9ChemIDplus
Citations