CHEBI:9440 - tenuazonic acid

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ChEBI Name tenuazonic acid
ChEBI ID CHEBI:9440
Definition A member of the class of pyrrolidin-2-ones that is 5-(butan-2-yl)pyrrolidine-2,4-dione carrying an additional acetyl group at position 3. A mycotoxin produced by various plant pathogenic fungi.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C10H15NO3
Net Charge 0
Average Mass 197.231
Monoisotopic Mass 197.105
InChI InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,7-8H,4H2,1-3H3,(H,11,14)/t5-,7?,8-/m0/s1
InChIKey KLBSRSYHIIAQTG-PZICIZFRSA-N
SMILES [C@]1(C(C(C(N1)=O)C(=O)C)=O)([C@H](CC)C)[H]
Metabolite of Species Details
Alternaria alternata (NCBI:txid5599) See: PubMed
Epicoccum sorghinum (NCBI:txid749593) See: PubMed
Homo sapiens (NCBI:txid9606) Found in urine (BTO:0001419). See: PubMed
Roles Classification
Biological Role(s): mycotoxin
Poisonous substance produced by fungi.
human urinary metabolite
Any metabolite (endogenous or exogenous) found in human urine samples.
protein synthesis inhibitor
A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
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ChEBI Ontology
Outgoing tenuazonic acid (CHEBI:9440) has role human urinary metabolite (CHEBI:84087)
tenuazonic acid (CHEBI:9440) has role mycotoxin (CHEBI:25442)
tenuazonic acid (CHEBI:9440) has role protein synthesis inhibitor (CHEBI:48001)
tenuazonic acid (CHEBI:9440) is a β-diketone (CHEBI:67265)
tenuazonic acid (CHEBI:9440) is a methyl ketone (CHEBI:51867)
tenuazonic acid (CHEBI:9440) is a pyrrolidin-2-ones (CHEBI:74223)
tenuazonic acid (CHEBI:9440) is conjugate acid of tenuazonic acid(1−) (CHEBI:136842)
Incoming tenuazonic acid(1−) (CHEBI:136842) is conjugate base of tenuazonic acid (CHEBI:9440)
IUPAC Name
(5S)-3-acetyl-5-[(2S)-butan-2-yl]pyrrolidine-2,4-dione
Synonyms Sources
Pyrrole-2,4-diol, 3-acetyl-5-sec-butyl- KEGG COMPOUND
Tenuazonic acid KEGG COMPOUND
Manual Xrefs Databases
C00001554 KNApSAcK
C08511 KEGG COMPOUND
CPD-19688 MetaCyc
Tenuazonic_acid Wikipedia
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Registry Numbers Types Sources
27778-66-1 CAS Registry Number KEGG COMPOUND
8485 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
07 July 2017