CHEBI:167320 - phevalin

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ChEBI Name phevalin
ChEBI ID CHEBI:167320
Definition A member of the class of pyrazinones that is pyrazin-2(1H)-one substituted by an isopropyl and benzyl groups at position 3 and 6, respectively. It is a natural product found in Staphylococcus aureus that inhibits calpain in a casein hydrolysis assay (IC50 = 1.3 μM), contributes to S. aureus infection in mice, and alters human keratinocyte gene expression.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Martin Larralde
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Formula C14H16N2O
Net Charge 0
Average Mass 228.295
Monoisotopic Mass 228.12626
InChI InChI=1S/C14H16N2O/c1-10(2)13-14(17)16-12(9-15-13)8-11-6-4-3-5-7-11/h3-7,9-10H,8H2,1-2H3,(H,16,17)
InChIKey CZUORGWXUVRUMV-UHFFFAOYSA-N
SMILES CC(C)C1=NC=C(CC2=CC=CC=C2)NC1=O
Metabolite of Species Details
Staphylococcus aureus (NCBI:txid1280) See: PubMed
Streptomyces sp. (NCBI:txid1931) of strain SC433 See: DOI
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
calpain inhibitor
An EC 3.4.22.* (cysteine endopeptidase) inhibitor that interferes with the action of any calpain.
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ChEBI Ontology
Outgoing phevalin (CHEBI:167320) has role bacterial metabolite (CHEBI:76969)
phevalin (CHEBI:167320) has role calpain inhibitor (CHEBI:82824)
phevalin (CHEBI:167320) is a benzenes (CHEBI:22712)
phevalin (CHEBI:167320) is a pyrazinone (CHEBI:167376)
IUPAC Name
6-benzyl-3-(propan-2-yl)pyrazin-2(1H)-one
Synonyms Sources
3-(1-methylethyl)-6-(phenylmethyl)-2(1H)-pyrazinone ChEBI
6-benzyl-3-(propan-2-yl)-1,2-dihydropyrazin-2-one ChEBI
6-benzyl-3-isopropyl-1H-pyrazin-2-one ChEBI
6-benzyl-3-propan-2-yl-1H-pyrazin-2-one ChEBI
aureusimine B SUBMITTER
Manual Xref Database
C00016595 KNApSAcK
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Registry Number Type Source
170713-71-0 CAS Registry Number SUBMITTER
Citations Waiting for Citations Types Sources
15896956 PubMed citation Europe PMC
22808288 PubMed citation SUBMITTER
23070851 PubMed citation SUBMITTER
23302043 PubMed citation SUBMITTER
27632173 PubMed citation Europe PMC
30549840 PubMed citation Europe PMC
30821453 PubMed citation Europe PMC
32649968 PubMed citation Europe PMC
7490226 PubMed citation Europe PMC
PMC3484167 PubMed Central citation Europe PMC
Last Modified
26 January 2021