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CHEBI:167320 - phevalin

ChEBI IDCHEBI:167320
ChEBI Namephevalin
Stars
DefinitionA 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.
Last Modified26 January 2021
SubmitterMartin Larralde
DownloadsMolfile
FormulaC14H16N2O
Net Charge0
Average Mass228.295
Monoisotopic Mass228.12626
SMILESCC(C)c1ncc(Cc2ccccc2)nc1=O
InChIInChI=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)
InChIKeyCZUORGWXUVRUMV-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Staphylococcus aureus (ncbitaxon:1280) - PubMed (23302043)
Streptomyces sp. (ncbitaxon:1931) - DOI (10.7164/antibiotics.48.1165) Strain: SC433
Escherichia coli (ncbitaxon:562) - PubMed (28111075)
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
aureusimine BSUBMITTER
6-benzyl-3-propan-2-yl-1H-pyrazin-2-oneChEBI
6-benzyl-3-isopropyl-1H-pyrazin-2-oneChEBI
6-benzyl-3-(propan-2-yl)-1,2-dihydropyrazin-2-oneChEBI
3-(1-methylethyl)-6-(phenylmethyl)-2(1H)-pyrazinoneChEBI
Manual XrefsDatabases
C00016595KNApSAcK
Registry NumbersSources
CAS:170713-71-0SUBMITTER
Citations