A natural pyrazinone
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Aureusimine B

Item No. 18752

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(1-methylethyl)-6-(phenylmethyl)-2(1H)-pyrazinone
CAS Number
170713-71-0
Synonyms
  • Phevalin​
Molecular Formula
C14H16N2O
Formula Weight
228.3
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly SolubleMethanol: Slightly Soluble
SMILES
CC(C)C1=NC=C(NC1=O)CC2=CC=CC=C2
InChi Code
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)
InChi Key
CZUORGWXUVRUMV-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $236

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    5 mg

    $1,053

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    Product Description

    Aureusimine B, also known as phevalin, is a natural pyrazinone produced by certain fungi and by Staphylococcus spp., including S. aureus.1,2 Its synthesis appears to be initiated by a conserved nonribosomal peptide synthetase that creates a dipeptide (phenylalanine-valine) aldehyde, which then undergoes cyclization and oxidation.2 Aureusimine B inhibits calpain in a casein hydrolysis assay (IC50 = 1.3 µM), contributes to S. aureus infection in mice, and alters human keratinocyte gene expression.1,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Alvarez, M.E., White, C.B., Gregory, J., et al. Phevalin, a new calpain inhibitor, from a Streptomyces sp. J. Antibiot. (Tokyo) 48(10), 1165-1167 (1995).

    2. Zimmermann, M., and Fischbach, M.A. A family of pyrazinone natural products from a conserved nonribosomal peptide synthetase in Staphylococcus aureus. Chem. Biol. 17(9), 925-930 (2010).

    3. Secor, P.R., Jennings, L.K., James, G.A., et al. Phevalin (aureusimine B) production by Staphylococcus aureus biofilm and impacts on human keratinocyte gene expression. PLoS One 7(7), (2012).

    4. Wyatt, M.A., Wang, W., Roux, C.M., et al. Staphylococcus aureus nonribosomal peptide secondary metabolites regulate virulence. Science 329(5989), 294-296 (2010).