ChemicalBook--->CAS DataBase List--->170713-71-0

170713-71-0

170713-71-0 Structure

170713-71-0 Structure
IdentificationBack Directory
[Name]

3-(1-Methylethyl)-6-(phenylMethyl)-2(1H)-pyrazinone
[CAS]

170713-71-0
[Synonyms]

Aureusimine B
6-BENZYL-3-ISOPROPYLPYRAZIN-2-ONE
6-benzyl-3-isopropylpyrazin-2(1H)-one
3-(1-Methylethyl)-6-(phenylMethyl)-2(1H)-pyrazinone
2(1H)-Pyrazinone, 3-(1-methylethyl)-6-(phenylmethyl)-
[Molecular Formula]

C14H16N2O
[MDL Number]

MFCD00930483
[MOL File]

170713-71-0.mol
[Molecular Weight]

228.29
Chemical PropertiesBack Directory
[Melting point ]

117-118 °C
[density ]

1.10±0.1 g/cm3(Predicted)
[storage temp. ]

Refrigerator
[solubility ]

Chloroform (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

11.65±0.60(Predicted)
[color ]

Off-White to Light Grey
Hazard InformationBack Directory
[Description]

Aureusimine B, also known as phevalin, is a natural pyrazinone produced by certain fungi and by Staphylococcus spp., including S. aureus. 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. 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.
[Uses]

Aureusimine B (phevalin) is a small molecular weight monoketopiperazine formed non-ribosomally by the fusion of phenylalanine and valine. Aureusimine B was isolated from S. aureus in 2010 as one of a pair of related metabolites, controversially identified as virulence factors in the pathology of Golden Staph. Aureusimine B is also an inhibitor of the protease, calpain.
[Uses]

Aureusimine B is a novel small molecule isolated from S. aureus as one of a pair of related metabolites controversially identified as virulence factors in the pathology of Golden Staph. Aureusimine B has also been reported as an inhibitor of the protease, calpain.
[Definition]

ChEBI: Phevalin is 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 muM), contributes to S. aureus infection in mice, and alters human keratinocyte gene expression. It has a role as a bacterial metabolite and a calpain inhibitor. It is a member of benzenes and a pyrazinone.
[storage]

Store at -20°C
Spectrum DetailBack Directory
[Spectrum Detail]

3-(1-Methylethyl)-6-(phenylMethyl)-2(1H)-pyrazinone(170713-71-0)1HNMR
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