Phevalin
Grundinformationen
- CAS
170713-71-0- Standard-SMILES
CC(C)c1ncc(Cc2ccccc2)[nH]c1=O- InChIKey
CZUORGWXUVRUMV-UHFFFAOYSA-N- Summenformel
- C14H16N2O
- Durchschnittliche Molmasse
- 228,29 g/mol
- Monoisotopische Masse
- 228,12626314
Überblick
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 M), 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 pyrazinone and a member of benzenes.
Namen und Bezeichner
- Bevorzugter Name
- Phevalin
- IUPAC
- 6-benzyl-3-propan-2-yl-1H-pyrazin-2-one
- Englischer Name
- 3-(1-Methylethyl)-6-(phenylMethyl)-2(1H)-pyrazinone
- Summenformel
- C14H16N2O
- Molmasse
- 228.28964
Namen und Synonyme
Aureusimine B170713-71-0Phevalin6-Benzyl-3-isopropyl-2(1H)-pyrazinone6-benzyl-3-propan-2-yl-1H-pyrazin-2-oneCHEBI:167320RefChem:1731496-Benzyl-3-isopropylpyrazin-2-one3-(1-Methylethyl)-6-(phenylmethyl)-2(1H)-pyrazinone6-Benzyl-3-isopropylpyrazin-2(1H)-one6-benzyl-3-(propan-2-yl)-1,2-dihydropyrazin-2-one6-Benzyl-3-isopropyl-1H-pyrazin-2-one
Weitere Namen anzeigen
Aureusimine B, 10 mM in DMSO2(1H)-Pyrazinone, 3-(1-methylethyl)-6-(phenylmethyl)-
CHEMBL419498MFCD009304833-(1-Methylethyl)-6-(phenylmethyl)-2(1H)-pyrazinone; Phevalin;orb1303765SCHEMBL16431626SCHEMBL21333942BDBM50104646EBC-39023
Datenbank-Bezeichner
- CAS
170713-71-0- PubChem CID
- 10376483
- ChEMBL
CHEMBL419498- ChEBI
CHEBI:167320
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,2
- Polarare Oberfläche (TPSA)
- 41,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 17
- Formalladung
- 0
- Komplexität
- 349
Physikochemische Eigenschaften
- Schmelzpunkt
- 117 · 117-118 °C
- Dichte
- 1.1 · 1.10±0.1 g/cm3(Predicted)
- storage temp.
- Refrigerator
- Löslichkeit
- Chloroform (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- pka
- 11.65 · 11.65±0.60(Predicted)
- Farbe
- Off-White to Light Grey
Chemie und Industrie
Anwendungen
BeschreibungAureusimine 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.
VerwendenAureusimine 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.
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成都市久鼎化学技术有限公司18584079237 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
孟成科技（上海）有限公司400-820-6829 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
成都赛诺宁科技有限公司28-87999436 02887999436 · [email protected]
上海陶术生物科技股份有限公司
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