Phevalin
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기본 정보
- CAS
170713-71-0- 표준 SMILES
CC(C)c1ncc(Cc2ccccc2)[nH]c1=O- InChIKey
CZUORGWXUVRUMV-UHFFFAOYSA-N- 분자식
- C14H16N2O
- 평균 분자량
- 228.29 g/mol
- 단동위원소 질량
- 228.12626314
개요
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.
이름 및 식별자
- 우선 이름
- Phevalin
- IUPAC
- 6-benzyl-3-propan-2-yl-1H-pyrazin-2-one
- 영어명
- 3-(1-Methylethyl)-6-(phenylMethyl)-2(1H)-pyrazinone
- 분자식
- C14H16N2O
- 분자량
- 228.28964
이름 및 동의어
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
이름 더 보기
Aureusimine B, 10 mM in DMSO2(1H)-Pyrazinone, 3-(1-methylethyl)-6-(phenylmethyl)-
CHEMBL419498MFCD009304833-(1-Methylethyl)-6-(phenylmethyl)-2(1H)-pyrazinone; Phevalin;orb1303765SCHEMBL16431626SCHEMBL21333942BDBM50104646EBC-39023
데이터베이스 식별자
- CAS
170713-71-0- PubChem CID
- 10376483
- ChEMBL
CHEMBL419498- ChEBI
CHEBI:167320- Nikkaji
- J697.856H
물성
구조 계산 물성보충 중
- XLogP
- 2.2
- 극성 표면적
- 41.5 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 3
- 무거운 원자 수
- 17
- 형식 전하
- 0
- 복잡도
- 349
물리화학적 성질
- 녹는점
- 117 · 117-118 °C
- 밀도
- 1.1 · 1.10±0.1 g/cm3(Predicted)
- 저장 조건
- Refrigerator
- 용해도
- 클로로포름(약간 용해됨), 메탄올(약간 용해됨)
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 11.65 · 11.65±0.60(Predicted)
- 색상
- 미색에서 밝은 회색까지
화학 및 산업
응용 분야
개요Aureusimine 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.
용도Aureusimine 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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