(2E,4E,6E)-N-[(2S)-1-Oxo-3-phenyl-1-[[(3S,7S,9R,13S,16S,19S)-9,13,16,17-tetramethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetrazatricyclo[17.3.0.07,11]docosan-3-yl]amino]propan-2-yl]octa-2,4,6-trienamide
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기본 정보
- CAS
95398-45-1- 표준 SMILES
C/C=C/C=C/C=C/C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@H]1COC(=O)[C@@H]2C[C@@H](C)CN2C(=O)[C@H](C)NC(=O)[C@H](C)N(C)C(=O)[C@@H]2CCCN2C1=O- InChIKey
ZGRSXMWWGUOTAO-VIEJTCJKSA-N- 분자식
- C38H50N6O8
- 평균 분자량
- 718.8 g/mol
개요
ADEP 1 is a cyclodepsipeptide.
이름 및 식별자
- 우선 이름
- (2E,4E,6E)-N-[(2S)-1-Oxo-3-phenyl-1-[[(3S,7S,9R,13S,16S,19S)-9,13,16,17-tetramethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetrazatricyclo[17.3.0.07,11]docosan-3-yl]amino]propan-2-yl]octa-2,4,6-trienamide
- IUPAC
- (2E,4E,6E)-N-[(2S)-1-oxo-3-phenyl-1-[[(3S,7S,9R,13S,16S,19S)-9,13,16,17-tetramethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetrazatricyclo[17.3.0.07,11]docosan-3-yl]amino]propan-2-yl]octa-2,4,6-trienamide
- 영어명
- A 54556A
- 분자식
- C38H50N6O8
- 분자량
- 718.839
이름 및 동의어
95398-45-1A-54556AADEP 1A 54556ACHEMBL3342324(2E,4E,6E)-N-[(2S)-1-Oxo-3-phenyl-1-[[(3S,7S,9R,13S,16S,19S)-9,13,16,17-tetramethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetrazatricyclo[17.3.0.07,11]docosan-3-yl]amino]propan-2-yl]octa-2,4,6-trienamideSCHEMBL15449217CHEBI:222868C38H50N6O8HY-P1926BDBM50028480MFCD28899144
이름 더 보기
A 54556A (~90%)Antibiotic A-54556APubChem ID: 24767779L-Proline, N-[(2E,4E,6E)-1-oxo-2,4,6-octatrien-1-yl]-L-phenylalanyl-L-seryl-L-prolyl-N-methyl-L-alanyl-L-alanyl-4-methyl-, (6→2)-lactone, (4R)-
(2E,4E,6E)-N-[(1S)-1-benzyl-2-oxo-2-[[(3S,7S,9R,13S,16S,19S)-9,13,16,17-tetramethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetrazatricyclo[17.3.0.07,11]docosan-3-yl]amino]ethyl]octa-2,4,6-trienamide
데이터베이스 식별자
- CAS
95398-45-1- ChEMBL
CHEMBL3342324- ChEBI
CHEBI:222868- Nikkaji
- J3.199.602C
물성
구조 계산 물성보충 중
- XLogP
- 2.9
- 극성 표면적
- 175 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 8
- 회전 가능 결합 수
- 8
- 무거운 원자 수
- 52
- 형식 전하
- 0
- 복잡도
- 1,440
물리화학적 성질
- 녹는점
- 180 oC · >180oC (dec.)
- 끓는 점
- 1086.9 · 1086.9±65.0 °C(Predicted)
- 밀도
- 1.28 · 1.28±0.1 g/cm3(Predicted)
- 저장 조건
- Amber Vial, Refrigerator
- 용해도
- 클로로포름(약간 용해됨), DMSO(약간 용해됨), 메탄올(약간 용해됨)
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 12.8 · 12.80±0.46(Predicted)
- 색상
- 연한 노란색에서 밝은 갈색까지
- 안정성
- 감광성
화학 및 산업
응용 분야
개요A-54556A is an acyldepsipeptide (ADEP) antibiotic that has been found in Streptomyces hawaiiensis. It is active against B. subtilis, S. pyogenes, and E. faecalis, as well as penicillin-resistant S. pneumoniae, vancomycin-resistant E. faecium, and methicillin-resistant S. aureus (MRSA; IC50s = 0.2, 0.4, 0.4, 1.6, 0.4, and 6.3 μg/ml, respectively). It binds to and activates caseinolytic protease P (ClpP), inducing degradation of β-casein by the B. subtilis ClpP in an ATPase-independent manner when used at concentrations of 2.5 and 5 μg/ml.
용도A 54556A is an unusual depsipeptide isolated from Streptomyces hawaiiensis by researchers at Eli Lilly in 1985, featuring a trienone side chain. A 54556A is potently active against Gram positive and Gram negative bacteria, including MRSA. A 54556A was the original lead structure of the recently re-discovered acyldepsipeptide (ADEP) antibiotics that act by activating and disregulating Clp-family proteins. ADEPs are considered important leads in the development of new generations of antibiotics against resistant bacteria.
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