플리티뎁신플리티뎁신
Plitidepsin
기본 정보
- CAS
137219-37-5- 표준 SMILES
CC[C@H](C)[C@H]1NC(=O)[C@@H](NC(=O)[C@@H](CC(C)C)N(C)C(=O)[C@@H]2CCCN2C(=O)C(C)=O)[C@@H](C)OC(=O)[C@H](Cc2ccc(OC)cc2)N(C)C(=O)[C@@H]2CCCN2C(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)C(=O)[C@H](C(C)C)OC(=O)C[C@@H]1O- InChIKey
UUSZLLQJYRSZIS-LXNNNBEUSA-N- 분자식
- C57H87N7O15
- 평균 분자량
- 1,110.3 g/mol
- 단동위원소 질량
- 1,109.62601509
개요
Plitidepsin is a didemnin that is didemin B in which the hydroxy group of the 1-(2-hydroxypropanoyl)-L-prolinamide moiety has been oxidised to the corresponding ketone. It was originally isolated from the Mediterranean tunicate Aplidium albicans. It has a role as an anticoronaviral agent, an antineoplastic agent and a marine metabolite.
이름 및 식별자
- 우선 이름
- Plitidepsin
- IUPAC
- (2S)-N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-N-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide
- 현지명
- 플리티뎁신플리티뎁신
- 영어명
- Plitidepsin
- 분자식
- C57H87N7O15
- 분자량
- 1110.34
이름 및 동의어
plitidepsinAplidine137219-37-5aplidinDehydrodidemnin BplitidepsinaplitidepsineY76ID234HW(2S)-N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-N-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamideCHEBI:90205NSC638719plitidepsinum
이름 더 보기
플리티뎁신플리티뎁신Plitidepsin top3cyclic peptide deriv.Plitidepsin (Aplidine)Aplidine, 10 mM in DMSODidemnin A, N-(1-(1,2-dioxopropyl)-L-prolyl)-2-9-Didemnin B, 2-(1-(1,2-dioxopropyl)-L-proline)-Inhibitor,DNA/RNA Synthesis,MOLT-4,SARS coronavirus,infection,SARS-CoV,Plitidepsin,Leukemia,VEGF,COVID-19,Antiviral,inhibit,Aplidine,advanced cancer,anticancer,Advanced Malignancies
물성
구조 계산 물성
- XLogP
- 5.7
- 극성 표면적
- 285 Ų
- 수소 결합 공여자 수
- 4
- 수소 결합 수용자 수
- 15
- 회전 가능 결합 수
- 15
- 무거운 원자 수
- 79
- 형식 전하
- 0
- 복잡도
- 2,200
물리화학적 성질
- 녹는점
- 152 · 152-160°
- 밀도
- 1.24 · 1.24±0.1 g/cm3(Predicted)
- 저장 조건
- -20 °C · -20°C
- 용해도
- DMSO: 용해될 수 있다
- 산도 계수 (pKa)
- 11.28 · 11.28±0.70(Predicted)
- 물리적 상태
- Solid
- 색상
- White to off-white
- InChIKey
- UUSZLLQJYRSZIS-NIORUGPLNA-N
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
안전 데이터
- 신호 어
- Danger
- 유해·위험 문구
- 암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H225
화학 및 산업
약리 정보
ATC Code
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Mechanism of Action
Plitidepsin has antineoplastic activity which stems from plitidepsin's ability to inhibit cell growth and induce apoptosis. Plitidepsin's primary intracellular target is the eukaryotic elongation factor 1A2 (eEF1A2). It also inhibits the growth and induces apoptosis in MOLT-4 cells by inhibiting VEGF secretion, which blocks the VEGF/VEGFR-1 autocrine loop that is required for the growth of the MOLT-4 cells. Through inhibition of eEF1A, plitidepsin also demonstrated antiviral activity against SARS-CoV-2. The exact mechanism of action is not fully understood and plitidepsin may have multiple modes of action.
Metabolism/MetabolitesHepatic
응용 분야
개요Plitidepsin is a cyclic depsipeptide that was first isolated from a Mediterranean marine tunicate (Aplidium albicans) and, at present, is manufactured by total synthesis and commercialized as Aplidin. Its antitumor activity, observed in preclinical in vitro and in vivo studies has prompted numerous clinical trials to be conducted over the last 17 years, alone or in combination with other anticancer agents.
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