야플라키놀라이드
Jasplakinolide
기본 정보
- CAS
102396-24-7- 표준 SMILES
C/C1=C\[C@H](C)C[C@H](C)OC(=O)C[C@H](c2ccc(O)cc2)NC(=O)[C@@H](Cc2c(Br)[nH]c3ccccc23)N(C)C(=O)[C@H](C)NC(=O)[C@@H](C)C1- InChIKey
GQWYWHOHRVVHAP-DHKPLNAMSA-N- 분자식
- C36H45BrN4O6
- 평균 분자량
- 709.7 g/mol
- 단동위원소 질량
- 708.25225
개요
Jaspamide is a cyclodepsipeptide isolated from Jaspis splendens and has been shown to exhibit antineoplastic activity. It is an actin polymerization and stabilization inducer. It has a role as an actin polymerisation inducer, an antineoplastic agent, an antifungal agent, a neuroprotective agent, an apoptosis inducer, an animal metabolite and a marine metabolite. It is a member of phenols and a cyclodepsipeptide.
이름 및 식별자
- 우선 이름
- Jasplakinolide
- IUPAC
- (4R,7R,10S,13S,15E,17R,19S)-7-[(2-bromo-1H-indol-3-yl)methyl]-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-1-oxa-5,8,11-triazacyclononadec-15-ene-2,6,9,12-tetrone
- 현지명
- 야플라키놀라이드
- 영어명
- JASPLAKINOLIDE
- 분자식
- C36H45BrN4O6
- 분자량
- 709.67
이름 및 동의어
jasplakinolideJaspamide102396-24-7(4R,7R,10S,13S,15E,17R,19S)-7-[(2-Bromo-1H-indol-3-yl)methyl]-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-1-oxa-5,8,11-triazacyclononadec-15-ene-2,6,9,12-tetroneDTXSID30893487CHEBI:66104NSC 613009beta-Alanine, N-(2-bromo-N-(N-(8-hydroxy-2,4,6-trimethyl-1-oxo-4-nonenyl)-L-alanyl)-N-methyl-D-tryptophyl)-L-3-(4-hydroxyphenyl)-, p-lactone, (2S-(2R*,4E,6S*,8R*))-(4R,7R,10S,13S,15E,17R,19S)-7-((2-bromo-1H-indol-3-yl)methyl)-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-1-oxa-5,8,11-triazacyclononadec-15-ene-2,6,9,12-tetroneRefChem:150384DTXCID801323504(3R,6S,9S,11E,13R,15S,19R)-3-((2-bromo-1H-indol-3-yl)methyl)-19-(4-hydroxyphenyl)-4,6,9,11,13,15-hexamethyl-1,4,7-triazacyclononadec-11-ene-2,5,8,17-tetrone
이름 더 보기
야플라키놀라이드JASPLAKINOLIDE, JASPIS JOHNSTONIJasplakinolide, Actin polymerization and stabilization inducerJasplakinolide, Jaspis johnstoni - CAS 102396-24-7 - CalbiochemCyclo[(3R)-3-(4-hydroxyphenyl)-β-alanyl-(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-L-alanyl-2-bromo-N-methyl-D-tryptophyl]
물성
구조 계산 물성
- XLogP
- 5.6
- 극성 표면적
- 141 Ų
- 수소 결합 공여자 수
- 4
- 수소 결합 수용자 수
- 6
- 회전 가능 결합 수
- 3
- 무거운 원자 수
- 47
- 형식 전하
- 0
- 복잡도
- 1,140
물리화학적 성질
- 녹는점
- 110 ℃ · 110℃ (decomposition)
- 저장 조건
- -20 °C · -20°C
- 용해도
- 2 mg/mL · DMSO: >2mg/mL
- 물리적 상태
- 회백색 고체
- 색상
- 오프 화이트부터 베이지까지
- InChIKey
- GQWYWHOHRVVHAP-DHKPLNAMSA-N
- SMILES
- C[C@H]1C[C@@H](C)\C=C(C)\C[C@H](C)C(=O)N[C@@H](C)C(=O)N(C)[C@H](Cc2c(Br)[nH]c3ccccc23)C(=O)N[C@H](CC(=O)O1)c4ccc(O)cc4
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
안전 데이터
- wgk
- 3
- rtecs
- GX7000000
- ridadr
- 3172
- 포장분류
- III
- 위험 등급
- 6.1(b)
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
MeSH Pharmacological Classification
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
응용 분야
개요Jasplakinolide is a natural macrocyclic peptide first isolated from a marine sponge. It potently inhibits the proliferation of PC3 prostate carcinoma cells (IC50 = 35 nM) by binding F-actin (KD = 15 nM). This binding of jasplakinolide to actin, which is competitive with phalloidin, stabilizes actin filaments in vitro but disrupts actin filaments and induces irregular polymerization of monomeric actin in vivo. This compound is used to investigate the role of actin in diverse cellular roles, such as motility, transport, and development.
용도Jasplakinolide is a potent inhibitor of prostrate and breast carcinoma cell proliferation. Also acts as an actin stabilizing agent, affecting chromosome movement in studies.
추가 설명
정의ChEBI: A cyclodepsipeptide isolated from Jaspis splendens and has been shown to exhibit antineoplastic activity.
관련 반응
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