기본 정보
- 표준 SMILES
C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1- InChIKey
QXRSDHAAWVKZLJ-PVYNADRNSA-N- 분자식
- C27H41NO6S
- 평균 분자량
- 507.7 g/mol
- 단동위원소 질량
- 507.26545903
개요
Epothilone B is an epithilone that is epithilone D in which the double bond in the macrocyclic ring has been oxidised to the corresponding epoxide (the S,S stereoisomer). It has a role as an antineoplastic agent, a microtubule-stabilising agent and an apoptosis inducer. It is an epoxide and an epothilone.
이름 및 식별자
- 우선 이름
- Epothilone B
- IUPAC
- (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
- 영어명
- Epothilone B
- 분자식
- C27H41NO6S
- 분자량
- 507.68
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
152044-54-7- PubChem CID
- 448013
- DTXSID
DTXSID4046862- ChEMBL
CHEMBL94657- ChEBI
CHEBI:31550- UNII
- UEC0H0URSE
- EC Number
- 604-822-6
물성
구조 계산 물성
- XLogP
- 4.2
- 극성 표면적
- 137 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 8
- 회전 가능 결합 수
- 2
- 무거운 원자 수
- 35
- 형식 전하
- 0
- 복잡도
- 815
실험 및 물리화학적 성질
물리화학적 성질
- 녹는점
- 95 · 95-97°C
- 끓는 점
- 680.2 · 680.2±55.0 °C(Predicted)
- 밀도
- 1.136 · 1.136
- 저장 조건
- -20 °C · Store at -20°C
- 용해도
- DMSO(최대 40mg/ml) 또는 에탄올(최대 35mg/ml)에 용해됩니다.
- 물리적 상태
- 흰색에서 회백색 고체
- 산도 계수 (pKa)
- 13.57 · 13.57±0.70(Predicted)
- 색상
- 무색의
- 생물학적 소스
- Sorangium cellulosum
- 안정성
- 2 · 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 또는 에탄올 용액은 -20°에서 최대 1개월 동안 보관할 수 있습니다.
- InChIKey
- QXRSDHAAWVKZLJ-PVYNADRNSA-N
- SMILES
- [C@]12([H])[C@](C)(O1)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O[C@H](/C(/C)=C/C1=CSC(C)=N1)C2
화학적 성질
White Powder
안전 및 규제
GHS 분류
GHS Classification
Danger
H300 (75%): Fatal if swallowed [Danger Acute toxicity, oral]
P203, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P333+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Regulatory Information
4,17-Dioxabicyclo14.1.0heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (1S,3S,7S,10R,11S,12S,16R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
안전 데이터
- wgk
- 3
- HS 번호
- 29419090
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
Mechanism of Action
The principal mechanism of the epothilone class is inhibition of microtubule function. Microtubules are essential to cell division, and epothilones therefore stop cells from properly dividing. Epothilone B possess the same biological effects as taxol both in vitro and in cultured cells. This is because they share the same binding site, as well as binding affinity to the microtubule. Like taxol, epothilone B binds to the αβ-tubulin heterodimer subunit. Once bound, the rate of αβ-tubulin dissociation decreases, thus stabilizing the microtubules. Furthermore, epothilone B has also been shown to induce tubulin polymerization into microtubules without the presence of GTP. This is caused by formation of microtubule bundles throughout the cytoplasm. Finally, epothilone B also causes cell cycle arrest at the G2-M transition phase, thus leading to cytotoxicity and eventually cell apoptosis.
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.
응용 분야
용도Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone B is what is known as a microtubule stabilizer. When a cell divides, the chromosomes that will end up in each cell are separated by thin filaments called microtubules. Normally these microtubules then break down as the cell division progresses. This class of cytotoxic chemo drugs prevents that break down and thus prevents cells from completing division.
일반 설명Epothilones has antimitotic properties. It prevents microtubule depolymerization and competitively blocks paclitaxel binding to microtubules. Epothilone B is used to treat metastatic breast cancer (MBC).
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
추가 설명
정의ChEBI: An epithilone that is epithilone D in which the double bond in the macrocyclic ring has been oxidised to the corresponding epoxide (the S,S stereoisomer).
관련 반응
연결된 노트
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