基本情報
- 標準SMILES
C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@@H]2CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1- InChIKey
HESCAJZNRMSMJG-KKQRBIROSA-N- 分子式
- C26H39NO6S
- 平均分子量
- 493.7 g/mol
- 単同位体質量
- 493.24980897
概要
Epothilone A is an epithilone that is epothilone C in which the double bond in the macrocyclic lactone ring has been oxidised to the corresponding epoxide (the 13R,14S diastereoisomer). It has a role as a metabolite, an antineoplastic agent, a tubulin modulator and a microtubule-stabilising agent. It is an epoxide and an epothilone.
名称と識別子
- 優先名称
- Epothilone A
- IUPAC
- (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-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
- 現地名
- エポチロンA
- 英語名
- Epothilone A
- 分子式
- C26H39NO6S
- 分子量
- 493.66
名称と別名
名称をさらに表示
データベース識別子
- CAS
152044-53-6- PubChem CID
- 448799
- DTXSID
DTXSID10332288- ChEMBL
CHEMBL329993- ChEBI
CHEBI:31549- UNII
- 51E07YBX96
物性
構造計算による物性
- XLogP
- 4
- 極性表面積
- 137 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 8
- 回転可能結合数
- 2
- 重原子数
- 34
- 形式電荷
- 0
- 複雑度
- 770
実験および物理化学的性質
物理化学的性質
- 融点
- 95 ℃ · 95℃
- 比旋光度
- 21 · D21 -47.1° (c = 1.0 in methanol)
- 沸点
- 683.3 · 683.3±55.0 °C(Predicted)
- 比重(密度)
- 1.143 · 1.143
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- クロロホルム(微量)、酢酸エチル(微量)
- 外見
- 個体
- 酸解離定数(Pka)
- 13.57 · 13.57±0.70(Predicted)
- 色
- ホワイトからオフホワイト
- 安定性
- Stable under recommended storage conditions., Stable Under Recommended Storage C
- InChIKey
- HESCAJZNRMSMJG-KKQRBIROSA-N
- SMILES
- [C@]12([H])[C@]([H])(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
安全と法規制
危険有害性情報
Regulatory Information
4,17-Dioxabicyclo14.1.0heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12-tetramethyl-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.
安全と保護具
毒性情報
Treatment
EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Toxicity Summary
The exact mechanism of toxicty of PBBs varies depending on the specific congener. The predominant interaction is believed to involve the aryl hydrocarbon receptor (AhR). PBBs bind to and activate the AhR, which in turn initiates the transcriptional upregulation of a number of genes, affecting biochemical and endocrine pathways, cell cycle regulation, morphogenesis, oxidative stress response, and various other processes. This results in the numerous toxic responses characteristic of PBBs. Some of the known induced genes include the cytochrome P-450-dependent monooxygenases CYP1A1 and CYP1A2. (L628)
安全データ
- wgk
- 3
化学と産業
薬理情報
Metabolism/Metabolites
PBBs can be absorbed via oral, inhalation, and dermal routes. Due to their lipophilic nature, PBBs, especially the highly brominated congeners, tend to accumulate in lipid-rich tissues such as the liver, adipose, skin, and breast milk. Certain PBB compounds are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 of the type induced by phenobarbital. The rate of metabolism may depends on the bromine substitution pattern. PBB congeners of low bromine content are transformed into hydroxylated derivatives that are predominately eliminated in the urine. Highly brominated congeners are either retained or excreted unchanged in the feces. (L628)
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.
用途と製造
Uses
PBBs can be used as flame retardants and may be added to the plastics used to make products like computer monitors, televisions, textiles, and plastic foams to make them difficult to burn. However, the use of PBBs is banned or restricted in most areas due to their toxicity and persistence in the environment. (L628, L629)
応用分野
使用The epothilones are a novel class of antineoplastic agents possessing antitubulin activity. Epothilone A, B isolated from Sorangium cellulosum was associated with cell cycle arrest at G2/M transition and apoptosis that was resisted with overexpression of β-tubulin and P-glycoprotein in human bladder carcinoma cell.
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補足説明
定義ChEBI: An epithilone that is epothilone C in which the double bond in the macrocyclic lactone ring has been oxidised to the corresponding epoxide (the 13R,14S diastereoisomer).
関連反応
関連ノート
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