エポチロンB
エポチロンB · エポチロンB, · エポチロンB (SYNTHETIC) · エポチロン B · (4S,7R,8S,9S,13R,14S,16S)-4,8-ジヒドロキシ-5,5,7,9,13-ペンタメチル-16-[(E)-1-メチル-2-(2-メチル-4-チアゾリル)エテニル]-13,14-エポキシ-1-オキサシクロヘキサデカン-2,6-ジオン · パツピロン · (-)-エポチロンB · (1S,3S,7S,10R,11S,12S,16R)-7,11-ジヒドロキシ-8,8,10,12,16-ペンタメチル-3-[(1E)-1-(2-メチル-1,3-チアゾール-4-イル)プロパ-1-エン-2-イル]-4,17-ジオキサビシクロ[14.1.0]ヘプタデカン-5,9-ジオン
識別子と物理属性
| CAS No. | 152044-54-7 |
|---|---|
| 分子式 | C27H41NO6S |
| 平均分子量 | 507.7 g/mol |
| 単同位体質量 | 507.26545903 g/mol |
| 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 |
| PubChem CID | 448013 |
| ChEMBL | CHEMBL94657 |
| ChEBI | CHEBI:31550 |
| EC No. | 604-822-6 |
| DTXSID | DTXSID4046862 |
| 現地名 | エポチロンB |
化学・物理的性質
| XLogP | 4.2 |
|---|---|
| 極性表面積 | 137 |
| 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 | 35 |
| 形式電荷 | 0 |
| 複雑度 | 815 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| 脂質 | Polyketides [PK] -> Macrolides and lactone polyketides [PK04] |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 融点 | 95-97°C |
| 比旋光度 | D21 -35° (c = 0.7 in methanol) |
| 沸点 | 680.2±55.0 °C(Predicted) |
| 密度 | 1.136 |
| 貯蔵条件 | Store at -20°C |
| 溶解度 | DMSO (最大 40mg/ml) またはエタノール (最大 35mg/ml) に可溶。 |
| 外観・状態 | 白からオフホワイトの固体 |
| pKa（酸解離定数） | 13.57±0.70(Predicted) |
| 色 | 無色 |
| 由来生物 | Sorangium cellulosum |
| 安定性 | 購入日から2年間安定です。この DMSO またはエタノール溶液は、-20°C で 1 か月間保存できます。 |
| 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 |
| CAS データベース | 152044-54-7 |
化学的特性
White Powder
安全性と法規制
| GHS 分類 | DangerH300 (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. |
|---|---|
| 規制情報 | 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. |
| Hazard Classes and Categories | Acute Tox. 1 (75%) |
| 水環境危害等級（WGK） | 3 |
| 税関コード | 29419090 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
天然物の起源
粘液細菌Sorangium cellulosum
使用
Epothilones 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.
一般的な説明
Epothilones has antimitotic properties. It prevents microtubule depolymerization and competitively blocks paclitaxel binding to microtubules. Epothilone B is used to treat metastatic breast cancer (MBC).