エポチロンD
Epothilone D
基本情報
- CAS
189453-10-9- 標準SMILES
C/C1=C/C[C@@H](/C(C)=C/c2csc(C)n2)OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC1- InChIKey
XOZIUKBZLSUILX-GIQCAXHBSA-N- 分子式
- C27H41NO5S
- 平均分子量
- 491.7 g/mol
- 単同位体質量
- 491.27054441
概要
Epothilone D is an epithilone that is epithilone C in which the hydrogen at position 13 of the oxacyclohexadec-13-ene-2,6-dione macrocycle has been replaced by a methyl group. It has a role as a microtubule-stabilising agent.
名称と識別子
- 優先名称
- Epothilone D
- IUPAC
- (4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
- 現地名
- エポチロンD
- 英語名
- Epothilone D
- 分子式
- C27H41NO5S
- 分子量
- 491.68
名称と別名
Epothilone D189453-10-9Desoxyepothilone b(-)-Desoxyepothilone BKOS-86212,13-Desoxyepothilone B(-)-Epothilone DEpothilon DNSC-703147KOS 86212,13-Deoxyepothilone BEpothiolone D
名称をさらに表示
エポチロンD(4S,13Z)-4α,8β-ジヒドロキシ-5,5,7α,9β,13-ペンタメチル-16β-[(E)-1-メチル-2-(2-メチル-4-チアゾリル)エテニル]-1-オキサシクロヘキサデカン-13-エン-2,6-ジオン(4S,7R,8S,9S,13Z,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]-1-オキサシクロヘキサデカ-13-エン-2,6-ジオン(12Z)-デスオキシエポチロンB(4S,7R,8S,9S,13Z,16S)-4,8-ジヒドロキシ-5,5,7,9,13-ペンタメチル-16-[(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]-1-オキサシクロヘキサデカ-13-エン-2,6-ジオンEpo DCS-1161Ebomycin12,13-Deoxyepo13-Desoxyepothilone BEpothilone D (KOS-862)
DEpoB cpdNSC 703147T0358E0YUFEpothilone B, desoxy12,13-desoxyepothilone b, cisKOS862Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)-R1492
物性
構造計算による物性
- XLogP
- 5
- 極性表面積
- 125 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 7
- 回転可能結合数
- 2
- 重原子数
- 34
- 形式電荷
- 0
- 複雑度
- 777
実験および物理化学的性質
LipidsPolyketides [PK] -> Macrolides and lactone polyketides [PK04]
物理化学的性質
- 融点
- 63 · 63-66°C
- 比旋光度
- 22 · D22 -61.3° (c = 2.5 in methanol)
- 沸点
- 663.7 · 663.7±55.0 °C(Predicted)
- 比重(密度)
- 1.084 · 1.084±0.06 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · -20°C Freezer
- 溶解性
- Soluble in DMSO
- 外見
- solid
- 酸解離定数(Pka)
- 13.47 · 13.47±0.70(Predicted)
- 色
- white to off-white
- InChIKey
- XOZIUKBZLSUILX-GIQCAXHBSA-N
- SMILES
- O1[C@H](/C(/C)=C/C2=CSC(C)=N2)CC=C(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC1=O |t:13|
化学的性質
化学的特性White Foam
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
危険有害性情報
Regulatory Information
Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (4S,7R,8S,9S,13Z,16S)-: 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.
化学と産業
薬理情報
ATC Code
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Mechanism of ActionThe 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.
MeSH Pharmacological ClassificationAgents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.
応用分野
説明Epothilones are microtubule-stabilizing agents with potential anti-neoplastic actions. They are natural macrolides that have high potency in both taxane-sensitive and taxane-resistant models. Epothilone D is a desoxy form of epothilone B (Item No. 10924) that inhibits the growth of a variety of cancer cells both in vitro (IC50 values range from 0.97 to 21 nM) and in mice. Epothilone D is brain penetrant and reduces neurodegeneration in aged tau transgenic mice. Effects include improved axonal transport, decreased tau neuropathology, and reduced hippocampal neuron loss. Epothilone D also rescues microtubule defects and attenuates nigrostriatal degeneration in a mouse model of Parkinson’s disease.
上流・下流製品情報
下流製品
補足説明
定義ChEBI: An epithilone that is epithilone C in which the hydrogen at position 13 of the oxacyclohexadec-13-ene-2,6-dione macrocycle has been replaced by a methyl group.
関連反応
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化合物ノート
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