エポチロンD

Epothilone D

HCID 447865CAS 189453-10-9

基本情報

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that is epithilone C in which the hydrogen at position 13 of the oxacyclohexadec-13-ene-2,6-dione macrocycle has been replaced by a methyl group.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

データベース識別子

CAS: 189453-10-9
PubChem CID: 447865
DTXSID: DTXSID70880053
ChEMBL: CHEMBL96172
ChEBI: CHEBI:29579
UNII: T0358E0YUF

物性

構造計算による物性

XLogP: 5
極性表面積: 125 Å²
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

危険有害性情報

Regulatory Information · 1 件

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 · 2 件

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 · 1 件

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

エポチロンB

サプライヤー50 社

南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]

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成都超九八生物科技有限公司13348960310 13348960310 · [email protected]

咸宁深蓝生物医药研发有限公司18171815831 · [email protected]

湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]

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.