CAS 56092-81-0 Ionomycin (HCID 6912226)

基本情報

CAS: 56092-81-0
標準SMILES: C[C@H](CCC(=O)O)C[C@H](C)C[C@H](C)C(=O)/C=C(\O)[C@H](C)C[C@H](C)C/C=C/[C@@H](C)[C@@H](O)[C@@H](C)[C@@H](O)C[C@@H]1CC[C@@](C)([C@H]2CC[C@@](C)([C@@H](C)O)O2)O1
InChIKey: PGHMRUGBZOYCAA-ADZNBVRBSA-N
分子式: C41H72O9
平均分子量: 709 g/mol
単同位体質量: 708.51763388

概要

Ionomycin is a very long-chain fatty acid that is docosa-10,16-dienoic acid which is substituted by methyl groups at positions 4, 6, 8, 12, 14, 18 and 20, by hydroxy groups at positions 11, 19 and 21, and by a (2',5-dimethyloctahydro-2,2'-bifuran-5-yl)ethanol group at position 21. An ionophore produced by Streptomyces conglobatus, it is used in research to raise the intracellular level of Ca2+ and as a research tool to understand Ca2+ transport across biological membranes. It has a role as a calcium ionophore and a metabolite. It is a polyunsaturated fatty acid, a very long-chain fatty acid, an enol and a cyclic ether.

名称と識別子

優先名称: Ionomycin
IUPAC: (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-trihydroxy-22-[(2S,5S)-5-[(2R,5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
現地名: イオノマイシン
英語名: IONOMYCIN
分子式: C41H72O9
分子量: 709.01

名称と別名

ionomycin56092-81-0SQ-23377SQ23377DTXSID2040521SQ 2337754V905V6AT(4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-trihydroxy-22-[(2S,5S)-5-[(2R,5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acidCHEBI:63954(4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-trihydroxy-22-{(2S,2'R,5S,5'S)-5'-[(1R)-1-hydroxyethyl]-2,5'-dimethyloctahydro-2,2'-bifuran-5-yl}-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid10,16-DOCOSADIENOIC ACID, 11,19,21-TRIHYDROXY-4,6,8,12,14,18,20-HEPTAMETHYL-22-((2S,2'R,5S,5'S)-OCTAHYDRO-5'-((1R)-1-HYDROXYETHYL)-2,5'-DIMETHYL(2,2'-BIFURAN)-5-YL)-9-OXO-, (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-(4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-trihydroxy-22-((2S,2'R,5S,5'S)-5'-((1R)-1-hydroxyethyl)-2,5'-dimethyloctahydro-2,2'-bifuran-5-yl)-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid

名称をさらに表示

イオノマイシンイオノマイシン, 遊離酸, STREPTOMYCES CONGLOBATUS由来

物性

構造計算による物性

XLogP: 7.5
極性表面積: 154 Å²
水素結合供与体数: 5
水素結合受容体数: 9
回転可能結合数: 22
重原子数: 50
形式電荷: 0
複雑度: 1,120

実験および物理化学的性質

DrugsPharmaceuticals -> Antibiotics

Human DrugsPharmaceuticals

物理化学的性質

沸点: 817.2 · 817.2±65.0 °C(Predicted)
比重(密度): 1.072 · 1.072±0.06 g/cm3(Predicted)
貯蔵温度: 20 °C · −20°C
溶解性: 10 mM、DMSO · エタノールに 10 mM、DMSO に 10 mM に可溶。
外見: ワックス状の固体
酸解離定数(Pka): 4.77 · 4.77±0.10(Predicted)
色: 黄色
BRN: 3642126 · 3642126
安定性: -20 °C · -20°C の DMSO またはエタノール溶液で最大 3 か月間保存できます。
InChIKey: PGHMRUGBZOYCAA-ADZNBVRBSA-N
SMILES: C[C@H](CCC(O)=O)C[C@H](C)C[C@H](C)C(=O)\C=C(/O)[C@H](C)C[C@H](C)C\C=C\[C@@H](C)[C@@H](O)[C@@H](C)[C@@H](O)C[C@@H]1CC[C@](C)(O1)[C@H]2CC[C@](C)(O2)[C@@H](C)O

化学的性質

化学的特性White powder

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 1 notifications to the ECHA C&L Inventory.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (100%)

安全データ

F: 8-10
wgk: 3
rtecs: NO0650000
hs_code: 29419090
risk_code: 22-36/37/38
hazard_code: Xn,Xi
safety_code: 36-36/37/39-27-26-24/25
hazard_class: 3
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

MeSH Pharmacological ClassificationChemical agents that increase the permeability of CELL MEMBRANES to CALCIUM ions.

用途と製造

Use ClassificationPharmaceuticals

応用分野 · 2 件

使用Ionomycin was isolated from Streptomyces conglobatus as a potent Gram positive antibiotic . During isolation, it was recognised that ionomycin exhibits a very high affinity and selectivity for calcium ions, suggesting the metabolite acts as a calcium ionophore. More recently, ionomycin has been used in cell biology as a universal calcium ionophore to explore the role of calcium regulation in the cell.

一般的な説明Highly specific for divalent cations (Ca2+ > Mg2+ >> Sr2+ = Ba2+). More effective than antibiotic A23187 as a mobile ion carrier for Ca2+. Complexes with Ca2+ between pH 7 and 9.5, causing significant absorption in the UV range; however, in contrast to A23187 (Cat. No. 100105), it is not fluorescent. Useful for studies of Ca2+ transport across biological membranes and measurement of cytoplasmic free Ca2+. Induces apoptotic neuronal degeneration in embryonic cortical neurons. Also induces cell cycle arrest in the G1 interval of mature Burkitt lymphoma cell lines.

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化合物ノート

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イオノマイシン