基本情報
- CAS
52665-69-7- 標準SMILES
CNc1ccc2oc(C[C@H]3O[C@@]4(CC[C@H]3C)O[C@H]([C@H](C)C(=O)c3ccc[nH]3)[C@H](C)C[C@H]4C)nc2c1C(=O)O- InChIKey
HIYAVKIYRIFSCZ-CYEMHPAKSA-N- 分子式
- C29H37N3O6
- 平均分子量
- 523.6 g/mol
- 単同位体質量
- 523.26823591
名称と識別子
- 優先名称
- Calcimycin
- IUPAC
- 5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid
- 現地名
- ビス[5-メチルアミノ-2-[[(6S)-3β,9α,11β-トリメチル-8α-[(S)-1-メチル-2-オキソ-2-(1H-ピロール-2-イル)エチル]-1,7-ジオキサスピロ[5.5]ウンデカ-2β-イル]メチル]-4-ベンゾオキサゾールカルボン酸]カルシウム
- 英語名
- A23187
- 分子式
- C29H37N3O6
- 分子量
- 523.62
名称と別名
Calcimycin52665-69-7antibiotic A-23187A2318737H9VM9WZLAntibiotic A23187DTXSID1040405A-23187A 231874-Benzoxazolecarboxylic acid, 5-(methylamino)-2-((3,9,11-trimethyl-8-(1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl)-1,7-dioxaspiro(5.5)undec-2-yl)methyl)-, (6S-(6alpha(2S*,3S*),8beta(R*),9beta,11alpha))-5-(Methylamino)-2-[[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-4-benzoxazolecarboxylic acid5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid
名称をさらに表示
5-メチルアミノ-2-[[(2R,3R,6S)-3,9α,11β-トリメチル-8α-[(S)-1-メチル-2-オキソ-2-(1H-ピロール-2-イル)エチル]-1,7-ジオキサスピロ[5.5]ウンデカ-2-イル]メチル]-4-ベンゾオキサゾールカルボン酸カルシウムイオノフォアA-23187カリマイシン抗生物質A-23187イオノホアA-23187ビス[5-メチルアミノ-2-[[(6S)-3β,9α,11β-トリメチル-8α-[(S)-1-メチル-2-オキソ-2-(1H-ピロール-2-イル)エチル]-1,7-ジオキサスピロ[5.5]ウンデカ-2β-イル]メチル]-4-ベンゾオキサゾールカルボン酸]カルシウム
物性
構造計算による物性
- XLogP
- 5.9
- 極性表面積
- 127 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 8
- 回転可能結合数
- 7
- 重原子数
- 38
- 形式電荷
- 0
- 複雑度
- 873
物理化学的性質
- 融点
- 187 · 187-190 °C
- 比旋光度
- 25 · D25 -56° (c = 1 in chloroform)
- 沸点
- 710.3 · 710.3±55.0 °C(Predicted)
- 比重(密度)
- 1.28 · 1.28±0.1 g/cm3(Predicted)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 加温または超音波処理により DMSO に可溶。エタノールまたは酢酸エチルにも可溶
- 外見
- 個体
- 酸解離定数(Pka)
- 1 · pKa1 6.9 in 90% DMSO
- 色
- 白色～淡黄色
- Merck
- 13 · 13,1639
- BRN
- 1096801 · 1096801
- 安定性
- 2 · 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 4 か月間保存できます。
- InChIKey
- HIYAVKIYRIFSCZ-CYEMHPAKSA-N
- SMILES
- [H][C@@]1(O[C@@]2(CC[C@@H](C)[C@@H](Cc3nc4c(C(O)=O)c(NC)ccc4o3)O2)[C@H](C)C[C@H]1C)[C@H](C)C(=O)c5ccc[nH]5
化学的性質
化学的特性white to off-white solid
安全と法規制
GHS分類
GHS Classification
Warning
H315 (95.2%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (95.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (95.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
危険有害性情報
Hazard Classes and CategoriesSkin Irrit. 2 (95.2%)；Eye Irrit. 2 (95.2%)；STOT SE 3 (95.2%)
安全データ
- F
- 8
- wgk
- 3
- rtecs
- DM4676000
- 毒性
- LD50 i.p. in mice: 10 mg/kg (Gale)
- hs_code
- 29349990
- risk_code
- 36/37/38-20/21/22
- hazard_code
- Xi,Xn
- safety_code
- 26-36
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
MeSH Pharmacological Classification
Substances that inhibit the growth or reproduction of BACTERIA.
Chemical agents that increase the permeability of CELL MEMBRANES to CALCIUM ions.
応用分野
使用A23187 (Mixed Calcium-Magnesium Salt) is used in cell activation experiments when calcium dose-response data are not required. Ca-Mg ratio ~ 1:1. it is widely used as a compound in cell activation. It is used as a highly selective Ca2+ ionophore. it is used in studies of intracellular Ca2+ mediated events. A23187 has been observed to induce cell activation, differentiation or proliferation. In vitro experimentation has shown A23187 to boost ROS generation and platelet fragmentation. A23187 is a widely used ionophore. It has the ability to increase the intracellular concentrations of cations and is widely used to increase the intracellular levels of calcium. Visualization of Synaptic Ca2+ Calmodulin-Dependent Protein Kinase II Activity in Living Neurons.
一般的な説明A mobile ion-carrier that forms stable complexes with divalent cations. Useful for increasing intracellular Ca2+ levels. Also acts as an uncoupler of oxidative phosphorylation and inhibitor of mitochondrial ATPase activity. An antibiotic with weak activity against Gram-positive bacteria. Also induces apoptosis in mouse lymphoma cell line (S49); however, A23187 has been shown to block apoptosis in other systems, such as when interleukin-3 (IL-3) is withdrawn from IL-3-dependent cells.
調製方法
純化方法It recrystallises from Me2CO as colourless needles. Protect it from light and moisture, store in a refrigerator. It is soluble in Me2SO or EtOH and can be stored for 3 months without loss of activity. The Mg and Ca salts are soluble in organic solvents and cross biological membranes. It has a pKa of 6.9 in 90% Me2SO. The Ca complex crystallises from 50% EtOH as colourless prisms. It is highly TOXIC. [Pressman Ann Rev Biochem 45 501 1976, Chaney et al. J Am Chem Soc 96 1932 1974, Chaney et al. J Antibiotics 29 124 1976, Suzuki et al. Anal Biochem 61 382 1989, Simon & Carafoli Methods Enzymol 56 439 1977.]
関連反応
4 件
化合物ノート
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