リアノドール3-(1H-ピロール-2-カルボキシラート)
Ryanodine
基本情報
- CAS
15662-33-6- 標準SMILES
CC(C)[C@@]1(O)[C@@H](OC(=O)c2ccc[nH]2)[C@@]2(O)[C@@]3(C)C[C@]4(O)O[C@@]5([C@H](O)[C@@H](C)CC[C@]35O)[C@@]2(O)[C@@]14C- InChIKey
JJSYXNQGLHBRRK-SFEDZAPPSA-N- 分子式
- C25H35NO9
- 平均分子量
- 493.5 g/mol
- 単同位体質量
- 493.23118169
概要
Ryanodine is an insecticide alkaloid isolated from South American plant Ryania speciosa. It has a role as a phytogenic insecticide and a ryanodine receptor modulator. It is an alkaloid and a cyclic hemiketal.
名称と識別子
- 優先名称
- Ryanodine
- IUPAC
- [(1R,2R,3S,6S,7S,9S,10R,11S,12R,13S,14R)-2,6,9,11,13,14-hexahydroxy-3,7,10-trimethyl-11-propan-2-yl-15-oxapentacyclo[7.5.1.01,6.07,13.010,14]pentadecan-12-yl] 1H-pyrrole-2-carboxylate
- 現地名
- リアノドール3-(1H-ピロール-2-カルボキシラート)
- 英語名
- Ryanodine
- 分子式
- C25H35NO9
- 分子量
- 493.55
名称と別名
ryanodine15662-33-6RyanodinRyanexRyanodol, 3-(1H-pyrrole-2-carboxylate)RyaniaRyanicideDTXSID0032574CHEBI:8925[(1R,2R,3S,6S,7S,9S,10R,11S,12R,13S,14R)-2,6,9,11,13,14-hexahydroxy-3,7,10-trimethyl-11-propan-2-yl-15-oxapentacyclo[7.5.1.01,6.07,13.010,14]pentadecan-12-yl] 1H-pyrrole-2-carboxylate(3S,4R,4aR,6S,6aR,7S,8R,8aS,8bR,9S,9aS)-4,6,7,8a,8b,9a-hexahydroxy-3,6a,9-trimethyl-7-(propan-2-yl)dodecahydro-6,9-methanobenzo[1,2]pentaleno[1,6-bc]furan-8-yl 1H-pyrrole-2-carboxylate1H-Pyrrole-2-carboxylic acid, (3S,4R,4aR,6S,6aS,7S,8R,8aS,8bR,9S,9aS)-dodecahydro-4,6,7,8a,8b,9a-hexahydroxy-3,6a,9-trimethyl-7-(1-methylethyl)-6,9-methanobenzo[1,2]pentaleno[1,6-bc]furan-8-yl ester
名称をさらに表示
リヤノジンリアノドール3-(1H-ピロール-2-カルボキシラート)リアノジンリアネックスリアニシドリアネクセルライアノジンリアニア(1R,2R,3S,6S,7S,9S,10S,11S,12R,13S,14R)-2,6,9,11,13,14-ヘキサヒドロキシ-3,7,10-トリメチル-11-(プロパン-2-イル)-15-オキサペンタシクロ[7.5.1.01,6.07,13.010,14]ペンタデカン-12-イル 1H-ピロール-2-カルボキシラート
物性
構造計算による物性
- XLogP
- -0.5
- 極性表面積
- 173 Ų
- 水素結合供与体数
- 7
- 水素結合受容体数
- 9
- 回転可能結合数
- 4
- 重原子数
- 35
- 形式電荷
- 0
- 複雑度
- 1,010
物理化学的性質
- 比旋光度
- 25 · D25 +26° (methanol)
- 沸点
- 586.95 °C · 586.95°C (rough estimate)
- 比重(密度)
- 1.2805 · 1.2805 (rough estimate)
- 屈折率
- 1.6 · 1.6000 (estimate)
- 貯蔵温度
- 2 · Sealed in dry,2-8°C
- 溶解性
- 10 mg/mL、透明 · DMSO：可溶10mg/mL、透明
- 外見
- 白い固体
- 融点
- 219 · 219-220 °C
- 酸解離定数(Pka)
- 10.66 · 10.66±0.70(Predicted)
- 色
- 白からベージュ
- 水溶解度
- 1 mg/mLmethanol: · water: 1mg/mLmethanol: 20mg/mL
- InChIKey
- JJSYXNQGLHBRRK-YSOSZROBSA-N
- SMILES
- [nH]1c(ccc1)C(=O)O[C@H]2[C@@]3([C@]4([C@]65O[C@]([C@]4([C@@]2(O)C(C)C)C)(C[C@]3([C@]6(CC[C@@H]([C@H]5O)C)O)C)O)O)O
- CAS データベース
- 15662 · 15662-33-6
- EPAの化学物質情報
- Ryanodine (15662-33-6)
化学的性質
化学的特性white to off-white solid
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。
GHS分類
GHS Classification
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)
Warning
H302+H312 (97.5%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]
P264, P270, P273, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)
危険有害性情報
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute toxicity - category 4
Acute Tox. 4 *
毒性情報
Toxicity Summary
Ryanodine has extremely high affinity to the open-form ryanodine receptor, a group of calcium channels found in skeletal muscle, smooth muscle, and heart muscle cells. It binds with such high affinity to the receptor that it was used as a label for the first purification of that class of ion channels and gave its name to it. At nanomolar concentrations, ryanodine locks the receptor in a half-open state, whereas it fully closes them at micromolarconcentration. The effect of the nanomolar-level binding is that ryanodine causes release of calcium from calcium stores as thesarcoplasmic reticulum in the cytoplasm, leading to massive muscular contractions. (Wikipedia)
Acute Toxicity LinkChemical: RYANIA
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
安全データ
化学と産業
用途と製造
UsesThis is a natural compound that is used as a pesticide.
Use ClassificationINSECTICIDES
応用分野
説明Ryania insecticide is the ground stem wood of the tropical tree Ryania speciosa Vahl., and it contains over a dozen of several structurally related alkaloids. Nowadays, this botanical preparation is of minor importance, but one of its major ingredients, ryanodine, is a widely used pharmacological tool in studies of the calcium release channels in sarcoplasmic reticulum membranes of skeletal and cardiac muscle of both insects and mammals (11,12).
使用Ryanodine is a potent inhibitor of Ca2+ release from sarcoplasmic reticulum with potential application towards the treatment of huntingtons disease.
補足説明
定義ChEBI: An insecticide alkaloid isolated from South American plant Ryania speciosa.
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