基本情報
- CAS
67526-95-8- 標準SMILES
C/C=C(/C)C(=O)O[C@H]1C(C)=C2[C@H]([C@@H]1OC(=O)CCCCCCC)[C@@](C)(OC(C)=O)C[C@H](OC(=O)CCC)[C@@]1(O)[C@H]2OC(=O)[C@@]1(C)O- InChIKey
IXFPJGBNCFXKPI-FSIHEZPISA-N- 分子式
- C34H50O12
- 平均分子量
- 650.8 g/mol
- 単同位体質量
- 650.33022703
概要
Thapsigargin is an organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca2+-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations. It has a role as a calcium channel blocker and an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor. It is an organic heterotricyclic compound, a sesquiterpene lactone and a butyrate ester.
名称と識別子
- 優先名称
- Thapsigargin
- IUPAC
- [(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-4-butanoyloxy-3,3a-dihydroxy-3,6,9-trimethyl-8-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] octanoate
- 現地名
- タプシガルギン
- 英語名
- Thapsigargin
- 分子式
- C34H50O12
- 分子量
- 650.75
名称と別名
thapsigargin67526-95-8(-)-ThapsigarginZ96BQ26RZDCHEBI:9516Octanoic acid, 6-(acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-((2-methyl-1-oxo-2-butenyl)oxy)-2-oxo-4-(1-oxobutoxy)azuleno(4,5-b)furan-7-yl ester, (3S-(3alpha,3abeta,4alpha,6beta,6abeta,7beta,8alpha(Z),9balpha))-(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl octanoate[(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-4-butanoyloxy-3,3a-dihydroxy-3,6,9-trimethyl-8-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] octanoate((3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-4-butanoyloxy-3,3a-dihydroxy-3,6,9-trimethyl-8-((Z)-2-methylbut-2-enoyl)oxy-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno(4,5-b)furan-7-yl) octanoate(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-(((2Z)-2-methylbut-2-enoyl)oxy)-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno(4,5-b)furan-7-yl octanoateRefChem:189119
物性
構造計算による物性
- XLogP
- 3.6
- 極性表面積
- 172 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 12
- 回転可能結合数
- 17
- 重原子数
- 46
- 形式電荷
- 0
- 複雑度
- 1,270
実験および物理化学的性質
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]
物理化学的性質
- 沸点
- 597.77 °C · 597.77°C (rough estimate)
- 比重(密度)
- 1.1521 · 1.1521 (rough estimate)
- 屈折率
- 1.639 · 1.6390 (estimate)
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- DMSO：可溶
- 外見
- 液体またはフィルム
- 酸解離定数(Pka)
- 10.57 · 10.57±0.70(Predicted)
- 色
- 無色
- 由来生物
- plant (Thapsia garganica)
- 安定性
- -20 °Cで最大1週間保存できます。 · DMSOまたはエタノール溶液で-20°Cで最大1週間保存できます。
- InChIKey
- IXFPJGBNCFXKPI-FSIHEZPISA-N
- SMILES
- [H][C@@]12C([C@H](OC([C@]3(O)C)=O)[C@]3(O)[C@@H](OC(CCC)=O)C[C@]2(C)OC(C)=O)=C(C)[C@H](OC(/C(C)=C(C)/[H])=O)[C@H]1OC(CCCCCCC)=O
- CAS データベース
- 67526 · 67526-95-8(CAS DataBase Reference)
化学的性質
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
Danger
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P233, P260, P261, P264, P264+P265, P271, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
安全データ
- wgk
- 3
- ridadr
- UN 2811 6.1/PG 2
- hs_code
- 29181990
- risk_code
- 36/37/38-42
- hazard_code
- Xn,T
- safety_code
- 26-36/37/39
- Hazard Classifications
- Eye Irrit. 2Resp. Sens. 1Skin Irrit. 2STOT SE 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
MeSH Pharmacological ClassificationCompounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
応用分野
説明Thapsigargin is a naturally occurring sesquiterpene lactone isolated from the umbelliferous plant Thapsia garganica. It is a non-competitive, cell permeable inhibitor of calcium transport by SERCAs (IC50 values are cell type-dependent and range from ~2-80 nM). This tumor promoter releases Ca2+ from intracellular stores by specifically inhibiting the endoplasmic reticulum Ca2+-ATPase; it does not directly affect plasma membrane Ca2+-ATPases, Ins 1,4,5-P3 production or protein kinase C activity. This effect is a result of emptying the intracellular calcium stores, which leads to a chain of events that causes apoptosis.
使用THAPSIGARGIN is a widely used inhibitor of the ubiquitous sarco-endoplasmic reticulum Ca(2+)-ATPases in mammalian cells. It acts as a potent, cell-permeable, IP3-independent intracellular calcium releaser that blocks the transient increase in intracellular Ca2+ induced by angiostatin and endostatin. It induces apoptosis by disrupting intracellular free Ca2+ levels.
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