基本情報
- CAS
73573-88-3- 標準SMILES
CC[C@H](C)C(=O)O[C@H]1CCC=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@H]21- InChIKey
AJLFOPYRIVGYMJ-INTXDZFKSA-N- 分子式
- C23H34O5
- 平均分子量
- 390.5 g/mol
- 単同位体質量
- 390.24062418
概要
Mevastatin is a carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals. It has a role as an antifungal agent, an apoptosis inducer, a fungal metabolite, a Penicillium metabolite and an EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor. It is a member of hexahydronaphthalenes, a polyketide, a carboxylic ester, a member of 2-pyranones and a statin (naturally occurring).
名称と識別子
- 優先名称
- Mevastatin
- IUPAC
- [(1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
- 現地名
- (2S)-2-メチル酪酸[(1S)-1,2,3,7,8,8aα-ヘキサヒドロ-7α-メチル-8α-[2-[(2R,4R)-テトラヒドロ-4-ヒドロキシ-6-オキソ-2H-ピラン-2-イル]エチル]ナフタレン-1β-イル]
- 英語名
- Mevastatin
- 分子式
- C23H34O5
- 分子量
- 390.51
名称と別名
Mevastatincompactin73573-88-3MevastatinaMevastatineMevastatinumAntibiotic ML 236BML-236B lactoneML-236BML 236 BCS 500ML236B lactone
名称をさらに表示
メバスタチン(2S)-2-メチルブタン酸[(1S)-1,2,3,7,8,8aα-ヘキサヒドロ-7α-メチル-8α-[2-[[(2R,4R)-テトラヒドロ-4β-ヒドロキシ-6-オキソ-2H-ピラン]-2α-イル]エチル]ナフタレン]-1β-イル(+)-コンパクチンコンパクチン(S)-2-メチル酪酸[(1S,7S,8S,8aR)-1,2,3,7,8,8a-ヘキサヒドロ-7-メチル-8-[2-[(2R,4R)-テトラヒドロ-4-ヒドロキシ-6-オキソ-2H-ピラン-2-イル]エチル]ナフタレン-1-イル](2S)-2-メチル酪酸[(1S)-1,2,3,7,8,8aα-ヘキサヒドロ-7α-メチル-8α-[2-[(2R,4R)-テトラヒドロ-4-ヒドロキシ-6-オキソ-2H-ピラン-2-イル]エチル]ナフタレン-1β-イル]抗生物質ML-236BスタチンI(2S)-2-メチルブタン酸(1S,7S,8S,8aR)-7-メチル-8-[2-[(2R,4R)-テトラヒドロ-4-ヒドロキシ-6-オキソ-2H-ピラン-2-イル]エチル]-1,2,3,7,8,8a-ヘキサヒドロナフタレン-1-イル(2S)-2-メチルブタン酸=(1S,7S,8S,8aR)-7-メチル-8-{2-[(2R,4R)テトラヒドロ-4-ヒドロキシ-6-オキソ-2H-ピラン-2-イル]エチル}-1,2,3,7,8,8a-ヘキサヒドロナフタレン-1-イルコンパクチンラクトンコンパクチン【ペニシリウム】
物性
構造計算による物性
- XLogP
- 3.9
- 極性表面積
- 72.8 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 5
- 回転可能結合数
- 7
- 重原子数
- 28
- 形式電荷
- 0
- 複雑度
- 637
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Statins
LogP3.85
Collision Cross Section
198.4 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
185.68 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 151 · 151-153 °C
- 比旋光度
- 22 · D22 +283° (c = 0.48 in acetone)
- 沸点
- 555 · 555.0±50.0 °C(Predicted)
- 比重(密度)
- 1.13 · 1.13±0.1 g/cm3(Predicted)
- 蒸気圧
- 0 Pa · 0Pa at 25℃
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 20 mg/mL · DMSO: 20 mg/mL
- 外見
- 粉
- 酸解離定数(Pka)
- 13.49 · 13.49±0.40(Predicted)
- 色
- 白い
- Merck
- 14 · 14,6164
- BRN
- 1269441 · 1269441
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
This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.
Danger
H317 (50%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P203, P260, P261, P263, P264, P270, P272, P273, P280, P302+P352, P318, P319, P321, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Not Classified
危険有害性情報
Regulatory InformationREACH registered substance: (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl(2S)-2-methylbutanoate (EC: 700-442-0)
Hazard Classes and Categories
Skin Sens. 1 (50%)
Not Classified
安全データ
- F
- 1-8-10
- wgk
- 3
- rtecs
- EK7907100
- hs_code
- 29322090
- risk_code
- 26/27/28
- hazard_code
- T+
- safety_code
- 22-24/25-45-36/37/39
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Pharmacodynamics
The primary cause of cardiovascular disease is atherosclerotic plaque formation. Mevastatin lowers hepatic production of cholesterol to reduce the risk of cardiovascular disease. Mevastatin competitively inhibits HMG-CoA reductase. This inhibition prevents the rate limiting step in cholesterol synthesis. Decreased hepatic cholesterol levels causes increased uptake of low density lipoprotein (LDL) cholesterol and reduces cholesterol levels in the circulation.
Mechanism of Action
Mevastatin is structurally similar to the HMG, a substituent of the endogenous substrate of HMG-CoA reductase. Mevastatin is a prodrug that is activated <i>in vivo</i> via hydrolysis of the lactone ring. The hydrolyzed lactone ring mimics the tetrahedral intermediate produced by the reductase allowing the agent to bind with 10,000 times greater affinity than its natural substrate. The bicyclic portion of mevastatin binds to the coenzyme A portion of the active site.
MeSH Pharmacological Classification
Substances used to lower plasma CHOLESTEROL levels.
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Compounds that inhibit HYDROXYMETHYLGLUTARYL COA REDUCTASES. They have been shown to directly lower CHOLESTEROL synthesis.
Substances that inhibit the growth or reproduction of BACTERIA.
応用分野
解説コンパクチン，C23H34O5(390.52)．Panicillium citrinumの培養液中よりコレステロール生合成阻害剤として発見された化合物．融点152 ℃．[α]D22"＋283°(アセトン)．コレステロールの生合成に関与する重要な調節酵素の一つである，3-ヒドロキシ-3-メチルグルタリルCoA還元酵素を特異的に阻害する．抗真菌作用をもつ．シンバスタチンは半合成誘導体である
用途病理研究用、昆虫神経ペプチド類の作用機構の研究用。
使用Mevastatin (compactin) is a diterpene produced by several species of the genera Penicillium and Monascus, first reported in 1976. Mevastatin, the prtotype of the statin class, is a potent competitive inhibitor of HMG-CoA reductase, a regulatory enzyme for cholesterol biosynthesis. Mevastatin has also been shown to induce apoptosis by inhibiting post-translational prenylation of proteins such as Ras, increasing eNOS mRNA and protein levels by blocking the geranylgeranylation of Rho, and inhibiting myoblast fusion. It induces cell cycle arrest in late G1 phase and may induce bone morphogenic protein-2 (BMP-2).
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