(1S)-1,6bβ,7,8,9a,10,11,11b-オクタヒドロ-11β-アセチルオキシ-1-(メトキシメチル)-9aα,11bα-ジメチル-3H-フロ[4,3,2-de]インデノ[4,5-h]-2-ベンゾピラン-3,6,9-トリオン

Wortmannin

HCID 312145
ノート反応
部分構造検索類似構造を探す

基本情報

CAS
19545-26-7
標準SMILES
COC[C@H]1OC(=O)c2coc3c2[C@@]1(C)C1=C(C3=O)[C@@H]2CCC(=O)[C@@]2(C)C[C@H]1OC(C)=O
InChIKey
QDLHCMPXEPAAMD-QAIWCSMKSA-N
分子式
C23H24O8
平均分子量
428.4 g/mol
単同位体質量
428.14711773

概要

Wortmannin is a delta-lactone, an organic heteropentacyclic compound, a cyclic ketone and an acetate ester. It has a role as a radiosensitizing agent, an anticoronaviral agent, a geroprotector, an antineoplastic agent, an EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor, a Penicillium metabolite and an autophagy inhibitor.

名称と識別子

優先名称
Wortmannin
IUPAC
[(1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),12(19),14-trien-3-yl] acetate
現地名
(1S)-1,6bβ,7,8,9a,10,11,11b-オクタヒドロ-11β-アセチルオキシ-1-(メトキシメチル)-9aα,11bα-ジメチル-3H-フロ[4,3,2-de]インデノ[4,5-h]-2-ベンゾピラン-3,6,9-トリオン
英語名
WORTMANNIN
分子式
C23H24O8
分子量
428.43

名称と別名

wortmannin19545-26-7WartmanninAntibiotic SL-2052SL-2052XVA4O219QWNSC221019DTXSID8040642NSC-627609CHEBI:52289NSC627609(1S,6bR,9aS,11R,11bR)-11-(Acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-3H-furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione
名称をさらに表示
ワートマニンウォルトマンニンウオルトマンニン(1S)-1,6bβ,7,8,9a,10,11,11b-オクタヒドロ-11β-アセチルオキシ-1-(メトキシメチル)-9aα,11bα-ジメチル-3H-フロ[4,3,2-de]インデノ[4,5-h]-2-ベンゾピラン-3,6,9-トリオンワートマニン 100ΜG/ML(+)-ウォルトマンニンワートマニン、調製済溶液ウォルトマンニン, Penicillium funiculosum1α-(メトキシメチル)-11α-アセトキシ-2-オキサアンドロスタ-5-エノ[6,5,4-bc]フラン-8-エン-3,7,17-トリオン(1R,3R,5S,9R,18S)-18-(メトキシメチル)-1,5-ジメチル-6,11,16-トリオキソ-13,17-ジオキサペンタシクロ[10.6.1.02,10.05,9.015,19]ノナデカ-2(10),12(19),14-トリエン-3-イル アセタートCS-731KY 1242KY 12420WortmamminWortmannin,98%WORTMANNINTOXINKY-12420antibioticsl-2052
[(1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),12(19),14-trien-3-yl] acetate(1S,6bR,9aS,11R,11bR)-9a,11b-dimethyl-1-[(methyloxy)methyl]-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetateMS54MS-54((1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo(10.6.1.02,10.05,9.015,19)nonadeca-2(10),12(19),14-trien-3-yl) acetate(1S,6bR,9aS,11R,11bR)-11-(Acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-3H-furo(4,3,2-de)indeno(4,5-h)-2-benzopyran-3,6,9-trione(1S,6bR,9aS,11R,11bR)-9a,11b-dimethyl-1-((methyloxy)methyl)-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo(4,3,2-de)indeno(4,5-h)isochromen-11-yl acetateRefChem:389363

データベース識別子

CAS
19545-26-7
PubChem CID
312145
DTXSID
DTXSID8040642
ChEMBL
CHEMBL428496
ChEBI
CHEBI:52289
UNII
XVA4O219QW
EC Number
606-337-5
Nikkaji
J13.549F

物性

構造計算による物性

XLogP
1.2
極性表面積
109 Ų
水素結合供与体数
0
水素結合受容体数
8
回転可能結合数
4
重原子数
31

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

物理化学的性質

融点
234 · 234-240 °C
沸点
463.31 °C · 463.31°C (rough estimate)
比旋光度
80 · +80.0~+105.0゜(20℃/D)(c=0.1,C2H5OH)
比重(密度)
1.2454 · 1.2454 (rough estimate)
屈折率
1.448 · 1.4480 (estimate)
闪点
2 ℃ · 2℃

化学的性質

化学的特性White to pale yellow powder

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 4 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 CategoriesAcute Tox. 2 (100%)

安全データ

F
3-8-10
wgk
3
rtecs
CB9641000
ridadr
UN 3462 6.1/PG 1
hs_code
29322090
risk_code
26/27/28-36/37/38-36-20/21/22-11

化学と産業

薬理情報

MeSH Pharmacological Classification · 5 件

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.

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.

Compounds which inhibit or antagonize the biosynthesis or action of insulin.

Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells.

Agents that inhibit PROTEIN KINASES.

応用分野 · 1 件

使用Wortmannin is a steroidal metabolite belonging to the viridin group, isolated from Penicillium wortmannii in 1957. The structure was finally solved in 1968. Wortmannin exhibits broad spectrum antifungal activity, together with antitumour and antiinflammatory activity. Wortmannin is a potent inhibitor of phosphoinositide 3-kinase and myosin light chain kinase. Wortmannin also activates neutrophil and formyl-Met-Leu-Phe-mediated phospholipase D, inhibits autophagy, potentiates LPS-induced NO production and induces Alzheimer-like hyperphosphorylation in tau in vivo.

上流・下流製品情報

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