プルンバギン

Plumbagin

HCID 10205CAS 481-42-5
部分構造検索類似構造を探す

基本情報

標準SMILES
CC1=CC(=O)c2c(O)cccc2C1=O
InChIKey
VCMMXZQDRFWYSE-UHFFFAOYSA-N
分子式
C11H8O3
平均分子量
188.18 g/mol
単同位体質量
188.04734412

概要

Plumbagin is a hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively. It has a role as a metabolite, an antineoplastic agent, an anticoagulant and an immunological adjuvant. It is a hydroxy-1,4-naphthoquinone and a member of phenols.

名称と識別子

優先名称
Plumbagin
IUPAC
5-hydroxy-2-methylnaphthalene-1,4-dione
現地名
プルンバギン
英語名
PLUMBAGIN
分子式
C11H8O3
分子量
188.18

名称と別名

Plumbagin481-42-55-hydroxy-2-methylnaphthalene-1,4-dionePlumbagine5-Hydroxy-2-methyl-1,4-naphthoquinone2-MethyljuglonePlumbaeinPlumbagone5-Hydroxy-2-methyl-1,4-naphthalenedione2-Methyl-5-hydroxy-1,4-naphthoquinone5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dioneNSC-236613
名称をさらに表示
プルンバギンプルムバギン5-ヒドロキシ-2-メチル-1,4-ナフタレンジオンプルンバゴン5-ヒドロキシ-2-メチル-1,4-ナフトキノン2-メチル-5-ヒドロキシナフタレン-1,4-ジオン3-メチル-8-ヒドロキシ-1,4-ナフトキノン2-メチル-5-ヒドロキシ-1,4-ナフトキノン5-ヒドロキシ-2-メチルナフタレン-1,4-ジオンプルンバギン PLUMBAGO INDICA(アカマツリ)由来3-メチル-8-ヒドロキシナフタレン-1,4-ジオン5-ヒドロキシ-2-メチル-1,4-ジヒドロナフタレン-1,4-ジオンplumaginplumbapinPLUMBAGANNSC 236613NSC 688284
YAS4TBQ4OQNSC-688284PCUR-101CHEBI:8273RefChem:863847PCUR101PCUR 101Synthetic Plumbagin PCUR-101

データベース識別子

CAS
481-42-5
PubChem CID
10205
DTXSID
DTXSID8075413
ChEMBL
CHEMBL295316
ChEBI
CHEBI:8273
UNII
YAS4TBQ4OQ
EC Number
207-569-6
Nikkaji
J5.778I

物性

構造計算による物性

XLogP
2.3
極性表面積
54.4 Ų
水素結合供与体数
1
水素結合受容体数
3
回転可能結合数
0
重原子数
14

実験および物理化学的性質

SpringerMaterials PropertiesChemical shift
Collision Cross Section · 2 件

124.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

134.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点
76 · 76-78 °C(lit.)
沸点
283.17 °C · 283.17°C (rough estimate)
比重(密度)
1.354 · 1.354
屈折率
1.631 · 1.6310 (estimate)
貯蔵温度
-20 °C · -20°C
溶解性
very faint turbidity in hot Methanol

化学的性質

化学的特性ORANGE CRYSTALLINE POWDER OR CRYSTALS

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P264+P265, P270, P280, P301+P316, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 69 reports by companies from 5 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. 3 (100%)

安全データ

wgk
3
rtecs
QL8500000
ridadr
UN 2923 8/PG 2
毒性
LD50 i.p. in mice: ~0.015 g/kg (Debray)
hs_code
29146990
risk_code
25-34-36/37/38

化学と産業

薬理情報

MeSH Pharmacological Classification · 6 件

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.

Agents that prevent BLOOD CLOTTING.

Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice.

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).

Chemical substances that prevent or reduce the probability of CONCEPTION.

応用分野 · 4 件

用途薬理研究用。

説明Plumbagin is a natural 1,4-naphthoquinone first isolated from plants of the genus Plumbago. It has diverse effects in cells and animals. Plumbagin causes the generation of reactive oxygen species and induces apoptosis in cancer cells. It activates signaling through Nrf2 and the antioxidant response element, inducing the expression of Nrf2 target genes, including NQO1 and heme oxygenase-1 in cultured neuronal cells. Plumbagin also inhibits NADPH oxidase 4 in a time- and dose-dependent manner. It can be protective against peroxide stress or deprivation of glucose or oxygen.

使用Plumbagin from Plumbago indica has been used: as a reactive oxygen species agent (ROS) to induce cytotoxicity in mouse embryonic fibroblastsas an oxidative stress inducer to generate superoxide anion in Saccharomyces cerevisiaeas a reference standard in thin layer chromatography and in spectrophotometric analysis for quantification of plumbagin in Plumbago auriculate samples

一般的な説明Plumbagin is a bioactive naphthoquinone present majorly in Plumbago indica L. It is a quinoid and is also derived from the roots of Plumbago zeylanicaroots.

調製方法

純化方法It crystallises in yellow needles from aqueous EtOH. It is soluble in organic solvents, it is steam volatile and it sublimes on heating in a vacuum. [Fieser & Dunn J Am Chem Soc 58 572 1936, Beilstein 8 III 2576, 8 IV 2376.]

上流・下流製品情報

サプライヤー50 社

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]

補足説明

定義ChEBI: A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.

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