1,2,5,6-テトラヒドロ-1-[3-(3,4,5-トリメトキシフェニル)-1-オキソ-2-プロペニル]ピリジン-2-オン

Piperlongumine

HCID 637858
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基本情報

CAS
20069-09-4
標準SMILES
COc1cc(/C=C/C(=O)N2CCC=CC2=O)cc(OC)c1OC
InChIKey
VABYUUZNAVQNPG-BQYQJAHWSA-N
分子式
C17H19NO5
平均分子量
317.34 g/mol
単同位体質量
317.12632271

概要

Piplartine is a member of cinnamamides and a dicarboximide.

名称と識別子

優先名称
Piperlongumine
IUPAC
1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
現地名
1,2,5,6-テトラヒドロ-1-[3-(3,4,5-トリメトキシフェニル)-1-オキソ-2-プロペニル]ピリジン-2-オン
英語名
PIPERLONGUMINE
分子式
C17H19NO5
分子量
317.34

名称と別名

PiperlonguminePiplartine20069-09-4SGD66V4SVJ1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one2(1H)-Pyridinone, 5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-, (E)-1-((E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl)-2,3-dihydropyridin-6-oneRefChem:455155,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-2(1H)pyridinone(E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-oneMFCD000757062(1H)-Pyridinone, 5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-
名称をさらに表示
ピプラルチン1,2,5,6-テトラヒドロ-1-[3-(3,4,5-トリメトキシフェニル)-1-オキソ-2-プロペニル]ピリジン-2-オンピペルロングミン5,6-ジヒドロ-1-[1-オキソ-3-(3,4,5-トリメトキシフェニル)-2-プロペニル]ピリジン-2(1H)-オン(E)-1-[3-(3,4,5-トリメトキシフェニル)アクリロイル]-5,6-ジヒドロピリジン-2(1H)-オン5,6-ジヒドロ-1-[1-オキソ-3-(3,4,5-トリメトキシフェニル)-trans-2-プロペニル]-2(1H)-ピリジノンピペロングミン (RG)ピペロングミンongPPLGMuminePiperLongumineacryloyl)PIPERLONGUMINPiperlorgumia
1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,2,5,6-tetrahydropyridin-2-oneCHEBI:8241ST079382BRD2293PiplartinBRD-2293(E)-1-[3-(3,4,5-Trimethoxyphenyl)acryloyl]-5,6-dihydropyridin-2(1H)-onePiplartine; (E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one

データベース識別子

CAS
20069-09-4
PubChem CID
637858
DTXSID
DTXSID801029762
ChEMBL
CHEMBL465843
ChEBI
CHEBI:8241
UNII
SGD66V4SVJ
EC Number
812-597-2
Nikkaji
J1.741.941B、J14.252B

物性

構造計算による物性

XLogP
2.1
極性表面積
65.1 Ų
水素結合供与体数
0
水素結合受容体数
5
回転可能結合数
5
重原子数
23

実験および物理化学的性質

Melting Point124 °C
Physical DescriptionSolid
Collision Cross Section · 2 件

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

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

物理化学的性質

融点
124 °C · 124°C
沸点
475.6 · 475.6±45.0 °C(Predicted)
比重(密度)
1.223 · 1.223±0.06 g/cm3(Predicted)
貯蔵温度
2 · 2-8°C
溶解性
60 ℃加温時≧5mg/mL · DMSO：60℃加温時≧5mg/mL
酸解離定数(Pka)
-1.88 · -1.88±0.20(Predicted)

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H302 (66.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 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. 4 (66.7%)

安全データ

wgk
3
rtecs
UU7785850
hs_code
2932209090
Hazard Classifications
Acute Tox. 4 Oral
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

Cellular LocationsCytoplasm
応用分野 · 3 件

説明A piperidinone alkaloid present in Piper longum, the structure has been shown to be N-(3:4:5-trimethoxycinnamoyl)-Lls-piperidin-2-one. In the plant, the base occurs mainly in the roots.

使用Piperlongumine (PL), a new alkaloid abundantly present in Piper longum fruits strongly inhibited platelet cell aggregation. It may have anti-cancer properties. It selectively targets and kills cancer cells but leaving normal cells unharmed.

一般的な説明Piperlongumine is an alkaloid, which is extracted from Piper longum Linn. It exhibits anti-atherosclerotic, anxiolytic, antidiabetic, antidepressant, antibacterial, anti-platelet, aggregation, anxiolytic and anti-inflammatory properties. Piperlongumine prevents the production of tumor necrosis factor-α and interleukin-6. It blocks the activation of nuclear factor-κB (NF-κB) against proinflammatory responses. Piperlongumine inhibits plaque formation and inhibits vascular smooth muscle cell migration. It is used to treat cough, respiratory infections and stomach-ache.

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補足説明

定義本品は、次の化学式で表される有機化合物である。

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