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アンドログラホリド

Andrographolide

HCID 5318517
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
5508-58-7
標準SMILES
C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1C/C=C1/C(=O)OC[C@H]1O
InChIKey
BOJKULTULYSRAS-OTESTREVSA-N
分子式
C20H30O5
平均分子量
350.4 g/mol
単同位体質量
350.20932406

概要

Andrographolide is a labdane diterpenoid isolated from the leaves and roots of Andrographis paniculata that exhibits anti-HIV, anti-inflammatory and antineoplastic properties. It has a role as a metabolite, an anti-inflammatory drug, an antineoplastic agent and an anti-HIV agent. It is a primary alcohol, a secondary alcohol, a labdane diterpenoid, a carbobicyclic compound and a gamma-lactone.

名称と識別子

優先名称
Andrographolide
IUPAC
(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
現地名
アンドログラホリド
英語名
Andrographolide
分子式
C20H30O5
分子量
350.45

名称と別名

Andrographolide5508-58-7DTXSID3045980HMPL004CHEBI:65408410105JHGRNSC-383468DTXCID10259803alpha,14,15,18-tetrahydroxy-5b,9bH,10a-labda-8(20),12-dien-16-oic acid gamma-Lactone(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one3-(2-(Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthyl)ethylidene)dihydro-4-hydroxyfuran-2(3H)-one(3E,4S)-4-hydroxy-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidenedecahydronaphthalen-1-yl]ethylidene}dihydrofuran-2(3H)-one
名称をさらに表示
(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-1,2,3,4,4a,5,6,7,8,8a-デカヒドロ-6-ヒドロキシ-5-(ヒドロキシメチル)-5,8a-ジメチル-2-メチレンナフタレン-1-イル]エチリデン]ジヒドロ-4-ヒドロキシ-2(3H)-フラノン(S)-3-[(E)-2-[[(1R,4aβ)-デカヒドロ-6α-ヒドロキシ-5α-ヒドロキシメチル-5,8aα-ジメチル-2-メチレンナフタレン]-1α-イル]エチリデン]ジヒドロ-4-ヒドロキシ-2(3H)-フラノンアンドログラホリド(3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-ヒドロキシ-5-(ヒドロキシメチル)-5,8a-ジメチル-2-メチリデン-デカヒドロナフタレン-1-イル]エチリデン}-4-ヒドロキシオキソラン-2-オン

物性

構造計算による物性補完中

XLogP
2.2
極性表面積
87 Ų
水素結合供与体数
3
水素結合受容体数
5
回転可能結合数
3
重原子数
25
形式電荷
0
複雑度
597

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
Dietary IngredientsAndrographis

物理化学的性質

融点
229 · 229-232 °C (lit.)
比旋光度
-126 · -126 º (c=1.5,HAc)
沸点
557.3 · 557.3±50.0 °C(Predicted)
比重(密度)
421 · d421 1.2317
貯蔵温度
2 · 2-8°C
溶解性
DMSO (最大 25mg/ml) またはエタノール (最大 8mg/ml) に可溶。
酸解離定数(Pka)
12.36 · 12.36±0.20(Predicted)
外見
オフホワイトの無地
色
オフホワイト
Merck
14 · 14,633
BRN
42762 · 42762
安定性
2 · 購入日から2年間安定です。この DMSO またはエタノール溶液は、-20°C で 3 か月間保存できます。
化粧品成分の機能
スキンコンディショニング
InChI
1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1

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 · 4 件

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Aggregated GHS information provided per 31 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 1 件

2(3H)-Furanone, 3-2-(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenylethylidenedihydro-4-hydroxy-, (3E,4S)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

安全データ

wgk
3
rtecs
LU3490750
hs_code
29322980
risk_code
20/21/22-36/37/38
hazard_code
Xn
safety_code
22-24/25-36-26
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

Mechanism of Action · 1 件

HMPL-004 acts on multiple cellular targets in the inflammatory signal transduction pathways resulting in suppressed inflammation cytokine expression including TNF-α, IL-1β and IL-6. HMPL-004 was demonstrated to inhibit TNF-α and IL-1β production in cell-based assays. HMPL-004 is also able to inhibit NF-kB activation. NF-kB is a family of transcriptional factors that regulate a wide spectrum of genes critically involved in host defence and inflammation. The mechanism of action of HMPL-004 was further supported in laboratory IBD animal models. Treatment of IBD rats with HMPL-004 caused a significant drop in plasma cytokine concentrations, including TNF-α and IL-1β.

MeSH Pharmacological Classification · 5 件

Substances that reduce or suppress INFLAMMATION.

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

Substances that are destructive to protozoans.

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.

用途と製造

Household ProductsInformation on 1 consumer products that contain Andrographolide in the following categories is provided:
応用分野

関連反応

3 件
反応記録を作成
HRID 384283 の反応式
HRID 384283反応物としてuspto-grants-2013_02
HRID 1019229 の反応式
HRID 1019229反応物としてuspto-grants-2002_11
HRID 1369023 の反応式
HRID 1369023反応物としてuspto-grants-2003_06

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
ANDRO
ANDROGRAPHIS
Andrographolid
(S,E)-4-Hydroxy-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxyMethyl)-5,8a-diMethyl-2-Methylenedecahydronaphthalen-1-yl)ethylidene)dihydrofuran-2(3H)-one
Andrograph
ent-(3β,12E,14R)-3,14,19-Trihydroxy-8(17),12-labdadien-16,15-olide
Androg
raphoL
Neoandrogr
AndrographoL
2(3H)-FURANONE, 3-(2-((1R,4AS,5R,6R,8AS)-DECAHYDRO-6-HYDROXY-5-(HYDROXYMETHYL)-5,8A-DIMETHYL-2-METHYLENE-1-NAPHTHALENYL)ETHYLIDENE)DIHYDRO-4-HYDROXY-, (3E,4S)-2(3H)-Furanone, 3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-, (1R-(1-alpha(E(S*)),4a-beta,5-alpha,6-alpha,8a-alpha))-2(3H)-Furanone, 3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-, (3E,4S)-(3E,4S)-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl)ethylidene)-4-hydroxyoxolan-2-one(3E,4S)-4-hydroxy-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidenedecahydronaphthalen-1-yl)ethylidene)dihydrofuran-2(3H)-oneRefChem:5554(1R-(1-alpha(E(S)),4a-beta,5alpha,6alpha,8a-alpha))-3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-2(3H)-furanone226-852-5

データベース識別子

CAS
5508-58-7
PubChem CID
5318517
DTXSID
DTXSID3045980
ChEMBL
CHEMBL186141
ChEBI
CHEBI:65408
UNII
410105JHGR
EC Number
226-852-5
Nikkaji
J13.236E
InChIKey
BOJKULTULYSRAS-QPSYGYIJSA-N
SMILES
C[C@@]1(CO)[C@H](O)CC[C@@]2(C)[C@H](C\C=C3/[C@H](O)COC3=O)C(=C)CC[C@H]12
LogP
0.424 · 0.424 (est)
CAS データベース
5508 · 5508-58-7
化学的性質 · 1 件

化学的特性white square prism or flaky crystals (ethanol or methanol) and odorless, with a bitter taste. dissolved in boiling ethanol, slightly soluble in methanol or ethanol, very slightly soluble in chloroform, and almost insoluble in water. Since andrographolide has an ester structure, it is easy to hydrolysis, open loop and isomerization in the aqueous solution to affect the drug stability. At lower temperature, the stability of andrographolide is better; it is unstable in alkaline conditions, and its instability increased with the increase in alkaline strength. The most stable pH value is 3–5. Andrographolide is more stable in chloroform.

· 6 件

用途薬理作用研究用。

説明Andrographolide is a diterpene lactone compound extracted from Andrographis. paniculata (Burm. F) Nees. Andrographis paniculata is also known as lanhelian, yijianxi, zhanshecao, kucao, kudancao, etc. Since this product originates in India, it is also known as Indian grass. This product is dry ground part of Jupiteraceae plant Andrographis paniculata (conus) may originate in South Asia. It is commonly cultivated in China such as in Fujian, Guangdong, Hainan, Guangxi, and Yunnan and also in Australia and was also introduced in Jiangsu and Shaanxi.Andrographis paniculata is commonly used in traditional Chinese medicine. Its ability of relieving “snake venom, and internal injuries cough” was recorded in “Lingnan herbal medicine records.” “Quanzhou Materia Medica” described it as “heat-clearing and detoxifying, anti-inflammatory, detumescence and inhibition throat inflammation, dysentery and high fever.”The above ground part of Andrographis paniculata contains andrographolide, neo-andrographolide, 14-deoxygenated andrographolide, etc., and the root contains mainly flavonoids.

天然物の起源Andrographis is found growing wild in India and Sri Lanka and is cultivated in many other parts of the world.

来歴In 1911, Gorter firstly isolated a crystalline substance from Andrographis paniculata, identified it as a diterpene lactone compound, and named it andrographolide .Andrographolide structure is complex and difficult to artificially synthesize, so it is often extracted from the plant.Andrographolide water solubility is poor and its bioavailability is low; its pharmacological effects are extensive but weak, so the preparation requirements are strict. Therefore, from the 1970s, drugs and organic chemical researchers have done a lot of work in the modification and transformation of andrographolide, mainly concentrated in the α, β-unsaturated lactone double bond Michael addition, redox, selective esterification of hydroxyl groups, oxidation and substitution reactions, intramolecular cyclization, replacement of lactone rings, etc. They had obtained a number of new derivatives. In the research of pharmacological effects, the main study of the andrographolide derivatives focuses on antitumor, antivirus, and other biological activities and has made some progress .

使用Andrographolide is a labdane diterpenoid. Andrographolide is the main bioactive component isolated from the medicinal plant Andrographis paniculata. It has a broad range of therapeutic applications including anti-inflammatory and anti-platelet aggregation activities and potential antineoplastic properties. Andrographolide showed significant antihepatotoxic action in P. berghei K173- induced hepatic damage in M. natalensis. Andrographolide inhibits tumor necrosis factor-α (TNF-α)-induced intercellular adhesion mol.-1 (ICAM-1) expression and adhesion of HL-60 cells onto human umbilical vein endothelial cells (HUVEC), which are associated with inflammatory diseases. These findings suggest that Andrographolide may have potential as a cardiovascular-protective agent.

一般的な説明Andrographolide, a bioactive diterpene lactone, is the main constituent of Andrographis paniculata, a plant used in traditional medicines. It is known to have different biological activities such as anti-inflammatory, anti-malarial, anti-cancer and hepatoprotective activity. It also shows potent anti-viral effect against dengue virus.

上流・下流製品情報

上流原料

エタノール
補足説明 · 2 件

定義本品は、次の化学式で表される二環式ジテルペンラクトンである。

定義ChEBI: Andrographolide is a labdane diterpenoid isolated from the leaves and roots of Andrographis paniculata that exhibits anti-HIV, anti-inflammatory and antineoplastic properties. It has a role as a metabolite, an anti-inflammatory drug, an anti-HIV agent and an antineoplastic agent. It is a gamma-lactone, a primary alcohol, a secondary alcohol, a labdane diterpenoid and a carbobicyclic compound.