2-メトキシ-5-[(Z)-2-(3,4,5-トリメトキシフェニル)エテニル]フェノール

Combretastatin A4

HCID 5351344

ノート反応

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基本情報

CAS: 117048-59-6
標準SMILES: COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1O
InChIKey: HVXBOLULGPECHP-WAYWQWQTSA-N
分子式: C18H20O5
平均分子量: 316.3 g/mol
単同位体質量: 316.13107374

概要

Combretastatin A4 is a stilbenoid.

名称と識別子

優先名称: Combretastatin A4
IUPAC: 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
現地名: 2-メトキシ-5-[(Z)-2-(3,4,5-トリメトキシフェニル)エテニル]フェノール
英語名: COMBRETASTATIN A-4
分子式: C18H20O5
分子量: 316.35

名称と別名

Combretastatin A4117048-59-6Combretastatin A-4Combrestatin A4Combretastatin 42'-deoxycombretastatin A12-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenolNSC-61372916U6OP69RQ3,4,5-Trimethoxy-3'-hydroxy-4'-methoxystilbene1-(3,4,5-Trimethoxyphenyl)-2-(3'-hydroxy-4'-methoxyphenyl)etheneDTXSID101025983

名称をさらに表示

(Z)-3',4,4',5'-テトラメトキシスチルベン-3-オールコンブレタスタチンA4コンブレタスタチンA-42-メトキシ-5-[(Z)-2-(3,4,5-トリメトキシフェニル)エテニル]フェノール(Z)-3,4,4',5-テトラメトキシ-3'-ヒドロキシスチルベン3-[(Z)-2-(3,4,5-トリメトキシフェニル)エテニル]-6-メトキシフェノール(Z)-コンブレタスタチンA45-[(Z)-2-(3,4,5-トリメトキシフェニル)エテニル]-2-メトキシフェノール(Z)-2-メトキシ-5-(3,4,5-トリメトキシスチリル)フェノール3'-ヒドロキシ-3,4,4',5-テトラメトキシ-cis-スチルベンコンブレタスタチン A-4CA4CoMbretastatin Acombretastatin A-4 (CA-4)CS-A4CS-284CRC 87-09NSC 817373NSC-817373

Phenol, 2-methoxy-5-(2-(3,4,5-trimethoxyphenyl)ethenyl)-, (Z)-NSC6137292-methoxy-5-((Z)-2-(3,4,5-trimethoxyphenyl)ethenyl)phenolRefChem:918948DTXCID80852504NSC817373631-427-6NSC609397

データベース識別子

CAS: 117048-59-6
PubChem CID: 5351344
DTXSID: DTXSID101025983
ChEMBL: CHEMBL67
ChEBI: CHEBI:181391
UNII: 16U6OP69RQ
EC Number: 631-427-6
Nikkaji: J424.288B

物性

構造計算による物性

XLogP: 3.7
極性表面積: 57.2 Å²
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: 6
重原子数: 23
形式電荷: 0
複雑度: 358

実験および物理化学的性質

Endocrine DisruptorsPotential endocrine disrupting compound

物理化学的性質

融点: 84.5 · 84.5-85.5°C
沸点: 490.3 · 490.3±45.0 °C(Predicted)
比重(密度): 1.184 · 1.184±0.06 g/cm3(Predicted)
貯蔵温度: -20 °C · -20°C
溶解性: 10 mg/mL · DMSO：>10mg/mL
酸解離定数(Pka): 9.65 · 9.65±0.10(Predicted)
外見: 粉
色: オフホワイト
Merck: 14 · 14,2494
InChI: InChI=1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3/b6-5-
InChIKey: HVXBOLULGPECHP-WAYWQWQTSA-N
SMILES: C1(O)=CC(/C=C\C2=CC(OC)=C(OC)C(OC)=C2)=CC=C1OC

化学的性質

化学的特性Crystalline Powder

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

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

P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 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

Hazard Classes and CategoriesAcute Tox. 3 (100%)

安全データ

wgk: 2
ridadr: UN 2811
hs_code: 29095000
risk_code: 23/24/25-41
hazard_code: T
safety_code: 26-36/37-39-45
hazard_class: 6.1
packing_group: Ⅲ
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Dam. 1
ストレージクラス: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

化学と産業

薬理情報

Metabolism/MetabolitesCombretastatin A4 has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenoxy]oxane-2-carboxylic acid.

MeSH Pharmacological ClassificationAgents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.

応用分野 · 3 件

説明Combrestatin A4 (CA4) is a potent inhibitor of tubulin polymerization and displays strong inhibitory activity on tumor cell growth. Combrestatin A4 was shown to inhibit tumor growth in several cell lines including IMR32 (neuroblastoma), Hs746T (gastric carcinoma), CFPAC-1 (pancreatic carcinoma), and MCF-7 (breast cancer) with IC50 values of 2.16, 5.20, 3.46, and 18.47 nM, respectively. CA4 inhibits tubulin polymerization with an IC50 value of 2.2 μM.

使用Combretastatin is a small organic molecule found in the bark of the African bush willow tree Combretum caffrum. Combretastatin-A4 Prodrug Induces Mitotic Catastrophe in Chronic Lymphocytic Leukemia Cell Line Independent of Caspase Activation and Poly(ADP-ribose) Polymerase Cleavage. A potent cytotoxic agent which strongly inhibits the polymerization of tubulin by binding to the colchicine site.

一般的な説明Combretastatin A4 belong to the class of colchicinoids compounds.

上流・下流製品情報

上流原料

イソバニリン銅キノリン無水酢酸トリエチルアミン 3,4,5-トリメトキシフェニル酢酸塩酸

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