基本情報
- CAS
519-23-3- 標準SMILES
Cc1c2ccncc2c(C)c2c1[nH]c1ccccc12- InChIKey
CTSPAMFJBXKSOY-UHFFFAOYSA-N- 分子式
- C17H14N2
- 平均分子量
- 246.31 g/mol
- 単同位体質量
- 246.11569845
概要
Ellipticine is a organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11. It has a role as an antineoplastic agent and a plant metabolite. It is an organonitrogen heterocyclic compound, an organic heterotetracyclic compound, a polycyclic heteroarene and an indole alkaloid.
名称と識別子
- 優先名称
- Ellipticine
- IUPAC
- 5,11-dimethyl-6H-pyrido[4,3-b]carbazole
- 現地名
- 5,11-ジメチル-6H-ピリド[4,3-b]カルバゾール
- 英語名
- ELLIPTICINE
- 分子式
- C17H14N2
- 分子量
- 246.31
名称と別名
ellipticine519-23-35,11-Dimethyl-6H-pyrido[4,3-b]carbazoleElliptisineNSC 71795NSC-71795elliptecine5,11-Dimethyl-6H-pyrido(4,3-b)carbazole117VLW7484CHEBI:4776DTXSID30199855RefChem:136522
名称をさらに表示
エリプチシン5,11-ジメチル-6H-ピリド[4,3-b]カルバゾールエリプティシン溶液エリプティシンK00071LP00531CS-1794icig770CP-3025CCG36483CCG 36483DB-052047CCG-36483LS-133282
DTXCID90122346208-264-0TCMDC-125546ICIG 770NSC71795MFCD00010524CHEMBL123MLS000028487
データベース識別子
- CAS
519-23-3- PubChem CID
- 3213
- DTXSID
DTXSID30199855- ChEMBL
CHEMBL123- ChEBI
物性
構造計算による物性
- XLogP
- 4.8
- 極性表面積
- 28.7 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 1
- 回転可能結合数
- 0
- 重原子数
- 19
- 形式電荷
- 0
- 複雑度
- 342
実験および物理化学的性質
LogP4.8
物理化学的性質
- 融点
- 316 · 316-318°C
- 沸点
- 379.31 °C · 379.31°C (rough estimate)
- 比重(密度)
- 1.257 · 1.257±0.06 g/cm3 (20 ºC 760 Torr)
- 屈折率
- 1.5794 · 1.5794 (estimate)
- 貯蔵温度
- 2 · Keep in dark place,Sealed in dry,2-8°C
- 溶解性
- DMSO：可溶
- 外見
- 明るい黄色の固体
- 酸解離定数(Pka)
- 16.59 · 16.59±0.40(Predicted)
- 色
- Light yellow to yellow
- Merck
- 13 · 13,3581
- InChI
- 1S/C17H14N2/c1-10-14-9-18-8-7-12(14)11(2)17-16(10)13-5-3-4-6-15(13)19-17/h3-9,19H,1-2H3
- InChIKey
- CTSPAMFJBXKSOY-UHFFFAOYSA-N
- SMILES
- [nH]1c2c(c4c1cccc4)c(c3c(c2C)ccnc3)C
- LogP
- 4.8 · 4.800
- CAS データベース
- 519 · 519-23-3(CAS DataBase Reference)
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
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 3 (100%)
安全データ
- wgk
- 3
- rtecs
- UU8825000
- ridadr
- UN 3462 6.1/PG 3
- 毒性
- LD50 in mice (mg/kg): 19.5-22.4 i.v.; 178-204 orally (Rakieten)
- risk_code
- 25
- hazard_code
- T
- safety_code
- 45
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard Classifications
- Acute Tox. 3 Oral
- 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
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Chemical agents that uncouple oxidation from phosphorylation in the metabolic cycle so that ATP synthesis does not occur. Included here are those IONOPHORES that disrupt electron transfer by short-circuiting the proton gradient across mitochondrial membranes.
応用分野
説明Ellipticine is an alkaloid isolated from Apocyanaceae plants that exhibits antitumor activities by intercalating into DNA and/or inhibiting DNA topoisomerase II. It forms covalent adducts in DNA after being enzymatically activated with cytochrome P450 isoforms (e.g., CYP3A4, CYP1A1, or CYP1A2) or by peroxidases in target tissues. Ellipticine has been shown to inhibit the proliferation of human breast adenocarcinoma MCF-7 cells, leukemia HL-60 and CCRF-CEM cells, neuroblastoma IMR-32, UKF-NB-3, and UKF-NB-4 cells, and U87MG glioblastoma cells with IC50 values ranging from 0.27-4.7 μM.
一般的な説明A topoisomerase II inhibitor. Acts as an intercalative alkaloid that stimulates topoisomerase II-mediated DNA breakage. Is also capable of uncoupling mitochondrial oxidative phosphorylation.
調製方法
純化方法This DNA intercalator is purified by recrystallisation from CHCl3 or MeOH and is dried in vacuo. The UV max values in aqueous EtOH/HCl are at 241, 249, 307, 335 and 426nm. [Marini-Bettolo & Schmutz Helv Chim Acta 42 2146 1959.] The methiodide has m 360o(dec), with UV (EtOH/KOH) at 223, 242, 251, 311, 362 and 432nm. [Goodwin et al. J Am max Chem Soc 81 1903 1959, Beilstein 23/9 V 417.]
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