基本情報
- CAS
34316-15-9- 標準SMILES
COc1ccc2c(c[n+](C)c3c4cc5c(cc4ccc23)OCO5)c1OC- InChIKey
LLEJIEBFSOEYIV-UHFFFAOYSA-N- 分子式
- C21H18NO4+
- 平均分子量
- 348.4 g/mol
- 単同位体質量
- 348.12358306
概要
Chelerythrine is a benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae. It has a role as an antibacterial agent, an antineoplastic agent and an EC 2.7.11.13 (protein kinase C) inhibitor. It is an organic cation and a benzophenanthridine alkaloid.
名称と識別子
- 優先名称
- Chelerythrine
- IUPAC
- 1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium
- 現地名
- 1,2-ジメトキシ-12-メチル[1,3]ベンゾジオキソロ[5,6-c]フェナントリジン-12-イウム
- 英語名
- Chelerythrine
- 分子式
- C21H18NO4+
- 分子量
- 348.37192
名称と別名
chelerythrine34316-15-9ToddalincheleritrineToddalinebroussonpapyrine[1,3]Benzodioxolo[5,6-c]phenanthridinium, 1,2-dimethoxy-12-methyl-1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-iumE3B045W6X0CHEBI:783731,2-Dimethoxy-12-methyl(1,3)benzodioxolo(5,6-c)phenanthridinium1,2-Dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridinium
名称をさらに表示
トッダリン1,2-ジメトキシ-12-メチル[1,3]ベンゾジオキソロ[5,6-c]フェナントリジン-12-イウムシェレリスリン2,3-(エポキシメタノキシ)-5-メチル-7,8-ジメトキシベンゾ[c]フェナントリジン-5-イウムケレリトリン2,3-(メチレンビスオキシ)-5-メチル-7,8-ジメトキシ-5-アゾニアクリセンケレリトリン(TODDALIトダリンケレリスリン5-メチル-9,10-ジメトキシ-2,3-(メチレンジオキシ)ベンゾ[c]フェナントリジン-5-イウム15,16-ジメトキシ-21-メチル-5,7-ジオキサ-21-アザペンタシクロ[11.8.0.02,10.04,8.014,19]ヘンイコサ-1(13),2,4(8),9,11,14,16,18,20-ノナエン-21-イウム17,18-ジメトキシ-21-メチル-5,7-ジオキサ-21-アザペンタシクロ[11.8.0.02,10.04,8.014,19]ヘンイコサ-1(13),2,4(8),9,11,14,16,18,20-ノナエン-21-イウムブロウッソンパピリン
物性
構造計算による物性
- XLogP
- 4.6
- 極性表面積
- 40.8 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 4
- 回転可能結合数
- 2
- 重原子数
- 26
- 形式電荷
- 1
- 複雑度
- 516
物理化学的性質
- 融点
- 195 · 195-205°C
- 沸点
- 496.37 °C · 496.37°C (rough estimate)
- 比重(密度)
- 1.2985 · 1.2985 (rough estimate)
- 屈折率
- 1.5614 · 1.5614 (estimate)
- 貯蔵温度
- -20 °C · Desiccate at -20°C
- 溶解性
- Chloroform (Slightly, Sonicated), DMSO (Slightly, Sonicated), Methanol (Slightly）
- 外見
- 個体
- 色
- ライトイエローからダークオレンジ
- 安定性
- 吸湿性
- InChI
- InChI=1S/C21H18NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-10H,11H2,1-3H3/q+1
- InChIKey
- LLEJIEBFSOEYIV-UHFFFAOYSA-N
- SMILES
- C[N+]1=CC2=C(C(OC)=CC=C2C2C=CC3C=C4OCOC4=CC=3C1=2)OC
- LogP
- -0.401 · -0.401 (est)
- CAS データベース
- 34316 · 34316-15-9(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
H300 (50%): Fatal if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, 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 2 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. 2 (50%)
毒性情報
Toxicity Summary
Chelerythrine is a potent, selective, and cell-permeable protein kinase C (PKC) inhibitor. It is also the major active natural product found in the plant Zanthoxylum clava-herculis, exhibiting anti-bacterial activity against Staphylococcus aureus. (Wikipedia) Chelerythrine is a selective inhibitor of group A and B PKC isoforms with an antitumor activity. Inhibition of PKC with chelerythrine chloride induces apoptosis by activation of a neutral sphingomyelinase, accumulation of ceramide, and depletion of sphingomyelin. Chelerythrine is at least 100-fold more selective for PKCs than for other kinases. Chelerythrine competes for the conserved catalytic sites of PKC and seems to be a potent and specific inhibitor of the group A and group B kinases. Chelerythrine exhibited cytotoxic activity against nine human tumor cell lines tested in vitro. Radioresistant and chemoresistant squamous cell carcinoma lines (HNSCC) undergo apoptosis rapidly after treatment with chelerythrine in vitro. Chelerythrine treatment of nude mice bearing SQ-20B HNSCC cells is associated with significant tumor growth delay. Also, treatment with chelerythrine resulted in minimal toxicity. (A15441)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
化学と産業
薬理情報
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Substances that inhibit the growth or reproduction of BACTERIA.
調製方法
純化方法Chelerythrine crystallises from CHCl3 on addition of MeOH [Manske Can J Res 21B 140 1943, UV: Hruban et al. Coll Czech Chem Commun 35 3420 1970]. The pseudo base is colourless while the salts are yellow in aqueous solution and are fluorescent.
上流・下流製品情報
下流製品
サプライヤー100 社
北京华美互利生物化工010-56205725 · [email protected]
成都曼思特生物科技有限公司18010516991 · [email protected]
南京普怡生物科技有限公司13814510036 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
成都健腾生物技术有限公司028-85159085 18080455027 · [email protected]
陕西帕尼尔生物科技有限公司
関連反応
0 件
現在のフィルター条件では反応記録がありません。
化合物ノート
読み込み中…