3,13,21-triazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one

• ChemBase编号: 72975
• 分子式: C18H13N3O
• 平均质量: 287.31532
• 单一同位素质量: 287.10586205
• SMILES: n12c(nc3c(c1=O)cccc3)c1c(CC2)c2c([nH]1)cccc2
• Canonical SMILES: O=c1c2ccccc2nc2n1CCc1c2[nH]c2c1cccc2
• InChI: InChI=1S/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2
• InChIKey: ACVGWSKVRYFWRP-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3,13,21-triazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one; 3,13,21-triazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one
• IUPAC传统名: rutaecarpine; 3,13,21-triazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one
• 别名: Rutecarpine; Rutacarpine; Rutaecarpin; Rhetine; Rutaecarpine; 7,8-dihydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(13H)-one; 8,13-Dihydro-indolo[2′,3′:3,4]pyrido[2,1-b]quinazolin-5(7H)-one; Rutaecarpine

登记号

• CAS号: 84-26-4
• MDL号: MFCD00210551
• PubChem SID: 24278677; 162037895
• PubChem CID: 65752

理论计算性质

• Acid pKa: 13.441173
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 2.9095914
• LogD (pH = 7.4): 2.9099379
• Log P: 2.9099426
• 摩尔折射率: 87.2307 cm^3
• 极化性: 32.738087 Å^3
• 极化表面积: 48.46 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: soluble18 mg/mL (clear yellow solution); H2O: insoluble
• 外观: white solid; Yellow powder

安全信息

• 保存条件: -20°C
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... CYP1A1(1543), CYP1A2(1544), CYP1B1(1545)
• 生物活性机理: Vasodilator

产品相关信息

• 纯度: >98% (HPLC); 97.5
• 成盐信息: Free Base
• 生物来源: A major component of the Chinese drug Wou-chou-yu (the dried fruit of Evodia rutaecarpa). Also isol. from the bark of Hortia arborea and Hortia badinii, and from the root wood of Zanthoxylum integrifoliolum (Rutaceae)
• 应用领域: Antihypertensive agent.; Evodia rutaecarpa is used in Chinese medicine against headache, abdominal pain, dysentery and cholera.
• Empirical Formula (Hill Notation): C18H13N3O

详细说明

Selleck Chemicals - S2349

Research Area: Cardiovascular Disease , Inflammation , Neurological Disease
Biological Activity:
Rutaecarpine is an indolopyridoquinazolinone alkaloid isolated from Evodia rutaecarpa and related herbs, which has shown a variety of intriguing biological properties such as anti-thrombotic, anticancer, anti-inflammatory and analgesic, anti-obesity and thermoregulatory, vasorelaxing activity, as well as effects on the cardiovascular and endocrine systems. [1] 

InterBioScreen - BB_NC-2569

Evodia rutaecarpa (Juss.) Benth

Sigma Aldrich - R3277

Biochem/physiol Actions
Delayed rectifier K+ channel blocker. Inhibits platelet aggregation; vasoldilator.

参考文献

• www.mdpi.com/1420-3049/13/2/272/pdf
• Yamazaki, M. et al., Tet. Lett., 1966, 3221; 1967, 3317
• Chiou, W.-F. et al., Eur. J. Pharmacol., 1994, 257, 59