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 ID: 72975
• Molecular Formular: C18H13N3O
• Molecular Mass: 287.31532
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: 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
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 13.441173
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.9095914
• LogD (pH = 7.4): 2.9099379
• Log P: 2.9099426
• Molar Refractivity: 87.2307 cm^3
• Polarizability: 32.738087 Å^3
• Polar Surface Area: 48.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble18 mg/mL (clear yellow solution); H2O: insoluble
• Apperance: white solid; Yellow powder

Safety Information

• Storage Condition: -20°C
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CYP1A1(1543), CYP1A2(1544), CYP1B1(1545)
• Mechanism of Action: Vasodilator

Product Information

• Purity: >98% (HPLC); 97.5
• Salt Data: Free Base
• Biological Source: 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)
• Application(s): Antihypertensive agent.; Evodia rutaecarpa is used in Chinese medicine against headache, abdominal pain, dysentery and cholera.
• Empirical Formula (Hill Notation): C18H13N3O

DETAILS

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.

REFERENCES

• 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