CAS 84-26-4|Rutaecarpin|Rutecarpine|Rhetine|Rutaecarpine|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|rutaecarpine|Rutacarpine|8,13-Di...

General Information

Structure

Molecular Formula

C₁₈H₁₃N₃O

Molecular Mass

287.31532

Exact Mass

287.10586205

Charge

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

Canonic Smiles

O=c1c2ccccc2nc2n1CCc1c2[nH]c2c1cccc2

Isomeric Smiles

n12c(nc3c(c1=O)cccc3)c1c(CC2)c2c([nH]1)cccc2

Calculated Properties

JChem

Acid pKa

13.441173

H Acceptors

H Donor

LogD (pH = 5.5)

2.9095914

LogD (pH = 7.4)

2.9099379

Log P

2.9099426

Molar Refractivity

87.2307

Polarizability

32.738087

Polar Surface Area

48.46

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

RutaecarpinRutecarpineRhetineRutaecarpineRutacarpine8,13-Dihydro-indolo[2′,3′:3,4]pyrido[2,1-b]quinazolin-5(7H)-oneRutaecarpine7,8-dihydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(13H)-one

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[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one

IUPAC Traditional name

rutaecarpine 3,13,21-triazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one

Names and Identifiers

Registration numbers

CAS Number

PubChem SID

MDL Number

PubChem CID

Registration numbers

Properties

Safety Information

Storage Condition

-20°C

Storage Temperature

2-8°C

Personal Protective Equipment

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

German water hazard class

MSDS Link

Download link

UN Number

2811

RID/ADR

UN 2811 6.1/PG 3

Packing Group

Hazard Class

6.1

Product Information

Salt Data

Free Base

Purity

>98% (HPLC)

97.5

Empirical Formula (Hill Notation)

C18H13N3O

Application(s)

Antihypertensive agent.

Evodia rutaecarpa is used in Chinese medicine against headache, abdominal pain, dysentery and cholera.

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)

Physical Property

Solubility

DMSO: soluble18 mg/mL (clear yellow solution)

H2O: insoluble

Apperance

white solid

Yellow powder

Pharmacology Properties

Gene Information

human ... CYP1A1(1543), CYP1A2(1544), CYP1B1(1545)

Mechanism of Action

Vasodilator

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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.

Molecule Details

References

PubChem Literature

From Data Sources

• www.mdpi.com/1420-3049/13/2/272/pdf

• Chiou, W.-F. et al., Eur. J. Pharmacol., 1994, 257, 59

• Yamazaki, M. et al., Tet. Lett., 1966, 3221; 1967, 3317

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

RutaecarpinRutecarpineRhetineRutaecarpineRutacarpine8,13-Dihydro-indolo[2′,3′:3,4]pyrido[2,1-b]quinazolin-5(7H)-oneRutaecarpine7,8-dihydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(13H)-one

IUPAC name

IUPAC Traditional name

rutaecarpine 3,13,21-triazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one

Registration numbers

CAS Number

PubChem SID

MDL Number

PubChem CID