Chelidonine

• CAS: 476-32-4
• Catalog Number: ACM476324
• Category: Inhibitors
• Molecular Weight: 353.4
• Molecular Formula: C20H19NO5
• Description: Chelidonine, an isoquinoline alkaloid, can be isolated from Chelidonium majus L.. Chelidonine causes G2/M arrest and induces caspase-dependent and caspase-independent apoptosis, and prevents cell cycle progression of stem cells in Dugesia japonica. Chelidonine has cytotoxic activity against melanoma cell lines. with anticancer and antiviral activity.
• Synonyms: Stylophorin
• Canonical SMILES: CN1[C@@]2([H])[C@@]([C@H](CC3=C2C=C4C(OCO4)=C3)O)([H])C5=C(C6=C(OCO6)C=C5)C1
• InChI: InChI=1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1
• InChI Key: GHKISGDRQRSCII-ZOCIIQOWSA-N
• Melting Point: 135-140 °C
• Appearance: Solid
• Storage: Powder-20°C, 3 years; 4°C, 2 years; In solvent-80°C, 6 months; -20°C, 1 month.
• Complexity: 560
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 3
• Exact Mass: 353.12632271
• Heavy Atom Count: 26
• Hydrogen Bond Acceptor Count: 6
• Hydrogen Bond Donor Count: 1
• Isomeric SMILES: CN1CC2=C(C=CC3=C2OCO3)[C@@H]4[C@H]1C5=CC6=C(C=C5C[C@@H]4O)OCO6
• Monoisotopic Mass: 353.12632271
• Physical State: Powder
• Rotatable Bond Count: 0
• Shipping: Can be shipped at room temperature, where not in use may vary.
• Source: PlantsPapaveraceaeChelidonium majus
• Topological Polar Surface Area: 60.4 Ų

Custom Q&A

What is the chemical formula of chelidonine?

The chemical formula of chelidonine is C20H19NO5.

What is the molecular weight of chelidonine?

The molecular weight of chelidonine is 353.37 g/mol.

What is the melting point of chelidonine?

The melting point of chelidonine is 135-140°C.

What is the solubility of chelidonine in water?

Chelidonine is insoluble in water.

What is the pharmacological action of chelidonine?

Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity.

How is chelidonine used in clinical treatment?

Chelidonine has been used as a painkiller in clinical treatment, based on its morphine-like analgesic effect.

What are some of the effects of chelidonine on the nervous system?

Chelidonine has analgesic and sedative effects on the nervous system.

What is the primary bioactive, isoquinoline alkaloid ingredient in Chelidonium majus?

Chelidonine is the major bioactive, isoquinoline alkaloid ingredient in Chelidonium majus.

In what year was chelidonine first isolated from Chelidonium majus?

Chelidonine was first isolated from Chelidonium majus in 1824.

What are some of the diseases that chelidonine has been used to treat traditionally?

Chelidonine has been used traditionally for the treatment of jaundice, biliary colic, cholelithiasis, and various other diseases like tuberculosis, inflammation, and cancer.