17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.02,10.04,8.014,19]henicosa-1(13),2,4(8),9,11,14(19),15,17,20-nonaen-21-ium chloride

• ChemBase ID: 72613
• Molecular Formular: C21H18ClNO4
• Molecular Mass: 383.82492
• Monoisotopic Mass: 383.09243574
• SMILES: c1c(c(c2c(c1)c1c([n+](c2)C)c2c(cc1)cc1c(c2)OCO1)OC)OC.[Cl-]
• Canonical SMILES: COc1c(OC)ccc2c1c[n+](C)c1c2ccc2c1cc1OCOc1c2.[Cl-]
• InChI: InChI=1S/C21H18NO4.ClH/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;1H/q+1;/p-1
• InChIKey: WEEFNMFMNMASJY-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^2,^1^0.0^4,^8.0^1^4,^1^9]henicosa-1(13),2,4(8),9,11,14(19),15,17,20-nonaen-21-ium chloride; 17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1(13),2,4(8),9,11,14,16,18,20-nonaen-21-ium chloride
• IUPAC Traditional name: 17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^2,^1^0.0^4,^8.0^1^4,^1^9]henicosa-1(13),2,4(8),9,11,14(19),15,17,20-nonaen-21-ium chloride; chelerythrine chloride
• Synonyms: 1,2-Dimethoxy-N-methyl(1,3)benzodioxolo(5,6-c)phenanthridinium chloride; Chelerythrine chloride; 1,2-Dimethoxy-N-methyl-[1,3]-benzodioxolo[5,6c]phenanthridinium; Chelerythrine Chloride

Database IDs

• CAS Number: 3895-92-9
• EC Number: 223-444-9
• MDL Number: MFCD00060717
• PubChem SID: 162037538; 24278305
• PubChem CID: 72311

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.8820726
• LogD (pH = 7.4): -0.8820726
• Log P: -0.8820726
• Molar Refractivity: 97.9779 cm^3
• Polarizability: 41.55171 Å^3
• Polar Surface Area: 40.8 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble2 mg/mL; H2O: soluble5 mg/mL
• Apperance: yellow to orange powder

Safety Information

• Storage Condition: 0°C; -20°C
• RTECS: FL9200000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: 20/21/22-36/37/38; R:25
• Safety Statements: 26-36; S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Storage Temperature: -20°C

Pharmacology Properties

• Target: PKC

Product Information

• Purity: ≥95% (TLC); 98%
• Salt Data: Chloride

DETAILS

MP Biomedicals - 02158888

Purity: 98%
Specifically inhibits protein kinase C.

Selleck Chemicals - S1292

Research Area: Inflammation
Biological Activity:
Chelerythrine is a benzophenanthridine alkaloid extracted from the plant Greater celandine (Chelidonium majus). It is a potent, selective, and cell-permeable PKC inhibitor (IC50 = 660 nM). It has a wide range of biological activities, including antiplatelet, anti-inflammatory, antibacterial and antitumor effects. [1,2]References on Chelerythrine Chloride[1] BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, November 15, 1990 , 172:993-999

Sigma Aldrich - C2932

Biochem/physiol Actions
Chelerythrine affects translocation of PKC from cytosol to plasma membrane. Shown to prevent neurite growth. Induces apoptosis in a concentration- and schedule-dependent manner.

REFERENCES

• Herbert, J.M., et al., Biochem. Biophys. Res. Commun. , 172 : 993 (1990).
• http://en.wikipedia.org/wiki/Chelerythrine