Basic information
- CAS
34316-15-9- Standard SMILES
COc1ccc2c(c[n+](C)c3c4cc5c(cc4ccc23)OCO5)c1OC- InChIKey
LLEJIEBFSOEYIV-UHFFFAOYSA-N- Molecular formula
- C21H18NO4+
- Average molar mass
- 348.4 g/mol
- Monoisotopic mass
- 348.12358306
Overview
Chelerythrine is a benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae. It has a role as an antibacterial agent, an antineoplastic agent and an EC 2.7.11.13 (protein kinase C) inhibitor. It is an organic cation and a benzophenanthridine alkaloid.
Names & identifiers
- Preferred name
- Chelerythrine
- IUPAC
- 1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium
- English name
- Chelerythrine
- Molecular formula
- C21H18NO4+
- Molecular weight
- 348.37192
Names & synonyms
chelerythrine34316-15-9ToddalincheleritrineToddalinebroussonpapyrine[1,3]Benzodioxolo[5,6-c]phenanthridinium, 1,2-dimethoxy-12-methyl-1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-iumE3B045W6X0CHEBI:783731,2-Dimethoxy-12-methyl(1,3)benzodioxolo(5,6-c)phenanthridinium1,2-Dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridinium
Show more names
Chelerythrine chlorideSibutramine Impurity 7helerythrineEinecs 251-930-0Chelerythrine (6CI)Chelerythrine chlorichelerythrine/toddaline
DTXSID20861211(1,3)BENZODIOXOLO(5,6-C)PHENANTHRIDINIUM, 1,2-DIMETHOXY-12-METHYL-1,2-DIMETHOXY-12-METHYL(1,3)DIOXOLO)4',5':4,5)BENZO(1,2-C)PHENANTHRIDINIUM1,2-dimethoxy-12-methyl-(1,3)benzodioxolo(5,6-c)phenanthridin-12-ium17,18-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-ium17,18-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-iumRefChem:32228DTXCID30208572
Properties
Computed structural properties
- XLogP
- 4.6
- Topological polar surface area
- 40.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 26
- Formal charge
- 1
- Complexity
- 516
Physicochemical properties
- Melting point
- 195 · 195-205°C
- Boiling point
- 496.37 °C · 496.37°C (rough estimate)
- Density
- 1.2985 · 1.2985 (rough estimate)
- refractive index
- 1.5614 · 1.5614 (estimate)
- storage temp.
- -20 °C · Desiccate at -20°C
- solubility
- Chloroform (Slightly, Sonicated), DMSO (Slightly, Sonicated), Methanol (Slightly）
- form
- Solid
- color
- Light Yellow to Dark Orange
- Stability
- Hygroscopic
- InChI
- InChI=1S/C21H18NO4/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/q+1
- InChIKey
- LLEJIEBFSOEYIV-UHFFFAOYSA-N
- SMILES
- C[N+]1=CC2=C(C(OC)=CC=C2C2C=CC3C=C4OCOC4=CC=3C1=2)OC
- LogP
- -0.401 · -0.401 (est)
- CAS DataBase Reference
- 34316 · 34316-15-9(CAS DataBase Reference)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (50%): Fatal if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 2 (50%)
Toxicology
Toxicity Summary
Chelerythrine is a potent, selective, and cell-permeable protein kinase C (PKC) inhibitor. It is also the major active natural product found in the plant Zanthoxylum clava-herculis, exhibiting anti-bacterial activity against Staphylococcus aureus. (Wikipedia) Chelerythrine is a selective inhibitor of group A and B PKC isoforms with an antitumor activity. Inhibition of PKC with chelerythrine chloride induces apoptosis by activation of a neutral sphingomyelinase, accumulation of ceramide, and depletion of sphingomyelin. Chelerythrine is at least 100-fold more selective for PKCs than for other kinases. Chelerythrine competes for the conserved catalytic sites of PKC and seems to be a potent and specific inhibitor of the group A and group B kinases. Chelerythrine exhibited cytotoxic activity against nine human tumor cell lines tested in vitro. Radioresistant and chemoresistant squamous cell carcinoma lines (HNSCC) undergo apoptosis rapidly after treatment with chelerythrine in vitro. Chelerythrine treatment of nude mice bearing SQ-20B HNSCC cells is associated with significant tumor growth delay. Also, treatment with chelerythrine resulted in minimal toxicity. (A15441)
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Substances that inhibit the growth or reproduction of BACTERIA.
Applications
DescriptionChelerythrine chloride is the chloride form of Chelerythrine chloride which is a benzophenanthridine alkaloid isolated from the plant Chelidonium majus (greater celandine). It is a kind of potent, selective, and cell-permeable protein kinase C inhibitor, an efficient antagonist of G-protein-coupled CB1 receptors, and an independent activator of MAPK pathways. It has a wide range of biological activities including antiplatelet, anti-inflammatory, antibacterial and antitumor effects. It has reported of that it is capable of inducing apoptosis in HL-60 human promyelocytic leukemia cells and several other cancer cell lines. The underlying mechanism is through its effects of inhibiting the binding of BclXL to Bax or Bad.
UsesChelerythrine Chloride is a cell permeable protein kinase C (PKC) inhibitor.
Upstream & downstream products
Downstream products
Suppliers100 total
北京华美互利生物化工010-56205725 · [email protected]
成都曼思特生物科技有限公司18010516991 · [email protected]
南京普怡生物科技有限公司13814510036 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
Related reactions
0 records
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Compound notes
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