| Record Information |
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| Version | 2.0 |
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| Creation Date | 2014-08-29 05:05:12 UTC |
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| Update Date | 2014-12-24 20:26:38 UTC |
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| Accession Number | T3D4086 |
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| Identification |
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| Common Name | Chelerythrine |
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| Class | Small Molecule |
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| Description | Chelerythrine is a benzophenanthridine alkaloid extracted from the plant Greater celandine (Chelidonium majus). It is a potent, selective, and cell-permeable protein kinase C inhibitor. |
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| Compound Type | - Ether
- Natural Compound
- Organic Compound
- Plant Toxin
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| Chemical Structure | |
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| Synonyms | | Synonym | | 1,2-Dimethoxy-12-methyl(1,3)benzodioxolo(5,6-c)phenanthridinium |
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| Chemical Formula | C21H18NO4 |
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| Average Molecular Mass | 348.371 g/mol |
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| Monoisotopic Mass | 348.123 g/mol |
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| CAS Registry Number | 34316-15-9 |
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| IUPAC Name | 17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaen-21-ium |
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| Traditional Name | chelerythrine |
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| SMILES | COC1=C(OC)C2=C[N+](C)=C3C4=CC5=C(OCO5)C=C4C=CC3=C2C=C1 |
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| InChI Identifier | 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 |
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| InChI Key | InChIKey=LLEJIEBFSOEYIV-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as quaternary benzophenanthridine alkaloids. These are alkaloids containing a quaternary N-demethylbenzophenanthridine skeleton, where the nitrogen atom of the phenanthridine moiety is part of four bonds. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Benzophenanthridine alkaloids |
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| Sub Class | Quaternary benzophenanthridine alkaloids |
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| Direct Parent | Quaternary benzophenanthridine alkaloids |
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| Alternative Parents | |
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| Substituents | - Quaternary benzophenanthridine alkaloid skeleton
- Benzoquinoline
- Phenanthridine
- Isoquinoline
- Naphthalene
- Quinoline
- Benzodioxole
- Anisole
- Alkyl aryl ether
- Benzenoid
- Pyridine
- Pyridinium
- Heteroaromatic compound
- Acetal
- Ether
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Organopnictogen compound
- Organic cation
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | - Acrosome
- Actin Cytoskeleton
- Actin Filament
- Apical Membrane
- Basolateral Membrane
- Caveolae
- Cell junction
- Cell surface
- Cytoplasm
- Cytoskeleton
- Cytosol
- Endocytic Vesicle
- Endoplasmic reticulum
- Endosome
- Extracellular
- Extracellular matrix
- Focal adhesion
- Golgi apparatus
- Intermediate Filament
- Lysosome
- Membrane Fraction
- Microsome
- Microtubule
- Mitochondrial Matrix
- Mitochondrial Membrane
- Mitochondrion
- Nuclear Membrane
- Perinuclear region
- Peroxisome
- Plasma Membrane
- Post Synaptic Density
- Sarcoplasmic Reticulum
- Secretory Granule
- Secretory vesicle
- Soluble Fraction
- Synaptic Vesicle
- Tubulin
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | | Name | SMPDB Link | KEGG Link |
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| Apoptosis | Not Available | map04210 | | Cell cycle | Not Available | map04110 | | Insulin secretion | Not Available | map04911 | | Oxidative phosphorylation | Not Available | map00190 | | Inositol Phosphate Metabolism | SMP00462 | map00562 | | Long-term potentiation | Not Available | map04720 | | Endocytosis | Not Available | map04144 | | Long-term depression | Not Available | map04730 | | Renin-angiotensin system | Not Available | map04614 | | Eicosanoids | Not Available | Not Available | | Vascular smooth muscle contraction | Not Available | map04270 | | Taste transduction | Not Available | map04742 | | Opioid Analgesics | Not Available | Not Available | | Metabolic Pathways | Not Available | Not Available | | Hippo signaling pathway | Not Available | map04390 | | Hiv Protease Inhibitors | Not Available | Not Available | | Gastric acid secretion | Not Available | map04971 | | Gabaergic synapse | Not Available | map04727 | | Circadian rhythm | Not Available | map04710 | | Cardiac muscle contraction | Not Available | map04260 | | Antifungal Agents | Not Available | Not Available | | Aminoglycosides | Not Available | Not Available |
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| Applications | |
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| Biological Roles | |
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| Chemical Roles | |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available | | LogP | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0009000000-d203afa4278759b82f7e | 2016-08-01 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0009000000-2bb5e50472f059eaa08d | 2016-08-01 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fsa-0059000000-250accb7a5a2c87754ac | 2016-08-01 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0009000000-5c16c2d1f705c69736a7 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0009000000-f7b3b2e0623f5657e36c | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0lfs-3059000000-35f6a4b40c5272241e1c | 2016-08-03 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | 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. (1) |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| PubChem Compound ID | 2703 |
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| ChEMBL ID | CHEMBL13045 |
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| ChemSpider ID | 2602 |
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| KEGG ID | C12227 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | CHEBI:78373 |
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| BioCyc ID | Not Available |
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| CTD ID | Not Available |
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| Stitch ID | Not Available |
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| PDB ID | Not Available |
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| ACToR ID | Not Available |
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| Wikipedia Link | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | T3D4086.pdf |
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| General References | - Chmura SJ, Dolan ME, Cha A, Mauceri HJ, Kufe DW, Weichselbaum RR: In vitro and in vivo activity of protein kinase C inhibitor chelerythrine chloride induces tumor cell toxicity and growth delay in vivo. Clin Cancer Res. 2000 Feb;6(2):737-42. [10690561 ]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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