ContaminantDB: Chelerythrine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:05:12 UTC

Update Date

2026-05-14 20:01:05 UTC

Accession Number

CHEM003046

Identification

Common Name

Chelerythrine

Class

Small Molecule

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.

Contaminant Sources

T3DB toxins

Contaminant Type

Ether
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1,2-Dimethoxy-12-methyl(1,3)benzodioxolo(5,6-c)phenanthridinium	ChEBI
Chelerythrine chloride	MeSH
Chelerythrine sulfate	MeSH
Chelerythrine hydroxide	MeSH
Norchelerythrine	MeSH

Chemical Formula

C₂₁H₁₈NO₄

Average Molecular Mass

348.372 g/mol

Monoisotopic Mass

348.124 g/mol

CAS Registry Number

34316-15-9

IUPAC Name

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

Traditional Name

chelerythrine

SMILES

COC1=C(OC)C2=C[N+](C)=C3C4=CC5=C(OCO5)C=C4C=CC3=C2C=C1

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

InChI Key

LLEJIEBFSOEYIV-UHFFFAOYSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Benzophenanthridine alkaloids

Sub Class

Quaternary benzophenanthridine alkaloids

Direct Parent

Quaternary benzophenanthridine alkaloids

Alternative Parents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic cation (CHEBI:78373 )
benzophenanthridine alkaloid (CHEBI:78373 )
Alkaloids (C12227 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

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

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
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

Applications

Biological Roles

Chemical Roles

EC 2.7.11.13 (protein kinase C) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.1e-05 g/L	ALOGPS
logP	-0.13	ALOGPS
logP	-0.88	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.8 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.98 m³·mol⁻¹	ChemAxon
Polarizability	38.2 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-d203afa4278759b82f7e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0009000000-2bb5e50472f059eaa08d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fsa-0059000000-250accb7a5a2c87754ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-5c16c2d1f705c69736a7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0009000000-f7b3b2e0623f5657e36c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0lfs-3059000000-35f6a4b40c5272241e1c	Spectrum

Toxicity Profile

Route of Exposure

Not Available

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)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available