<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4140</id>
  <title>T3D4086</title>
  <common-name>Chelerythrine</common-name>
  <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.</description>
  <cas>34316-15-9</cas>
  <pubchem-id>2703</pubchem-id>
  <chemical-formula>C21H18NO4</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <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. (A15441)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source nil="true"/>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T05:05:12Z</created-at>
  <updated-at type="dateTime">2026-05-14T20:01:05Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C12227</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>CHEBI:78373</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB17024</drugbank-id>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>COC1=C(OC)C2=C[N+](C)=C3C4=CC5=C(OCO5)C=C4C=CC3=C2C=C1</moldb-smiles>
  <moldb-formula>C21H18NO4</moldb-formula>
  <moldb-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</moldb-inchi>
  <moldb-inchikey>LLEJIEBFSOEYIV-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">348.3719</moldb-average-mass>
  <moldb-mono-mass type="decimal">348.123583069</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>-0.88</logp>
  <hmdb-id nil="true"/>
  <chembl-id>CHEMBL13045</chembl-id>
  <chemspider-id>2602</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003046</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id nil="true"/>
  <iupac>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</iupac>
  <moldb-polar-surface-area>40.8</moldb-polar-surface-area>
  <moldb-refractivity>97.97789999999998</moldb-refractivity>
  <moldb-polarizability>38.20012426749034</moldb-polarizability>
  <moldb-rotatable-bond-count>2</moldb-rotatable-bond-count>
  <moldb-acceptor-count>4</moldb-acceptor-count>
  <moldb-donor-count>0</moldb-donor-count>
  <moldb-pka-strongest-acidic nil="true"/>
  <moldb-pka-strongest-basic>-4.387090973095842</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>5</moldb-number-of-rings>
  <moldb-alogps-logp>-0.13</moldb-alogps-logp>
  <moldb-alogps-logs>-6.97</moldb-alogps-logs>
  <moldb-alogps-solubility>4.08e-05 g/l</moldb-alogps-solubility>
</compound>
