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کلریت‌رین

Structure via PubChem · Public domain (PubChem)

EntityQ5089853· pop 11· linked from 223 articles

کلریت‌رین

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Also known as broussonpapyrine, cheleritrine, chelerythrine hydroxide, toddalin, 1,2-Dimethoxy-12-methyl(1,3)benzodioxolo(5,6-c)phenanthridinium

Chelerythrine is a benzophenanthridine alkaloid present in the plant Chelidonium majus (greater celandine). It is a potent, selective, and cell-permeable protein kinase C inhibitor in vitro. And an efficacious antagonist of G-protein-coupled CB1 receptors. This molecule also exhibits anticancer qualities and it has served as a base for many potential novel drugs against cancer. Structurally, this molecule has two distinct conformations, one being a positively charged iminium form, and the other being an uncharged form, a pseudo-base.

Chemical data

Formula
C21H18NO4+
Molecular weight
348.4 g/mol
IUPAC name
1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium
SMILES
C[N+]1=C2C(=C3C=CC(=C(C3=C1)OC)OC)C=CC4=CC5=C(C=C42)OCO5
InChIKey
LLEJIEBFSOEYIV-UHFFFAOYSA-N
XLogP
4.6
Polar surface area
40.8 Ų
H-bond donors
0
H-bond acceptors
4
Formal charge
1

via PubChem

Drug data · ChEMBL

Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Mass
348.124
Show 5 more facts
found in taxon
Macleaya cordata
canonical SMILES
C[N+]1=C2C(=C3C=CC(=C(C3=C1)OC)OC)C=CC4=CC5=C(C=C42)OCO5
subject has role
antineoplastic
Commons category
Chelerythrine
chemical formula
C₂₁H₁₈NO₄⁺
Sources (3)

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