Compound: chelerythrine
SMILES: O1c2c(cc3ccc4c(c3c2)[n+](cc5c(OC)c(OC)ccc45)C)OC1
InChIKey: LLEJIEBFSOEYIV-UHFFFAOYSA-N
Synonyms: chelerythrine, 34316-15-9, Toddalin, cheleritrine, Toddaline, broussonpapyrine, [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-ium, E3B045W6X0, CHEBI:78373, 1,2-Dimethoxy-12-methyl(1,3)benzodioxolo(5,6-c)phenanthridinium, DTXSID20861211, 1,2-Dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridinium, (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)PHENANTHRIDINIUM, 1,2-dimethoxy-12-methyl-(1,3)benzodioxolo(5,6-c)phenanthridin-12-ium, 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, 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, RefChem:32228, DTXCID30208572, 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, 251-930-0, EINECS 251-930-0, 1,2-Dimethoxy-12-Methyl[1,3]benzodioxolo[5,6-C]phenanthridin-12-Ium, 1,2-Dimethoxy-12-methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-12-ium, CHEMBL13045, 1,2-Dimethoxy-12-methyl-[1,3]dioxolo-[4',5':4,5]benzo[1,2-c]phenanthridin-12-ium, NSC646662, 1,2-Dimethoxy-N-methyl(1,3)benzodioxolo(5,6-c)phenanthridinium chloride, Chelerytherine, Chelerythrine?, UNII-E3B045W6X0, SR-01000075750, Lopac-C-2932, CHELERYTHRINE [MI], Lopac0_000241, BSPBio_001558, SCHEMBL288915, CHELERYTHRINE [WHO-DD], GTPL5953, MEGxp0_001953, orb1300271, SCHEMBL29357531, SCHEMBL30527167, SCHEMBL30527168, BDBM25524, HMS1791N20, HMS1989N20, HMS3402N20, HY-N2359, MFCD00270393, MSK157280, STL581484, AKOS028108433, CCG-204336, FC73805, NCGC00015225-01, NCGC00015225-02, NCGC00015225-03, NCGC00015225-04, NCGC00015225-05, NCGC00015225-06, NCGC00015225-07, NCGC00162102-01, NCGC00162102-02, NCGC00162102-03, NCGC00162102-04, NCGC00162102-05, NCI60_003349, NCI60_041672, DB-050176, CS-0022541, NS00089928, Q5089853, SR-01000075750-5, BRD-K87904882-001-02-3, 1,2-Dimethoxy-12-methyl-9H-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium, 1,2-Dimethoxy-12-methyl-12lambda~5~-[1,3]benzodioxolo[5,6-c]phenanthridine hydrochloride, 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(19),15,17,20-nonaen-21-ium
Theoretical properties:
molecular_formula: C21H18NO4+
molecular_weight: 348.4 g/mol
exact_mass: 348.12358306 g/mol
formal_charge: 1
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 2
heavy_atom_count: 26
topological_polar_surface_area: 40.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: 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.
chebi: A benzophenanthridine alkaloid isolated from the root of <em>Zanthoxylum simulans</em>, <em>Chelidonium majus L.</em>, and other <em>Papaveraceae</em>.
chembl: CHELERYTHRINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 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.
It is also found in the plants Zanthoxylum clava-herculis and Zanthoxylum rhoifolium, exhibiting antibacterial activity against Staphylococcus aureus and other human pathogens.