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Chelerythrine information


Chelerythrine
Skeletal formula of chelerythrine
Ball-and-stick model of the chelerythrine molecule
Names
Preferred IUPAC name
1,2-Dimethoxy-12-methyl-9H-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium
Identifiers
CAS Number
  • 34316-15-9 checkY
  • chloride: 3895-92-9
3D model (JSmol)
  • Interactive image
  • chloride: Interactive image
ChEBI
  • CHEBI:78373 checkY
ChEMBL
  • chloride: ChEMBL258893 checkY
ChemSpider
  • 2602 checkY
  • chloride: 65262
ECHA InfoCard 100.047.194 Edit this at Wikidata
EC Number
  • 251-930-0
  • chloride: 223-444-9
IUPHAR/BPS
  • 5953
KEGG
  • C12227
PubChem CID
  • 2703
  • chloride: 72311
UNII
  • E3B045W6X0 checkY
  • chloride: 7IC98TZ0PZ
CompTox Dashboard (EPA)
  • DTXSID20861211 Edit this at Wikidata
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 checkY
    Key: LLEJIEBFSOEYIV-UHFFFAOYSA-N checkY
  • InChI=1/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
    Key: LLEJIEBFSOEYIV-UHFFFAOYAP
  • chloride: InChI=1S/C21H18NO4.ClH/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;1H/q+1;/p-1
    Key: WEEFNMFMNMASJY-UHFFFAOYSA-M
SMILES
  • O1c3c(OC1)cc2ccc4c5c(c[n+](c4c2c3)C)c(OC)c(OC)cc5
  • chloride: C[n+]1cc2c(ccc(c2OC)OC)c3c1c4cc5c(cc4cc3)OCO5.[Cl-]
Properties
Chemical formula
C21H18NO4
Molar mass 348.378 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

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.[1] And an efficacious antagonist of G-protein-coupled CB1 receptors.[2] 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.[3]

It is also found in the plants Zanthoxylum clava-herculis and Zanthoxylum rhoifolium, exhibiting antibacterial activity against Staphylococcus aureus and other human pathogens.[4][5]

  1. ^ Chelerythrine Chloride from Fermentek
  2. ^ Dhopeshwarkar, Amey S.; Jain, Saurabh; Liao, Chengyong; Ghose, Sudip K.; Bisset, Kathleen M.; Nicholson, Russell A. (2011-03-01). "The actions of benzophenanthridine alkaloids, piperonyl butoxide and (S)-methoprene at the G-protein coupled cannabinoid CB₁ receptor in vitro". European Journal of Pharmacology. 654 (1): 26–32. doi:10.1016/j.ejphar.2010.11.033. ISSN 1879-0712. PMID 21172340.
  3. ^ Dostál, Jiří; Táborská, Eva; Slavík, Jiří; Potáček, Milan; de Hoffmann, Edmond (May 1995). "Structure of Chelerythrine Base". Journal of Natural Products. 58 (5): 723–729. doi:10.1021/np50119a010. ISSN 0163-3864.
  4. ^ Gibbons, Simon; Leimkugel, Julia; Oluwatuyi, Moyo; et al. (2003). "<Activity of Zanthoxylum clava-herculis extracts against multi-drug resistant methicillin-resistant Staphylococcus aureus (mdr-MRSA)>". Phytotherapy Research. 17 (3): 274–275. doi:10.1002/ptr.1112. PMID 12672160. S2CID 32722743.
  5. ^ Tavares, Luciana de C; Zanon, Graciane; Weber, Andréia D.; et al. (2014). "<Structure-activity relationship of benzophenanthridine alkaloids from Zanthoxylum rhoifolium having antimicrobial activity>". PLOS ONE. 9 (5): e97000. Bibcode:2014PLoSO...997000T. doi:10.1371/journal.pone.0097000. PMC 4019524. PMID 24824737.

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Chelerythrine

Last Update:

Chelerythrine is a benzophenanthridine alkaloid present in the plant Chelidonium majus (greater celandine). It is a potent, selective, and cell-permeable...

Word Count : 1388

Chelidonium majus

Last Update:

homochelidonine, norchelidonine, berberine, chelidonine, sanguinarine, chelerythrine, and 8-hydroxydihydrosanguinarine. Sanguinarine is particularly toxic...

Word Count : 1846

Sanguinaria

Last Update:

Sanguinaria root is rich in isoquinoline alkaloids, mainly sanguinarine and chelerythrine. Sanguinarine is a benzophenanthridine alkaloid (see phenanthridine)...

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Argemone mexicana

Last Update:

A and B (protopine type), coptisine, cryptopine, allocryptopine and chelerythrine have also been found in this plant. The seed pods secrete a pale yellow...

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Nucleotide

Last Update:

A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 3299

Alkaloid

Last Update:

antiarrhythmic (e.g. quinidine), analgesic (e.g. morphine), antibacterial (e.g. chelerythrine), and antihyperglycemic activities (e.g. berberine). Many have found...

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Caffeine

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A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 19836

Quercetin

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A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 2467

Methotrexate

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A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 3144

Uric acid

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A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 3692

Purine

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A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 2510

Ivermectin

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A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 7752

Allopurinol

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A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 2753

Pentoxifylline

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A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 1818

Lamprocapnos

Last Update:

corydine, and protopine. a Korean source lists also cryptopine, coptisine, chelerythrine, chelirubine, chelilutine and reticuline. The alkaloids sanguinarine...

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Fenethylline

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A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 4646

Ticagrelor

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A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 3096

List of poisonous plants

Last Update:

and root is coptisine, with berberine, chelidonine, sanguinarine, and chelerythrine also present. Sanguinarine is particularly toxic with an LD50 of only...

Word Count : 4901

Cinnamaldehyde

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A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 1911

Theobromine

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A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 2126

Phenolphthalein

Last Update:

A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 1809

Cilostazol

Last Update:

A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 689

Inositol

Last Update:

A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 3949

Propolis

Last Update:

A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 1279

Uracil

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A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 2942

Adenosine

Last Update:

A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 3346

Coomassie brilliant blue

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A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans blue Gefapixant GW-791343 HMA...

Word Count : 2577

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