Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H19NO5 |
Molecular Weight | 353.3686 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12[C@@H](O)CC3=CC4=C(OCO4)C=C3[C@@]1([H])N(C)CC5=C2C=CC6=C5OCO6
InChI
InChIKey=GHKISGDRQRSCII-ZOCIIQOWSA-N
InChI=1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1
Molecular Formula | C20H19NO5 |
Molecular Weight | 353.3686 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11211931
https://www.ncbi.nlm.nih.gov/pubmed/26626193
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11211931
https://www.ncbi.nlm.nih.gov/pubmed/26626193
Chelidonine is the major alkaloid component of Chelidonium majus. Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase (a nonspecific cholinesterase) inhibitory activity. It showed strong cytotoxicity in cancer cells. While several modes of death have been identified, most of anti-cancer attempts have focused on stimulation of cells to undergo apoptosis. Chelidonine seems to trigger multiple mechanisms in MCF-7 breast cancer cells. It induces both apoptosis and autophagy modes of cell death in a dose dependent manner. Alteration of expression levels of bax/bcl2, and dapk1a by increasing concentration of chelidonine approves switching the death mode from apoptosis induced by very low to autophagy by high concentrations of this compound. On the other hand, submicromolar concentrations of chelidonine strongly suppressed telomerase at both enzyme activity and hTERT transcriptional level. Long exposure of the cells to 50 nanomolar concentration of chelidonine considerably accelerated senescence. Altogether, chelidonine may provide a promising chemistry from nature to treat cancer. Chelidonine exhibits a broad spectrum of pharmacological properties, such as anti-inflammatory and antiviral activities Its biological activities and clinical applications have been extensively investigated. Especially the usage of chelidonine as an anticancer drug is very important lately. It also has profound inhibitory effects on airway inflammation, which means chelidonine can improve allergic asthma in mice and may also work for human medicine.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
34.51 µM [IC50] | |||
Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27420038 |
3.85 µM [IC50] | ||
Target ID: CHEMBL614909 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26677104 |
23.13 µM [IC50] | ||
Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21213973 |
26.8 µM [IC50] | ||
Target ID: CHEMBL1914 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21213973 |
31.9 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
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HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products. | 1992 May 29 |
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[The inhibition enzymatic hydrolysis of acetylthiocholine by acetylcholinesterase using principal alkaloids isolated from celandine and macleya and their derivatives]. | 2001 |
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Effect of a homeopathic drug, Chelidonium, in amelioration of p-DAB induced hepatocarcinogenesis in mice. | 2002 Apr 10 |
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[Inhibition by various alkaloids of acetylcholinesterase and butyrylcholinesterase from human blood]. | 2002 Jan-Feb |
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NSC-631570 (Ukrain) in the palliative treatment of pancreatic cancer. Results of a phase II trial. | 2002 Mar |
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Inhibitory activity on binding of specific ligands to the human angiotensin II AT(1) and endothelin 1 ET(A) receptors: bioactive benzo[c]phenanthridine alkaloids from the root of Bocconia frutescens. | 2002 Sep |
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[Inhibition of liver mitochondrial monoamine oxidase activity by alkaloids isolated from Chelidonium and Macleaya and by their derivative drugs]. | 2003 |
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Cytotoxic activity and quality control determinations on Chelidonium majus. | 2003 Feb |
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Preliminary evaluation of CNS effects of 6-O-substituted chelidonine derivatives. | 2003 Mar-Apr |
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Ukrain - a new cancer cure? A systematic review of randomised clinical trials. | 2005 Jul 1 |
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Intestinal spasmolytic effects of STW 5 (Iberogast) and its components. | 2006 |
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Simultaneous determination of seven main alkaloids of Chelidonium majus L. by ultra-performance LC with photodiode-array detection. | 2010 Apr |
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Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae). | 2010 Nov |
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Multiple mechanisms of cell death induced by chelidonine in MCF-7 breast cancer cell line. | 2014 Nov 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23850776
Mice: mice were fed once/day for 14 consecutive days of the experimental period, respectively, with 50 mg/kg, 75 mg/kg and 100 mg/kg body weight (bw) of chelidonine dissolved in sterile saline.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27420038
2.5 uM chelidonine arrested the cell cycle in the G2/M
phase with an increase from 25.67% to 88.27% in HeLa cells
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:19:31 GMT 2023
by
admin
on
Sat Dec 16 09:19:31 GMT 2023
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Record UNII |
4UDG3LY0GT
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Record Status |
Validated (UNII)
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Record Version |
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m3322
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PRIMARY | Merck Index | ||
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Chelidonine
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4UDG3LY0GT
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20267-87-2
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197810
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