Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H14NO4 |
Molecular Weight | 320.3188 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 1 |
SHOW SMILES / InChI
SMILES
C1OC2=C(O1)C=C3C(CC[N+]4=C3C=C5C=CC6=C(OCO6)C5=C4)=C2
InChI
InChIKey=XYHOBCMEDLZUMP-UHFFFAOYSA-N
InChI=1S/C19H14NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,5-8H,3-4,9-10H2/q+1
Molecular Formula | C19H14NO4 |
Molecular Weight | 320.3188 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Coptisine (COP), a protoberberine alkaloid, is widely found in Chinese medicinal plants (family Berberidaceae, Ranunculaceae and Papaveraceae). It is reported that COP has a wide range of pharmacological and biological activities, including antibacterial, hypoglycemic, anti-tumorigenic, and gastric-mucous membrane protection. Considerable attention has been focused on its activity against central nervous system disorders, such as improving the symptoms of Alzheimer’s disease and even preventing its onset, by exerting antidepressant effects as a potent type A monoamine oxidase inhibitor. Coptisine was found to be an efficient uncompetitive Indoleamine 2,3-dioxygenase inhibitor. Coptisine is a potent inhibitor of human organic cation transporters.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459 |
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Target ID: GO:0070371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459 |
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Target ID: CHEMBL5685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304 |
0.9 µM [IC50] | ||
Target ID: CHEMBL1743122 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304 |
2.3 µM [IC50] | ||
Target ID: CHEMBL2073673 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304 |
2.3 µM [IC50] | ||
Target ID: CHEMBL4685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25079795 |
6.3 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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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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Inhibition of type A monoamine oxidase by coptisine in mouse brain. | 2001 Dec 28 |
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[The effects of kampo-formulation and the constituting crude drugs, prescribed for the treatment of peptic ulcer on H,K-ATPase activity]. | 2001 Feb |
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Structural elucidation and identification of alkaloids in Rhizoma Coptidis by electrospray ionization tandem mass spectrometry. | 2004 Nov |
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Improved detection of Coptidis alkaloids by field-amplified sample stacking in capillary electrophoresis. | 2004 Sep 21 |
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[Quality assessment of Coptis chinensis in China]. | 2005 Apr |
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Sensitivity improvement on detection of Coptidis alkaloids by sweeping in capillary electrophoresis. | 2005 Feb 7 |
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[Studies on the alkaloids from herb of Corydalis adunca]. | 2005 Nov |
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Double blockade of cell cycle progression by coptisine in vascular smooth muscle cells. | 2005 Oct 15 |
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[Qualitative and quantitative determination of the main components of huanglianjiedu decoction by HPLC-UV/MS]. | 2006 Apr |
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Simultaneous determination of four active alkaloids from a traditional Chinese medicine Corydalis saxicola Bunting. (Yanhuanglian) in plasma and urine samples by LC-MS-MS. | 2006 Feb 2 |
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Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway. | 2006 Jan 17 |
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[Fingerprints of Rhizoma Coptidis from Shizhu by HPLC]. | 2006 Jul |
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Bioavailabilty and pharmacokinetics of four active alkaloids of traditional Chinese medicine Yanhuanglian in rats following intravenous and oral administration. | 2006 Jun 16 |
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[Effect of alkaloids from celandine on calcium accumulation and oxidative phosphorylation in mitochondria depending on their DNA intercalating properties]. | 2006 Mar-Apr |
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Selective inhibition of vascular smooth muscle cell proliferation by coptisine isolated from Coptis rhizoma, one of the crude drugs composing Kampo medicines Unsei-in. | 2006 May |
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Simultaneous analysis of nine active components in Gegen Qinlian preparations by high-performance liquid chromatography with diode array detection. | 2006 Sep |
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Simultaneous analysis of alkaloids from Zanthoxylum nitidum by high performance liquid chromatography-diode array detector-electrospray tandem mass spectrometry. | 2006 Sep 18 |
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High performance liquid chromatography-mass spectrometry analysis of protoberberine alkaloids in medicine herbs. | 2007 Apr |
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Analysis of Central European Corydalis species by nonaqueous capillary electrophoresis-electrospray ion trap mass spectrometry. | 2007 Aug 3 |
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[Absorption of coptisine chloride and berberrubine across human intestinal epithelial by using human Caco-2 cell monolayers]. | 2007 Dec |
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Comparative analysis of the chemical profile of wild and cultivated populations of Corydalis saxicola by high-performance liquid chromatography. | 2007 Sep-Oct |
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Covalent bonding of azoles to quaternary protoberberine alkaloids. | 2008 Dec |
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[Analysis of the main components of coptis-evodia herb couple by HPLC-DAD-MS]. | 2008 Mar |
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Alkaloids from Corydalis saxicola and their anti-hepatitis B virus activity. | 2008 May |
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Inhibitory activities of the alkaloids from Coptidis Rhizoma against aldose reductase. | 2008 Nov |
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Anti-Alzheimer and antioxidant activities of Coptidis Rhizoma alkaloids. | 2009 Aug |
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Significant differences in alkaloid content of Coptis chinensis (Huanglian), from its related American species. | 2009 Aug 24 |
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[Effect of additives on absorption of Coptis chinensis total alkaloids and pharmacokinetics in mice]. | 2009 Feb |
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Bear bile: dilemma of traditional medicinal use and animal protection. | 2009 Jan 12 |
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Hydroxyl radical scavenging activities of isoquinoline alkaloids isolated from Coptis chinensis. | 2009 Mar |
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Inhibitory Effects of Coptidis rhizoma and Berberine on Cocaine-induced Sensitization. | 2009 Mar |
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Development of a rapid resolution liquid chromatographic method for simultaneous analysis of four alkaloids in Rhizoma coptidis under different cultivation conditions. | 2009 Mar-Apr |
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Purification of alkaloids from Corydalis yanhusuo W. T. Wang using preparative 2-D HPLC. | 2009 May |
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Investigation of the anti-fungal activity of coptisine on Candida albicans growth by microcalorimetry combined with principal component analysis. | 2009 Oct |
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[Simultaneous determination of the five alkaloids in Rhizoma Coptidis by nonaqueous capillary electrophoresis]. | 2010 Apr |
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[Metabolism, transformation and distribution of Coptis chinensis total alkaloids in rat]. | 2010 Aug |
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[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis]. | 2010 Dec |
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Quality assurance for Chinese herbal formulae: standardization of IBS-20, a 20-herb preparation. | 2010 Feb 22 |
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[Pharmacodyamic material basis of rhizoma coptidis on insulin resistance]. | 2010 Jul |
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JinQi-Jiangtang tablet, a Chinese patent medicine, for pre-diabetes: a randomized controlled trial. | 2010 Mar 10 |
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[Simultaneous determination of six alkaloids in Coptis chinensis of different regions by RP-HPLC]. | 2010 Oct |
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Simultaneous analysis of seven alkaloids in Coptis-Evodia herb couple and Zuojin pill by UPLC with accelerated solvent extraction. | 2010 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459
Mice: 50,100 or 150mg/kg body weight daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459
In HCT-116 cells, Coptisine exhibited cell cytotoxicity at a high rate (IC50 was 27.13 μg/mL vs 282.2 μg/mL in human colorectal epithelial cells FHC). Besides, Coptisine (2.5 μg/mL) decreased the survival rate of cells time-dependently .
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:49:54 GMT 2023
by
admin
on
Fri Dec 15 19:49:54 GMT 2023
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Record UNII |
0GCL71VN14
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Record Status |
Validated (UNII)
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Record Version |
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-
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8323
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3486-66-6
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m3782
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COPTISINE
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72322
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DTXSID10188404
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0GCL71VN14
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C034384
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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