Basic information
- Standard SMILES
COc1ccc2cc3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2- InChIKey
YBHILYKTIRIUTE-UHFFFAOYSA-N- Molecular formula
- C20H18NO4+
- Average molar mass
- 336.4 g/mol
- Monoisotopic mass
- 336.12303448
Overview
Berberine is a berberine alkaloid, an organic heteropentacyclic compound, an alkaloid antibiotic and a botanical anti-fungal agent. It has a role as a geroprotector, an antioxidant, a metabolite, a hypoglycemic agent, an EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor, an antineoplastic agent, an antilipemic drug, an EC 3.1.1.8 (cholinesterase) inhibitor, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 3.1.1.4 (phospholipase A2) inhibitor, a potassium channel blocker, an EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor, an EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, an EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor, an EC 1.21.3.3 (reticuline oxidase) inhibitor, an EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor, an EC 2.7.11.10 (IkappaB kinase) inhibitor and an EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor.
Names & identifiers
- Preferred name
- Berberine
- IUPAC
- 16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene
- English name
- Berberine
- Molecular formula
- C20H18NO4
- Molecular weight
- 336.36
Names & synonyms
Show more names
Database identifiers
- CAS
2086-83-1- PubChem CID
- 2353
- DTXSID
DTXSID9043857- ChEMBL
CHEMBL295124- ChEBI
CHEBI:16118- UNII
- 0I8Y3P32UF
- EC Number
- 218-229-1
- Nikkaji
- J7.320B
Properties
Computed structural properties
- XLogP
- 3.6
- Topological polar surface area
- 40.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 25
- Formal charge
- 1
- Complexity
- 488
Experimental & physicochemical properties
Physical Description
Yellow solid; [Merck Index]
Solid
Physicochemical properties
- Melting point
- 204 · 204-206 °C (dec.)
- Boiling point
- 486.8 °C · 486.8°C (rough estimate)
- Density
- 1.2976 · 1.2976 (rough estimate)
- refractive index
- 1.58 · 1.5800 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- powder
- pka
- 2.47 · 2.47(at 25℃)
- color
- White to yellow crystals
- Water Solubility
- 43.48 g/L · 43.48g/L(25 ºC)
- InChI
- InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1
- InChIKey
- YBHILYKTIRIUTE-UHFFFAOYSA-N
- SMILES
- O(C1C(=CC=C2C=1C=[N+]1CCC3=CC4OCOC=4C=C3C1=C2)OC)C
- LogP
- -0.99 · -0.990 (est)
- CAS DataBase Reference
- 2086 · 2086-83-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 0 I8Y3P32UF · 0I8Y3P32UF
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- RIDADR
- 1544 · 1544
- WGK Germany
- 2 · 2
- RTECS
- 9866400 · DR9866400
- F
- 3 · 3-10
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- Toxicity
- 50 orl-mus: · LD50 orl-mus: 329 mg/kg YKKZAJ 82,726,62
Safety & regulation
Hazard information
Toxicology
Hepatotoxicity
Berberine has not been linked to serum enzyme elevations during therapy, although there have been few prospective studies in humans that have reported on its effects on laboratory test results in any detail. In published trials, berberine has appeared to be well tolerated with only minor and few adverse effects which have been similar in frequency among persons receiving placebo. Despite wide scale use as an herbal supplement, berberine has not been linked to published instances of clinically apparent liver injury. The frequency of hypersensitivity reactions to berberine is also not known.
Toxicity Summary
Sanguinarine [13-methyl (1,3) benzodioxolo(5,6-c)-1,3-dioxolo (4,5) phenanthridinium] kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. Berberine, on the other hand, has been reported to cause cytotoxicity and adversely influence the synthesis of DNA. Studies have reported various pharmacological properties of these alkaloids, e.g., they exhibit antibacterial, antiasthma, anticancer, anti-inflammatory, and antidiabetic activities.
Safety data
- F
- 3-10
- wgk
- 2
- rtecs
- DR9866400
- ridadr
- 1544
- Toxicity
- LD50 orl-mus: 329 mg/kg YKKZAJ 82,726,62
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
Mechanism of Action
This publication noted that berberine is an alkaloid from Hydrastis canadensis L., Chinese herb Huanglian, and many other plants. It is widely used in traditional Chinese medicine as an antimicrobial in the treatment of dysentery and infectious diarrhea. The authors describe the cardiovascular effects of berberine and its derivatives, tetrahydroberberine and 8-oxoberberine, e.g., berberine has positive inotropic, negative chronotropic, antiarrhythmic, and vasodilator properties. Some cardiovascular effects of berberine and its derivatives are attributed to the blockade of K+ channels (delayed rectifier and K(ATP)) and stimulation of Na+ -Ca(2+) exchanger. Also, berberine prolongs the duration of ventricular action potential. Its vasodilator activity has been attributed to multiple cellular mechanisms. The authors note that the cardiovascular effects of berberine suggest its possible clinical usefulness in the treatment of arrhythmias and/or heart failure.
Berberine, an isoquinoline alkaloid isolated from the Chinese herb Coptis chinensis and other Berberis plants, has a wide range of pharmacological properties. This publication notes the mechanisms of berberine's functions have been extensively explored, and that berberine: 1) can be used to treat many diseases, such as cancer and digestive, metabolic, cardiovascular, and neurological diseases, 2) has protective capacities in digestive diseases, 3) can inhibit toxins and bacteria, including Helicobacter pylori, protect the intestinal epithelial barrier from injury, and ameliorate liver injury, 4) inhibits the proliferation of various types of cancer cells and impedes invasion and metastasis, 5) improves the efficacy and safety of chemoradiotherapies, 6) regulates glycometabolism and lipid metabolism, improves energy expenditure, reduces body weight, and alleviates nonalcoholic fatty liver disease, 7) improves cardiovascular hemodynamics, suppresses ischemic arrhythmias, attenuates the development of atherosclerosis, and reduces hypertension, 8) shows potent neuroprotective effects, including antioxidative, antiapoptotic, and anti-ischemic, and 9) exerts protective effects against other diseases.
Uses & manufacturing
Applications
DescriptionCoptis chinensis was widely used in China as a folk medicine by Shennong around 3000 BC. Coptis chinensis was first described in the ancient Chinese medical book The Divine Farmer's Herb-Root Classic. Coptis chinensis was used to treat intestinal bacterial infections and antipyretic analgesic for thousands of years agoCoptis chinensis also called zhilian, chuanlian, weilian, jizhualian, shanglian, and xuanlian in Chinese history. Coptis chinensis was accepted by most physicians, and the Chinese pharmacopoeia also uses Coptis chinensis as its official name. Coptis chinensis mainly grows in Anhui, Hunan, Sichuan, and Yunnan and has been cultivated in Sichuan since the Ming dynasty, which has a long history of cultivation. Other species of Coptis chinensis from different places were used as medicine. However, commodity circulation of wild Rhizoma coptidis has not been formed . Coptis chinensis is national three level protection plants at present and majorly produced in Shizhu of Chongqing, West Hubei, Shanxi, and Gansu.Berberine is a quaternary ammonium salt from the protoberberine group of isoquinoline alkaloids. It is found in some plants such as huanglian (Rhizoma coptidis), huangbo (Phellodendri Chinensis) Cortex), sankezhenthree needles (Berberidis Radix), and so on.The components of Coptis chinensis which have antibacterial and antiinflammatory effects are original alkaloid berberine class, including berberine, coptisine, palmatine, epiberberine, columbamine, jatrorrhizine, worenine, and magnoflorine, with berberine having the highest content (5–8%).
HistoryBerberine is often used in the form of quaternary ammonium alkali. The solubility of berberine in water is lower, for example, berberine hydrochloride is 1:500, and berberine sulfate is 1:30. In 1926, berberine was first separated from bark of Zanthoxylum clava. Modern pharmacology study showed that berberine has defined structure and is a monomer of traditional Chinese medicine. Berberine can be obtained from many sources and is used in clinics, with reliable pharmacological effects and various and unique mechanisms. At present, berberine can be synthesized by industrial biosynthesis. A series of derivatives can also be synthesized by structure modification, and the pharmacological activities of these derivatives have been tested.
UsesAntiseptic drug.Treat intestinal infection caused from dysentery bacillus and E.coil
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: Berberine is an organic heteropentacyclic compound, an alkaloid antibiotic, a botanical anti-fungal agent and a berberine alkaloid. It has a role as an antilipemic drug, a hypoglycemic agent, an antioxidant, a potassium channel blocker, an antineoplastic agent, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor, an EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor, an EC 1.21.3.3 (reticuline oxidase) inhibitor, an EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor, an EC 3.1.1.4 (phospholipase A2) inhibitor, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, an EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor, an EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 3.1.1.8 (cholinesterase) inhibitor, an EC 2.7.11.10 (IkappaB kinase) inhibitor, an EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor, a geroprotector and a metabolite.
Related reactions
Linked notes
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