Record Information
Version1.0
Creation date2011-09-21 00:25:37 UTC
Update date2021-05-25 17:27:34 UTC
Primary IDFDB023165
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBerberine
DescriptionBerberine is a quaternary ammonium salt that belongs to the protoberberine group of benzylisoquinoline alkaloids. Chemically, berberine is classified as an isoquinoline alkaloid. More specifically, berberine is a plant alkaloid derived from tyrosine through a complex 8 step biosynthetic process. Berberine is found in plants such as Berberis vulgaris (barberry), Berberis aristata (tree turmeric), Mahonia aquifolium (Oregon grape) and Hydrastis canadensis (goldenseal). Two other known berberine-containing plants are Phellodendron chinense and Phellodendron amurense. Berberine is usually found in the roots, rhizomes, stems, and bark of Berberis plants. Due to berberine's intense yellow color, plants that contain berberine were traditionally used to dye wool, leather, and wood. Under ultraviolet light, berberine shows a strong yellow fluorescence, making it useful in histology for staining heparin in mast cells. Berberine is a bioactive plant compound that has been frequently used in traditional medicine. Among the known physiological effects or bioactivities are: 1) Antimicrobial action against bacteria, fungi, protozoa, viruses, helminthes, and Chlamydia; 2) Antagonism against the effects of cholera and E coli heat-stable enterotoxin; 3) Inhibition of intestinal ion secretion and of smooth muscle contraction; 4) Reduction of inflammation and 5) Stimulation of bile secretion and bilirubin discharge (PMID: 32335802). Berberine can inhibit bacterial growth in the gut, including Helicobacter pylori, protect the intestinal epithelial barrier from injury, and ameliorate liver injury. Currently, berberine is sold as an Over-the-Counter (OTC) drug for treating gastrointestinal infections in China (PMID: 18442638). Berberine also inhibits the proliferation of various types of cancer cells and impedes invasion and metastasis (PMID: 32335802). Recent evidence has also confirmed that berberine improves the efficacy and safety of both chemo and radiotherapies for cancer treatment (PMID: 32335802). Berberine has also been shown to regulate glucose and lipid metabolism in vitro and in vivo (PMID: 18442638). In fact, berberine is the main active component of an ancient Chinese herb Coptis chinensis French, which has been used to treat diabetes for thousands of years. As an anti-diabetic, berberine increases glucose uptake by muscle fibers independent of insulin levels. It triggers AMPK activation and increases glycolysis, leading to decreased insulin resistance and decreased oxygen respiration. The same mechanism leads to a reduction in gluconeogenesis in the liver. AMPK activation by berberine also leads to an antiatherosclerotic effect in mice. Berberine's AMPK activation may also underlie berberine’s anti-obesity effects and favorable influence on weight loss (PMID: 18442638). While its use as a medication is widely touted, it is important to remember that berberine inhibits CYP2D6 and CYP3A4 enzymes, both of which are involved in the metabolism of many endogenous substances and xenobiotics, including a number of prescription drugs. Berberine is a bitter tasting compound.
CAS Number2086-83-1
Structure
Thumb
Synonyms
SynonymSource
7,8,13,13a-Tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbiniumChEBI
9,10-Dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbiniumChEBI
BerberinChEBI
Coptis rhizomeHMDB
Umbellatinehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00035 g/LALOGPS
logP-0.18ALOGPS
logP-1.3ChemAxon
logS-6ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.8 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.52 m³·mol⁻¹ChemAxon
Polarizability36.92 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H18NO4
IUPAC name16,17-dimethoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium
InChI IdentifierInChI=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
InChI KeyYBHILYKTIRIUTE-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C2C=C3C4=CC5=C(OCO5)C=C4CC[N+]3=CC2=C1OC
Average Molecular Weight336.3612
Monoisotopic Molecular Weight336.123583069
Classification
Description Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassProtoberberine alkaloids and derivatives
Sub ClassNot Available
Direct ParentProtoberberine alkaloids and derivatives
Alternative Parents
Substituents
  • Protoberberine skeleton
  • Isoquinoline
  • Benzodioxole
  • Anisole
  • Alkyl aryl ether
  • Pyridine
  • Pyridinium
  • Benzenoid
  • Heteroaromatic compound
  • Acetal
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSBerberine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4l-0059000000-2d03f2d248021273bb66Spectrum
Predicted GC-MSBerberine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0009000000-19928d40d547cbbc26dcSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-0029000000-42f72c3da8025ad70c4dSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0103-0089000000-dbcf680bd232ed620a00Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000i-0009000000-2993f75f22b9532dc39fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-0009000000-1d4cdb20920f8c900320Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0079-0019000000-4995338b7526764bbad3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00dl-0059000000-ab35b8a7ec73f1063bb2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00fu-0089000000-09273e18fcd3186156f0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0039000000-3a3f7eba3883c388e58cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0006-0092000000-6f10979e1ecdd29611b1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0006-0090000000-bacf940c54361560b64bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (Shimadzu LC20A-IT-TOFMS) , Positivesplash10-000i-0009000000-3d6d1928f5797f4633e4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-000i-0009000000-6337ae6880e36d106adfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-0039000000-5d1ff6b7636484db90d1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-0059000000-131055c16d28a84b6130Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0009000000-9d8986d4bd9f3b6d634dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0009000000-4459c8c8f7b607ad7b49Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dr-0019000000-a0c1c55261d223b09256Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dl-0069000000-437bdc5509b367efef25Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-41bc0e7901cbc892051cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009000000-b2e1ddadd60e4f52d2ddSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0iki-0179000000-85594d2e5f4b265077abSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-604df9f348201c3c531eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-34b3c7d90696ff194395Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0nnc-3095000000-2e76003cd5b376964ba8Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID2263
ChEMBL IDCHEMBL295124
KEGG Compound IDC00757
Pubchem Compound ID2353
Pubchem Substance IDNot Available
ChEBI ID16118
Phenol-Explorer IDNot Available
DrugBank IDDB04115
HMDB IDHMDB03409
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDBER
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDBerberine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference