Berberine
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Identification
- Generic Name
- Berberine
- DrugBank Accession Number
- DB04115
- Background
An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 336.3612
Monoisotopic: 336.123583069 - Chemical Formula
- C20H18NO4
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ATelomerase reverse transcriptase inhibitorHumans UBaculoviral IAP repeat-containing protein 5 Not Available Humans UHTH-type transcriptional regulator QacR Not Available Staphylococcus haemolyticus - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Berberine chloride UOT4O1BYV8 633-65-8 VKJGBAJNNALVAV-UHFFFAOYSA-M Berberine sulfate anhydrous FST3E667FF 316-41-6 OJVABJMSSDUECT-UHFFFAOYSA-L
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Protoberberine alkaloids and derivatives
- Sub Class
- Not Available
- Direct Parent
- Protoberberine alkaloids and derivatives
- Alternative Parents
- Isoquinolines and derivatives / Benzodioxoles / Anisoles / Alkyl aryl ethers / Pyridinium derivatives / Heteroaromatic compounds / Oxacyclic compounds / Azacyclic compounds / Acetals / Organopnictogen compounds show 3 more
- Substituents
- Acetal / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzodioxole / Ether / Heteroaromatic compound / Hydrocarbon derivative show 12 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organic heteropentacyclic compound, berberine alkaloid, alkaloid antibiotic, botanical anti-fungal agent (CHEBI:16118) / Alkaloids, Isoquinoline alkaloids (C00757) / a small molecule (BERBERINE)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 0I8Y3P32UF
- CAS number
- 2086-83-1
- InChI Key
- YBHILYKTIRIUTE-UHFFFAOYSA-N
- 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
- IUPAC Name
- 16,17-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
- SMILES
- COC1=CC=C2C=C3C4=CC5=C(OCO5)C=C4CC[N+]3=CC2=C1OC
References
- Synthesis Reference
Christopher W. Grote, Frank W. Moser, John E. Johnson, JR., "Berberine compounds and processes for the preparation of berberine compounds." U.S. Patent US20100081821, issued April 01, 2010.
US20100081821- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0003409
- KEGG Drug
- D00092
- KEGG Compound
- C00757
- PubChem Compound
- 2353
- PubChem Substance
- 46506051
- ChemSpider
- 2263
- BindingDB
- 50203126
- 1437
- ChEBI
- 16118
- ChEMBL
- CHEMBL295124
- ZINC
- ZINC000003779067
- Therapeutic Targets Database
- DNC000385
- PharmGKB
- PA165860812
- PDBe Ligand
- BER
- Wikipedia
- Berberine
- PDB Entries
- 1jum / 2qvd / 3bti / 3d6y / 3np6 / 3r6r / 3vw2 / 4dbk / 5y0v / 6jwd … show 8 more
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Syndrome, Metabolic 1 somestatus stop reason just information to hide Not Available Completed Treatment Berberine Hydrochloride 1 somestatus stop reason just information to hide Not Available Completed Treatment Females / Schizophrenia / Syndrome, Metabolic 1 somestatus stop reason just information to hide Not Available Completed Treatment Schizophrenia 1 somestatus stop reason just information to hide Not Available Completed Treatment Schizophrenia / Therapeutics 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Granule 25 kg/25kg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 145 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.000354 mg/mL ALOGPS logP -0.18 ALOGPS logP -1.3 Chemaxon logS -6 ALOGPS pKa (Strongest Basic) -4.4 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 40.8 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 93.52 m3·mol-1 Chemaxon Polarizability 36.92 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.5 Blood Brain Barrier + 0.9279 Caco-2 permeable + 0.8726 P-glycoprotein substrate Non-substrate 0.6002 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Non-inhibitor 0.8435 Renal organic cation transporter Inhibitor 0.6035 CYP450 2C9 substrate Non-substrate 0.876 CYP450 2D6 substrate Non-substrate 0.5937 CYP450 3A4 substrate Substrate 0.6738 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Inhibitor 0.8933 CYP450 2C19 inhibitor Non-inhibitor 0.7463 CYP450 3A4 inhibitor Non-inhibitor 0.5873 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9003 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9539 Biodegradation Not ready biodegradable 0.8408 Rat acute toxicity 2.7834 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8367 hERG inhibition (predictor II) Non-inhibitor 0.8734
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 194.2343576 predictedDarkChem Lite v0.1.0 [M-H]- 174.7241576 predictedDarkChem Lite v0.1.0 [M-H]- 182.91756 predictedDeepCCS 1.0 (2019) [M+H]+ 195.2280576 predictedDarkChem Lite v0.1.0 [M+H]+ 175.6461576 predictedDarkChem Lite v0.1.0 [M+H]+ 185.89343 predictedDeepCCS 1.0 (2019) [M+Na]+ 195.5482576 predictedDarkChem Lite v0.1.0 [M+Na]+ 174.5871576 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.56412 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsTelomerase reverse transcriptase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Telomerase is a ribonucleoprotein enzyme essential for the replication of chromosome termini in most eukaryotes. Active in progenitor and cancer cells. Inactive, or very low activity, in normal somatic cells. Catalytic component of the teleromerase holoenzyme complex whose main activity is the elongation of telomeres by acting as a reverse transcriptase that adds simple sequence repeats to chromosome ends by copying a template sequence within the RNA component of the enzyme. Catalyzes the RNA-dependent extension of 3'-chromosomal termini with the 6-nucleotide telomeric repeat unit, 5'-TTAGGG-3'. The catalytic cycle involves primer binding, primer extension and release of product once the template boundary has been reached or nascent product translocation followed by further extension. More active on substrates containing 2 or 3 telomeric repeats. Telomerase activity is regulated by a number of factors including telomerase complex-associated proteins, chaperones and polypeptide modifiers. Modulates Wnt signaling. Plays important roles in aging and antiapoptosis
- Specific Function
- DNA binding
- Gene Name
- TERT
- Uniprot ID
- O14746
- Uniprot Name
- Telomerase reverse transcriptase
- Molecular Weight
- 126995.435 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Multitasking protein that has dual roles in promoting cell proliferation and preventing apoptosis (PubMed:20627126, PubMed:21364656, PubMed:25778398, PubMed:28218735, PubMed:9859993). Component of a chromosome passage protein complex (CPC) which is essential for chromosome alignment and segregation during mitosis and cytokinesis (PubMed:16322459). Acts as an important regulator of the localization of this complex; directs CPC movement to different locations from the inner centromere during prometaphase to midbody during cytokinesis and participates in the organization of the center spindle by associating with polymerized microtubules (PubMed:20826784). Involved in the recruitment of CPC to centromeres during early mitosis via association with histone H3 phosphorylated at 'Thr-3' (H3pT3) during mitosis (PubMed:20929775). The complex with RAN plays a role in mitotic spindle formation by serving as a physical scaffold to help deliver the RAN effector molecule TPX2 to microtubules (PubMed:18591255). May counteract a default induction of apoptosis in G2/M phase (PubMed:9859993). The acetylated form represses STAT3 transactivation of target gene promoters (PubMed:20826784). May play a role in neoplasia (PubMed:10626797). Inhibitor of CASP3 and CASP7 (PubMed:21536684). Essential for the maintenance of mitochondrial integrity and function (PubMed:25778398). Isoform 2 and isoform 3 do not appear to play vital roles in mitosis (PubMed:12773388, PubMed:16291752). Isoform 3 shows a marked reduction in its anti-apoptotic effects when compared with the displayed wild-type isoform (PubMed:10626797)
- Specific Function
- cobalt ion binding
- Gene Name
- BIRC5
- Uniprot ID
- O15392
- Uniprot Name
- Baculoviral IAP repeat-containing protein 5
- Molecular Weight
- 16388.555 Da
References
- Wang Z, Guo X, Liu Z, Cui M, Song F, Liu S: Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry. J Mass Spectrom. 2008 Mar;43(3):327-35. [Article]
3. DetailsHTH-type transcriptional regulator QacR
- Kind
- Protein
- Organism
- Staphylococcus haemolyticus
- Pharmacological action
- Unknown
- General Function
- Transcriptional repressor of qacA. Binds to IR1, an unusually long 28 bp operator, which is located downstream from the qacA promoter and overlaps its transcription start site. QacR is induced from its IR1 site by binding to one of many structurally dissimilar cationic lipophilic compounds, which are also substrates of QacA (By similarity).
- Specific Function
- DNA binding
- Gene Name
- qacR
- Uniprot ID
- P0A0N5
- Uniprot Name
- HTH-type transcriptional regulator QacR
- Molecular Weight
- 22174.175 Da
References
- Crystal Binding Structure [Link]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:24