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Berberine (sulfate) (Standard)

CAT: 0804-HY-N0716BR-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0716BR-01Size:5 mg
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Description
Berberine (sulfate) (Standard) is the analytical standard of Berberine (sulfate) . This product is intended for research and analytical applications. Berberine sulfate is an alkaloid isolated from the Chinese herbal medicine Huanglian, as an antibiotic. Berberine sulfate induces reactive oxygen species (ROS) generation and inhibits DNA topoisomerase. Berberine sulfate has antineoplastic properties. The sulfate form improves bioavailability[1][2].
CAS Number
633-66-9
Product Name Alternative
Natural Yellow 18 (sulfate) (Standard)
UNSPSC
12352005
Target
Akt; Antibiotic; AP-1; Apoptosis; Autophagy; Bacterial; Caspase; JNK; NF-κB; Parasite; PI3K; Reactive Oxygen Species (ROS) ; Reference Standards; Topoisomerase
Related Pathways
Anti-infection; Apoptosis; Autophagy; Cell Cycle/DNA Damage; Immunology/Inflammation; MAPK/ERK Pathway; Metabolic Enzyme/Protease; NF-κB; Others; PI3K/Akt/mTOR
Field of Research
Cancer; Infection; Metabolic Disease; Inflammation/Immunology; Neurological Disease; Cardiovascular Disease
Smiles
COC1=C(OC)C2=C[N+]3=C(C(C(CC3)=C4)=CC5=C4OCO5)C=C2C=C1.O=S(O)([O-])=O
Molecular Formula
C20H19NO8S
Molecular Weight
433.43
References & Citations
[1]Cai Y, et al. Berberine inhibits the growth of human colorectal adenocarcinoma in vitro and in vivo. J Nat Med. 2014 Jan;68 (1) :53-62.|[2]Cui HX, et al. Preparation and Evaluation of Antidiabetic Agents of Berberine Organic Acid Salts for Enhancing the Bioavailability. Molecules. 2018 Dec 28;24 (1) :103.|[3]Boberek JM, et al., Genetic evidence for inhibition of bacterial division protein FtsZ by berberine. PLoS One. 2010 Oct 29;5 (10) :e13745. |[4]Remppis A, et al., Rhizoma Coptidis inhibits LPS-induced MCP-1/CCL2 production in murine macrophages via an AP-1 and NFkappaB-dependent pathway. Mediators Inflamm. 2010;2010:194896.|[5]Bae J, et al., Berberine protects 6-hydroxydopamine-induced human dopaminergic neuronal cell death through the induction of heme oxygenase-1. Mol Cells. 2013 Feb;35 (2) :151-7. |[6]Ye Y, et al., Efficacy and Safety of Berberine Alone for Several Metabolic Disorders: A Systematic Review and Meta-Analysis of Randomized Clinical Trials. Front Pharmacol. 2021 Apr 26;12:653887.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Berberine bisulfate
CAS Number633-66-9
PubChem CID12457
IUPAC Name16,17-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;hydrogen sulfate
Molecular FormulaC20H19NO8S
Molecular Weight433.4
Topological Polar Surface Area127
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count2
Heavy Atom Count30
Formal Charge0
Complexity564
SMILES
COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC.OS(=O)(=O)[O-]
InChI
InChI=1S/C20H18NO4.H2O4S/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;1-5(2,3)4/h3-4,7-10H,5-6,11H2,1-2H3;(H2,1,2,3,4)/q+1;/p-1
InChIKey
JISRTQBQFQMSLG-UHFFFAOYSA-M
Chemical Structure
2D Structure
2D structure of Berberine bisulfate
CAS: 633-66-9
CID: 12457
Formula: C20H19NO8S
MW: 433.4
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight433.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count2
Exact Mass433.08313774
Monoisotopic Mass433.08313774
Topological Polar Surface Area127 Ų
Heavy Atom Count30
Formal Charge0
Complexity564
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes