bis(16,17-dimethoxy-5,7-dioxa-13λ5-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2(10),3,8,13,15,17,19-octaen-13-ylium) sulfate

• ChemBase ID: 106008
• Molecular Formular: C40H36N2O12S
• Molecular Mass: 768.78504
• Monoisotopic Mass: 768.1988956
• SMILES: COc1c(OC)c2c(cc1)cc1c3c(CC[n+]1c2)cc1OCOc1c3.COc1c(OC)c2c(cc1)cc1c3c(CC[n+]1c2)cc1OCOc1c3.[O-]S(=O)(=O)[O-]
• Canonical SMILES: [O-]S(=O)(=O)[O-].COc1c(OC)ccc2c1c[n+]1CCc3c(c1c2)cc1c(c3)OCO1.COc1c(OC)ccc2c1c[n+]1CCc3c(c1c2)cc1c(c3)OCO1
• InChI: InChI=1S/2C20H18NO4.H2O4S/c2*1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2;1-5(2,3)4/h2*3-4,7-10H,5-6,11H2,1-2H3;(H2,1,2,3,4)/q2*+1;/p-2
• InChIKey: OJVABJMSSDUECT-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(16,17-dimethoxy-5,7-dioxa-13λ^5-azapentacyclo[11.8.0.0^2,^1^0.0^4,^8.0^1^5,^2^0]henicosa-1(21),2(10),3,8,13,15,17,19-octaen-13-ylium) sulfate; bis(16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2(10),3,8,13,15,17,19-octaen-13-ylium) sulfate; bis(16,17-dimethoxy-5,7-dioxa-13$l^{5}-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) sulfate
• IUPAC Traditional name: bis(16,17-dimethoxy-5,7-dioxa-13λ^5-azapentacyclo[11.8.0.0^2,^1^0.0^4,^8.0^1^5,^2^0]henicosa-1(21),2(10),3,8,13,15,17,19-octaen-13-ylium) sulfate; bis(16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2(10),3,8,13,15,17,19-octaen-13-ylium) sulfate; bis(berberine) sulfate
• Synonyms: Berberine hemisulfate salt; Natural Yellow 18; C.I. 75160; BERBERINE HEMISULFATE SALT; BERBERINE SULFATE; 黄连素

Database IDs

• CAS Number: 69352-97-2; 633-66-9
• EC Number: 211-196-4
• MDL Number: MFCD00031743
• PubChem SID: 24891718; 162093879
• PubChem CID: 9424
• Color Index Number: 75160

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -1.2833123
• LogD (pH = 7.4): -1.2833123
• Log P: -1.2833123
• Molar Refractivity: 93.5233 cm^3
• Polarizability: 38.453724 Å^3
• Polar Surface Area: 40.8 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: DR9867000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95%; ≥95%

DETAILS

MP Biomedicals - 05204456

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02195858

Hemisulfate Salt
Purity: >95%
Apoptosis inhibitor in leukemia HL-60 cells and inhibitor of platelet aggregation induced by ADP, arachidonic acid and collagen in rates. A reversible competitive inhibitor of acetylcholinesterase (ACE).

Sigma Aldrich - B3412

Application
Fluorescent stain for heparin in mast cells
Biochem/physiol Actions
An alkaloid with weak antibiotic properties. Substrate for MDR efflux pumps. Antimicrobial activities of berberine is potentiated by the MDR inhibitor 5′-methoxyhydnocarpin (5′-MHC). Berberine upregulates the expression of Pgp in hepatoma cells. Treatment with berberine potentially results in the reduced accumulation of chemotherapeutic drugs.