Dihydroberberine - ≥98% , CAS No.483-15-8

CAS: 483-15-8 Cat. No.: D651092 Molecular Weight: 337.37 EC Number: 683-111-2 PubChem CID: 10217

GRADE & PURITY ≥98%

Synonyms

BERBINE, 13,13a-DIDEHYDRO-9,10-DIMETHOXY-2,3-(METHYLENEDIOXY)- | Dihydroberberine | Dihydroberberine/dihydroumbellatine | lambertin | 3bti | 9,10-Dimethoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline | Dihydroberbine | FT-0701465 | CHEBI

Storage

Store at 2-8°C,Protected from light,Desiccated

Shipped In

Wet ice

Overview

Dihydroberberine inhibits human ether-a-go-go-related gene (hERG) channels and remarkably reduces heat shock protein 90 (Hsp90) expression and its interaction with hERG. Dihydroberberine has anti-inflammatory, anti-atherosclerotic, hypolipidemic and antitumor activities

Form:Solid

IC50& Target:HSP90

Specifications

Synonyms

BERBINE, 13, 13a-DIDEHYDRO-9, 10-DIMETHOXY-2, 3-(METHYLENEDIOXY)- | Dihydroberberine | Dihydroberberine/dihydroumbellatine | lambertin | 3bti | 9, 10-Dimethoxy-5, 8-dihydro-6H-[1, 3]dioxolo[4, 5-g]isoquino[3, 2-a]isoquinoline | Dihydroberbine | FT-0701465 | CHEBI

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Dihydroberberine inhibits human ether-a-go-go-related gene (hERG) channels and remarkably reduces heat shock protein 90 (Hsp90) expression and its interaction with hERG. Dihydroberberine has anti-inflammatory, anti-atherosclerotic, hypolipidemic and antit

Storage

Store at 2-8°C, Protected from light, Desiccated

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Canonical Smiles: COC1=C(C2=C(C=C1)C=C3C4=CC5=C(C=C4CCN3C2)OCO5)OC
• IUPAC Name: 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaene
• InChIKey: FZAGOOYMTPGPGF-UHFFFAOYSA-N
• INCHI: 1S/C20H19NO4/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/h3-4,7-9H,5-6,10-11H2,1-2H3
• Isomeric SMILES: COC1=C(C2=C(C=C1)C=C3C4=CC5=C(C=C4CCN3C2)OCO5)OC
• Alternate CAS: 120834-89-1,483-15-8
• PubChem CID: 10217
• NSC Number: 331264
• MeSH Entry Terms: dihydroberberine;dihydroberberine hydrochloride
• Molecular Weight: 337.37

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Protoberberine alkaloids and derivatives

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Protoberberine alkaloids and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Protoberberine alkaloids and derivatives
• Alternative Parents: Tetrahydroisoquinolines Benzodioxoles Anisoles Aralkylamines Alkyl aryl ethers Trialkylamines Oxacyclic compounds Enamines Azacyclic compounds Acetals Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Protoberberine skeleton - Tetrahydroisoquinoline - Benzodioxole - Anisole - Alkyl aryl ether - Aralkylamine - Benzenoid - Tertiary aliphatic amine - Tertiary amine - Acetal - Organoheterocyclic compound - Oxacycle - Azacycle - Enamine - Ether - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Organic nitrogen compound - Amine - Organopnictogen compound - Aromatic heteropolycyclic compound
• 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.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CEL Tchem Cholesterol esterase (33 Activities)

Discover Target: CEL

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Associated Targets(non-human)

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

Discover Target: pol

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Plasmodium falciparum (966862 Activities)

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Toxoplasma gondii (4585 Activities)

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Human betaherpesvirus 5 (5122 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 20 mg/mL (59.28 mM; ultrasonic and warming and heat to 70°C)
• Molecular Weight: 337.400 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 337.131 Da
• Monoisotopic Mass: 337.131 Da
• Topological Polar Surface Area: 40.200 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 538.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1