Epiberberine - 10mM in DMSO , CAS No.6873-09-2

CAS: 6873-09-2 Cat. No.: E425480 Molecular Weight: 336.36

GRADE & PURITY 10mM in DMSO

Synonyms

EWV | SMR000232286 | 16,17-dimethoxy-5,7-dioxa-1-azoniapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),2,4(8),9,11,14,16,18-octaene | s9152 | EPIBERBERINE ION | BENZO(A)-1,3-BENZODIOXOLO(4,5-G)QUINOLIZINIUM, 11,12-DIHYDRO-8,9-DIMETHOXY- | EPIBERBERINE

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells.

Specifications

Synonyms

EWV | SMR000232286 | 16, 17-dimethoxy-5, 7-dioxa-1-azoniapentacyclo[11.8.0.03, 11.04, 8.014, 19]henicosa-1(13), 2, 4(8), 9, 11, 14, 16, 18-octaene | s9152 | EPIBERBERINE ION | BENZO(A)-1, 3-BENZODIOXOLO(4, 5-G)QUINOLIZINIUM, 11, 12-DIHYDRO-8, 9-DIMETHOXY- | EPIBERBERINE

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Epiberberine is a protoberberine alkaloid extracted from Coptis chinensis with natural biological activity. Coptis and its alkaloids have a variety of activities, including antioxidant activity and neuroprotection

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Action Type

INHIBITOR

Product Properties

• ALogP: 3.962
• hba_count: 4
• Rotatable Bond: 2

Names and Identifiers

• Canonical Smiles: COC1=C(C=C2C(=C1)CC[N+]3=C2C=C4C=CC5=C(C4=C3)OCO5)OC
• IUPAC Name: 16,17-dimethoxy-5,7-dioxa-1-azoniapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),2,4(8),9,11,14,16,18-octaene
• InChIKey: FPJQGFLUORYYPE-UHFFFAOYSA-N
• INCHI: 1S/C20H18NO4/c1-22-18-8-13-5-6-21-10-15-12(3-4-17-20(15)25-11-24-17)7-16(21)14(13)9-19(18)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1
• Isomeric SMILES: COC1=C(C=C2C(=C1)CC[N+]3=C2C=C4C=CC5=C(C4=C3)OCO5)OC
• Molecular Weight: 336.36
• Reaxy-Rn: 4159683
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4159683&ln=

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: Isoquinolines and derivatives Benzodioxoles Anisoles Alkyl aryl ethers Pyridinium derivatives Heteroaromatic compounds Oxacyclic compounds Azacyclic compounds Acetals Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives Organic cations
• Molecular Framework: Aromatic heteropolycyclic compounds
• 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
• 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)

KDM1A Tchem Lysine-specific histone demethylase 1A (1 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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MAOB Tclin Monoamine oxidase B (8835 Activities)

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POLB Tchem DNA polymerase beta (23632 Activities)

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PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)

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HaCaT (4069 Activities)

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FEN1 Tchem Flap endonuclease 1 (12055 Activities)

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GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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POLH Tchem DNA polymerase eta (21678 Activities)

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KDM1A Tchem Lysine-specific histone demethylase 1 (3916 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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TSG101 Tbio Tumor susceptibility gene 101 protein (2874 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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SMN1 Tchem Survival motor neuron protein (34246 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

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GMNN Tbio Geminin (128009 Activities)

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MBNL1 Tbio Muscleblind-like protein 1 (34431 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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APOBEC3F Tbio DNA dC->dU-editing enzyme APOBEC-3F (14861 Activities)

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RAPGEF3 Tchem Rap guanine nucleotide exchange factor 3 (15528 Activities)

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RAPGEF4 Tchem Rap guanine nucleotide exchange factor 4 (11476 Activities)

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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SAE1 Tbio SUMO-activating enzyme (861 Activities)

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Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

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Salmon testes DNA (254 Activities)

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C2C12 (756 Activities)

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Npsr1 Neuropeptide S receptor (260 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

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ORF 73 (309 Activities)

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clpP ATP-dependent Clp protease proteolytic subunit (245 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• DMSO(mg / mL) Max Solubility: 12
• DMSO(mM) Max Solubility: 35.6759319638572
• Molecular Weight: 336.400 g/mol
• XLogP3: 3.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 336.124 Da
• Monoisotopic Mass: 336.124 Da
• Topological Polar Surface Area: 40.800 Ų
• Heavy Atom Count: 25
• Formal Charge: 1
• Complexity: 488.000
• 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

References

1. Weijuan Du, Lisha Jin, Liping Li, Wei Wang, Su Zeng, Huidi Jiang, Hui Zhou.  (2018)  Development and Validation of a HPLC-ESI-MS/MS Method for Simultaneous Quantification of Fourteen Alkaloids in Mouse Plasma after Oral Administration of the Extract of Corydalis yanhusuo Tuber: Application to Pharmacokinetic Study.  MOLECULES,  23  (4): (714).  [PMID:29561801] [10.3390/molecules23040714]

2. Bingyu Chen, Ke Liu, Yaya Guo, Jingwei Zhao, Yanhua Wang.  (2026)  Epi-Berberine Alleviates Ulcerative Colitis, Protects the Intestinal Mucosal Barrier, and Inhibits Colonic Inflammation via Glutaminyl-Peptide Cyclotransferase in a Mouse Model of DSS-Induced Colitis.  PHYTOTHERAPY RESEARCH,      [PMID:] [10.1002/ptr.70300]