EPIBERBERINE ION

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H18NO4
Molecular Weight	336.3612
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C=C2C(CC[N+]3=CC4=C(C=CC5=C4OCO5)C=C23)=C1

InChI

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

HIDE SMILES / InChI

Molecular Formula	C20H18NO4
Molecular Weight	336.3612
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Potency
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/30155694	Antagonist 2778	2.3 µM [IC50]
Angiotensin-converting enzyme 97 Target ID: CHEMBL2096989 Sources: https://www.ncbi.nlm.nih.gov/pubmed/30391811	Inhibitor 8297
Cytochrome P450 2D6 61 Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29343943	Inhibitor 8297	25.44 µM [Ki]
Cytochrome P450 2C9 50 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29343943	Inhibitor 8297	5.64 µM [Ki]

PubMed

Title	Date	PubMed
[Determination of six alkaloids in six types of Coptidis Rhizoma pieces by RP-HPLC and spectrum-effect relationships with anti-diabetes pharmacodynamics data].	2016 Dec	28936841
Transcriptome analyses provide insights into the difference of alkaloids biosynthesis in the Chinese goldthread (Coptis chinensis Franch.) from different biotopes.	2017	28533961
Development and Validation of an UPLC-MS/MS Method for Pharmacokinetic Comparison of Five Alkaloids from JinQi Jiangtang Tablets and Its Monarch Drug Coptidis Rhizoma.	2017 Dec 29	29286316
Inhibition activity of a traditional Chinese herbal formula Huang-Lian-Jie-Du-Tang and its major components found in its plasma profile on neuraminidase-1.	2017 Nov 14	29138445
The oral bioavailability, excretion and cytochrome P450 inhibition properties of epiberberine: an in vivo and in vitro evaluation.	2018	29343943
Discovery of novel antagonists on β(2)-adrenoceptor from natural products using a label-free cell phenotypic assay.	2018 Dec	30155694
Rapid and simultaneous analysis of five alkaloids in four parts of Coptidis Rhizoma by near-infrared spectroscopy.	2018 Jan 5	28780486
Comparative pharmacokinetics study of five alkaloids in rat plasma and related compound-herb interactions mechanism after oral administration of Shuanghua Baihe tablets.	2018 Sep	28871816
Ligand Selectivity in the Recognition of Protoberberine Alkaloids by Hybrid-2 Human Telomeric G-Quadruplex: Binding Free Energy Calculation, Fluorescence Binding, and NMR Experiments.	2019 Apr 21	31010072
Molecular Recognition of the Hybrid-Type G-Quadruplexes in Human Telomeres.	2019 Apr 22	31013622
A method using angiotensin converting enzyme immobilized on magnetic beads for inhibitor screening.	2019 Feb 5	30391811
Large-scale separation of acetylcholinesterase inhibitors from Zanthoxylum nitidum by pH-zone-refining counter-current chromatography target-guided by ultrafiltration high-performance liquid chromatography with ultraviolet and mass spectrometry screening.	2019 Mar	30638299
A review on analytical methods for natural berberine alkaloids.	2019 May	30793835
Rhizoma Coptidis for Alzheimer's Disease and Vascular Dementia: A Literature Review.	2020	31291876

Substance Class	Chemical Created by `admin` on `Sat Dec 16 19:01:09 UTC 2023` Edited by `admin` on `Sat Dec 16 19:01:09 UTC 2023`
Record UNII	VWP9N35AYS
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

EPIBERBERINE ION

Common Name

English

Epiberberine [WHO-DD]

Common Name

English

11,12-DIHYDRO-8,9-DIMETHOXYBENZO(A)-1,3-BENZODIOXOLO(4,5-G)QUINOLIZINIUM

Systematic Name

English

EPIBERBERINE CATION

Common Name

English

BENZO(A)-1,3-BENZODIOXOLO(4,5-G)QUINOLIZINIUM, 11,12-DIHYDRO-8,9-DIMETHOXY-

Systematic Name

English

DEHYDROSINACTINE

Common Name

English

EPIBERBERINE

Common Name

English

Code System Code Type Description

PUBCHEM

160876

Created by admin on Sat Dec 16 19:01:09 UTC 2023 , Edited by admin on Sat Dec 16 19:01:09 UTC 2023

PRIMARY

EPA CompTox

DTXSID90218854

Created by admin on Sat Dec 16 19:01:09 UTC 2023 , Edited by admin on Sat Dec 16 19:01:09 UTC 2023

PRIMARY

CAS

6873-09-2

Created by admin on Sat Dec 16 19:01:09 UTC 2023 , Edited by admin on Sat Dec 16 19:01:09 UTC 2023

PRIMARY

FDA UNII

VWP9N35AYS

Created by admin on Sat Dec 16 19:01:09 UTC 2023 , Edited by admin on Sat Dec 16 19:01:09 UTC 2023

PRIMARY

Related Record Type Details


					VWP9N35AYS

EPIBERBERINE ION

IONIC MOIETY

Amount:


					ND559X5J59

EPIBERBERINE CHLORIDE

SALT/SOLVATE -> PARENT

Amount:

Related Record Type Details


					VWP9N35AYS

EPIBERBERINE ION

ACTIVE MOIETY

Amount: