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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 of BERBERINE

SMILES

COC1=C(OC)C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(OCO5)C=C4CC3

InChI

InChIKey=YBHILYKTIRIUTE-UHFFFAOYSA-N
InChI=1S/C20H18NO4/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/h3-4,7-10H,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

Description
Curator's Comment: description was created based on several sources, including: https://examine.com/supplements/berberine/ | https://www.ncbi.nlm.nih.gov/pubmed/19686830 | https://www.ncbi.nlm.nih.gov/pubmed/25610485

Berberine, an alkaloid isolated from Rhizoma Coptidis, is known to have a wide array of therapeutic effects including antimicrobial, antineoplastic, and hepatoprotective effects. It is found in several plants including European barberry, goldenseal, goldthread, Oregon grape, phellodendron, and tree tumeric. Berberine seems to slightly reduce blood sugar levels in people with diabetes. Berberine might lower blood pressure. Berberine is possibly safe for most adults for short-term use when taken by mouth or applied to the skin.

CNS Activity

Originator

Approval Year

2023
455
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Activator
1430
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase IV
63
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products.
1992 May 29
The effect of Kampo formulae on bone resorption in vitro and in vivo. I. Active constituents of Tsu-kan-gan.
1998 Dec
Analysis of coptisine, berberine and palmatine in adulterated Chinese medicine by capillary electrophoresis-electrospray ion trap mass spectrometry.
2000 Jan 14
Antimicrobial activity of berberine--a constituent of Mahonia aquifolium.
2002
Potential antimutagenic activity of berberine, a constituent of Mahonia aquifolium.
2002 Feb 19
Identification of three sulfate-conjugated metabolites of berberine chloride in healthy volunteers' urine after oral administration.
2002 Jan
[The interaction of berberine and human serum albumin].
2004 Jan
Effect of artemisinin/artesunate as inhibitors of hepatitis B virus production in an "in vitro" replicative system.
2005 Nov
Activation of the aryl hydrocarbon receptor by berberine in HepG2 and H4IIE cells: Biphasic effect on CYP1A1.
2005 Sep 15
Berberine, a natural product, induces G1-phase cell cycle arrest and caspase-3-dependent apoptosis in human prostate carcinoma cells.
2006 Feb
Combination of simvastatin with berberine improves the lipid-lowering efficacy.
2008 Aug
Berberine enhances inhibition of glioma tumor cell migration and invasiveness mediated by arsenic trioxide.
2008 Feb 25
Protection by and anti-oxidant mechanism of berberine against rat liver fibrosis induced by multiple hepatotoxic factors.
2008 Mar
Anti-diabetic effects of cinnamaldehyde and berberine and their impacts on retinol-binding protein 4 expression in rats with type 2 diabetes mellitus.
2008 Nov 5
Effect of berberine on the antioxidant status, ultrastructural modifications and protein bound carbohydrates in azoxymethane-induced colon cancer in rats.
2009 Feb 12
Berberine suppresses intestinal disaccharidases with beneficial metabolic effects in diabetic states, evidences from in vivo and in vitro study.
2010 Apr
[Controlling effect of berberine on in vitro synthesis and metabolism of steroid hormones in insulin resistant ovary].
2010 Feb
Berberine attenuates lipopolysaccharide-induced impairments of intestinal glutamine transport and glutaminase activity in rat.
2011 Apr
Berberine protects liver from ethanol-induced oxidative stress and steatosis in mice.
2014 Dec
Multiple mechanisms of cell death induced by chelidonine in MCF-7 breast cancer cell line.
2014 Nov 5
The neuroprotective effect of berberine in mercury-induced neurotoxicity in rats.
2015 Aug
Berberine promotes bone marrow-derived mesenchymal stem cells osteogenic differentiation via canonical Wnt/β-catenin signaling pathway.
2016 Jan 5
Patents

Patents

JP2001064108A
7
JP2001503768A
14
JP2005132788A
7
JPH01146809A
7
JPH02101076A
7
JPH03247666A
7
JPH0899813A
8
JPH11255651A
7
JPS61285988A
7
JPS6322507A
7

Sample Use Guides

In Vivo Use Guide
500 mg of berberine 2-3 times daily for up to 3 months
Route of Administration: Oral
In Vitro Use Guide
Berberine acted cytotoxically on both tumour cell lines. The melanoma B16 cells were much more sensitive to berberine treatment than the U937 cells. The value of IC(100) was below 100 ug/ml for the U937 cells and below 1 ug/ml for the B16 cells. As for both cell lines under the long-term influence the values of IC(50) were found to be less than 4 ug/ml.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:05:25 GMT 2023
Edited
by admin
on Fri Dec 15 15:05:25 GMT 2023
Record UNII
0I8Y3P32UF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BERBERINE
MART.   MI   VANDF   WHO-DD  
Common Name English
5,6-DIHYDRO-9,10-DIMETHOXY-1,3-BENZODIOXOLO(5,6-A)BENZO(G)QUINOLIZINIUM
Systematic Name English
UMBELLATINE
Common Name English
BENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINIUM, 5,6-DIHYDRO-9,10-DIMETHOXY-
Systematic Name English
BERBERICINE
Common Name English
THALSINE
Common Name English
Berberine [WHO-DD]
Common Name English
BERBERONE
Common Name English
BERBERINE [MI]
Common Name English
BERBERINE [MART.]
Common Name English
BERBERINE [VANDF]
Common Name English
MAJARINE
Common Name English
BERBERINE (CONSTITUENT OF GOLDENSEAL) [DSC]
Common Name English
UMBELLATIN
Common Name English
5,6-DIHYDRO-9,10-DIMETHOXYBENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINIUM
Systematic Name English
9,10-DIMETHOXY-5,6-DIHYDRO(1,3)DIOXOLO(4,5-G)ISOQUINO(3,2-A)ISOQUINOLIN-7-IUM
Systematic Name English
BERBERIN
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C221
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
DSLD 1060 (Number of products:199)
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C83551
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
MERCK INDEX
m2426
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB04115
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
NCI_THESAURUS
C1505
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
CONCEPT Dietary Supplement
WIKIPEDIA
BERBERINE
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
SMS_ID
100000077167
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID9043857
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
FDA UNII
0I8Y3P32UF
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
PUBCHEM
2353
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
ALANWOOD
berberine
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
EVMPD
SUB13044MIG
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
CAS
2086-83-1
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
MESH
D001599
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
RXCUI
1437
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY RxNorm
CHEBI
16118
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
ECHA (EC/EINECS)
218-229-1
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
Related Record Type Details
SANGUINARIA CANADENSIS ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of BERBERINE CHLORIDE DIHYDRATE
SALT/SOLVATE -> PARENT
Structure of BERBERINE SULFATE ANHYDROUS
SALT/SOLVATE -> PARENT
BERBERIS ARISTATA STEM
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of BERBERINE SULFATE TRIHYDRATE
SALT/SOLVATE -> PARENT
CHELIDONIUM MAJUS FLOWERING TOP
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of BERBERINE BISULFATE
SALT/SOLVATE -> PARENT
GOLDENSEAL
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of Berberine Ursodeoxycholate
SALT/SOLVATE -> PARENT
Structure of BERBERINE CHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of COLUMBAMINE-2-O-BETA-D-GLUCURONIDE
METABOLITE -> PARENT
URINE
Structure of 3,10-DEMETHYLPALMATINE-10-O-SULFATE
METABOLITE -> PARENT
URINE
Structure of DEMETHYLENEBERBERINE-2-O-SULFATE
METABOLITE -> PARENT
URINE
Structure of JATRORRHIZINE O-GLUCURONIDE
METABOLITE -> PARENT
URINE
Structure of BERBERRUBINE-9-O-.BETA.-D-GLUCURONIDE
METABOLITE -> PARENT
URINE
Structure of JATRORRHIZINE 3-O-SULFATE
METABOLITE -> PARENT
URINE
Structure of THALIFENDINE 10-O-.BETA.-D-GLUCURONIDE
METABOLITE -> PARENT
URINE
Related Record Type Details
Structure of BERBERINE
ACTIVE MOIETY
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