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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

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
Record UNII
0I8Y3P32UF
Record Status Validated (UNII)
Record Version