BERBERINE

Search structure
Synonyms:
Status: Approved
Entry Type: Small molecule
Molecule Category: Parent
UNII: 0I8Y3P32UF

Structure
InChI Key YBHILYKTIRIUTE-UHFFFAOYSA-N
Smile COc1ccc2cc3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2
InChI
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H18NO4+
Molecular Weight 336.37
AlogP 3.1
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 2.0
Polar Surface Area 40.8
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 25.0

Pharmacology

Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1B Cytochrome P450 1B1
- 94-2500 - 44 -
Enzyme Hydrolase
- 374-1600 - 14300 -
Enzyme Isomerase
- - - - 72
Enzyme Oxidoreductase
- 6710 - - -
Enzyme Phosphatase Protein Phosphatase Tyrosine protein phosphatase
- 67000 - - -
Enzyme Transferase
- 37000 - - -
Enzyme
- 374-1600 - 14300 72
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 66069 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 19
Transporter Primary active transporter Oxidoreduction-driven transporters
- - - - 15-16

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Diabetes Mellitus, Type 2 3 D003924 ClinicalTrials
Non-alcoholic Fatty Liver Disease 2 D065626 ClinicalTrials
Adenoma 2 D000236 ClinicalTrials
Prediabetic State 2 D011236 ClinicalTrials
Hyperlipidemia, Familial Combined 2 D006950 ClinicalTrials
Adenocarcinoma of Lung 2 D000077192 ClinicalTrials

Related Entries

Scaffolds

UNKNOWN
Salt

Cross References

Resources Reference
CAS NUMBER 2086-83-1
ChEBI 16118
ChEMBL CHEMBL295124
DrugBank DB04115
EPA CompTox DTXSID9043857
FDA SRS 0I8Y3P32UF
Human Metabolome Database HMDB0003409
KEGG C00757
PDB BER
PharmGKB PA165860812
PubChem 2353
SureChEMBL SCHEMBL25632
ZINC ZINC000003779067
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