BERBERINE

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Synonyms
Status
Molecule Category Free-form
UNII 0I8Y3P32UF
EPA CompTox DTXSID9043857

Structure

InChI Key YBHILYKTIRIUTE-UHFFFAOYSA-N
Smiles 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
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
- 94-330 - 44 -
Enzyme Hydrolase
- 100-700 - - -
Enzyme Isomerase
- - - - 71.9
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 18.5-32
Transporter Primary active transporter Oxidoreduction-driven transporters
- - - - 15-16
EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Electrophorus electricus
- 374-374 - - -
Homo sapiens
- 94-700 - 44 15-71.9
Influenza A virus (A/Puerto Rico/8/1934(H1N1))
- - - - 12.1
Mus musculus
- - - - 4.1-67
Mycobacterium tuberculosis
- - - - 79
Zika virus
- - - - 77.6

Cross References

Resources Reference
ChEBI 16118
ChEMBL CHEMBL295124
DrugBank DB04115
FDA SRS 0I8Y3P32UF
Human Metabolome Database HMDB0003409
KEGG C00757
PDB BER
PharmGKB PA165860812
PubChem 2353
SureChEMBL SCHEMBL25632
ZINC ZINC000003779067
CONTENTS