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
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
Assay Description Organism Bioactivity Reference
Inhibition of self-mediated amyloid beta (1 to 42) aggregation at 10 uM after 48 hrs by thioflavin T fluorescence assay None 8.9 %
Inhibition of self-mediated amyloid beta (1 to 42) aggregation at 20 uM after 48 hrs by thioflavin T fluorescence assay None 36.3 %
Inhibition of electric eel AChE using acetylthiocholine chloride substrate as substrate preincubated for 15 mins by Ellman's method Electrophorus electricus 374.0 nM
Inhibition of electric eel AChE using acetylcholine as substrate by Ellman's method Electrophorus electricus 374.0 nM
Inhibition of amyloid beta (1 to 42) self aggregation at 20 uM after 48 hrs by thioflavin T fluorescence assay None 36.3 %
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 32.0 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 19.4 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 18.5 %
Antiamoebic activity against Entamoeba histolytica Entamoeba histolytica 1.0 ug.mL-1
Inhibition of Sus scrofa (pig) pancreatic lipase type 2 using PNPB as substrate pre-incubated with enzyme for 5 min prior to substrate addition measured for 5 min by spectrophotometric analysis Sus scrofa 106.0 ug.mL-1
Binding affinity to poly(A) tail mRNA (unknown origin) assessed as cooperative binding constant by absorption spectroscopy Not specified 1.21 10'-4/M
Binding affinity to poly(A) tail mRNA (unknown origin) assessed as apparent binding constant by absorption spectroscopy Not specified 410.0 nM
Binding affinity to poly(A) tail mRNA (unknown origin) assessed as cooperative binding constant by fluorimetric analysis Not specified 0.98 10'-4/M
Binding affinity to poly(A) tail mRNA (unknown origin) assessed as apparent binding constant by fluorimetric analysis Not specified 400.0 nM
Inhibition of FtsZ (unknown origin) assessed as reduction in frequency of Z-rings per unit cell length Not specified 50.0 %
Inhibition of AChE (unknown origin) using acetylthiocholine as substrate assessed as substrate hydrolysis by spectrophotometric/Ellman method Homo sapiens 100.0 nM
Inhibition of recombinant Mycobacterium tuberculosis FtsZ GTPase activity expressed in Escherichia coli assessed as inorganic phosphate release at 50 uM measured after 15 mins in presence of GTP using malachite green dye by fluorescence spectrophotometry relative to control Mycobacterium tuberculosis 79.0 %
Inhibition of human CYP1B1 expressed in Escherichia coli DH5alpha coexpressing human NADPH-P450 reductase using 4-estradiol as substrate in presence of NADP+ by Michaelis-Menten plot analysis Homo sapiens 44.0 nM
Inhibition of human CYP1B1 expressed in Escherichia coli DH5alpha coexpressing human NADPH-P450 reductase using 4-estradiol as substrate in presence of NADP+ by HPLC analysis Homo sapiens 330.0 nM
Inhibition of COX2 in human A375 cells assessed as reduction in PGE2 production up to 20 uM by immunoblot analysis relative to control Homo sapiens 15.0 %
Inhibition of COX2 in human Hs294 cells assessed as reduction in PGE2 production up to 20 uM by immunoblot analysis relative to control Homo sapiens 16.0 %
Inhibition of mPGES1 in human HeLa cells assessed as reduction in PGE2 production at 50 uM by enzyme immunoassay relative to control Homo sapiens 71.9 %
Antiviral activity against Influenza A virus (A/Puerto Rico/8/1934(H1N1)) infected in MDCK cells assessed as reduction in virus-induced cytopathogenicity incubated for 48 hrs by SRB assay Influenza A virus (A/Puerto Rico/8/1934(H1N1)) 31.35 ug.mL-1
Antiviral activity against Influenza A virus (A/Puerto Rico/8/1934(H1N1)) infected in MDCK cells assessed as reduction in virus-induced cytopathogenicity at 1 ug/ml treated before virus infection and measured after 48 hrs by SRB assay relative to untreated control Influenza A virus (A/Puerto Rico/8/1934(H1N1)) 12.1 %
Inhibition of human CYP1B1 expressed in Escherichia coli DH5alpha cell membranes coexpressing human NADPH-cytochrome P450 reductase using 7-Ethoxyresorufin as substrate by EROD assay Homo sapiens 94.0 nM
Inhibition of PCSK9 mRNA level in mouse RAW264.7 cells at 20 uM by qRT-PCR assay relative to control Mus musculus 67.0 %
Inhibition of human AChE using acetylthiocholine iodide as substrate measured for 1 min by Ellman's method Homo sapiens 700.0 nM
Cytotoxicity against human HeLa cells measured after 48 hrs by MTT assay Homo sapiens 12.08 ug.mL-1
Cytotoxicity against African green monkey Vero cells measured after 48 hrs by MTT assay Chlorocebus sabaeus 71.14 ug.mL-1
Antiviral activity against Zika virus infected in African green monkey Vero E6 cells assessed as reduction in virus infectivity at 160 uM preincubated with virus for 1 hr followed by cell infection and measured after 96 hrs by crystal violet staining based assay relative to control Zika virus 77.6 %
Cytotoxicity against human HepG2 cells assessed as reduction in cell viability after 48 hrs by MTT assay Homo sapiens 46.9 ug.mL-1
Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed inhibition of TNFalpha release at 0.5 uM incubated for 24 hrs in presence of LPS by ELISA Mus musculus 4.1 %
Inhibition of Staphylococcus aureus sortase A using Abz-LPETGK(Dnp)-NH2 fluorescent peptide as a substrate assessed as substrate cleavage measured over 60 mins by FRET assay Staphylococcus aureus 6.9 ug.mL-1

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