BERBERINE CHLORIDE

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Synonyms
UNII UOT4O1BYV8
Source Gaulton A, Kale N, van Westen GJ, Bellis LJ, Bento AP, Davies M, Hersey A, Papadatos G, Forster M, Wege P, Overington JP. A large-scale crop protection bioassay data set. Sci Data. 2015 Jul 7;2:150032. Read more ...

Structure

InChI Key VKJGBAJNNALVAV-UHFFFAOYSA-M
Smiles [Cl-].COc1ccc2cc3c4cc5OCOc5cc4CC[n+]3cc2c1OC
InChI
InChI=1S/C20H18NO4.ClH/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;1H/q+1;/p-1

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H18ClNO4
Molecular Weight 371.81
AlogP 3.96
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 2.0
Polar Surface Area 40.79
Molecular species None
Aromatic Rings 3.0
Heavy Atoms 25.0
Assay Description Organism Bioactivity Reference
Antihyperlipidemic activity in high fat-high cholesterol fed New Zealand Oryctolagus cuniculus (rabbit) assessed as high-density lipoprotein-cholesterol level in blood at 15 mg/kg, po for 40 days (Rvb = 0.67 +/- 0.22 mmol/l) Oryctolagus cuniculus 0.7 nmol/L
Antihyperlipidemic activity in high fat-high cholesterol fed New Zealand Oryctolagus cuniculus (rabbit) assessed as low-density lipoprotein-cholesterol level in blood at 15 mg/kg, po for 40 days (Rvb = 3.45 +/- 0.56 mmol/l) Oryctolagus cuniculus 3.27 nmol/L
Antihyperlipidemic activity in high fat-high cholesterol fed New Zealand Oryctolagus cuniculus (rabbit) assessed as triglyceride level in blood at 15 mg/kg, po for 40 days (Rvb = 2.11 +/- 0.43 mmol/l) Oryctolagus cuniculus 2.02 nmol/L
Antihyperlipidemic activity in high fat-high cholesterol fed New Zealand Oryctolagus cuniculus (rabbit) assessed as total cholesterol level in blood at 15 mg/kg, po for 40 days (Rvb = 8.89 +/- 0.53 mmol/l) Oryctolagus cuniculus 7.94 nmol/L
Toxicity in Mus musculus Kunming (mouse) Mus musculus 763.5 mg.kg-1
Inhibition of HMGR isolated from Mus musculus (mouse) liver assessed as change in NADPH at 8 umol/l by HPLC analysis Mus musculus None
Cytotoxicity against Mus musculus (mouse) L929 cells assessed as metabolically active cells at 200 ug/ml after 24 hr by MTT assay relative to control Mus musculus 23.57 %
Cytotoxicity against Mus musculus (mouse) L929 cells assessed as metabolically active cells at 150 ug/ml after 24 hr by MTT assay relative to control Mus musculus 41.77 %
Cytotoxicity against Mus musculus (mouse) L929 cells assessed as metabolically active cells at 100 ug/ml after 24 hr by MTT assay relative to control Mus musculus 67.41 %
Cytotoxicity against Mus musculus (mouse) L929 cells assessed as metabolically active cells at 50 ug/ml after 24 hr by MTT assay relative to control Mus musculus 106.45 %
Herbicidal activity against Lemna minor (common duckweed) at 1 ppm after 9 days relative to control Lemna minor 75.0 %
Herbicidal activity against Agrostis stolonifera var. palustris at 1 ppm after 9 days relative to control Agrostis stolonifera var. palustris 0.0 %
Antifungal activity against Puccinia recondita on wheat plant assessed as disease control at 100 ppm after 24 hr Puccinia recondita 0.0 %
Antifungal activity against Phytophthora infestans on potato plant assessed as disease control at 100 ppm after 24 hr Phytophthora infestans 0.0 %
Antifungal activity against Phaeosphaeria nodorum on wheat plant assessed as disease control at 100 ppm after 24 hr Phaeosphaeria nodorum 0.0 %
Antifungal activity against Blumeria graminis f. sp. tritici on wheat plant assessed as disease control at 100 ppm after 24 hr Blumeria graminis f. sp. tritici 0.0 %

Cross References

Resources Reference
ChEMBL CHEMBL12089
FDA SRS UOT4O1BYV8
PubChem 6426334
SureChEMBL SCHEMBL153906
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