PIPERINE

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Synonyms
UNII U71XL721QK
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 MXXWOMGUGJBKIW-YPCIICBESA-N
Smiles O=C(\C=C\C=C\c1ccc2OCOc2c1)N3CCCCC3
InChI
InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+

Physicochemical Descriptors

Property Name Value
Molecular Formula C17H19NO3
Molecular Weight 285.34
AlogP 2.86
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 3.0
Polar Surface Area 38.77
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 21.0
Assay Description Organism Bioactivity Reference
Cytotoxicity against Homo sapiens (human) COLO205 cells by SRB assay Homo sapiens 46000.0 nM
Cytotoxicity against Homo sapiens (human) Hep2 cells by SRB assay Homo sapiens 70000.0 nM
Cytotoxicity against Homo sapiens (human) DU145 cells by SRB assay Homo sapiens 50000.0 nM
Cytotoxicity against Homo sapiens (human) PC3 cells by SRB assay Homo sapiens 50000.0 nM
Cytotoxicity against Homo sapiens (human) IMR32 cells by SRB assay Homo sapiens 89000.0 nM
Cytotoxicity against Homo sapiens (human) MCF7 cells by SRB assay Homo sapiens 99000.0 nM
Fungicidal activity against Blumeria graminis infected barley assessed as reduction in powdery mildew disease at 500 mg/l applied for 1 day prior to infection relative to untreated control Blumeria graminis 0.0 %
Fungicidal activity against Blumeria graminis infected barley assessed as reduction in powdery mildew disease at 1000 mg/l applied for 1 day prior to infection relative to untreated control Blumeria graminis 0.0 %
Fungicidal activity against Puccinia recondita infected wheat assessed as reduction in wheat leaf rust disease at 500 mg/l applied for 1 day prior to infection relative to untreated control Puccinia recondita 0.0 %
Fungicidal activity against Puccinia recondita infected wheat assessed as reduction in wheat leaf rust disease at 1000 mg/l applied for 1 day prior to infection relative to untreated control Puccinia recondita 0.0 %
Fungicidal activity against Phytophthora infestans infected tomato assessed as reduction in tomato late blight disease at 500 mg/l applied for 1 day prior to infection relative to untreated control Phytophthora infestans 0.0 %
Fungicidal activity against Phytophthora infestans infected tomato assessed as reduction in tomato late blight disease at 1000 mg/l applied for 1 day prior to infection relative to untreated control Phytophthora infestans 0.0 %
Fungicidal activity against Botryotinia fuckeliana infected cucumber assessed as reduction in cucumber gray mold disease at 500 mg/l applied for 1 day prior to infection relative to untreated control Botryotinia fuckeliana 0.0 %
Fungicidal activity against Botryotinia fuckeliana infected cucumber assessed as reduction in cucumber gray mold disease at 1000 mg/l applied for 1 day prior to infection relative to untreated control Botryotinia fuckeliana 0.0 %
Fungicidal activity against Rhizoctonia solani infected rice assessed as reduction in rice sheath blight disease at 500 mg/l applied for 1 day prior to infection relative to untreated control Rhizoctonia solani 0.0 %
Fungicidal activity against Rhizoctonia solani infected rice assessed as reduction in rice sheath blight disease at 1000 mg/l applied for 1 day prior to infection relative to untreated control Rhizoctonia solani 0.0 %
Fungicidal activity against Magnaporthe grisea infected rice assessed as reduction in rice blast disease at 500 mg/l applied for 1 day prior to infection relative to untreated control Magnaporthe grisea 0.0 %
Fungicidal activity against Magnaporthe grisea infected rice assessed as reduction in rice blast disease at 1000 mg/l applied for 1 day prior to infection relative to untreated control Magnaporthe grisea 0.0 %
Antitrypanosomal activity against epimastigote forms of Trypanosoma cruzi Y after 72 hr Trypanosoma cruzi 233000.0 nM
Insecticidal activity against Aedes aegypti assessed as lethal compound dose per mosquito measured after 24 hr post topical application Aedes aegypti 8.13 ug
Inhibition of cathepsin D (unknown origin) using hemoglobin as substrate after 30 min by spectrophotometric analysis Homo sapiens 42300.0 nM
Antibacterial activity against Pseudomonas aeruginosa assessed as growth inhibition after 24 hr by two-fold serial dilution method Pseudomonas aeruginosa 100.0 ug.mL-1
Antibacterial activity against Staphylococcus aureus assessed as growth inhibition after 24 hr by two fold serial dilution method Staphylococcus aureus 300.0 ug.mL-1
Antibacterial activity against Bacillus subtilis assessed as growth inhibition after 24 hr by two fold serial dilution method Bacillus subtilis 500.0 ug.mL-1
Antibacterial activity against Shigella dysenteriae assessed as growth inhibition after 24 hr by two-fold serial dilution method Shigella dysenteriae 600.0 ug.mL-1
Antibacterial activity against Salmonella enterica subsp. enterica serovar Typhi assessed as growth inhibition after 24 hr by two fold serial dilution method Salmonella enterica subsp. enterica serovar Typhi 200.0 ug.mL-1
Antibacterial activity against Klebsiella pneumoniae assessed as growth inhibition after 24 hr by two-fold serial dilution method Klebsiella pneumoniae 200.0 ug.mL-1
Antibacterial activity against Escherichia coli assessed as growth inhibition after 24 hr by two-fold serial dilution method Escherichia coli 300.0 ug.mL-1

Cross References

Resources Reference
ChEMBL CHEMBL43185
FDA SRS U71XL721QK
PubChem 638024
SureChEMBL SCHEMBL94058
ZINC ZINC01529772
CONTENTS