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Piperstachine; (E,E,E)-form, 8,9-Dihydro 

AlkaPlorer ID: AK310590

Synonym: 11-(3,4-Methylenedioxyphenyl)-2,10-undecadienoic acid isobutylamide, Piperchabamide D

IUPAC Name: (2E,10E)-11-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,10-dienamide

Structure

SMILES: CC(C)CN=C(O)/C=C/CCCCCC/C=C/C1=CC=C2OCOC2=C1

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InChI: InChI=1S/C22H31NO3/c1-18(2)16-23-22(24)12-10-8-6-4-3-5-7-9-11-19-13-14-20-21(15-19)26-17-25-20/h9-15,18H,3-8,16-17H2,1-2H3,(H,23,24)/b11-9+,12-10+

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InChIKey: DOGZABSTLUIXJO-WGDLNXRISA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Crocus corsicus Crocus Iridaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Brickellia longifolia Brickellia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Silene banksia Silene Caryophyllaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cochlearia officinalis Cochlearia Brassicaceae Brassicales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Frullania brasiliensis Frullania Frullaniaceae Porellales Jungermanniopsida Streptophyta Viridiplantae Eukaryota
Didymosphaeria enalia Didymosphaeria Didymosphaeriaceae Pleosporales Dothideomycetes Ascomycota Fungi Eukaryota
Matsumurella chinensis Matsumurella Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dichotomanthes tristaniicarpa Dichotomanthes Rosaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Agaricus xanthodermus Agaricus Agaricaceae Agaricales Agaricomycetes Basidiomycota Fungi Eukaryota
Piper longum Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Piper retrofractum Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Verbesina virginica Verbesina Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Piper nigrum Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Mycoplasma mycoides Mycoplasma Mycoplasmataceae Mycoplasmatales Mollicutes Mycoplasmatota None Bacteria
Penicillium tardum Penicillium Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota
Bupleurum rigidum Bupleurum Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Palisota barteri Palisota Commelinaceae Commelinales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Carpesium longifolium Carpesium Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
None Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Photorhabdus luminescens Photorhabdus Morganellaceae Enterobacterales Gammaproteobacteria Pseudomonadota None Bacteria
Leifsonia aquatica Leifsonia Microbacteriaceae Micrococcales Actinomycetes Actinomycetota None Bacteria
Coelogyne nitida Coelogyne Orchidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
None Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 357.494

TPSA？: 51.05000000000001

MolLogP？: 5.9378000000000055

Number of H-Donors: 1

Number of H-Acceptors: 3

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens Intercellular adhesion molecule-1 IC50 30.0 ug.mL-1 10.1016/j.bmcl.2008.07.045
Homo sapiens Intercellular adhesion molecule-1 Inhibition 15.6 % 10.1016/j.bmcl.2008.07.045
Homo sapiens Intercellular adhesion molecule-1 Inhibition 20.9 % 10.1016/j.bmcl.2008.07.045
Homo sapiens Intercellular adhesion molecule-1 Inhibition 26.9 % 10.1016/j.bmcl.2008.07.045
Homo sapiens Intercellular adhesion molecule-1 Inhibition 42.6 % 10.1016/j.bmcl.2008.07.045
Homo sapiens THP-1 Activity nan None 10.1016/j.bmcl.2008.07.045
Mus musculus 3T3-L1 Activity 1.7 % 10.1016/j.bmcl.2008.04.052
Mus musculus 3T3-L1 Activity 4.7 % 10.1016/j.bmcl.2008.04.052
Mus musculus 3T3-L1 Activity 8.0 % 10.1016/j.bmcl.2008.04.052
Mus musculus 3T3-L1 Activity 8.5 % 10.1016/j.bmcl.2008.04.052
Mus musculus Hepatocyte IC50 3000.0 nM 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 37.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 37.0 % 10.1016/j.bmcl.2008.01.101
Mus musculus Hepatocyte Inhibition 57.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 57.0 % 10.1016/j.bmcl.2008.01.101
Mus musculus Hepatocyte Inhibition 77.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 77.0 % 10.1016/j.bmcl.2008.01.101
Mus musculus L929 Inhibition -23.0 % 10.1016/j.bmc.2009.08.050
Mus musculus L929 Inhibition -20.0 % 10.1016/j.bmc.2009.08.050
Mus musculus L929 Inhibition -3.0 % 10.1016/j.bmc.2009.08.050
Mus musculus L929 Inhibition 8.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Mus musculus Activity nan None 10.1016/j.bmcl.2008.07.045
None Peritoneal macrophage cell Inhibition -1.0 % 10.1016/j.bmc.2009.08.050
None Peritoneal macrophage cell Inhibition 7.0 % 10.1016/j.bmc.2009.08.050
None Peritoneal macrophage cell Inhibition 10.0 % 10.1016/j.bmc.2009.08.050
None Peritoneal macrophage cell Inhibition 22.0 % 10.1016/j.bmc.2009.08.050

Metabolism Information