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Guineensine; (E,E,E)-form 

AlkaPlorer ID: AK299775

Synonym: None

IUPAC Name: (2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide

Structure

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

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InChI: InChI=1S/C24H33NO3/c1-20(2)18-25-24(26)14-12-10-8-6-4-3-5-7-9-11-13-21-15-16-22-23(17-21)28-19-27-22/h8,10-17,20H,3-7,9,18-19H2,1-2H3,(H,25,26)/b10-8+,13-11+,14-12+

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InChIKey: FPMPOFBEYSSYDQ-AUVZEZIHSA-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
Hippocrepis emerus Hippocrepis Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Oocystis polymorpha Oocystis Oocystaceae Chlorellales Trebouxiophyceae Chlorophyta Viridiplantae Eukaryota
Rubus pileatus Rubus Rosaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Didymosphaeria enalia Didymosphaeria Didymosphaeriaceae Pleosporales Dothideomycetes Ascomycota Fungi Eukaryota
Piper attenuatum Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Plenckia populnea Plenckia Celastraceae Celastrales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Piper amalago Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Matsumurella chinensis Matsumurella Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Piper guineense Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dichotomanthes tristaniicarpa Dichotomanthes Rosaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Agaricus xanthodermus Agaricus Agaricaceae Agaricales Agaricomycetes Basidiomycota Fungi Eukaryota
Pinus aristata Pinus Pinaceae Pinales Pinopsida Streptophyta Viridiplantae Eukaryota
Phoebe grandis Phoebe Lauraceae Laurales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dryopteris arguta Dryopteris Dryopteridaceae Polypodiales Polypodiopsida Streptophyta Viridiplantae 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
Bellardia viscosa Bellardia Orobanchaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ardisia japonica Ardisia Primulaceae Ericales 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
Gyalolechia fulgida Gyalolechia Teloschistaceae Teloschistales Lecanoromycetes Ascomycota Fungi Eukaryota
Bupleurum rigidum Bupleurum Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Piper sarmentosum Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Palisota barteri Palisota Commelinaceae Commelinales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Carpesium longifolium Carpesium Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Photorhabdus luminescens Photorhabdus Morganellaceae Enterobacterales Gammaproteobacteria Pseudomonadota None Bacteria
Aglaia perviridis Aglaia Meliaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Leifsonia aquatica Leifsonia Microbacteriaceae Micrococcales Actinomycetes Actinomycetota None Bacteria
Acanthosyris paulo-alvinii Acanthosyris Cervantesiaceae Santalales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Coelogyne nitida Coelogyne Orchidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Betula alnoides Betula Betulaceae Fagales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 383.5320000000001

TPSA？: 51.05000000000001

MolLogP？: 6.494000000000007

Number of H-Donors: 1

Number of H-Acceptors: 3

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Aedes aegypti Aedes aegypti LC50 0.89 ppm 10.1016/j.ejmech.2015.04.061
Bacillus subtilis Bacillus subtilis MIC 163000.0 nM 10.1021/np900341f
Hepatitis B virus Hepatitis B virus IC50 50000.0 nM 10.1016/j.bmcl.2013.01.118
Homo sapiens Anandamide amidohydrolase IC50 46800.0 nM 10.1021/acs.jnatprod.8b00874
Homo sapiens Anandamide amidohydrolase Inhibition 59.0 % 10.1021/acs.jnatprod.8b00874
Homo sapiens Cannabinoid CB1 receptor Ki 20000.0 nM 10.1021/acs.jnatprod.8b00874
Homo sapiens Cannabinoid CB2 receptor Ki 38300.0 nM 10.1021/acs.jnatprod.8b00874
Homo sapiens Fatty acid binding protein epidermal Ki 100000.0 nM 10.1021/acs.jnatprod.8b00874
Homo sapiens Geminin Potency 410.9 nM None
Homo sapiens Intercellular adhesion molecule-1 Activity nan None 10.1016/j.bmcl.2008.07.045
Homo sapiens Intercellular adhesion molecule-1 IC50 50.0 ug.mL-1 10.1016/j.bmcl.2008.07.045
Homo sapiens Intercellular adhesion molecule-1 Inhibition 14.9 % 10.1016/j.bmcl.2008.07.045
Homo sapiens Intercellular adhesion molecule-1 Inhibition 31.7 % 10.1016/j.bmcl.2008.07.045
Homo sapiens Intercellular adhesion molecule-1 Inhibition 36.8 % 10.1016/j.bmcl.2008.07.045
Homo sapiens Monoglyceride lipase Ki 100000.0 nM 10.1021/acs.jnatprod.8b00874
Homo sapiens Parathyroid hormone receptor Potency 25118.9 nM None
Homo sapiens THP-1 Activity nan None 10.1016/j.bmcl.2008.07.045
Homo sapiens U-937 EC50 290.0 nM 10.1021/acs.jnatprod.8b00874
Homo sapiens U-937 Efficacy 65.0 % 10.1021/acs.jnatprod.8b00874
Mus musculus 3T3-L1 Activity 0.8 % 10.1016/j.bmcl.2008.04.052
Mus musculus 3T3-L1 Activity 1.5 % 10.1016/j.bmcl.2008.04.052
Mus musculus 3T3-L1 Activity 2.0 % 10.1016/j.bmcl.2008.04.052
Mus musculus 3T3-L1 Activity 9.7 % 10.1016/j.bmcl.2008.04.052
Mus musculus Hepatocyte Inhibition -20.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 6.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 7.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 12.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 12.0 % 10.1016/j.bmcl.2008.01.101
Mus musculus Hepatocyte Inhibition 26.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 26.0 % 10.1016/j.bmcl.2008.01.101
Mus musculus Hepatocyte Inhibition 33.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 33.0 % 10.1016/j.bmcl.2008.01.101
Mus musculus Hepatocyte Inhibition nan % 10.1016/j.bmc.2009.08.050
Mus musculus L929 Inhibition -18.0 % 10.1016/j.bmc.2009.08.050
Mus musculus L929 Inhibition -9.0 % 10.1016/j.bmc.2009.08.050
Mus musculus L929 Inhibition 2.0 % 10.1016/j.bmc.2009.08.050
Mus musculus L929 Inhibition 9.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Mus musculus Activity nan None 10.1016/j.bmcl.2008.07.045
Plasmodium falciparum Plasmodium falciparum IC50 3700.0 nM 10.1021/np900341f
Pseudomonas agarici Pseudomonas agarici MIC 81500.0 nM 10.1021/np900341f
Streptococcus minor Streptococcus minor Activity nan None 10.1021/np900341f
None ADMET CC50 150000.0 nM 10.1016/j.bmcl.2013.01.118
None Unchecked Ratio CC50/IC50 3.0 None 10.1016/j.bmcl.2013.01.118

Metabolism Information