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Retrofractamides; Retrofractamide A

AlkaPlorer ID: AK312361

Synonym: None

IUPAC Name: (2E,4E,8E)-9-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,4,8-trienamide

Structure

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

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InChI: InChI=1S/C20H25NO3/c1-16(2)14-21-20(22)10-8-6-4-3-5-7-9-17-11-12-18-19(13-17)24-15-23-18/h4,6-13,16H,3,5,14-15H2,1-2H3,(H,21,22)/b6-4+,9-7+,10-8+

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InChIKey: BPSWISYORIWKCT-FCGWLDPVSA-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
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

Properties Information

Molecule Weight: 327.4240000000001

TPSA？: 51.05000000000001

MolLogP？: 4.933600000000004

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 0.04 ppm 10.1016/j.ejmech.2015.04.061
Homo sapiens HCT-116 IC50 20000.0 nM 10.1016/j.bmcl.2011.06.046
Homo sapiens Histone deacetylase 1 Inhibition 50.0 % 10.1016/j.bmcl.2011.06.046
Homo sapiens Histone deacetylase 3 Inhibition 50.0 % 10.1016/j.bmcl.2011.06.046
Homo sapiens Histone deacetylase 6 Inhibition 50.0 % 10.1016/j.bmcl.2011.06.046
Mus musculus 3T3-L1 Activity 6.5 % 10.1016/j.bmcl.2013.06.101
Mus musculus 3T3-L1 Activity 14.1 % 10.1016/j.bmcl.2013.06.101
Mus musculus 3T3-L1 Activity 22.9 % 10.1016/j.bmcl.2013.06.101
Mus musculus 3T3-L1 Activity 25.1 % 10.1016/j.bmcl.2008.04.052
Mus musculus 3T3-L1 Activity 27.3 % 10.1016/j.bmcl.2008.04.052
Mus musculus 3T3-L1 Activity 27.8 % 10.1016/j.bmcl.2008.04.052
Mus musculus 3T3-L1 Activity 33.3 % 10.1016/j.bmcl.2008.04.052
Mus musculus 3T3-L1 Activity 33.4 % 10.1016/j.bmcl.2013.06.101
Mus musculus 3T3-L1 Activity 38.0 % 10.1016/j.bmcl.2013.06.101
Mus musculus 3T3-L1 Activity 98.1 % 10.1016/j.bmcl.2013.06.101
Mus musculus 3T3-L1 Activity 100.2 % 10.1016/j.bmcl.2013.06.101
Mus musculus 3T3-L1 Activity 107.8 % 10.1016/j.bmcl.2013.06.101
Mus musculus 3T3-L1 Activity 109.0 % 10.1016/j.bmcl.2013.06.101
Mus musculus 3T3-L1 Activity 109.4 % 10.1016/j.bmcl.2013.06.101
Mus musculus 3T3-L1 Activity nan None 10.1016/j.bmcl.2008.04.052
Mus musculus Hepatocyte IC50 21000.0 nM 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 1.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 2.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 3.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 7.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 32.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 32.0 % 10.1016/j.bmcl.2008.01.101
Mus musculus Hepatocyte Inhibition 35.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 35.0 % 10.1016/j.bmcl.2008.01.101
Mus musculus Hepatocyte Inhibition 40.0 % 10.1016/j.bmcl.2008.01.101
Mus musculus Hepatocyte Inhibition 60.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 60.0 % 10.1016/j.bmcl.2008.01.101
None Peritoneal macrophage cell Inhibition -14.0 % 10.1016/j.bmc.2009.08.050
None Peritoneal macrophage cell Inhibition -12.0 % 10.1016/j.bmc.2009.08.050
None Peritoneal macrophage cell Inhibition -8.0 % 10.1016/j.bmc.2009.08.050
None Peritoneal macrophage cell Inhibition 4.0 % 10.1016/j.bmc.2009.08.050

Metabolism Information