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Retrofractamides; Retrofractamide A, 4,5-Dihydro

AlkaPlorer ID: AK312362

Synonym: Retrofractamide C

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

Structure

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

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InChI: InChI=1S/C20H27NO3/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/h7-13,16H,3-6,14-15H2,1-2H3,(H,21,22)/b9-7+,10-8+

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InChIKey: PAXQNYHJDFKFEU-FIFLTTCUSA-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
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: 329.44000000000005

TPSA？: 51.05000000000001

MolLogP？: 5.157600000000005

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 A549 IC50 40000.0 nM 10.1016/j.bmcl.2014.08.063
Homo sapiens DU-145 IC50 40000.0 nM 10.1016/j.bmcl.2014.08.063
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 29.9 % 10.1016/j.bmcl.2008.07.045
Homo sapiens Intercellular adhesion molecule-1 Inhibition 35.9 % 10.1016/j.bmcl.2008.07.045
Homo sapiens Intercellular adhesion molecule-1 Inhibition 36.0 % 10.1016/j.bmcl.2008.07.045
Homo sapiens KB IC50 40000.0 nM 10.1016/j.bmcl.2014.08.063
Homo sapiens MCF7 IC50 40000.0 nM 10.1016/j.bmcl.2014.08.063
Homo sapiens MDA-MB-231 IC50 40000.0 nM 10.1016/j.bmcl.2014.08.063
Homo sapiens SK-BR-3 IC50 40000.0 nM 10.1016/j.bmcl.2014.08.063
Homo sapiens THP-1 Activity nan None 10.1016/j.bmcl.2008.07.045
Homo sapiens ZR-75-1 IC50 40000.0 nM 10.1016/j.bmcl.2014.08.063
Mus musculus 3T3-L1 Activity 9.7 % 10.1016/j.bmcl.2008.04.052
Mus musculus 3T3-L1 Activity 15.0 % 10.1016/j.bmcl.2008.04.052
Mus musculus 3T3-L1 Activity 15.4 % 10.1016/j.bmcl.2008.04.052
Mus musculus 3T3-L1 Activity 22.2 % 10.1016/j.bmcl.2008.04.052
Mus musculus Hepatocyte Inhibition -18.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 0.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 1.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 30.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 30.0 % 10.1016/j.bmcl.2008.01.101
Mus musculus Hepatocyte Inhibition 31.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 31.0 % 10.1016/j.bmcl.2008.01.101
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 51.0 % 10.1016/j.bmc.2009.08.050
Mus musculus Hepatocyte Inhibition 51.0 % 10.1016/j.bmcl.2008.01.101
Mus musculus Mus musculus Activity nan None 10.1016/j.bmcl.2008.07.045
None NON-PROTEIN TARGET IC50 40000.0 nM 10.1016/j.bmcl.2014.08.063

Metabolism Information