Showing chemical card for N-trans-feruloyltyramine (CFc000010610)
Record Information
Version
1.0
Creation Date
2022-08-28 10:25:12 UTC
Update Date
2022-09-13 18:58:06 UTC
Chemfont ID
CFc000010610
Molecule Identification
Common Name
N-trans-feruloyltyramine
Definition
N-trans-feruloyltyramine (NFT), also known as Moupinamide or Alfrutamide or N-feruloyltyramine or trans-N-Feruloyltyramine, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is also classified as a phenylpropanoid amide. Phenylpropanoids consist of a six-carbon, aromatic phenyl group and a three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. A phenylpropanoid amide has an amide group incorporated into its propanoid chain. There are two known isomers of N-Feruloyltyramine, N-trans-Feruloyltyramine and N-cis-Feruloyltyramine. N-trans-feruloyltyramine (Moupinamide) is a largely neutral molecule, that is somewhat insoluble in water. It exists as a white crystalline solid. Moupinamide or N-trans-Feruloyltyramine is one of the major phenylpropanoid amides that have been identified in the cannabis plant (PMID:6991645 ). It is also found in black and white peppers, the leaves of the Chinese pepper tree as well as eggplant (PMID: 34335243 ). This could make moupinamide a potential biomarker for the consumption of these plants/foods. Moupinamide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases, they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. N-trans-feruloyltyramine or NFT has a number of potential therapeutic or beneficial effects in humans. It is an inhibitor of COX 1 and COX 2 and has potential antioxidant properties (PMID: 19807156 ). More recently, trans-N-Caffeoyltyramine has been identified to by a potent HNF4α agonist (PMID: 35087037 ). HNF4A or HNF4α is also known as Hepatocyte nuclear factor 4 alpha. It is also known as NR2A1 (nuclear receptor subfamily 2, group A, member 1 and) is a nuclear receptor that in humans is encoded by the HNF4A gene. Moupinamide (NFT) has been found to promote weight loss by inducing an increase in mitochondrial mass and function, including fatty acid oxidation. It also promotes the reversal of hepatic steatosis through a mechanism involving the stimulation of lipophagy by dihydroceramides (PMID: 34117215 ). This has made Moupinamide or NFT a strong candidate as a NAFLD (non-alcoholic fatty liver disease) therapeutic.
Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
