1.0 2010-04-08 22:09:25 UTC 2022-12-14 16:43:52 UTC FDB011018 N-trans-Caffeoyltyramine N-trans-Caffeoyltyramine also known as trans-N-Caffeoyltyramine or TNC, belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing a cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. N-trans-Caffeoyltyramine 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-Caffeoyltyramine, N-trans-Caffeoyltyramine and N-cis-Caffeoyltyramine. N-trans-Caffeoyltyramine is a largely neutral molecule that is somewhat insoluble in water. N-trans-caffeoyltyramine is one of the major phenylpropanoid amides that have been identified in the cannabis plant (PMID:6991645 ) N-trans-Caffeoyltyramine has also been found in the plant Tribulus terrestris (also known as Bindi or puncture vine, a fruit-producing Mediterranean plant that's covered with spines) (PMID: 26239676). N-trans-Caffeoyltyramine is also known to be found in Lycium chinense root bark (which produces goji berry or wolfberry) (PMID: 12214850). N-trans-Caffeoyltyramine has both arginase inhibitory properties and a strong antioxidant capacity (DOI: 10.1055/s-0042-119400). These properties may make it useful for the design and development of new drugs for the treatment of endothelial dysfunction associated with cardiovascular diseases. N-Caffeoyltyramine has exhibited anti-cancer activities and appears to inhibit the epidermal growth factor receptor (EGFR) and its protein tyrosine kinase activity. In addition, N-Caffeoyltyramine appears to activate caspase 3 activity (PMID: 14643446). N-trans-caffeoyltyramine, in particular, has been found to have strong anti-oxidant properties (PMID: 12214850; PMID: 28715870), and potent anti-fungal activities (PMID: 15266117). More recently N-trans-caffeoyltyramine has been identified to be a potent HNF4α agonist (PMID: 35087037). It 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 TNC a strong candidate as a NAFLD (non-alcoholic fatty liver disease) therapeutic. N-cis-Caffeoyltyramine C17H17NO4 299.3212 299.115758037 (E,2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid (E,2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid 219773-48-5 OC1=CC=C(CCNC(=O)\C=C\C2=CC=C(O)C(O)=C2)C=C1 InChI=1S/C17H17NO4/c19-14-5-1-12(2-6-14)9-10-18-17(22)8-4-13-3-7-15(20)16(21)11-13/h1-8,11,19-21H,9-10H2,(H,18,22)/b8-4+ VSHUQLRHTJOKTA-XBXARRHUSA-N belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. Hydroxycinnamic acids and derivatives Organic compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Carbonyl compounds Catechols Cinnamic acid amides Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Secondary carboxylic acid amides Styrenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxamide group Carboxylic acid derivative Catechol Cinnamic acid amide Hydrocarbon derivative Hydroxycinnamic acid or derivatives Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol Secondary carboxylic acid amide Styrene logp 2.26 ALOGPS logs -3.90 ALOGPS solubility 3.80e-02 g/l ALOGPS logp 2.92 ChemAxon pka_strongest_acidic 4.36 ChemAxon pka_strongest_basic 6.32 ChemAxon iupac (E,2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid ChemAxon average_mass 299.3212 ChemAxon mono_mass 299.115758037 ChemAxon smiles OC1=CC=C(CCNC(=O)\C=C\C2=CC=C(O)C(O)=C2)C=C1 ChemAxon formula C17H17NO4 ChemAxon inchi InChI=1S/C17H17NO4/c19-14-5-1-12(2-6-14)9-10-18-17(22)8-4-13-3-7-15(20)16(21)11-13/h1-8,11,19-21H,9-10H2,(H,18,22)/b8-4+ ChemAxon inchikey VSHUQLRHTJOKTA-XBXARRHUSA-N ChemAxon polar_surface_area 93.28 ChemAxon refractivity 85.61 ChemAxon polarizability 31.73 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 20477 Specdb::CMs 43063 Specdb::CMs 167108 Specdb::MsMs 262656 Specdb::MsMs 262657 Specdb::MsMs 262658 Specdb::MsMs 282588 Specdb::MsMs 282589 Specdb::MsMs 282590 Specdb::MsMs 2762083 Specdb::MsMs 2762084 Specdb::MsMs 2762085 Specdb::MsMs 2947545 Specdb::MsMs 2947546 Specdb::MsMs 2947547 HMDB33026 Y13 #<Reference:0x000055ce32597ee0> Fruits Unknown generic