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Showing Compound N-trans-Caffeoyltyramine (FDB011018)

Record Information
Version1.0
Creation date2010-04-08 22:09:25 UTC
Update date2022-12-14 16:43:52 UTC
Primary IDFDB011018
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-trans-Caffeoyltyramine
DescriptionN-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.
CAS Number219773-48-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.038 g/LALOGPS
logP2.26ALOGPS
logP2.92ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)6.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area93.28 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity85.61 m³·mol⁻¹ChemAxon
Polarizability31.73 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H17NO4
IUPAC name(E,2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid
InChI IdentifierInChI=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+
InChI KeyVSHUQLRHTJOKTA-XBXARRHUSA-N
Isomeric SMILESOC1=CC=C(CCNC(=O)\C=C\C2=CC=C(O)C(O)=C2)C=C1
Average Molecular Weight299.3212
Monoisotopic Molecular Weight299.115758037
Classification
Description 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids and derivatives
Alternative Parents
Substituents
  • Cinnamic acid amide
  • Hydroxycinnamic acid or derivatives
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSN-trans-Caffeoyltyramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-0910000000-1c173cf7b0466780ad35Spectrum
Predicted GC-MSN-trans-Caffeoyltyramine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-2214490000-6874f89c7d4c31b6fc55Spectrum
Predicted GC-MSN-trans-Caffeoyltyramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0902000000-bb08be6dcc7c2a45bf352017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0900000000-c6428a4104f73aef3c4b2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05w0-4900000000-4fca258d19782c0fb73f2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0390000000-bc4e0e59663ef50085452017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06tk-0940000000-bb3d5ef1352903365d4d2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7900000000-9b04559c19d2c27de1e72017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-ee9973b640e1d151e6682021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-0960000000-63c941ca4aabf16712022021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2910000000-97509ed3cb2dd7b98ff92021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0609000000-b6bd2633941fd45aa3ac2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0911000000-fd9a2c7ec9b5be9edabb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i0-4930000000-5dfe8817cc8d0f88a5ef2021-09-24View Spectrum
NMRNot Available
ChemSpider ID8170478
ChEMBL IDCHEMBL206646
KEGG Compound IDNot Available
Pubchem Compound ID9994897
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB08754
HMDB IDHMDB33026
CRC / DFC (Dictionary of Food Compounds) IDBCB62-V:FYF81-K
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDY13
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
No data available in table
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Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference