Showing Compound Card for N-trans-Caffeoyltyramine (CDB000363)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 6 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:33:02 UTC
Updated at2022-12-14 16:18:28 UTC
CannabisDB IDCDB000363
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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.
Structure
Data
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
trans-N-CaffeoyltyramineHMDB
(2E)-3-(3,4-Dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidateHMDB
N-CaffeoyltyramineHMDB
TypheramideHMDB
(2E)-3-(3,4-Dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-2-propenamide HMDB
N-trans-Caffeoyltyramine HMDB
TNCHMDB
Chemical FormulaC17H17NO4
Average Molecular Weight299.3212
Monoisotopic Molecular Weight299.115758037
IUPAC Name(E,2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid
Traditional Name(E,2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid
CAS Registry Number219773-48-5
SMILES
OC1=CC=C(CCNC(=O)\C=C\C2=CC=C(O)C(O)=C2)C=C1
InChI Identifier
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+
InChI KeyVSHUQLRHTJOKTA-XBXARRHUSA-N
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Arginase-1ARG16q23P05089 details
Epidermal growth factor receptorEGFR7p12P00533 details
Caspase-3CASP34q35.1P42574 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Arginase-1ARG16q23P05089 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Epidermal growth factor receptorEGFR7p12P00533 details
Caspase-3CASP34q35.1P42574 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0033026
DrugBank IDDB08754
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011018
KNApSAcK IDC00000662
Chemspider ID8170478
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9994897
PDB IDY13
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Park JB, Schoene N: N-Caffeoyltyramine arrests growth of U937 and Jurkat cells by inhibiting protein tyrosine phosphorylation and inducing caspase-3. Cancer Lett. 2003 Dec 30;202(2):161-71. doi: 10.1016/j.canlet.2003.08.010. [PubMed:14643446 ]

Enzymes

Enzyme Details
1. Arginase-1
General function:
Involved in arginase activity
Specific function:
Not Available
Gene Name:
ARG1
Uniprot ID:
P05089
Molecular weight:
34734.655
Enzyme Details
2. Epidermal growth factor receptor
General function:
Involved in transmembrane receptor protein tyrosine kinase activity
Specific function:
Isoform 2 may act as an antagonist of EGF action
Gene Name:
EGFR
Uniprot ID:
P00533
Molecular weight:
134276.2
Enzyme Details
3. Caspase-3
General function:
protein-containing complex binding
Specific function:
Involved in the activation cascade of caspases responsible for apoptosis execution. At the onset of apoptosis it proteolytically cleaves poly(ADP-ribose) polymerase (PARP) at a '216-Asp-|-Gly-217' bond. Cleaves and activates sterol regulatory element binding proteins (SREBPs) between the basic helix-loop-helix leucine zipper domain and the membrane attachment domain. Cleaves and activates caspase-6, -7 and -9. Involved in the cleavage of huntingtin. Triggers cell adhesion in sympathetic neurons through RET cleavage.
Gene Name:
CASP3
Uniprot ID:
P42574
Molecular weight:
31607.58