NP-MRD: Showing NP-Card for N-trans-Caffeoyltyramine (NP0045035)

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Record Information

Version

2.0

Created at

2022-03-10 18:53:06 UTC

Updated at

2022-12-14 16:27:40 UTC

NP-MRD ID

NP0045035

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-trans-Caffeoyltyramine

Description

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.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.1690    2.4733   -0.2145 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3380    1.3333   -0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7759    1.2186    0.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4666    0.1202    0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9160    0.0382    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5227   -1.2134    0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8888   -1.3532    0.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7043   -0.2364    0.4896 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0583   -0.3914    0.5992 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1399    1.0161    0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9800    2.1180    0.3287 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7721    1.1112    0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4760    0.1787   -0.0603 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9267    0.3402   -0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6090   -1.0322   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0690   -0.7617   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8831   -0.5379    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2275   -0.2916    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8155   -0.2584   -0.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1808   -0.0069   -0.7138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9995   -0.4825   -1.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6547   -0.7290   -1.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661    2.1488   -0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8939   -0.8113    0.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8820   -2.0924    0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3672   -2.3267    0.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7416    0.3283    0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5566    3.0297    0.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3647    2.1034    0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1038   -0.7797    0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0941    0.8187   -1.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3137    0.9922    0.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3545   -1.5572    0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3041   -1.6416   -0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4623   -0.5559    1.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8990   -0.1100    1.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7963   -0.8220   -0.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4026   -0.4683   -2.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9937   -0.9091   -2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 16 22  1  0
 22 21  2  0
 21 19  1  0
 12  5  1  0
 20 37  1  0
 18 36  1  0
 17 35  1  0
 15 33  1  0
 15 34  1  0
 14 31  1  0
 14 32  1  0
 13 30  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 22 39  1  0
 21 38  1  0
M  END


  Mrv1652303202019022D          

 22 23  0  0  0  0            999 V2000
   -2.2266    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9469    0.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5889    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5889   -0.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9469   -1.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2266   -0.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -1.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7835   -0.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7835    0.0007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0605    0.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0605    1.2020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3105    0.4007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1044    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3828    0.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6611    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1483   -0.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -1.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5752   -0.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5297    0.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7929    0.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2197    0.5244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3105   -1.1236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3 12  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 15  1  0  0  0  0
 13 14  1  0  0  0  0
 13 16  2  0  0  0  0
 13 20  1  0  0  0  0
 14 15  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045035

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
VSHUQLRHTJOKTA-XBXARRHUSA-N

> <FORMULA>
C17H17NO4

> <MOLECULAR_WEIGHT>
299.3212

> <EXACT_MASS>
299.115758037

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.73140322622816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(E,2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.921375411442294

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.075826369280593

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.359309020442711

> <JCHEM_PKA_STRONGEST_BASIC>
6.319368426582382

> <JCHEM_POLAR_SURFACE_AREA>
93.28000000000002

> <JCHEM_REFRACTIVITY>
85.6108

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(E,2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      -4.156   0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.501   0.748   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.699   0.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.699  -1.494   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.501  -2.244   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.156  -1.494   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.810  -2.244   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.463  -1.494   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.463   0.001   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.113   0.748   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.113   2.244   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -8.046   0.748   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.928   0.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.581   0.748   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.234   0.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.010  -1.538   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.383  -2.244   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.674  -1.400   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.589   0.137   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.213   0.833   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.877   0.979   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.046  -2.097   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10                                                            
CONECT   12    3                                                            
CONECT   13   14   16   20                                                  
CONECT   14   13   15                                                       
CONECT   15   10   14                                                       
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   13   19                                                       
CONECT   21   19                                                            
CONECT   22   18                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
trans-N-Caffeoyltyramine	HMDB
(2E)-3-(3,4-Dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidate	Generator
N-Caffeoyltyramine	MeSH

Chemical Formula

C₁₇H₁₇NO₄

Average Mass

299.3212 Da

Monoisotopic Mass

299.11576 Da

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 Number

219773-48-5

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 Key

VSHUQLRHTJOKTA-XBXARRHUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Annona cherimola	Plant	KNApSAcK
Annona crassiflora	LOTUS Database	35616633
Annona montana	LOTUS Database	35616633
Cannabis sativa	NULL	Not Available
Ceratostigma willmottianum	LOTUS Database	35616633
Crinum asiaticum	LOTUS Database	35616633
Limoniastrum guyonianum	LOTUS Database	35616633
Limonium sinense	LOTUS Database	35616633
Lycium chinense	LOTUS Database	35616633
Mitrephora tomentosa	LOTUS Database	35616633
Piper umbellatum	LOTUS Database	35616633
Populus trichocarpa	Plant	KNApSAcK
Tetragonia tetragonioides	LOTUS Database	35616633
Tinospora crispa	Plant	KNApSAcK
Tribulus terrestris	Plant	KNApSAcK
Xylopia aethiopica	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.26	ALOGPS
logP	2.92	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	6.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	93.28 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.61 m³·mol⁻¹	ChemAxon
Polarizability	31.73 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033026

DrugBank ID

DB08754

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011018

KNApSAcK ID

Not Available

Chemspider ID

8170478

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9994897

PDB ID

Y13

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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 ]
Han SH, Lee HH, Lee IS, Moon YH, Woo ER: A new phenolic amide from Lycium chinense Miller. Arch Pharm Res. 2002 Aug;25(4):433-7. doi: 10.1007/BF02976596. [PubMed:12214850 ]
Lee DG, Park Y, Kim MR, Jung HJ, Seu YB, Hahm KS, Woo ER: Anti-fungal effects of phenolic amides isolated from the root bark of Lycium chinense. Biotechnol Lett. 2004 Jul;26(14):1125-30. doi: 10.1023/B:BILE.0000035483.85790.f7. [PubMed:15266117 ]
Olatunji OJ, Chen H, Zhou Y: Neuroprotective effect of trans-N-caffeoyltyramine from Lycium chinense against H(2)O(2) induced cytotoxicity in PC12 cells by attenuating oxidative stress. Biomed Pharmacother. 2017 Sep;93:895-902. doi: 10.1016/j.biopha.2017.07.013. Epub 2017 Jul 13. [PubMed:28715870 ]
Veeriah V, Lee SH, Levine F: Long-term oral administration of an HNF4alpha agonist prevents weight gain and hepatic steatosis by promoting increased mitochondrial mass and function. Cell Death Dis. 2022 Jan 27;13(1):89. doi: 10.1038/s41419-022-04521-5. [PubMed:35087037 ]

Showing NP-Card for N-trans-Caffeoyltyramine (NP0045035)

MOL for NP0045035 (N-trans-Caffeoyltyramine)

3D MOL for NP0045035 (N-trans-Caffeoyltyramine)

3D SDF for NP0045035 (N-trans-Caffeoyltyramine)

3D-SDF for NP0045035 (N-trans-Caffeoyltyramine)

PDB for NP0045035 (N-trans-Caffeoyltyramine)

3D PDB for NP0045035 (N-trans-Caffeoyltyramine)

SMILES for NP0045035 (N-trans-Caffeoyltyramine)

INCHI for NP0045035 (N-trans-Caffeoyltyramine)

Structure for NP0045035 (N-trans-Caffeoyltyramine)

3D Structure for NP0045035 (N-trans-Caffeoyltyramine)