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enzymes (4) Show 4 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2022-07-13 16:52:13 UTC

Update Date

2022-07-15 03:19:41 UTC

HMDB ID

HMDB0341059

Secondary Accession Numbers

None

Metabolite 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 3D SDF PDB 3D PDB SMILES InChI

HMDB0033026
     RDKit          3D
N-cis-Caffeoyltyramine
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.3188    0.7340    1.6173 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267    0.0224    0.7387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932    0.1538    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4403   -0.5117   -0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -0.3836   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5565   -1.1503   -1.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9224   -1.0923   -1.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6683   -0.2601   -0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0399   -0.2514   -0.8158 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0190    0.4925    0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7536    1.3313    1.1503 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6317    0.4358    0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431   -0.8135   -0.0678 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -0.8762    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5630    0.4768   -0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0475    0.4241   -0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8258    0.1042   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2127    0.0539   -1.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8501    0.3155    0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2364    0.2667    0.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0615    0.6344    1.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6842    0.6857    1.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295    0.8232    1.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9316   -1.1852   -0.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9648   -1.8169   -1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4270   -1.7026   -2.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7228    0.2766   -0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7495    1.3802    1.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2043    1.0472    1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0437   -1.4056   -0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2756   -1.1815    1.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3744   -1.6623   -0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2871    0.7939   -1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1722    1.2451    0.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3404   -0.1065   -2.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8447   -0.1974   -1.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7862    1.1225    0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5705    0.8412    2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0674    0.9359    1.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 12  5  1  0
 22 16  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
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  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>
HMDB0341059

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0033026
     RDKit          3D
N-cis-Caffeoyltyramine
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.3188    0.7340    1.6173 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267    0.0224    0.7387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932    0.1538    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4403   -0.5117   -0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -0.3836   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5565   -1.1503   -1.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9224   -1.0923   -1.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6683   -0.2601   -0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0399   -0.2514   -0.8158 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0190    0.4925    0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7536    1.3313    1.1503 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6317    0.4358    0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431   -0.8135   -0.0678 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -0.8762    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5630    0.4768   -0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0475    0.4241   -0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8258    0.1042   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2127    0.0539   -1.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8501    0.3155    0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2364    0.2667    0.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0615    0.6344    1.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6842    0.6857    1.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295    0.8232    1.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9316   -1.1852   -0.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9648   -1.8169   -1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4270   -1.7026   -2.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7228    0.2766   -0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7495    1.3802    1.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2043    1.0472    1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0437   -1.4056   -0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2756   -1.1815    1.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3744   -1.6623   -0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2871    0.7939   -1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1722    1.2451    0.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3404   -0.1065   -2.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8447   -0.1974   -1.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7862    1.1225    0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5705    0.8412    2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0674    0.9359    1.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 12  5  1  0
 22 16  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
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  0
M  END

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

COMPND    HMDB0033026
HETATM    1  O1  UNL     1      -0.319   0.734   1.617  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.227   0.022   0.739  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.693   0.154   0.650  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.440  -0.512  -0.209  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.901  -0.384  -0.301  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.557  -1.150  -1.258  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.922  -1.092  -1.412  1.00  0.00           C  
HETATM    8  C7  UNL     1       6.668  -0.260  -0.606  1.00  0.00           C  
HETATM    9  O2  UNL     1       8.040  -0.251  -0.816  1.00  0.00           O  
HETATM   10  C8  UNL     1       6.019   0.493   0.335  1.00  0.00           C  
HETATM   11  O3  UNL     1       6.754   1.331   1.150  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.632   0.436   0.494  1.00  0.00           C  
HETATM   13  N1  UNL     1      -0.543  -0.814  -0.068  1.00  0.00           N  
HETATM   14  C10 UNL     1      -1.977  -0.876   0.081  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.563   0.477  -0.215  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.047   0.424  -0.073  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.826   0.104  -1.166  1.00  0.00           C  
HETATM   18  C14 UNL     1      -6.213   0.054  -1.038  1.00  0.00           C  
HETATM   19  C15 UNL     1      -6.850   0.315   0.157  1.00  0.00           C  
HETATM   20  O4  UNL     1      -8.236   0.267   0.291  1.00  0.00           O  
HETATM   21  C16 UNL     1      -6.061   0.634   1.244  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.684   0.686   1.122  1.00  0.00           C  
HETATM   23  H1  UNL     1       2.229   0.823   1.309  1.00  0.00           H  
HETATM   24  H2  UNL     1       1.932  -1.185  -0.877  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.965  -1.817  -1.905  1.00  0.00           H  
HETATM   26  H4  UNL     1       6.427  -1.703  -2.172  1.00  0.00           H  
HETATM   27  H5  UNL     1       8.723   0.277  -0.338  1.00  0.00           H  
HETATM   28  H6  UNL     1       7.750   1.380   1.045  1.00  0.00           H  
HETATM   29  H7  UNL     1       4.204   1.047   1.242  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.044  -1.406  -0.797  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.276  -1.182   1.112  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.374  -1.662  -0.607  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.287   0.794  -1.260  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.172   1.245   0.457  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.340  -0.107  -2.122  1.00  0.00           H  
HETATM   36  H14 UNL     1      -6.845  -0.197  -1.891  1.00  0.00           H  
HETATM   37  H15 UNL     1      -8.786   1.123   0.120  1.00  0.00           H  
HETATM   38  H16 UNL     1      -6.570   0.841   2.190  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.067   0.936   1.975  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   23
CONECT    4    5   24
CONECT    5    6    6   12
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   10
CONECT    9   27
CONECT   10   11   12   12
CONECT   11   28
CONECT   12   29
CONECT   13   14   30
CONECT   14   15   31   32
CONECT   15   16   33   34
CONECT   16   17   17   22
CONECT   17   18   35
CONECT   18   19   19   36
CONECT   19   20   21
CONECT   20   37
CONECT   21   22   22   38
CONECT   22   39
END

HMDB0033026
     RDKit          3D
N-cis-Caffeoyltyramine
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.3188    0.7340    1.6173 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267    0.0224    0.7387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932    0.1538    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4403   -0.5117   -0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -0.3836   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5565   -1.1503   -1.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9224   -1.0923   -1.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6683   -0.2601   -0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0399   -0.2514   -0.8158 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0190    0.4925    0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7536    1.3313    1.1503 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6317    0.4358    0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431   -0.8135   -0.0678 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -0.8762    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5630    0.4768   -0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0475    0.4241   -0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8258    0.1042   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2127    0.0539   -1.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8501    0.3155    0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2364    0.2667    0.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0615    0.6344    1.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6842    0.6857    1.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295    0.8232    1.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9316   -1.1852   -0.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9648   -1.8169   -1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4270   -1.7026   -2.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7228    0.2766   -0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7495    1.3802    1.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2043    1.0472    1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0437   -1.4056   -0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2756   -1.1815    1.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3744   -1.6623   -0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2871    0.7939   -1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1722    1.2451    0.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3404   -0.1065   -2.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8447   -0.1974   -1.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7862    1.1225    0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5705    0.8412    2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0674    0.9359    1.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 12  5  1  0
 22 16  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
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

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

Chemical Formula

C₁₇H₁₇NO₄

Average Molecular Weight

299.3212

Monoisotopic Molecular Weight

299.115758037

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 Number

Not Available

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

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

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	169.077	30932474
DeepCCS	[M-H]-	166.719	30932474
DeepCCS	[M-2H]-	200.521	30932474
DeepCCS	[M+Na]+	176.52	30932474
AllCCS	[M+H]+	170.9	32859911
AllCCS	[M+H-H2O]+	167.5	32859911
AllCCS	[M+NH4]+	174.1	32859911
AllCCS	[M+Na]+	175.0	32859911
AllCCS	[M-H]-	173.3	32859911
AllCCS	[M+Na-2H]-	173.0	32859911
AllCCS	[M+HCOO]-	172.8	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-cis-Caffeoyltyramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0910000000-1c173cf7b0466780ad35	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-cis-Caffeoyltyramine GC-MS (3 TMS) - 70eV, Positive	splash10-0udi-2214490000-6874f89c7d4c31b6fc55	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-cis-Caffeoyltyramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-trans-Caffeoyltyramine 10V, Positive-QTOF	splash10-0f79-0902000000-bb08be6dcc7c2a45bf35	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-trans-Caffeoyltyramine 20V, Positive-QTOF	splash10-00kr-0900000000-c6428a4104f73aef3c4b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-trans-Caffeoyltyramine 40V, Positive-QTOF	splash10-05w0-4900000000-4fca258d19782c0fb73f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-trans-Caffeoyltyramine 10V, Negative-QTOF	splash10-0002-0390000000-bc4e0e59663ef5008545	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-trans-Caffeoyltyramine 20V, Negative-QTOF	splash10-06tk-0940000000-bb3d5ef1352903365d4d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-trans-Caffeoyltyramine 40V, Negative-QTOF	splash10-0006-7900000000-9b04559c19d2c27de1e7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-trans-Caffeoyltyramine 10V, Negative-QTOF	splash10-0002-0090000000-ee9973b640e1d151e668	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-trans-Caffeoyltyramine 20V, Negative-QTOF	splash10-000b-0960000000-63c941ca4aabf1671202	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-trans-Caffeoyltyramine 40V, Negative-QTOF	splash10-000i-2910000000-97509ed3cb2dd7b98ff9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-trans-Caffeoyltyramine 10V, Positive-QTOF	splash10-0udi-0609000000-b6bd2633941fd45aa3ac	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-trans-Caffeoyltyramine 20V, Positive-QTOF	splash10-0fk9-0911000000-fd9a2c7ec9b5be9edabb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-trans-Caffeoyltyramine 40V, Positive-QTOF	splash10-05i0-4930000000-5dfe8817cc8d0f88a5ef	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08754

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011018

KNApSAcK ID

C00000662

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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
Lee SH, Veeriah V, Levine F: Liver fat storage is controlled by HNF4alpha through induction of lipophagy and is reversed by a potent HNF4alpha agonist. Cell Death Dis. 2021 Jun 11;12(6):603. doi: 10.1038/s41419-021-03862-x. [PubMed:34117215 ]
Ko HJ, Ahn EK, Oh JS: Ntransrhocaffeoyl tyramine isolated from Tribulus terrestris exerts antiinflammatory effects in lipopolysaccharidestimulated RAW 264.7 cells. Int J Mol Med. 2015 Oct;36(4):1042-8. doi: 10.3892/ijmm.2015.2301. Epub 2015 Aug 3. [PubMed:26239676 ]
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 ]
Olatunji OJ, Chen H, Zhou Y: Neuroprotective effect of trans-N-caffeoyltyramine from Lycium chinense against H2O2 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 ]

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. Hepatocyte nuclear factor 4-alpha

General function:: Not Available
Specific function:: Transcriptional regulator which controls the expression of hepatic genes during the transition of endodermal cells to hepatic progenitor cells, facilitating the recruitment of RNA pol II to the promoters of target genes. Activates the transcription of CYP2C38. Represses the CLOCK-ARNTL/BMAL1 transcriptional activity and is essential for circadian rhythm maintenance and period regulation in the liver and colon cells.
Gene Name:: HNF4A
Uniprot ID:: P41235
Molecular weight:: Not Available

Enzyme Details

4. Caspase-3

General function:: Not Available
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. Cleaves and inhibits serine/threonine-protein kinase AKT1 in response to oxidative stress. Acts as an inhibitor of type I interferon production during virus-induced apoptosis by mediating cleavage of antiviral proteins CGAS, IRF3 and MAVS, thereby preventing cytokine overproduction. Cleaves XRCC4 and phospholipid scramblase proteins XKR4, XKR8 and XKR9, leading to promote phosphatidylserine exposure on apoptotic cell surface.
Gene Name:: CASP3
Uniprot ID:: P42574
Molecular weight:: 31.0

Showing metabocard for N-trans-Caffeoyltyramine (HMDB0341059)

MOL for HMDB0341059 (N-trans-Caffeoyltyramine)

3D MOL for HMDB0341059 (N-trans-Caffeoyltyramine)

3D SDF for HMDB0341059 (N-trans-Caffeoyltyramine)

3D-SDF for HMDB0341059 (N-trans-Caffeoyltyramine)

PDB for HMDB0341059 (N-trans-Caffeoyltyramine)

3D PDB for HMDB0341059 (N-trans-Caffeoyltyramine)

SMILES for HMDB0341059 (N-trans-Caffeoyltyramine)

INCHI for HMDB0341059 (N-trans-Caffeoyltyramine)

Structure for HMDB0341059 (N-trans-Caffeoyltyramine)

3D Structure for HMDB0341059 (N-trans-Caffeoyltyramine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

Enzymes