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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:29:59 UTC

Update Date

2022-07-15 00:38:55 UTC

HMDB ID

HMDB0029365

Secondary Accession Numbers

HMDB29365

Metabolite Identification

Common Name

N-trans-feruloyltyramine

Description

N-trans-feruloyltyramine (NFT), also known as Moupinamide or Alfrutamide or N-feruloyltyramine or trans-N-Feruloyltyramine, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It 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-Feruloyltyramine, N-trans-Feruloyltyramine and N-cis-Feruloyltyramine. N-trans-feruloyltyramine (Moupinamide) is a largely neutral molecule, that is somewhat insoluble in water. It exists as a white crystalline solid. Moupinamide or N-trans-Feruloyltyramine is one of the major phenylpropanoid amides that have been identified in the cannabis plant (PMID:6991645 ). It is also found in black and white peppers, the leaves of the Chinese pepper tree as well as eggplant (PMID: 34335243 ). This could make moupinamide a potential biomarker for the consumption of these plants/foods. Moupinamide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases, they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. N-trans-feruloyltyramine or NFT has a number of potential therapeutic or beneficial effects in humans. It is an inhibitor of COX 1 and COX 2 and has potential antioxidant properties (PMID: 19807156 ). More recently, trans-N-Caffeoyltyramine has been identified to by a potent HNF4α agonist (PMID: 35087037 ). HNF4A or HNF4α is also known as Hepatocyte nuclear factor 4 alpha. It is also known as NR2A1 (nuclear receptor subfamily 2, group A, member 1 and) is a nuclear receptor that in humans is encoded by the HNF4A gene. Moupinamide (NFT) 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 Moupinamide or NFT a strong candidate as a NAFLD (non-alcoholic fatty liver disease) therapeutic.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0029365
     RDKit          3D
Moupinamide
 42 43  0  0  0  0  0  0  0  0999 V2000
   -6.2417    1.3215   -2.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5223    0.0213   -1.7719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6028   -0.8236   -1.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2933   -0.3687   -1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2894   -1.1270   -0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9199   -0.6893   -0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5211    0.4966   -0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1487    1.0077   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1188    2.1743   -0.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    0.2066    0.0984 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1849    0.7281    0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1095   -0.2858    0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4779    0.2555    1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8612    0.9335    2.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1383    1.4495    2.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0809    1.2934    1.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3776    1.7965    1.4601 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6916    0.6125    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4209    0.1017    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6132   -2.4116   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8860   -2.8872   -0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8783   -2.0949   -0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1555   -2.6040   -0.9118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5681    1.2562   -3.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7036    1.8653   -1.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1422    1.8874   -2.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0711    0.6451   -1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2196   -1.3661    0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2514    1.1762   -1.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6301   -0.7501    0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    1.6709    0.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6466    0.9720   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0822   -1.2282    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6923   -0.5305    1.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1544    1.0726    2.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4526    1.9832    3.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6429    2.7249    1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3838    0.4561   -0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1378   -0.4360   -0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597   -3.0535    0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0975   -3.9081    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3600   -3.5436   -0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 23 42  1  0
M  END


  Mrv1652303202019012D          

 23 24  0  0  0  0            999 V2000
   -3.2614   -1.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9221   -0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9221   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2614    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5182   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5182   -0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7750   -1.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0319   -0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0319   -0.0004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6652    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0046   -1.2383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2614   -0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008   -1.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576   -0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886    1.2383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2614   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9221    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6652   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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 18  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 21  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029365

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(\C=C\C(=O)NCCC2=CC=C(O)C=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO4/c1-23-17-12-14(4-8-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5+

> <INCHI_KEY>
NPNNKDMSXVRADT-WEVVVXLNSA-N

> <FORMULA>
C18H19NO4

> <MOLECULAR_WEIGHT>
313.3478

> <EXACT_MASS>
313.131408101

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.55616315060448

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
3.0512487574095197

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.380955402735097

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.410052460238977

> <JCHEM_PKA_STRONGEST_BASIC>
6.377417070219201

> <JCHEM_POLAR_SURFACE_AREA>
82.28000000000002

> <JCHEM_REFRACTIVITY>
90.09309999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029365
     RDKit          3D
Moupinamide
 42 43  0  0  0  0  0  0  0  0999 V2000
   -6.2417    1.3215   -2.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5223    0.0213   -1.7719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6028   -0.8236   -1.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2933   -0.3687   -1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2894   -1.1270   -0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9199   -0.6893   -0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5211    0.4966   -0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1487    1.0077   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1188    2.1743   -0.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    0.2066    0.0984 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1849    0.7281    0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1095   -0.2858    0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4779    0.2555    1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8612    0.9335    2.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1383    1.4495    2.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0809    1.2934    1.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3776    1.7965    1.4601 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6916    0.6125    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4209    0.1017    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6132   -2.4116   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8860   -2.8872   -0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8783   -2.0949   -0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1555   -2.6040   -0.9118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5681    1.2562   -3.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7036    1.8653   -1.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1422    1.8874   -2.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0711    0.6451   -1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2196   -1.3661    0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2514    1.1762   -1.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6301   -0.7501    0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    1.6709    0.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6466    0.9720   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0822   -1.2282    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6923   -0.5305    1.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1544    1.0726    2.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4526    1.9832    3.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6429    2.7249    1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3838    0.4561   -0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1378   -0.4360   -0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597   -3.0535    0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0975   -3.9081    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3600   -3.5436   -0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 23 42  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      -6.088  -2.311   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.321  -1.541   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.321  -0.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.088   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.701  -0.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.701  -1.541   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.313  -2.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.926  -1.541   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.926  -0.001   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -8.708   0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.475  -2.311   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.088  -1.541   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.855  -2.311   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.468  -1.541   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.468  -0.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.080   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.847  -0.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.539   0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.539   2.311   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.855   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.088  -0.001   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.321   0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.708  -0.001   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   18                                                       
CONECT   10    3                                                            
CONECT   11   12                                                            
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18    9   17   19                                                  
CONECT   19   18                                                            
CONECT   20   15   21                                                       
CONECT   21   12   20   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0029365
HETATM    1  C1  UNL     1      -6.242   1.322  -2.206  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.522   0.021  -1.772  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.603  -0.824  -1.199  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.293  -0.369  -1.031  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.289  -1.127  -0.470  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.920  -0.689  -0.280  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.521   0.497  -0.639  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.149   1.008  -0.477  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.119   2.174  -0.863  1.00  0.00           O  
HETATM   10  N1  UNL     1       0.844   0.207   0.098  1.00  0.00           N  
HETATM   11  C8  UNL     1       2.185   0.728   0.248  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.110  -0.286   0.889  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.478   0.255   1.038  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.861   0.933   2.172  1.00  0.00           C  
HETATM   15  C12 UNL     1       6.138   1.449   2.334  1.00  0.00           C  
HETATM   16  C13 UNL     1       7.081   1.293   1.339  1.00  0.00           C  
HETATM   17  O3  UNL     1       8.378   1.796   1.460  1.00  0.00           O  
HETATM   18  C14 UNL     1       6.692   0.612   0.203  1.00  0.00           C  
HETATM   19  C15 UNL     1       5.421   0.102   0.047  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.613  -2.412  -0.053  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.886  -2.887  -0.202  1.00  0.00           C  
HETATM   22  C18 UNL     1      -5.878  -2.095  -0.774  1.00  0.00           C  
HETATM   23  O4  UNL     1      -7.155  -2.604  -0.912  1.00  0.00           O  
HETATM   24  H1  UNL     1      -5.568   1.256  -3.086  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.704   1.865  -1.398  1.00  0.00           H  
HETATM   26  H3  UNL     1      -7.142   1.887  -2.500  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.071   0.645  -1.370  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.220  -1.366   0.169  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.251   1.176  -1.097  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.630  -0.750   0.416  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.217   1.671   0.838  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.647   0.972  -0.750  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.082  -1.228   0.312  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.692  -0.531   1.896  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.154   1.073   2.965  1.00  0.00           H  
HETATM   36  H13 UNL     1       6.453   1.983   3.218  1.00  0.00           H  
HETATM   37  H14 UNL     1       8.643   2.725   1.157  1.00  0.00           H  
HETATM   38  H15 UNL     1       7.384   0.456  -0.615  1.00  0.00           H  
HETATM   39  H16 UNL     1       5.138  -0.436  -0.867  1.00  0.00           H  
HETATM   40  H17 UNL     1      -2.860  -3.053   0.397  1.00  0.00           H  
HETATM   41  H18 UNL     1      -5.097  -3.908   0.141  1.00  0.00           H  
HETATM   42  H19 UNL     1      -7.360  -3.544  -0.598  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   27
CONECT    5    6   20   20
CONECT    6    7    7   28
CONECT    7    8   29
CONECT    8    9    9   10
CONECT   10   11   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   14   19
CONECT   14   15   35
CONECT   15   16   16   36
CONECT   16   17   18
CONECT   17   37
CONECT   18   19   19   38
CONECT   19   39
CONECT   20   21   40
CONECT   21   22   22   41
CONECT   22   23
CONECT   23   42
END

HMDB0029365
     RDKit          3D
Moupinamide
 42 43  0  0  0  0  0  0  0  0999 V2000
   -6.2417    1.3215   -2.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5223    0.0213   -1.7719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6028   -0.8236   -1.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2933   -0.3687   -1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2894   -1.1270   -0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9199   -0.6893   -0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5211    0.4966   -0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1487    1.0077   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1188    2.1743   -0.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    0.2066    0.0984 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1849    0.7281    0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1095   -0.2858    0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4779    0.2555    1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8612    0.9335    2.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1383    1.4495    2.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0809    1.2934    1.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3776    1.7965    1.4601 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6916    0.6125    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4209    0.1017    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6132   -2.4116   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8860   -2.8872   -0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8783   -2.0949   -0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1555   -2.6040   -0.9118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5681    1.2562   -3.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7036    1.8653   -1.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1422    1.8874   -2.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0711    0.6451   -1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2196   -1.3661    0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2514    1.1762   -1.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6301   -0.7501    0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    1.6709    0.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6466    0.9720   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0822   -1.2282    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6923   -0.5305    1.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1544    1.0726    2.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4526    1.9832    3.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6429    2.7249    1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3838    0.4561   -0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1378   -0.4360   -0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597   -3.0535    0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0975   -3.9081    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3600   -3.5436   -0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 23 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-[(e)-Feruloyl]tyramine	ChEBI
trans-N-Feruloyltyramine	ChEBI
Feruloyltyramine, (Z)-isomer	MeSH
N-Feruloyltyramine	MeSH
Feruloyltyramine	MeSH
Feruloyltyramine, (e)-isomer	MeSH
(2,3)trans-N-(P-Hydroxyphenethyl)ferulamide	HMDB
N-trans-Feruloyltyramine	HMDB
Moupinamide	ChEBI
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidate	HMDB
(2,3) trans-N-(P-Hydroxyphenethyl)ferulamide	HMDB
(2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-2-propenamide	HMDB
(2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide	HMDB
NFT	HMDB
Alfrutamide	HMDB
3-(4-hydroxy-3-methoxyphenyl)-N-(2-(4-hydroxyphenyl)ethyl)-2-Propenamide	HMDB

Chemical Formula

C₁₈H₁₉NO₄

Average Molecular Weight

313.3478

Monoisotopic Molecular Weight

313.131408101

IUPAC Name

(Z,2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid

Traditional Name

(Z,2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid

CAS Registry Number

66648-43-9

SMILES

COC1=CC(\C=C\C(=O)NCCC2=CC=C(O)C=C2)=CC=C1O

InChI Identifier

InChI=1S/C18H19NO4/c1-23-17-12-14(4-8-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5+

InChI Key

NPNNKDMSXVRADT-WEVVVXLNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Carboximidic acid
Carboximidic acid derivative
Ether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tyramines (CHEBI:17818 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029365)
Cytoplasm (HMDB: HMDB0029365)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029365)

Source

Endogenous

Endogenous (HMDB: HMDB0029365)

Plant

Animal

Animal (HMDB: HMDB0029365)

Exogenous

Food

Food (HMDB: HMDB0029365)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Exogenous (HMDB: HMDB0029365)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	144.5 - 145 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	382.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	2.46	ALOGPS
logP	3.05	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.41	ChemAxon
pKa (Strongest Basic)	6.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.28 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	90.09 m³·mol⁻¹	ChemAxon
Polarizability	34.56 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]+	171.872	30932474
DeepCCS	[M-H]-	169.514	30932474
DeepCCS	[M-2H]-	203.518	30932474
DeepCCS	[M+Na]+	178.987	30932474
AllCCS	[M+H]+	175.5	32859911
AllCCS	[M+H-H2O]+	172.2	32859911
AllCCS	[M+NH4]+	178.6	32859911
AllCCS	[M+Na]+	179.5	32859911
AllCCS	[M-H]-	177.6	32859911
AllCCS	[M+Na-2H]-	177.5	32859911
AllCCS	[M+HCOO]-	177.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.11 minutes	32390414
Predicted by Siyang on May 30, 2022	11.5471 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.62 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1837.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	230.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	162.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	142.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	540.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	402.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	127.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1068.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	437.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1226.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	303.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	351.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	286.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	227.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	20.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Moupinamide	COC1=CC(\C=C\C(=O)NCCC2=CC=C(O)C=C2)=CC=C1O	4532.8	Standard polar	33892256
Moupinamide	COC1=CC(\C=C\C(=O)NCCC2=CC=C(O)C=C2)=CC=C1O	3004.2	Standard non polar	33892256
Moupinamide	COC1=CC(\C=C\C(=O)NCCC2=CC=C(O)C=C2)=CC=C1O	3323.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Moupinamide,1TMS,isomer #1	COC1=CC(/C=C/C(=O)NCCC2=CC=C(O[Si](C)(C)C)C=C2)=CC=C1O	3250.6	Semi standard non polar	33892256
Moupinamide,1TMS,isomer #2	COC1=CC(/C=C/C(=O)NCCC2=CC=C(O)C=C2)=CC=C1O[Si](C)(C)C	3286.1	Semi standard non polar	33892256
Moupinamide,1TMS,isomer #3	COC1=CC(/C=C/C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C)=CC=C1O	3255.3	Semi standard non polar	33892256
Moupinamide,2TMS,isomer #1	COC1=CC(/C=C/C(=O)NCCC2=CC=C(O[Si](C)(C)C)C=C2)=CC=C1O[Si](C)(C)C	3316.2	Semi standard non polar	33892256
Moupinamide,2TMS,isomer #2	COC1=CC(/C=C/C(=O)N(CCC2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)=CC=C1O	3177.3	Semi standard non polar	33892256
Moupinamide,2TMS,isomer #3	COC1=CC(/C=C/C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3244.2	Semi standard non polar	33892256
Moupinamide,3TMS,isomer #1	COC1=CC(/C=C/C(=O)N(CCC2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3225.4	Semi standard non polar	33892256
Moupinamide,3TMS,isomer #1	COC1=CC(/C=C/C(=O)N(CCC2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2960.5	Standard non polar	33892256
Moupinamide,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)NCCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O	3543.7	Semi standard non polar	33892256
Moupinamide,1TBDMS,isomer #2	COC1=CC(/C=C/C(=O)NCCC2=CC=C(O)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3560.7	Semi standard non polar	33892256
Moupinamide,1TBDMS,isomer #3	COC1=CC(/C=C/C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O	3494.3	Semi standard non polar	33892256
Moupinamide,2TBDMS,isomer #1	COC1=CC(/C=C/C(=O)NCCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3839.5	Semi standard non polar	33892256
Moupinamide,2TBDMS,isomer #2	COC1=CC(/C=C/C(=O)N(CCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O	3684.1	Semi standard non polar	33892256
Moupinamide,2TBDMS,isomer #3	COC1=CC(/C=C/C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3726.3	Semi standard non polar	33892256
Moupinamide,3TBDMS,isomer #1	COC1=CC(/C=C/C(=O)N(CCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3948.7	Semi standard non polar	33892256
Moupinamide,3TBDMS,isomer #1	COC1=CC(/C=C/C(=O)N(CCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3534.5	Standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280537

PDB ID

Not Available

ChEBI ID

17818

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1808791

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 ]
Song Y, Mei T, Liu Y, Kong S, Zhang J, Xie M, Ou S, Liang M, Wang Q: Metabolites Identification of Chemical Constituents From the Eggplant (Solanum melongena L.) Calyx in Rats by UPLC/ESI/qTOF-MS Analysis and Their Cytotoxic Activities. Front Pharmacol. 2021 Jul 15;12:655008. doi: 10.3389/fphar.2021.655008. eCollection 2021. [PubMed:34335243 ]
Park JB: Isolation and characterization of N-feruloyltyramine as the P-selectin expression suppressor from garlic (Allium sativum). J Agric Food Chem. 2009 Oct 14;57(19):8868-72. doi: 10.1021/jf9018382. [PubMed:19807156 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for N-trans-feruloyltyramine (HMDB0029365)

MOL for HMDB0029365 (N-trans-feruloyltyramine)

3D MOL for HMDB0029365 (N-trans-feruloyltyramine)

3D SDF for HMDB0029365 (N-trans-feruloyltyramine)

3D-SDF for HMDB0029365 (N-trans-feruloyltyramine)

PDB for HMDB0029365 (N-trans-feruloyltyramine)

3D PDB for HMDB0029365 (N-trans-feruloyltyramine)

SMILES for HMDB0029365 (N-trans-feruloyltyramine)

INCHI for HMDB0029365 (N-trans-feruloyltyramine)

Structure for HMDB0029365 (N-trans-feruloyltyramine)

3D Structure for HMDB0029365 (N-trans-feruloyltyramine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized