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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:31:09 UTC

Update Date

2022-07-15 01:31:02 UTC

HMDB ID

HMDB0036381

Secondary Accession Numbers

HMDB36381

Metabolite Identification

Common Name

N-cis-feruloyltyramine

Description

N-cis-feruloyltyramine or cis-N-Feruloyltyramine (CFT) 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. Moupinamide is a largely neutral molecule, that is somewhat insoluble in water. It exists as a pale yellow oil. N-cis-Feruloyltyramine 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-cis-Feruloyltyramine has been found within a few different foods or plants (especially their stems), such as yellow bell peppers, red bell peppers, orange bell peppers and green bell peppers (Capsicum annuum) (PMID: 21425680 ). This could make N-cis-feruloyltyramine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-cis-Feruloyltyramine.

Structure

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

HMDB0036381
     RDKit          3D
N-cis-Feruloyltyramine
 42 43  0  0  0  0  0  0  0  0999 V2000
    6.0736    0.2998   -2.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5128    1.1705   -1.4538 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4779    0.7611   -0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650   -0.4979   -0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9174   -0.9627    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5512   -2.3242    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660   -2.8190    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -2.0937    0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9949   -2.9200    0.5885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231   -0.8725    0.4837 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4108   -0.2957    0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3352   -0.4060   -0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6287    0.2393   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6134   -0.5204    0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8082    0.0571    0.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0622    1.4002    0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2783    1.9819    1.0468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0656    2.1392    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8657    1.5759   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4513   -0.0513    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9707    1.2594    1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865    1.6634    0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4926    2.9540    0.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6303   -0.5135   -1.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6249    0.8543   -3.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025   -0.1698   -2.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3580   -1.2143   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3899   -3.0829   -0.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2466   -3.9443    0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1768   -3.5019   -0.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2656    0.7951    0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9430   -0.6921    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -1.4246   -0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8999    0.1638   -1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4829   -1.5927    0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6097   -0.5115    1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3543    2.3698    1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2818    3.2032   -0.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0883    2.1648   -0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -0.2553    1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877    1.9736    1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1690    3.6396    1.0303 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
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  6  7  2  0
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M  END


  Mrv0541 05061309062D          

 23 24  0  0  0  0            999 V2000
   -8.5737   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
 11 10  1  0  0  0  0
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 17 12  1  0  0  0  0
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 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 22 18  1  0  0  0  0
 23  1  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036381

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C/C(/O)=N/CCC2=CC=C(O)C=C2)=C1

> <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-UITAMQMPSA-N

> <FORMULA>
C18H19NO4

> <MOLECULAR_WEIGHT>
313.3478

> <EXACT_MASS>
313.131408101

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.822034820731396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
3.620756252333333

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.386374784984497

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.58430193677384

> <JCHEM_PKA_STRONGEST_BASIC>
4.850258367533686

> <JCHEM_POLAR_SURFACE_AREA>
82.28000000000002

> <JCHEM_REFRACTIVITY>
90.09309999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036381
     RDKit          3D
N-cis-Feruloyltyramine
 42 43  0  0  0  0  0  0  0  0999 V2000
    6.0736    0.2998   -2.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5128    1.1705   -1.4538 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4779    0.7611   -0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650   -0.4979   -0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9174   -0.9627    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5512   -2.3242    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660   -2.8190    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -2.0937    0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9949   -2.9200    0.5885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231   -0.8725    0.4837 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4108   -0.2957    0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3352   -0.4060   -0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6287    0.2393   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6134   -0.5204    0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8082    0.0571    0.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0622    1.4002    0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2783    1.9819    1.0468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0656    2.1392    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8657    1.5759   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4513   -0.0513    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9707    1.2594    1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865    1.6634    0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4926    2.9540    0.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6303   -0.5135   -1.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6249    0.8543   -3.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025   -0.1698   -2.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3580   -1.2143   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3899   -3.0829   -0.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2466   -3.9443    0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1768   -3.5019   -0.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2656    0.7951    0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9430   -0.6921    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -1.4246   -0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8999    0.1638   -1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4829   -1.5927    0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6097   -0.5115    1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3543    2.3698    1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2818    3.2032   -0.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0883    2.1648   -0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -0.2553    1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877    1.9736    1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1690    3.6396    1.0303 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  1  0
  8 10  2  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
  9 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                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0     -16.004 -13.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.336 -14.630   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -6.668 -11.550   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0     -14.671 -11.550   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0     -14.671 -14.630   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2    6   13                                                       
CONECT    3    7   13                                                       
CONECT    4    8   14                                                       
CONECT    5    9   14                                                       
CONECT    6    2   15                                                       
CONECT    7    3   15                                                       
CONECT    8    4   16                                                       
CONECT    9    5   18                                                       
CONECT   10   11   13                                                       
CONECT   11   10   19                                                       
CONECT   12   14   17                                                       
CONECT   13    2    3   10                                                  
CONECT   14    4    5   12                                                  
CONECT   15    6    7   20                                                  
CONECT   16    8   17   21                                                  
CONECT   17   12   16   23                                                  
CONECT   18    9   19   22                                                  
CONECT   19   11   18                                                       
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   18                                                            
CONECT   23    1   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0036381
HETATM    1  C1  UNL     1       6.074   0.300  -2.418  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.513   1.170  -1.454  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.478   0.761  -0.613  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.965  -0.498  -0.688  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.917  -0.963   0.140  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.551  -2.324   0.078  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.366  -2.819   0.207  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.168  -2.094   0.418  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.995  -2.920   0.589  1.00  0.00           O  
HETATM   10  N1  UNL     1      -0.123  -0.872   0.484  1.00  0.00           N  
HETATM   11  C8  UNL     1      -1.411  -0.296   0.708  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.335  -0.406  -0.477  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.629   0.239  -0.083  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.613  -0.520   0.505  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.808   0.057   0.873  1.00  0.00           C  
HETATM   16  C13 UNL     1      -6.062   1.400   0.670  1.00  0.00           C  
HETATM   17  O3  UNL     1      -7.278   1.982   1.047  1.00  0.00           O  
HETATM   18  C14 UNL     1      -5.066   2.139   0.082  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.866   1.576  -0.291  1.00  0.00           C  
HETATM   20  C16 UNL     1       2.451  -0.051   1.033  1.00  0.00           C  
HETATM   21  C17 UNL     1       2.971   1.259   1.123  1.00  0.00           C  
HETATM   22  C18 UNL     1       3.986   1.663   0.296  1.00  0.00           C  
HETATM   23  O4  UNL     1       4.493   2.954   0.389  1.00  0.00           O  
HETATM   24  H1  UNL     1       6.630  -0.513  -1.945  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.625   0.854  -3.193  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.202  -0.170  -2.946  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.358  -1.214  -1.412  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.390  -3.083  -0.106  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.247  -3.944   0.148  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.177  -3.502  -0.227  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.266   0.795   0.897  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.943  -0.692   1.583  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.561  -1.425  -0.783  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.900   0.164  -1.321  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.483  -1.593   0.697  1.00  0.00           H  
HETATM   36  H13 UNL     1      -6.610  -0.512   1.340  1.00  0.00           H  
HETATM   37  H14 UNL     1      -7.354   2.370   1.992  1.00  0.00           H  
HETATM   38  H15 UNL     1      -5.282   3.203  -0.072  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.088   2.165  -0.753  1.00  0.00           H  
HETATM   40  H17 UNL     1       1.708  -0.255   1.804  1.00  0.00           H  
HETATM   41  H18 UNL     1       2.588   1.974   1.837  1.00  0.00           H  
HETATM   42  H19 UNL     1       4.169   3.640   1.030  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   10   10
CONECT    9   30
CONECT   10   11
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

HMDB0036381
     RDKit          3D
N-cis-Feruloyltyramine
 42 43  0  0  0  0  0  0  0  0999 V2000
    6.0736    0.2998   -2.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5128    1.1705   -1.4538 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4779    0.7611   -0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650   -0.4979   -0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9174   -0.9627    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5512   -2.3242    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660   -2.8190    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -2.0937    0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9949   -2.9200    0.5885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231   -0.8725    0.4837 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4108   -0.2957    0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3352   -0.4060   -0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6287    0.2393   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6134   -0.5204    0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8082    0.0571    0.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0622    1.4002    0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2783    1.9819    1.0468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0656    2.1392    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8657    1.5759   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4513   -0.0513    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9707    1.2594    1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865    1.6634    0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4926    2.9540    0.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6303   -0.5135   -1.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6249    0.8543   -3.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025   -0.1698   -2.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3580   -1.2143   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3899   -3.0829   -0.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2466   -3.9443    0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1768   -3.5019   -0.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2656    0.7951    0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9430   -0.6921    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -1.4246   -0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8999    0.1638   -1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4829   -1.5927    0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6097   -0.5115    1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3543    2.3698    1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2818    3.2032   -0.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0883    2.1648   -0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -0.2553    1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877    1.9736    1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1690    3.6396    1.0303 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  1  0
  8 10  2  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
  9 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
cis-N-Feruloyltyramine	HMDB
N-cis-Feruloyl tyramine	HMDB
(2Z)-3-(4-Hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidate	HMDB
N-cis-Feruloyltyramine	HMDB
(2,3) cis-N-(P-Hydroxyphenethyl)ferulamide	HMDB
(2Z)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-2-propenamide	HMDB
(2Z)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide	HMDB
Feruloyltyramine	HMDB
Feruloyltyramine, (Z)-isomer	HMDB
NCT	HMDB
N-[(Z)-Feruloyl]tyramine	HMDB
N-Feruloyltyramine	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,2Z)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]propa-2-enimidic acid

Traditional Name

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

CAS Registry Number

80510-09-4

SMILES

COC1=C(O)C=CC(\C=C/C(/O)=N/CCC2=CC=C(O)C=C2)=C1

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-UITAMQMPSA-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
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036381)
Cytoplasm (HMDB: HMDB0036381)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036381)

Source

Exogenous

Exogenous (HMDB: HMDB0036381)

Food

Food (HMDB: HMDB0036381)

Fruit

Tropical fruit

Cherimoya (FooDB: FOOD00326)

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Orange bell pepper (FooDB: FOOD00879)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0036381)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036381)

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
Water Solubility	0.021 g/L	ALOGPS
logP	3.12	ALOGPS
logP	3.62	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.58	ChemAxon
pKa (Strongest Basic)	4.85	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	33.82 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]+	186.737	30932474
DeepCCS	[M-H]-	184.379	30932474
DeepCCS	[M-2H]-	218.529	30932474
DeepCCS	[M+Na]+	194.011	30932474
AllCCS	[M+H]+	175.5	32859911
AllCCS	[M+H-H2O]+	172.1	32859911
AllCCS	[M+NH4]+	178.5	32859911
AllCCS	[M+Na]+	179.4	32859911
AllCCS	[M-H]-	177.9	32859911
AllCCS	[M+Na-2H]-	177.6	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.	4.67 minutes	32390414
Predicted by Siyang on May 30, 2022	10.7947 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.53 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1644.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	215.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	153.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	123.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	498.0 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	345.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	125.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	937.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	410.6 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	1125.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	285.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	325.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	287.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	236.8 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	17.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-cis-Feruloyltyramine	COC1=C(O)C=CC(\C=C/C(/O)=N/CCC2=CC=C(O)C=C2)=C1	4750.4	Standard polar	33892256
N-cis-Feruloyltyramine	COC1=C(O)C=CC(\C=C/C(/O)=N/CCC2=CC=C(O)C=C2)=C1	3079.0	Standard non polar	33892256
N-cis-Feruloyltyramine	COC1=C(O)C=CC(\C=C/C(/O)=N/CCC2=CC=C(O)C=C2)=C1	3151.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-cis-Feruloyltyramine,1TMS,isomer #1	COC1=CC(/C=C\C(O)=N\CCC2=CC=C(O)C=C2)=CC=C1O[Si](C)(C)C	3166.2	Semi standard non polar	33892256
N-cis-Feruloyltyramine,1TMS,isomer #2	COC1=CC(/C=C\C(=N\CCC2=CC=C(O)C=C2)O[Si](C)(C)C)=CC=C1O	3170.0	Semi standard non polar	33892256
N-cis-Feruloyltyramine,1TMS,isomer #3	COC1=CC(/C=C\C(O)=N\CCC2=CC=C(O[Si](C)(C)C)C=C2)=CC=C1O	3104.9	Semi standard non polar	33892256
N-cis-Feruloyltyramine,2TMS,isomer #1	COC1=CC(/C=C\C(=N\CCC2=CC=C(O)C=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3131.8	Semi standard non polar	33892256
N-cis-Feruloyltyramine,2TMS,isomer #2	COC1=CC(/C=C\C(O)=N\CCC2=CC=C(O[Si](C)(C)C)C=C2)=CC=C1O[Si](C)(C)C	3109.8	Semi standard non polar	33892256
N-cis-Feruloyltyramine,2TMS,isomer #3	COC1=CC(/C=C\C(=N\CCC2=CC=C(O[Si](C)(C)C)C=C2)O[Si](C)(C)C)=CC=C1O	3094.3	Semi standard non polar	33892256
N-cis-Feruloyltyramine,3TMS,isomer #1	COC1=CC(/C=C\C(=N\CCC2=CC=C(O[Si](C)(C)C)C=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3117.7	Semi standard non polar	33892256
N-cis-Feruloyltyramine,1TBDMS,isomer #1	COC1=CC(/C=C\C(O)=N\CCC2=CC=C(O)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3431.3	Semi standard non polar	33892256
N-cis-Feruloyltyramine,1TBDMS,isomer #2	COC1=CC(/C=C\C(=N\CCC2=CC=C(O)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O	3451.9	Semi standard non polar	33892256
N-cis-Feruloyltyramine,1TBDMS,isomer #3	COC1=CC(/C=C\C(O)=N\CCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O	3377.2	Semi standard non polar	33892256
N-cis-Feruloyltyramine,2TBDMS,isomer #1	COC1=CC(/C=C\C(=N\CCC2=CC=C(O)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3659.8	Semi standard non polar	33892256
N-cis-Feruloyltyramine,2TBDMS,isomer #2	COC1=CC(/C=C\C(O)=N\CCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3611.2	Semi standard non polar	33892256
N-cis-Feruloyltyramine,2TBDMS,isomer #3	COC1=CC(/C=C\C(=N\CCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O	3634.8	Semi standard non polar	33892256
N-cis-Feruloyltyramine,3TBDMS,isomer #1	COC1=CC(/C=C\C(=N\CCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3843.5	Semi 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

FDB015259

KNApSAcK ID

C00025324

Chemspider ID

4944914

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440659

PDB ID

Not Available

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

Chen CY, Yeh YT, Yang WL: Amides from the stem of Capsicum annuum. Nat Prod Commun. 2011 Feb;6(2):227-9. [PubMed:21425680 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for N-cis-feruloyltyramine (HMDB0036381)

MOL for HMDB0036381 (N-cis-feruloyltyramine)

3D MOL for HMDB0036381 (N-cis-feruloyltyramine)

3D SDF for HMDB0036381 (N-cis-feruloyltyramine)

3D-SDF for HMDB0036381 (N-cis-feruloyltyramine)

PDB for HMDB0036381 (N-cis-feruloyltyramine)

3D PDB for HMDB0036381 (N-cis-feruloyltyramine)

SMILES for HMDB0036381 (N-cis-feruloyltyramine)

INCHI for HMDB0036381 (N-cis-feruloyltyramine)

Structure for HMDB0036381 (N-cis-feruloyltyramine)

3D Structure for HMDB0036381 (N-cis-feruloyltyramine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized