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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:00:29 UTC

Update Date

2022-03-07 02:56:14 UTC

HMDB ID

HMDB0039521

Secondary Accession Numbers

HMDB39521

Metabolite Identification

Common Name

N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide

Description

N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide has been detected, but not quantified in, several different foods, such as red onion, green onion, onion-family vegetables, garden onions (Allium cepa), and pulses. This could make N-(p-hydroxyphenyl)ethyl p-hydroxycinnamide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide.

Structure

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

HMDB0039521
     RDKit          3D
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide
 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.2359    0.6067   -1.7853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4214    0.0617   -0.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8514    0.2954   -0.8079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6701   -0.2041    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0914    0.0851    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749   -0.5009    1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2193   -0.2903    1.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8665    0.5239    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2304    0.7558    0.2688 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1198    1.1130   -0.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7465    0.8717   -0.8160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2286   -0.7607    0.0664 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6618   -1.0049    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4024    0.2844    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8629    0.1396    0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6399    0.2049   -0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0071    0.0630   -0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6439   -0.1568    0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0283   -0.2980    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9023   -0.2291    1.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5143   -0.0801    1.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258    0.9477   -1.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2690   -0.8458    0.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4180   -1.1363    1.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8090   -0.7503    1.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8096    0.3357    0.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5825    1.7486   -1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2238    1.3584   -1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3467   -1.2085    0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9541   -1.5752   -0.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9072   -1.6603    0.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331    0.7747    1.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1453    1.0368   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1503    0.3739   -1.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5313    0.1298   -1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4833   -0.4572    1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4344   -0.4018    2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0100   -0.1504    2.2966 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  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 11  5  1  0
 21 15  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END


  Mrv1652303202019012D          

 21 22  0  0  0  0            999 V2000
   -2.9310   -1.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916   -0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916   -0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9310    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1879   -0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1879   -0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4447   -1.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015   -0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015   -0.0003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3348    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879   -0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9310   -1.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916   -0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3348   -1.2383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916   -0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9310    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879   -0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841   -0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    1.2383    0.0000 O   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 20  1  0  0  0  0
 11 12  1  0  0  0  0
 11 17  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039521

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(CCNC(=O)\C=C\C2=CC=C(O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H17NO3/c19-15-6-1-13(2-7-15)5-10-17(21)18-12-11-14-3-8-16(20)9-4-14/h1-10,19-20H,11-12H2,(H,18,21)/b10-5+

> <INCHI_KEY>
RXGUTQNKCXHALN-BJMVGYQFSA-N

> <FORMULA>
C17H17NO3

> <MOLECULAR_WEIGHT>
283.3218

> <EXACT_MASS>
283.120843415

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.6725567651728

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
3.1898446827683755

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.210308329258071

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.55870756219977

> <JCHEM_PKA_STRONGEST_BASIC>
6.5203904119245815

> <JCHEM_POLAR_SURFACE_AREA>
73.05000000000001

> <JCHEM_REFRACTIVITY>
83.62989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039521
     RDKit          3D
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide
 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.2359    0.6067   -1.7853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4214    0.0617   -0.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8514    0.2954   -0.8079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6701   -0.2041    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0914    0.0851    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749   -0.5009    1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2193   -0.2903    1.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8665    0.5239    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2304    0.7558    0.2688 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1198    1.1130   -0.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7465    0.8717   -0.8160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2286   -0.7607    0.0664 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6618   -1.0049    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4024    0.2844    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8629    0.1396    0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6399    0.2049   -0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0071    0.0630   -0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6439   -0.1568    0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0283   -0.2980    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9023   -0.2291    1.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5143   -0.0801    1.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258    0.9477   -1.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2690   -0.8458    0.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4180   -1.1363    1.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8090   -0.7503    1.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8096    0.3357    0.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5825    1.7486   -1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2238    1.3584   -1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3467   -1.2085    0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9541   -1.5752   -0.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9072   -1.6603    0.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331    0.7747    1.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1453    1.0368   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1503    0.3739   -1.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5313    0.1298   -1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4833   -0.4572    1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4344   -0.4018    2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0100   -0.1504    2.2966 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  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 11  5  1  0
 21 15  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  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      -5.471  -2.311   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.704  -1.541   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.704  -0.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.471   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.084  -0.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.084  -1.541   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.697  -2.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.309  -1.541   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.309  -0.001   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -8.092   0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.084  -1.541   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.471  -2.311   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.704  -1.541   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.092  -2.311   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.704  -0.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.471   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.084  -0.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.697   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.464  -0.001   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.076   0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.076   2.311   0.000  0.00  0.00           O+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   20                                                       
CONECT   10    3                                                            
CONECT   11   12   17                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   11   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20    9   19   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0039521
HETATM    1  O1  UNL     1      -0.236   0.607  -1.785  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.421   0.062  -0.873  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.851   0.295  -0.808  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.670  -0.204   0.086  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.091   0.085   0.073  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.875  -0.501   1.075  1.00  0.00           C  
HETATM    7  C6  UNL     1       6.219  -0.290   1.148  1.00  0.00           C  
HETATM    8  C7  UNL     1       6.866   0.524   0.219  1.00  0.00           C  
HETATM    9  O2  UNL     1       8.230   0.756   0.269  1.00  0.00           O  
HETATM   10  C8  UNL     1       6.120   1.113  -0.777  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.746   0.872  -0.816  1.00  0.00           C  
HETATM   12  N1  UNL     1      -0.229  -0.761   0.066  1.00  0.00           N  
HETATM   13  C10 UNL     1      -1.662  -1.005   0.021  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.402   0.284   0.178  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.863   0.140   0.148  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.640   0.205  -0.984  1.00  0.00           C  
HETATM   17  C14 UNL     1      -6.007   0.063  -0.969  1.00  0.00           C  
HETATM   18  C15 UNL     1      -6.644  -0.157   0.238  1.00  0.00           C  
HETATM   19  O3  UNL     1      -8.028  -0.298   0.232  1.00  0.00           O  
HETATM   20  C16 UNL     1      -5.902  -0.229   1.397  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.514  -0.080   1.343  1.00  0.00           C  
HETATM   22  H1  UNL     1       2.326   0.948  -1.564  1.00  0.00           H  
HETATM   23  H2  UNL     1       2.269  -0.846   0.847  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.418  -1.136   1.812  1.00  0.00           H  
HETATM   25  H4  UNL     1       6.809  -0.750   1.927  1.00  0.00           H  
HETATM   26  H5  UNL     1       8.810   0.336   0.991  1.00  0.00           H  
HETATM   27  H6  UNL     1       6.583   1.749  -1.513  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.224   1.358  -1.614  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.347  -1.208   0.821  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.954  -1.575  -0.881  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.907  -1.660   0.881  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.133   0.775   1.155  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.145   1.037  -0.594  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.150   0.374  -1.913  1.00  0.00           H  
HETATM   35  H14 UNL     1      -6.531   0.130  -1.912  1.00  0.00           H  
HETATM   36  H15 UNL     1      -8.483  -0.457   1.112  1.00  0.00           H  
HETATM   37  H16 UNL     1      -6.434  -0.402   2.319  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.010  -0.150   2.297  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   22
CONECT    4    5   23
CONECT    5    6    6   11
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9   10
CONECT    9   26
CONECT   10   11   11   27
CONECT   11   28
CONECT   12   13   29
CONECT   13   14   30   31
CONECT   14   15   32   33
CONECT   15   16   16   21
CONECT   16   17   34
CONECT   17   18   18   35
CONECT   18   19   20
CONECT   19   36
CONECT   20   21   21   37
CONECT   21   38
END

HMDB0039521
     RDKit          3D
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide
 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.2359    0.6067   -1.7853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4214    0.0617   -0.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8514    0.2954   -0.8079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6701   -0.2041    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0914    0.0851    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749   -0.5009    1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2193   -0.2903    1.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8665    0.5239    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2304    0.7558    0.2688 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1198    1.1130   -0.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7465    0.8717   -0.8160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2286   -0.7607    0.0664 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6618   -1.0049    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4024    0.2844    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8629    0.1396    0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6399    0.2049   -0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0071    0.0630   -0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6439   -0.1568    0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0283   -0.2980    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9023   -0.2291    1.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5143   -0.0801    1.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258    0.9477   -1.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2690   -0.8458    0.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4180   -1.1363    1.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8090   -0.7503    1.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8096    0.3357    0.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5825    1.7486   -1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2238    1.3584   -1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3467   -1.2085    0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9541   -1.5752   -0.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9072   -1.6603    0.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331    0.7747    1.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1453    1.0368   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1503    0.3739   -1.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5313    0.1298   -1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4833   -0.4572    1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4344   -0.4018    2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0100   -0.1504    2.2966 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  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 11  5  1  0
 21 15  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-trans-Coumaroyltyramine	ChEMBL, HMDB
trans-N-Hydroxycinnamoyltyramine	ChEMBL, HMDB
N-P-Coumaroyltyramine	ChEMBL, HMDB
N-P-trans-Coumaroyltyramine	HMDB
Paprazine	HMDB
4-Coumaroyltyramine	MeSH, HMDB
N-(4-Hydroxy-beta-phenethyl)-4-hydroxycinnamide	MeSH, HMDB
P-Coumaroyltyramine	MeSH, HMDB
N-(P-Hydroxy-beta-phenethyl)-P-hydroxy-trans-cinnamide	MeSH, HMDB
N-HBPHTC	MeSH, HMDB
(2E)-3-(4-Hydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidate	Generator
trans-N-p-Coumaroyl tyramine	MeSH

Chemical Formula

C₁₇H₁₇NO₃

Average Molecular Weight

283.3218

Monoisotopic Molecular Weight

283.120843415

IUPAC Name

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

Traditional Name

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

CAS Registry Number

36417-86-4

SMILES

OC1=CC=C(CCNC(=O)\C=C\C2=CC=C(O)C=C2)C=C1

InChI Identifier

InChI=1S/C17H17NO3/c19-15-6-1-13(2-7-15)5-10-17(21)18-12-11-14-3-8-16(20)9-4-14/h1-10,19-20H,11-12H2,(H,18,21)/b10-5+

InChI Key

RXGUTQNKCXHALN-BJMVGYQFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Cinnamic acid amide
Coumaric acid or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroxycinnamic acid (CHEBI:65665 )

Ontology

Not Available

Not Available

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	260 - 261 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	405.8 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	0.016 g/L	ALOGPS
logP	2.58	ALOGPS
logP	3.19	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.56	ChemAxon
pKa (Strongest Basic)	6.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.63 m³·mol⁻¹	ChemAxon
Polarizability	31.67 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]+	166.954	30932474
DeepCCS	[M-H]-	164.596	30932474
DeepCCS	[M-2H]-	197.482	30932474
DeepCCS	[M+Na]+	173.047	30932474
AllCCS	[M+H]+	167.6	32859911
AllCCS	[M+H-H2O]+	164.0	32859911
AllCCS	[M+NH4]+	170.8	32859911
AllCCS	[M+Na]+	171.8	32859911
AllCCS	[M-H]-	171.1	32859911
AllCCS	[M+Na-2H]-	170.8	32859911
AllCCS	[M+HCOO]-	170.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide	OC1=CC=C(CCNC(=O)\C=C\C2=CC=C(O)C=C2)C=C1	4330.7	Standard polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide	OC1=CC=C(CCNC(=O)\C=C\C2=CC=C(O)C=C2)C=C1	2539.2	Standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide	OC1=CC=C(CCNC(=O)\C=C\C2=CC=C(O)C=C2)C=C1	3223.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCNC(=O)/C=C/C2=CC=C(O)C=C2)C=C1	3086.8	Semi standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=CC=C(O)C=C2)C=C1	3124.0	Semi standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,1TMS,isomer #3	C[Si](C)(C)N(CCC1=CC=C(O)C=C1)C(=O)/C=C/C1=CC=C(O)C=C1	3094.5	Semi standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=CC=C(O[Si](C)(C)C)C=C2)C=C1	3156.2	Semi standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CCN(C(=O)/C=C/C2=CC=C(O)C=C2)[Si](C)(C)C)C=C1	3124.7	Semi standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C)C=C1	3145.0	Semi standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C=C1	3092.4	Semi standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C=C1	2863.3	Standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCNC(=O)/C=C/C2=CC=C(O)C=C2)C=C1	3356.4	Semi standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=CC=C(O)C=C2)C=C1	3399.0	Semi standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC1=CC=C(O)C=C1)C(=O)/C=C/C1=CC=C(O)C=C1	3358.4	Semi standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C1	3718.3	Semi standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN(C(=O)/C=C/C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C=C1	3630.0	Semi standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C=C1	3647.1	Semi standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/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)C=C1	3851.6	Semi standard non polar	33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/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)C=C1	3440.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-052b-0910000000-6be5a92b4c900bc4314d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide GC-MS (2 TMS) - 70eV, Positive	splash10-03di-5886900000-4e07b44443bb550b6f3a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 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-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 10V, Positive-QTOF	splash10-0019-0940000000-67eca6cd4610cdb6385c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 20V, Positive-QTOF	splash10-00kr-0900000000-76a2a687a7fdc6dff8ac	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 40V, Positive-QTOF	splash10-0ap0-2900000000-37f55b85aa3f8f38b0ac	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 10V, Negative-QTOF	splash10-001i-0390000000-c6c693214244c760e76d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 20V, Negative-QTOF	splash10-03e9-0940000000-629ce8460c91a8cf71ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 40V, Negative-QTOF	splash10-0006-7900000000-670117754556b9bfd737	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 10V, Positive-QTOF	splash10-001i-0490000000-eb6448de7547cc12159f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 20V, Positive-QTOF	splash10-00e9-0940000000-110219e85b66ace2e7eb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 40V, Positive-QTOF	splash10-0600-3900000000-3336c5e4da5dd7892b8a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 10V, Negative-QTOF	splash10-001i-0190000000-1ca5c616e12c1f59d6cd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 20V, Negative-QTOF	splash10-053r-1970000000-ba1058b269f97d0521a5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 40V, Negative-QTOF	splash10-014i-2920000000-ed1f42ff191ef6b46296	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB019132

KNApSAcK ID

C00028801

Chemspider ID

4523095

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5372945

PDB ID

Not Available

ChEBI ID

65665

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1878051

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide (HMDB0039521)

MOL for HMDB0039521 (N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide)

3D MOL for HMDB0039521 (N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide)

3D SDF for HMDB0039521 (N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide)

3D-SDF for HMDB0039521 (N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide)

PDB for HMDB0039521 (N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide)

3D PDB for HMDB0039521 (N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide)

SMILES for HMDB0039521 (N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide)

INCHI for HMDB0039521 (N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide)

Structure for HMDB0039521 (N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide)

3D Structure for HMDB0039521 (N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra