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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:56 UTC

Update Date

2022-03-07 02:53:28 UTC

HMDB ID

HMDB0032806

Secondary Accession Numbers

HMDB32806

Metabolite Identification

Common Name

p-Hydroxyphenethyl trans-ferulate

Description

p-Hydroxyphenethyl trans-ferulate 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. p-Hydroxyphenethyl trans-ferulate has been detected, but not quantified in, herbs and spices. This could make p-hydroxyphenethyl trans-ferulate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on p-Hydroxyphenethyl trans-ferulate.

Structure

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

HMDB0032806
     RDKit          3D
p-Hydroxyphenethyl trans-ferulate
 41 42  0  0  0  0  0  0  0  0999 V2000
    6.7105    2.2214   -0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0179    0.8840   -0.6302 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9836    0.0046   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6606    0.3886   -0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6240   -0.4895   -0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2558    0.0002   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1806   -0.7209    0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -0.1165   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    1.0893   -0.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2938   -0.8713    0.2024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5521   -0.2371    0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6957   -1.1476    0.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9556   -0.4014    0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5968   -0.3721   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7761    0.3288   -1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3687    1.0246   -0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5488    1.7201   -0.2571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7127    0.9834    1.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5326    0.2852    1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9636   -1.7763    0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2920   -2.1658    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3225   -1.2974    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6551   -1.7047    0.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6459    2.8427   -0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2293    2.2846   -1.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0040    2.6949   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583    1.4238   -0.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    1.0422   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3026   -1.7488    0.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6429    0.0472   -1.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5365    0.6471    0.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6942   -1.9632   -0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6073   -1.6549    1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1475   -0.9144   -1.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2904    0.3611   -2.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9313    2.2067    0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1328    1.5153    1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0044    0.2465    2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1687   -2.4641    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5269   -3.1864    0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3540   -1.0098   -0.1510 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
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 23 41  1  0
M  END

  Mrv0541 05061306422D          

 23 24  0  0  0  0            999 V2000
    2.8579    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.1250    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
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    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
    0.0000    4.1250    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
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    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
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.8875    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
    2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    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
 13  2  2  0  0  0  0
 13  3  1  0  0  0  0
 13 10  1  0  0  0  0
 14  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14 12  2  0  0  0  0
 15  6  2  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  2  0  0  0  0
 18  9  1  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 18  2  0  0  0  0
 22  1  1  0  0  0  0
 22 17  1  0  0  0  0
 23 11  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032806

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)OCCC2=CC=C(O)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O5/c1-22-17-12-14(4-8-16(17)20)5-9-18(21)23-11-10-13-2-6-15(19)7-3-13/h2-9,12,19-20H,10-11H2,1H3/b9-5+

> <INCHI_KEY>
JMSFLLZUCIXALN-WEVVVXLNSA-N

> <FORMULA>
C18H18O5

> <MOLECULAR_WEIGHT>
314.3325

> <EXACT_MASS>
314.115423686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.77984269179677

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-hydroxyphenyl)ethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
3.7636460626666666

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.023884397719568

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.347661371641264

> <JCHEM_PKA_STRONGEST_BASIC>
-4.888719674964705

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
87.62159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-hydroxyphenyl)ethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032806
     RDKit          3D
p-Hydroxyphenethyl trans-ferulate
 41 42  0  0  0  0  0  0  0  0999 V2000
    6.7105    2.2214   -0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0179    0.8840   -0.6302 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9836    0.0046   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6606    0.3886   -0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6240   -0.4895   -0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2558    0.0002   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1806   -0.7209    0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -0.1165   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    1.0893   -0.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2938   -0.8713    0.2024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5521   -0.2371    0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6957   -1.1476    0.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9556   -0.4014    0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5968   -0.3721   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7761    0.3288   -1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3687    1.0246   -0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5488    1.7201   -0.2571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7127    0.9834    1.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5326    0.2852    1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9636   -1.7763    0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2920   -2.1658    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3225   -1.2974    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6551   -1.7047    0.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6459    2.8427   -0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2293    2.2846   -1.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0040    2.6949   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583    1.4238   -0.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    1.0422   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3026   -1.7488    0.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6429    0.0472   -1.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5365    0.6471    0.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6942   -1.9632   -0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6073   -1.6549    1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1475   -0.9144   -1.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2904    0.3611   -2.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9313    2.2067    0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1328    1.5153    1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0044    0.2465    2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1687   -2.4641    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5269   -3.1864    0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3540   -1.0098   -0.1510 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
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 23 41  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       5.335  12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002   7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335   7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.336   5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -10.669   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668  10.010   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  11.550   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667   7.700   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
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   23                                                       
CONECT   12   14   17                                                       
CONECT   13    2    3   10                                                  
CONECT   14    4    5   12                                                  
CONECT   15    6    7   19                                                  
CONECT   16    8   17   20                                                  
CONECT   17   12   16   22                                                  
CONECT   18    9   21   23                                                  
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   18                                                            
CONECT   22    1   17                                                       
CONECT   23   11   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0032806
HETATM    1  C1  UNL     1       6.711   2.221  -0.995  1.00  0.00           C  
HETATM    2  O1  UNL     1       7.018   0.884  -0.630  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.984   0.005  -0.340  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.661   0.389  -0.395  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.624  -0.489  -0.105  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.256   0.000  -0.188  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.181  -0.721   0.059  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.158  -0.117  -0.056  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.285   1.089  -0.391  1.00  0.00           O  
HETATM   10  O3  UNL     1      -1.294  -0.871   0.202  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.552  -0.237   0.075  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.696  -1.148   0.378  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.956  -0.401   0.219  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.597  -0.372  -1.002  1.00  0.00           C  
HETATM   15  C12 UNL     1      -6.776   0.329  -1.143  1.00  0.00           C  
HETATM   16  C13 UNL     1      -7.369   1.025  -0.097  1.00  0.00           C  
HETATM   17  O4  UNL     1      -8.549   1.720  -0.257  1.00  0.00           O  
HETATM   18  C14 UNL     1      -6.713   0.983   1.116  1.00  0.00           C  
HETATM   19  C15 UNL     1      -5.533   0.285   1.267  1.00  0.00           C  
HETATM   20  C16 UNL     1       3.964  -1.776   0.244  1.00  0.00           C  
HETATM   21  C17 UNL     1       5.292  -2.166   0.299  1.00  0.00           C  
HETATM   22  C18 UNL     1       6.323  -1.297   0.013  1.00  0.00           C  
HETATM   23  O5  UNL     1       7.655  -1.705   0.073  1.00  0.00           O  
HETATM   24  H1  UNL     1       7.646   2.843  -0.943  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.229   2.285  -1.988  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.004   2.695  -0.267  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.458   1.424  -0.678  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.108   1.042  -0.475  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.303  -1.749   0.344  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.643   0.047  -1.014  1.00  0.00           H  
HETATM   31  H8  UNL     1      -2.537   0.647   0.731  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.694  -1.963  -0.394  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.607  -1.655   1.356  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.148  -0.914  -1.843  1.00  0.00           H  
HETATM   35  H12 UNL     1      -7.290   0.361  -2.093  1.00  0.00           H  
HETATM   36  H13 UNL     1      -8.931   2.207   0.540  1.00  0.00           H  
HETATM   37  H14 UNL     1      -7.133   1.515   1.983  1.00  0.00           H  
HETATM   38  H15 UNL     1      -5.004   0.246   2.225  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.169  -2.464   0.470  1.00  0.00           H  
HETATM   40  H17 UNL     1       5.527  -3.186   0.577  1.00  0.00           H  
HETATM   41  H18 UNL     1       8.354  -1.010  -0.151  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
CONECT   11   12   30   31
CONECT   12   13   32   33
CONECT   13   14   14   19
CONECT   14   15   34
CONECT   15   16   16   35
CONECT   16   17   18
CONECT   17   36
CONECT   18   19   19   37
CONECT   19   38
CONECT   20   21   39
CONECT   21   22   22   40
CONECT   22   23
CONECT   23   41
END

HMDB0032806
     RDKit          3D
p-Hydroxyphenethyl trans-ferulate
 41 42  0  0  0  0  0  0  0  0999 V2000
    6.7105    2.2214   -0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0179    0.8840   -0.6302 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9836    0.0046   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6606    0.3886   -0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6240   -0.4895   -0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2558    0.0002   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1806   -0.7209    0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -0.1165   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    1.0893   -0.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2938   -0.8713    0.2024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5521   -0.2371    0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6957   -1.1476    0.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9556   -0.4014    0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5968   -0.3721   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7761    0.3288   -1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3687    1.0246   -0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5488    1.7201   -0.2571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7127    0.9834    1.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5326    0.2852    1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9636   -1.7763    0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2920   -2.1658    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3225   -1.2974    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6551   -1.7047    0.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6459    2.8427   -0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2293    2.2846   -1.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0040    2.6949   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583    1.4238   -0.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    1.0422   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3026   -1.7488    0.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6429    0.0472   -1.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5365    0.6471    0.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6942   -1.9632   -0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6073   -1.6549    1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1475   -0.9144   -1.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2904    0.3611   -2.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9313    2.2067    0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1328    1.5153    1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0044    0.2465    2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1687   -2.4641    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5269   -3.1864    0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3540   -1.0098   -0.1510 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
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
p-Hydroxyphenethyl trans-ferulic acid	Generator
Hydroxyphenethylferulate	HMDB, MeSH
2-(4-Hydroxyphenyl)ethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid	Generator
p-Hydroxyphenethyl trans-ferulate	MeSH

Chemical Formula

C₁₈H₁₈O₅

Average Molecular Weight

314.3325

Monoisotopic Molecular Weight

314.115423686

IUPAC Name

2-(4-hydroxyphenyl)ethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

2-(4-hydroxyphenyl)ethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

84873-15-4

SMILES

COC1=C(O)C=CC(\C=C\C(=O)OCCC2=CC=C(O)C=C2)=C1

InChI Identifier

InChI=1S/C18H18O5/c1-22-17-12-14(4-8-16(17)20)5-9-18(21)23-11-10-13-2-6-15(19)7-3-13/h2-9,12,19-20H,10-11H2,1H3/b9-5+

InChI Key

JMSFLLZUCIXALN-WEVVVXLNSA-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

Coumaric acid or derivatives
Cinnamic acid ester
Methoxyphenol
Tyrosol derivative
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032806)
Cell membrane (HMDB: HMDB0032806)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032806)

Source

Exogenous

Exogenous (HMDB: HMDB0032806)

Food

Food (HMDB: HMDB0032806)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0032806)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032806)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165 - 166 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	46.13 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	0.025 g/L	ALOGPS
logP	3.16	ALOGPS
logP	3.76	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.35	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	87.62 m³·mol⁻¹	ChemAxon
Polarizability	33.78 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]+	181.83	30932474
DeepCCS	[M-H]-	179.472	30932474
DeepCCS	[M-2H]-	213.016	30932474
DeepCCS	[M+Na]+	188.242	30932474
AllCCS	[M+H]+	174.8	32859911
AllCCS	[M+H-H2O]+	171.5	32859911
AllCCS	[M+NH4]+	177.9	32859911
AllCCS	[M+Na]+	178.8	32859911
AllCCS	[M-H]-	177.3	32859911
AllCCS	[M+Na-2H]-	176.9	32859911
AllCCS	[M+HCOO]-	176.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
p-Hydroxyphenethyl trans-ferulate	COC1=C(O)C=CC(\C=C\C(=O)OCCC2=CC=C(O)C=C2)=C1	4852.5	Standard polar	33892256
p-Hydroxyphenethyl trans-ferulate	COC1=C(O)C=CC(\C=C\C(=O)OCCC2=CC=C(O)C=C2)=C1	2871.9	Standard non polar	33892256
p-Hydroxyphenethyl trans-ferulate	COC1=C(O)C=CC(\C=C\C(=O)OCCC2=CC=C(O)C=C2)=C1	3043.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
p-Hydroxyphenethyl trans-ferulate,1TMS,isomer #1	COC1=CC(/C=C/C(=O)OCCC2=CC=C(O)C=C2)=CC=C1O[Si](C)(C)C	3045.5	Semi standard non polar	33892256
p-Hydroxyphenethyl trans-ferulate,1TMS,isomer #2	COC1=CC(/C=C/C(=O)OCCC2=CC=C(O[Si](C)(C)C)C=C2)=CC=C1O	3002.2	Semi standard non polar	33892256
p-Hydroxyphenethyl trans-ferulate,2TMS,isomer #1	COC1=CC(/C=C/C(=O)OCCC2=CC=C(O[Si](C)(C)C)C=C2)=CC=C1O[Si](C)(C)C	3046.3	Semi standard non polar	33892256
p-Hydroxyphenethyl trans-ferulate,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)OCCC2=CC=C(O)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3327.7	Semi standard non polar	33892256
p-Hydroxyphenethyl trans-ferulate,1TBDMS,isomer #2	COC1=CC(/C=C/C(=O)OCCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O	3278.5	Semi standard non polar	33892256
p-Hydroxyphenethyl trans-ferulate,2TBDMS,isomer #1	COC1=CC(/C=C/C(=O)OCCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3580.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - p-Hydroxyphenethyl trans-ferulate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-0900000000-40a06cb9ad006d8c105c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Hydroxyphenethyl trans-ferulate GC-MS (2 TMS) - 70eV, Positive	splash10-0096-2692600000-ed47c38069517756c31a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Hydroxyphenethyl trans-ferulate 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 - p-Hydroxyphenethyl trans-ferulate 10V, Positive-QTOF	splash10-014i-0916000000-c43dcbd0efa6f59d2a55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenethyl trans-ferulate 20V, Positive-QTOF	splash10-00fr-0900000000-7ed25e9b41142ef56b38	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenethyl trans-ferulate 40V, Positive-QTOF	splash10-05i0-3900000000-a0be17be1ffdc3c42fdd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenethyl trans-ferulate 10V, Negative-QTOF	splash10-03fr-0906000000-9f1edd9a6bd7a2e141a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenethyl trans-ferulate 20V, Negative-QTOF	splash10-004i-0900000000-e981c6d30cf94fe46851	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenethyl trans-ferulate 40V, Negative-QTOF	splash10-056r-1900000000-0669350d67f653f1cb53	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenethyl trans-ferulate 10V, Negative-QTOF	splash10-03di-0709000000-6913e1c6010d1114fa74	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenethyl trans-ferulate 20V, Negative-QTOF	splash10-03gj-0901000000-5768e5fb19d06adf1014	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenethyl trans-ferulate 40V, Negative-QTOF	splash10-02aj-0921000000-2d5a6e11e0bab2469fdd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenethyl trans-ferulate 10V, Positive-QTOF	splash10-00or-0915000000-95721fc05ca52b8b6964	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenethyl trans-ferulate 20V, Positive-QTOF	splash10-00di-0910000000-31b2f91e500b92742fcb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenethyl trans-ferulate 40V, Positive-QTOF	splash10-00dj-2900000000-33b4579dda413a09c14f	2021-09-23	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

FDB010780

KNApSAcK ID

C00041758

Chemspider ID

552938

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

637308

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1831741

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 p-Hydroxyphenethyl trans-ferulate (HMDB0032806)

MOL for HMDB0032806 (p-Hydroxyphenethyl trans-ferulate)

3D MOL for HMDB0032806 (p-Hydroxyphenethyl trans-ferulate)

3D SDF for HMDB0032806 (p-Hydroxyphenethyl trans-ferulate)

3D-SDF for HMDB0032806 (p-Hydroxyphenethyl trans-ferulate)

PDB for HMDB0032806 (p-Hydroxyphenethyl trans-ferulate)

3D PDB for HMDB0032806 (p-Hydroxyphenethyl trans-ferulate)

SMILES for HMDB0032806 (p-Hydroxyphenethyl trans-ferulate)

INCHI for HMDB0032806 (p-Hydroxyphenethyl trans-ferulate)

Structure for HMDB0032806 (p-Hydroxyphenethyl trans-ferulate)

3D Structure for HMDB0032806 (p-Hydroxyphenethyl trans-ferulate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra