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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:52:32 UTC

Update Date

2022-03-07 02:55:49 UTC

HMDB ID

HMDB0038551

Secondary Accession Numbers

HMDB38551

Metabolite Identification

Common Name

Methyl 3,4,5-trimethoxycinnamate

Description

Methyl 3,4,5-trimethoxycinnamate, also known as 3,4,5-trimethoxycinnamate methyl ester, 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. Methyl 3,4,5-trimethoxycinnamate has been detected, but not quantified in, herbs and spices. This could make methyl 3,4,5-trimethoxycinnamate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Methyl 3,4,5-trimethoxycinnamate.

Structure

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

HMDB0038551
     RDKit          3D
Methyl 3,4,5-trimethoxycinnamate
 34 34  0  0  0  0  0  0  0  0999 V2000
    5.8278    0.4459    1.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4813    0.2762    1.2032 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7896    1.3370    0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4172    2.4106    0.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4032    1.2208    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7137    0.1053    0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3383   -0.0907   -0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2588   -1.3402    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647   -1.5676   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1752   -2.7848   -0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241   -3.8259    0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2696   -0.5386   -0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5696   -0.7370   -1.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6850   -0.5073   -0.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944    0.7057   -0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4737    1.6940   -1.5806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8672    2.9540   -1.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3609    0.9432   -0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3642    1.0709    0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8897    1.0338    2.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3430   -0.5167    1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9347    2.0819   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2683   -0.7311    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182   -2.1161    0.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0150   -4.7627    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4573   -3.9571    0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1781   -3.4785    1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8964    0.5816   -0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4916   -0.7661    0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5810   -1.0259   -0.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0777    2.9024   -2.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6151    3.6997   -2.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4681    3.3538   -0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346    1.9297   -0.8224 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
M  END


  Mrv0541 05061310312D          

 18 18  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  6  1  0  0  0  0
 13 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 15  1  1  0  0  0  0
 15 10  1  0  0  0  0
 16  2  1  0  0  0  0
 16 11  1  0  0  0  0
 17  3  1  0  0  0  0
 17 12  1  0  0  0  0
 18  4  1  0  0  0  0
 18 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038551

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O5/c1-15-10-7-9(5-6-12(14)17-3)8-11(16-2)13(10)18-4/h5-8H,1-4H3/b6-5+

> <INCHI_KEY>
KLXHCGFNNUQTEY-AATRIKPKSA-N

> <FORMULA>
C13H16O5

> <MOLECULAR_WEIGHT>
252.2631

> <EXACT_MASS>
252.099773622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.604991402962103

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.0422998523333336

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4447330085380585

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
67.21860000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.86e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038551
     RDKit          3D
Methyl 3,4,5-trimethoxycinnamate
 34 34  0  0  0  0  0  0  0  0999 V2000
    5.8278    0.4459    1.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4813    0.2762    1.2032 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7896    1.3370    0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4172    2.4106    0.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4032    1.2208    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7137    0.1053    0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3383   -0.0907   -0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2588   -1.3402    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647   -1.5676   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1752   -2.7848   -0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241   -3.8259    0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2696   -0.5386   -0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5696   -0.7370   -1.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6850   -0.5073   -0.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944    0.7057   -0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4737    1.6940   -1.5806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8672    2.9540   -1.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3609    0.9432   -0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3642    1.0709    0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8897    1.0338    2.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3430   -0.5167    1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9347    2.0819   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2683   -0.7311    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182   -2.1161    0.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0150   -4.7627    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4573   -3.9571    0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1781   -3.4785    1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8964    0.5816   -0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4916   -0.7661    0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5810   -1.0259   -0.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0777    2.9024   -2.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6151    3.6997   -2.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4681    3.3538   -0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346    1.9297   -0.8224 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5    6    9                                                       
CONECT    6    5   12                                                       
CONECT    7    9   10                                                       
CONECT    8    9   11                                                       
CONECT    9    5    7    8                                                  
CONECT   10    7   13   15                                                  
CONECT   11    8   13   16                                                  
CONECT   12    6   14   17                                                  
CONECT   13   10   11   18                                                  
CONECT   14   12                                                            
CONECT   15    1   10                                                       
CONECT   16    2   11                                                       
CONECT   17    3   12                                                       
CONECT   18    4   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0038551
HETATM    1  C1  UNL     1       5.828   0.446   1.596  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.481   0.276   1.203  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.790   1.337   0.624  1.00  0.00           C  
HETATM    4  O2  UNL     1       4.417   2.411   0.480  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.403   1.221   0.200  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.714   0.105   0.337  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.338  -0.091  -0.057  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.259  -1.340   0.155  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.565  -1.568  -0.205  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.175  -2.785  -0.008  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.424  -3.826   0.585  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.270  -0.539  -0.778  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.570  -0.737  -1.146  1.00  0.00           O  
HETATM   14  C10 UNL     1      -4.685  -0.507  -0.309  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.694   0.706  -0.996  1.00  0.00           C  
HETATM   16  O5  UNL     1      -2.474   1.694  -1.581  1.00  0.00           O  
HETATM   17  C12 UNL     1      -1.867   2.954  -1.793  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.361   0.943  -0.630  1.00  0.00           C  
HETATM   19  H1  UNL     1       6.364   1.071   0.823  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.890   1.034   2.551  1.00  0.00           H  
HETATM   21  H3  UNL     1       6.343  -0.517   1.738  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.935   2.082  -0.240  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.268  -0.731   0.797  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.318  -2.116   0.603  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.015  -4.763   0.631  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.457  -3.957   0.066  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.178  -3.479   1.620  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.896   0.582  -0.348  1.00  0.00           H  
HETATM   29  H11 UNL     1      -4.492  -0.766   0.750  1.00  0.00           H  
HETATM   30  H12 UNL     1      -5.581  -1.026  -0.708  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.078   2.902  -2.582  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.615   3.700  -2.147  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.468   3.354  -0.834  1.00  0.00           H  
HETATM   34  H16 UNL     1       0.035   1.930  -0.822  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   22
CONECT    6    7   23
CONECT    7    8    8   18
CONECT    8    9   24
CONECT    9   10   12   12
CONECT   10   11
CONECT   11   25   26   27
CONECT   12   13   15
CONECT   13   14
CONECT   14   28   29   30
CONECT   15   16   18   18
CONECT   16   17
CONECT   17   31   32   33
CONECT   18   34
END

HMDB0038551
     RDKit          3D
Methyl 3,4,5-trimethoxycinnamate
 34 34  0  0  0  0  0  0  0  0999 V2000
    5.8278    0.4459    1.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4813    0.2762    1.2032 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7896    1.3370    0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4172    2.4106    0.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4032    1.2208    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7137    0.1053    0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3383   -0.0907   -0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2588   -1.3402    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647   -1.5676   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1752   -2.7848   -0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241   -3.8259    0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2696   -0.5386   -0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5696   -0.7370   -1.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6850   -0.5073   -0.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944    0.7057   -0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4737    1.6940   -1.5806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8672    2.9540   -1.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3609    0.9432   -0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3642    1.0709    0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8897    1.0338    2.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3430   -0.5167    1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9347    2.0819   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2683   -0.7311    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182   -2.1161    0.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0150   -4.7627    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4573   -3.9571    0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1781   -3.4785    1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8964    0.5816   -0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4916   -0.7661    0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5810   -1.0259   -0.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0777    2.9024   -2.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6151    3.6997   -2.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4681    3.3538   -0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346    1.9297   -0.8224 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4,5-Trimethoxycinnamic acid methyl ester	ChEBI
3,4,5-Trimethoxycinnamate methyl ester	Generator
Methyl 3,4,5-trimethoxycinnamic acid	Generator
Methyl-3,4,5-trimethoxy cinnamic acid	HMDB

Chemical Formula

C₁₃H₁₆O₅

Average Molecular Weight

252.2631

Monoisotopic Molecular Weight

252.099773622

IUPAC Name

methyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate

Traditional Name

methyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate

CAS Registry Number

20329-96-8

SMILES

COC(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C13H16O5/c1-15-10-7-9(5-6-12(14)17-3)8-11(16-2)13(10)18-4/h5-8H,1-4H3/b6-5+

InChI Key

KLXHCGFNNUQTEY-AATRIKPKSA-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
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

methoxybenzene (CHEBI:86898 )
alkyl cinnamate (CHEBI:86898 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038551)

Cellular substructure

Membrane (HMDB: HMDB0038551)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038551)

Source

Exogenous

Food

Food (HMDB: HMDB0038551)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0038551)

Not Available

Nutrient (HMDB: HMDB0038551)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	99 - 100 °C	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	0.079 g/L	ALOGPS
logP	2.53	ALOGPS
logP	2.04	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	67.22 m³·mol⁻¹	ChemAxon
Polarizability	26.6 Å³	ChemAxon
Number of Rings	1	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
DarkChem	[M+H]+	163.734	31661259
DarkChem	[M-H]-	163.275	31661259
DeepCCS	[M+H]+	160.594	30932474
DeepCCS	[M-H]-	158.22	30932474
DeepCCS	[M-2H]-	191.106	30932474
DeepCCS	[M+Na]+	166.671	30932474
AllCCS	[M+H]+	157.7	32859911
AllCCS	[M+H-H2O]+	154.0	32859911
AllCCS	[M+NH4]+	161.1	32859911
AllCCS	[M+Na]+	162.1	32859911
AllCCS	[M-H]-	159.9	32859911
AllCCS	[M+Na-2H]-	160.2	32859911
AllCCS	[M+HCOO]-	160.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl 3,4,5-trimethoxycinnamate	COC(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1	3184.2	Standard polar	33892256
Methyl 3,4,5-trimethoxycinnamate	COC(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1	1938.8	Standard non polar	33892256
Methyl 3,4,5-trimethoxycinnamate	COC(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1	2102.3	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 - Methyl 3,4,5-trimethoxycinnamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00du-0690000000-36255dc7ae0bd83ff8a5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate , positive-QTOF	splash10-022c-0940000000-96354eb898855b8e905d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate , positive-QTOF	splash10-000i-1920000000-f2f693c1c78cd6ef2b29	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 10V, Positive-QTOF	splash10-00di-0290000000-c8ecf3965a9c83a56381	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 20V, Positive-QTOF	splash10-022c-0940000000-8b93bb36ccc3e076e945	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 40V, Positive-QTOF	splash10-07mv-4900000000-c635331ee3e0b65d7741	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 10V, Negative-QTOF	splash10-0udi-0090000000-fe93b401f1321fcc37ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 20V, Negative-QTOF	splash10-0uy0-0290000000-2807d3e5a8560757b050	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 40V, Negative-QTOF	splash10-0a59-1930000000-e4ce758b6ce5a108f57b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 10V, Negative-QTOF	splash10-0uxr-0090000000-df5f63af7cb771b611ad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 20V, Negative-QTOF	splash10-0i0c-0980000000-6c28694657f3a00eeed1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 40V, Negative-QTOF	splash10-06vj-1910000000-5ba44afb44d12123a066	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 10V, Positive-QTOF	splash10-0fk9-0090000000-c8e7b119aab8b699ab7c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 20V, Positive-QTOF	splash10-0fk9-1390000000-117d5df646bc9ca49010	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 40V, Positive-QTOF	splash10-0a4l-2940000000-ab5ee043bc5d575d6fdd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 10V, Positive-QTOF	splash10-0uk9-0090000000-76606a89e13ac877c163	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 20V, Positive-QTOF	splash10-0fkc-0490000000-93a87722bafafb173972	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 40V, Positive-QTOF	splash10-0a4j-0910000000-6811633d14eb7b224c9e	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

FDB017938

KNApSAcK ID

C00057228

Chemspider ID

643000

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

735846

PDB ID

Not Available

ChEBI ID

86898

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

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

Showing metabocard for Methyl 3,4,5-trimethoxycinnamate (HMDB0038551)

MOL for HMDB0038551 (Methyl 3,4,5-trimethoxycinnamate)

3D MOL for HMDB0038551 (Methyl 3,4,5-trimethoxycinnamate)

3D SDF for HMDB0038551 (Methyl 3,4,5-trimethoxycinnamate)

3D-SDF for HMDB0038551 (Methyl 3,4,5-trimethoxycinnamate)

PDB for HMDB0038551 (Methyl 3,4,5-trimethoxycinnamate)

3D PDB for HMDB0038551 (Methyl 3,4,5-trimethoxycinnamate)

SMILES for HMDB0038551 (Methyl 3,4,5-trimethoxycinnamate)

INCHI for HMDB0038551 (Methyl 3,4,5-trimethoxycinnamate)

Structure for HMDB0038551 (Methyl 3,4,5-trimethoxycinnamate)

3D Structure for HMDB0038551 (Methyl 3,4,5-trimethoxycinnamate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra