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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:55 UTC

Update Date

2022-09-22 18:34:55 UTC

HMDB ID

HMDB0002511

Secondary Accession Numbers

HMDB02511

Metabolite Identification

Common Name

3,4,5-Trimethoxycinnamic acid

Description

3, 4, 5-trimethoxycinnamic acid is a methoxycinnamic acid with three methoxy substituents at the 3-, 4- and 5-positions. It has a role as an allergen. It is a conjugate acid of a 3,4,5-trimethoxycinnamate. 3, 4, 5-Trimethoxycinnamic acid is an organic acid found in normal human urine (PMID:6992730 , 6511847 ). Trimethoxycinnamate is a natural aromatic ester from Piper longum that inhibits expression of cell adhesion molecules on endothelial cells (TNF- -induced expression of intercellular adhesion molecule-1 (ICAM-1) and E-Selectin and vascular adhesion molecules-1 (VCAM-1)), without being toxic to endothelial cells. (PMID:16313198 ).

Structure

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

HMDB0002511
     RDKit          3D
3,4,5-Trimethoxycinnamic acid
 31 31  0  0  0  0  0  0  0  0999 V2000
   -1.4446   -3.2478   -1.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9269   -1.9238   -0.9362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0947   -0.8779   -0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2688   -1.0475   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0494    0.0209    0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4791   -0.1134    0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0711   -1.2784    0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158   -1.3752    0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1244   -2.4623    0.2792 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2123   -0.2431    0.7528 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4371    1.2791    0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9065    1.4560   -0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409    2.6867    0.0861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8734    3.8646    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6697    0.3672   -0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0285    0.5291   -0.6381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8699    0.3442    0.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -3.5586   -0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3124   -3.8689   -1.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7216   -3.2312   -1.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6419   -2.0483   -0.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0731    0.7683    0.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5461   -2.1843   -0.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0756    0.5990    0.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0573    2.1119    0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2120    3.6555    1.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2979    4.2038   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244    4.6460    0.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726   -0.6227    0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9315    0.4238    0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5436    1.1275    1.2400 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
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 15  3  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
 10 24  1  0
 11 25  1  0
 14 26  1  0
 14 27  1  0
 14 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
M  END


  Mrv1652305261923582D          

 17 17  0  0  0  0            999 V2000
   21.2735  -11.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8445  -10.9620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7024  -10.9620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7024   -6.8369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2735   -6.8369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5591  -12.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1300  -10.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4170  -10.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9880   -7.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9880   -8.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2735   -8.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2735  -10.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9880  -10.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5591  -10.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2735   -9.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5591   -9.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9880   -9.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 12  1  0  0  0  0
  2  7  1  0  0  0  0
  2 14  1  0  0  0  0
  3  8  1  0  0  0  0
  3 13  1  0  0  0  0
  4  9  1  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 15  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 17  1  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002511

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b5-4+

> <INCHI_KEY>
YTFVRYKNXDADBI-SNAWJCMRSA-N

> <FORMULA>
C12H14O5

> <MOLECULAR_WEIGHT>
238.2366

> <EXACT_MASS>
238.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.16535914536337

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
1.6630724629999993

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.708908487912579

> <JCHEM_PKA_STRONGEST_BASIC>
-4.446646512913645

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
62.449500000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trimethoxycinnamic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002511
     RDKit          3D
3,4,5-Trimethoxycinnamic acid
 31 31  0  0  0  0  0  0  0  0999 V2000
   -1.4446   -3.2478   -1.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9269   -1.9238   -0.9362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0947   -0.8779   -0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2688   -1.0475   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0494    0.0209    0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4791   -0.1134    0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0711   -1.2784    0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158   -1.3752    0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1244   -2.4623    0.2792 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2123   -0.2431    0.7528 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4371    1.2791    0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9065    1.4560   -0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409    2.6867    0.0861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8734    3.8646    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6697    0.3672   -0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0285    0.5291   -0.6381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8699    0.3442    0.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -3.5586   -0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3124   -3.8689   -1.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7216   -3.2312   -1.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6419   -2.0483   -0.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0731    0.7683    0.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5461   -2.1843   -0.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0756    0.5990    0.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0573    2.1119    0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2120    3.6555    1.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2979    4.2038   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244    4.6460    0.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726   -0.6227    0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9315    0.4238    0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5436    1.1275    1.2400 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
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 15  3  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
 10 24  1  0
 11 25  1  0
 14 26  1  0
 14 27  1  0
 14 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      39.711 -22.003   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      37.043 -20.462   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      42.378 -20.462   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      42.378 -12.762   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      39.711 -12.762   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      38.377 -22.773   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      35.709 -19.692   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      43.712 -19.692   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      41.044 -13.532   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      41.044 -15.072   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      39.711 -15.842   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      39.711 -20.462   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      41.044 -19.692   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.377 -19.692   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      39.711 -17.382   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.377 -18.152   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      41.044 -18.152   0.000  0.00  0.00           C+0
CONECT    1    6   12                                                       
CONECT    2    7   14                                                       
CONECT    3    8   13                                                       
CONECT    4    9                                                            
CONECT    5    9                                                            
CONECT    6    1                                                            
CONECT    7    2                                                            
CONECT    8    3                                                            
CONECT    9    4    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   15                                                       
CONECT   12    1   13   14                                                  
CONECT   13    3   12   17                                                  
CONECT   14    2   12   16                                                  
CONECT   15   11   16   17                                                  
CONECT   16   14   15                                                       
CONECT   17   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0002511
HETATM    1  C1  UNL     1      -1.445  -3.248  -1.118  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.927  -1.924  -0.936  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.095  -0.878  -0.564  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.269  -1.047  -0.343  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.049   0.021   0.024  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.479  -0.113   0.265  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.071  -1.278   0.137  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.516  -1.375   0.389  1.00  0.00           C  
HETATM    9  O2  UNL     1       5.124  -2.462   0.279  1.00  0.00           O  
HETATM   10  O3  UNL     1       5.212  -0.243   0.753  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.437   1.279   0.168  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.907   1.456  -0.048  1.00  0.00           C  
HETATM   13  O4  UNL     1      -1.541   2.687   0.086  1.00  0.00           O  
HETATM   14  C10 UNL     1      -0.873   3.865   0.454  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.670   0.367  -0.416  1.00  0.00           C  
HETATM   16  O5  UNL     1      -3.029   0.529  -0.638  1.00  0.00           O  
HETATM   17  C12 UNL     1      -3.870   0.344   0.511  1.00  0.00           C  
HETATM   18  H1  UNL     1      -0.981  -3.559  -0.183  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.312  -3.869  -1.429  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.722  -3.231  -1.978  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.642  -2.048  -0.479  1.00  0.00           H  
HETATM   22  H5  UNL     1       3.073   0.768   0.559  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.546  -2.184  -0.148  1.00  0.00           H  
HETATM   24  H7  UNL     1       5.076   0.599   0.209  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.057   2.112   0.456  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.212   3.655   1.310  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.298   4.204  -0.450  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.624   4.646   0.661  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.573  -0.623   0.964  1.00  0.00           H  
HETATM   30  H13 UNL     1      -4.931   0.424   0.266  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.544   1.127   1.240  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   15
CONECT    4    5   21
CONECT    5    6   11   11
CONECT    6    7    7   22
CONECT    7    8   23
CONECT    8    9    9   10
CONECT   10   24
CONECT   11   12   25
CONECT   12   13   15   15
CONECT   13   14
CONECT   14   26   27   28
CONECT   15   16
CONECT   16   17
CONECT   17   29   30   31
END

HMDB0002511
     RDKit          3D
3,4,5-Trimethoxycinnamic acid
 31 31  0  0  0  0  0  0  0  0999 V2000
   -1.4446   -3.2478   -1.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9269   -1.9238   -0.9362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0947   -0.8779   -0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2688   -1.0475   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0494    0.0209    0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4791   -0.1134    0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0711   -1.2784    0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158   -1.3752    0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1244   -2.4623    0.2792 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2123   -0.2431    0.7528 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4371    1.2791    0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9065    1.4560   -0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409    2.6867    0.0861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8734    3.8646    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6697    0.3672   -0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0285    0.5291   -0.6381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8699    0.3442    0.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -3.5586   -0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3124   -3.8689   -1.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7216   -3.2312   -1.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6419   -2.0483   -0.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0731    0.7683    0.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5461   -2.1843   -0.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0756    0.5990    0.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0573    2.1119    0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2120    3.6555    1.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2979    4.2038   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244    4.6460    0.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726   -0.6227    0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9315    0.4238    0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5436    1.1275    1.2400 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
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 15  3  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
 10 24  1  0
 11 25  1  0
 14 26  1  0
 14 27  1  0
 14 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4,5-Trimethoxycinnamate	Generator
3-(3,4,5-Trimethoxyphenyl)-2-propenoic acid	MeSH
3,4,5-Trimethoxy cinnamate	HMDB
3,4,5-Trimethoxy cinnamic acid	HMDB
3,4,5-Trimethoxyphenylacrylate	HMDB
3,4,5-Trimethoxyphenylacrylic acid	HMDB
O-Methylsinapate	HMDB
O-Methylsinapic acid	HMDB
(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoate	Generator, HMDB
3,4,5-Trimethoxycinnamic acid	MeSH

Chemical Formula

C₁₂H₁₄O₅

Average Molecular Weight

238.2366

Monoisotopic Molecular Weight

238.084123558

IUPAC Name

(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid

Traditional Name

3,4,5-trimethoxycinnamic acid

CAS Registry Number

90-50-6

SMILES

COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b5-4+

InChI Key

YTFVRYKNXDADBI-SNAWJCMRSA-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
Coumaric acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 19812218)

Source

Endogenous

Endogenous (HMDB: HMDB0002511)

Plant

Plant (HMDB: HMDB0002511)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	126 - 128 °C	Not Available
Boiling Point	396.39 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	3040 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.001 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	2.24	ALOGPS
logP	1.66	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.45 m³·mol⁻¹	ChemAxon
Polarizability	24.17 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]+	159.807	31661259
DarkChem	[M-H]-	158.64	31661259
DeepCCS	[M+H]+	155.457	30932474
DeepCCS	[M-H]-	153.099	30932474
DeepCCS	[M-2H]-	186.058	30932474
DeepCCS	[M+Na]+	161.55	30932474
AllCCS	[M+H]+	153.6	32859911
AllCCS	[M+H-H2O]+	149.7	32859911
AllCCS	[M+NH4]+	157.1	32859911
AllCCS	[M+Na]+	158.1	32859911
AllCCS	[M-H]-	154.1	32859911
AllCCS	[M+Na-2H]-	154.4	32859911
AllCCS	[M+HCOO]-	154.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	5.19 minutes	32390414
Predicted by Siyang on May 30, 2022	11.2344 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.3 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1738.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	289.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	142.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	83.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	394.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	438.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	131.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	960.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	360.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1142.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	280.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	363.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	356.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	18.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4,5-Trimethoxycinnamic acid	COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC	3667.2	Standard polar	33892256
3,4,5-Trimethoxycinnamic acid	COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC	1994.7	Standard non polar	33892256
3,4,5-Trimethoxycinnamic acid	COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC	2108.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4,5-Trimethoxycinnamic acid,1TMS,isomer #1	COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C1OC	2139.4	Semi standard non polar	33892256
3,4,5-Trimethoxycinnamic acid,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	2399.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3,4,5-Trimethoxycinnamic acid GC-MS (1 TMS)	splash10-0019-5980000000-481902850188a4b983e1	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4,5-Trimethoxycinnamic acid EI-B (Non-derivatized)	splash10-000i-0290000000-577fe3f81fdd216fe76b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4,5-Trimethoxycinnamic acid GC-MS (Non-derivatized)	splash10-0019-5980000000-481902850188a4b983e1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4,5-Trimethoxycinnamic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-1690000000-4bdc2e168c37e0d8c46e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4,5-Trimethoxycinnamic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00dm-7390000000-279ac79fde7a9d1eb827	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4,5-Trimethoxycinnamic acid 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 - 3,4,5-Trimethoxycinnamic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0890000000-73d378c5d062a4380537	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-014r-0900000000-7d415b23b8c22936e972	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0006-9000000000-b27641d2926e1d3e69ed	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-qTof , Positive-QTOF	splash10-03dl-2900000000-a43198a76493a4d0f488	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Linear Ion Trap , negative-QTOF	splash10-0f89-0910000000-f321fbc297d524d25e5e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Linear Ion Trap , negative-QTOF	splash10-0f89-0910000000-098ef1a616ba7aacdd8b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-QTOF , positive-QTOF	splash10-00di-0190000000-a53a43c16d61d22ba5fd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-QTOF , positive-QTOF	splash10-00dl-0970000000-e99d426adbbcf08b402b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-QTOF , positive-QTOF	splash10-01ox-0910000000-eb35950d925bbd52e2e7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-ITFT , positive-QTOF	splash10-00di-0190000000-c166d05b1d38a4369d13	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-ITFT , positive-QTOF	splash10-00di-0190000000-8e02e6181e389f2fce58	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-ITFT , positive-QTOF	splash10-00di-0190000000-b96acc7d851ea2cbe471	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-ITFT , positive-QTOF	splash10-00di-0190000000-c690fb44764739147531	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Linear Ion Trap , positive-QTOF	splash10-00dj-0690000000-37f50a89d80a7d8e7b7c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Linear Ion Trap , positive-QTOF	splash10-00dj-0790000000-a0f7d5eacf28002d6c1e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Linear Ion Trap , positive-QTOF	splash10-001i-0590000000-5e15df23e1760f95e514	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Linear Ion Trap , positive-QTOF	splash10-001i-0490000000-528be5b0367f05c60956	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid , positive-QTOF	splash10-03dl-2900000000-a43198a76493a4d0f488	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid , positive-QTOF	splash10-01vo-0920000000-f5f28fbcb7e0a5bb9b80	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid 10V, Positive-QTOF	splash10-00di-0190000000-f80ae28c9584a754308f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid 20V, Positive-QTOF	splash10-00dl-1980000000-6202f47e101d4e1eb445	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid 40V, Positive-QTOF	splash10-01tc-4900000000-467e437210b7102853bc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid 10V, Negative-QTOF	splash10-000i-0190000000-43a9af4188e370a734b8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid 20V, Negative-QTOF	splash10-00kr-0590000000-cc97b3e7c9a32a9bebd2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid 40V, Negative-QTOF	splash10-03dm-1900000000-e915c52fc0eac0cfe2b9	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected and Quantified	0.046 +/- 0.009 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	19812218	details

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

FDB023019

KNApSAcK ID

Not Available

Chemspider ID

642910

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6705

PubChem Compound

735755

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1182681

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Jenner AM, Rafter J, Halliwell B: Human fecal water content of phenolics: the extent of colonic exposure to aromatic compounds. Free Radic Biol Med. 2005 Mar 15;38(6):763-72. [PubMed:15721987 ]
Todoriki H, Hayashi T, Naruse H: High-performance liquid chromatographic method for screening disorders of aromatic acid metabolism using a multi-detection system. J Chromatogr. 1984 Oct 12;310(2):273-81. [PubMed:6511847 ]
Kissling E: [The detection of Azotobacter and its significance in criminal technical soil examinations]. Arch Kriminol. 1980;165(1-2):27-34. [PubMed:6992730 ]
Kumar S, Arya P, Mukherjee C, Singh BK, Singh N, Parmar VS, Prasad AK, Ghosh B: Novel aromatic ester from Piper longum and its analogues inhibit expression of cell adhesion molecules on endothelial cells. Biochemistry. 2005 Dec 6;44(48):15944-52. [PubMed:16313198 ]

Showing metabocard for 3,4,5-Trimethoxycinnamic acid (HMDB0002511)

MOL for HMDB0002511 (3,4,5-Trimethoxycinnamic acid)

3D MOL for HMDB0002511 (3,4,5-Trimethoxycinnamic acid)

3D SDF for HMDB0002511 (3,4,5-Trimethoxycinnamic acid)

3D-SDF for HMDB0002511 (3,4,5-Trimethoxycinnamic acid)

PDB for HMDB0002511 (3,4,5-Trimethoxycinnamic acid)

3D PDB for HMDB0002511 (3,4,5-Trimethoxycinnamic acid)

SMILES for HMDB0002511 (3,4,5-Trimethoxycinnamic acid)

INCHI for HMDB0002511 (3,4,5-Trimethoxycinnamic acid)

Structure for HMDB0002511 (3,4,5-Trimethoxycinnamic acid)

3D Structure for HMDB0002511 (3,4,5-Trimethoxycinnamic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra