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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-02-26 10:58:06 UTC

Update Date

2020-02-26 21:35:44 UTC

HMDB ID

HMDB0011721

Secondary Accession Numbers

HMDB11721

Metabolite Identification

Common Name

Trans-2, 3, 4-Trimethoxycinnamate

Description

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

HMDB0011721
     RDKit          3D
Trans-2, 3, 4-Trimethoxycinnamate
 31 31  0  0  0  0  0  0  0  0999 V2000
   -3.3737    1.0134    2.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0739    0.5895    1.2936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428    0.3742    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280    0.5711    1.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5665    0.3438    1.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8504   -0.0699    0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2318   -0.3205   -0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3040   -0.1788    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6506   -0.4405    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9033   -0.8196   -1.1536 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7159   -0.2648    0.8695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1950   -0.2669   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1086   -0.6731   -1.9622 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2404   -1.9151   -2.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4913   -0.0428   -0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5044   -0.2405   -1.2548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341    0.8317   -2.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4548    1.1241    2.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8164    1.9810    2.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9293    0.3084    3.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522    0.9049    2.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3645    0.4934    2.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261   -0.6523   -1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1840    0.1428    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8001    0.6196    1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5261   -1.8097   -3.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536   -2.4780   -2.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514   -2.5609   -2.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075    0.7392   -3.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5389    1.7957   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0325    0.9005   -2.0809 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 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
  5 22  1  0
  7 23  1  0
  8 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


  Mrv0541 02241201522D          

 17 17  0  0  0  0            999 V2000
   12.1453   -7.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1453   -8.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4308   -7.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4308   -8.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7163   -7.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7163   -8.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8598   -8.9061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5742   -8.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4308   -9.7311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1453  -10.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0019   -8.9061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0019   -9.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8598   -7.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5742   -7.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2888   -7.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0032   -7.6686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2888   -6.4311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
  2  7  1  0  0  0  0
 10  9  1  0  0  0  0
  4  9  1  0  0  0  0
 12 11  1  0  0  0  0
  6 11  1  0  0  0  0
 13  1  1  0  0  0  0
 14 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011721

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O5/c1-15-9-6-4-8(5-7-10(13)14)11(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b7-5+

> <INCHI_KEY>
ZYOPDNLIHHFGEC-FNORWQNLSA-N

> <FORMULA>
C12H14O5

> <MOLECULAR_WEIGHT>
238.2366

> <EXACT_MASS>
238.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
24.164069659006476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
1.6630724629999993

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7233652357846596

> <JCHEM_PKA_STRONGEST_BASIC>
-4.450388100499459

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
62.4495

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011721
     RDKit          3D
Trans-2, 3, 4-Trimethoxycinnamate
 31 31  0  0  0  0  0  0  0  0999 V2000
   -3.3737    1.0134    2.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0739    0.5895    1.2936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428    0.3742    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280    0.5711    1.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5665    0.3438    1.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8504   -0.0699    0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2318   -0.3205   -0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3040   -0.1788    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6506   -0.4405    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9033   -0.8196   -1.1536 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7159   -0.2648    0.8695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1950   -0.2669   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1086   -0.6731   -1.9622 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2404   -1.9151   -2.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4913   -0.0428   -0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5044   -0.2405   -1.2548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341    0.8317   -2.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4548    1.1241    2.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8164    1.9810    2.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9293    0.3084    3.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522    0.9049    2.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3645    0.4934    2.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261   -0.6523   -1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1840    0.1428    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8001    0.6196    1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5261   -1.8097   -3.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536   -2.4780   -2.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514   -2.5609   -2.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075    0.7392   -3.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5389    1.7957   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0325    0.9005   -2.0809 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 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
  5 22  1  0
  7 23  1  0
  8 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                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      22.671 -14.315   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.671 -15.855   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.337 -13.545   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.337 -16.625   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.004 -14.315   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.004 -15.855   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      24.005 -16.625   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      25.339 -15.855   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      21.337 -18.165   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      22.671 -18.935   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      18.670 -16.625   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      18.670 -18.165   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.005 -13.545   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.339 -14.315   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.672 -13.545   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      28.006 -14.315   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      26.672 -12.005   0.000  0.00  0.00           O+0
CONECT    1    2    3   13                                                  
CONECT    2    1    4    7                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6    9                                                  
CONECT    5    3    6                                                       
CONECT    6    4    5   11                                                  
CONECT    7    8    2                                                       
CONECT    8    7                                                            
CONECT    9   10    4                                                       
CONECT   10    9                                                            
CONECT   11   12    6                                                       
CONECT   12   11                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0011721
HETATM    1  C1  UNL     1      -3.374   1.013   2.593  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.074   0.590   1.294  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.743   0.374   0.950  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.728   0.571   1.863  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.567   0.344   1.470  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.850  -0.070   0.200  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.232  -0.321  -0.246  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.304  -0.179   0.503  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.651  -0.440   0.012  1.00  0.00           C  
HETATM   10  O2  UNL     1       4.903  -0.820  -1.154  1.00  0.00           O  
HETATM   11  O3  UNL     1       5.716  -0.265   0.869  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.195  -0.267  -0.722  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.109  -0.673  -1.962  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.240  -1.915  -2.529  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.491  -0.043  -0.340  1.00  0.00           C  
HETATM   16  O5  UNL     1      -2.504  -0.240  -1.255  1.00  0.00           O  
HETATM   17  C12 UNL     1      -2.934   0.832  -2.091  1.00  0.00           C  
HETATM   18  H1  UNL     1      -4.455   1.124   2.780  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.816   1.981   2.760  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.929   0.308   3.346  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.952   0.905   2.889  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.365   0.493   2.171  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.426  -0.652  -1.273  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.184   0.143   1.517  1.00  0.00           H  
HETATM   25  H8  UNL     1       5.800   0.620   1.352  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.526  -1.810  -3.602  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.054  -2.478  -2.024  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.651  -2.561  -2.511  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.507   0.739  -3.108  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.539   1.796  -1.671  1.00  0.00           H  
HETATM   31  H14 UNL     1      -4.032   0.901  -2.081  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    6   22
CONECT    6    7   12
CONECT    7    8    8   23
CONECT    8    9   24
CONECT    9   10   10   11
CONECT   11   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

HMDB0011721
     RDKit          3D
Trans-2, 3, 4-Trimethoxycinnamate
 31 31  0  0  0  0  0  0  0  0999 V2000
   -3.3737    1.0134    2.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0739    0.5895    1.2936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428    0.3742    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280    0.5711    1.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5665    0.3438    1.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8504   -0.0699    0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2318   -0.3205   -0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3040   -0.1788    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6506   -0.4405    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9033   -0.8196   -1.1536 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7159   -0.2648    0.8695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1950   -0.2669   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1086   -0.6731   -1.9622 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2404   -1.9151   -2.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4913   -0.0428   -0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5044   -0.2405   -1.2548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341    0.8317   -2.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4548    1.1241    2.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8164    1.9810    2.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9293    0.3084    3.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522    0.9049    2.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3645    0.4934    2.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261   -0.6523   -1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1840    0.1428    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8001    0.6196    1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5261   -1.8097   -3.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536   -2.4780   -2.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514   -2.5609   -2.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075    0.7392   -3.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5389    1.7957   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0325    0.9005   -2.0809 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 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
  5 22  1  0
  7 23  1  0
  8 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
trans-2, 3, 4-Trimethoxycinnamic acid	Generator
(2E)-3-(2,3,4-Trimethoxyphenyl)-2-propenoate	HMDB
(2E)-3-(2,3,4-Trimethoxyphenyl)-2-propenoic acid	HMDB
3-(2,3,4-Trimethoxyphenyl)-2-propenoate	HMDB
3-(2,3,4-Trimethoxyphenyl)-2-propenoic acid	HMDB
3-(2,3,4-Trimethoxyphenyl)acrylic acid	MeSH, HMDB
(Z)-3-(2,3,4-Trimethoxyphenyl)acrylic acid	MeSH, HMDB
(2E)-3-(2,3,4-Trimethoxyphenyl)prop-2-enoate	Generator, HMDB
trans-2,3,4-Trimethoxycinnamic acid	Generator, HMDB

Chemical Formula

C₁₂H₁₄O₅

Average Molecular Weight

238.2366

Monoisotopic Molecular Weight

238.084123558

IUPAC Name

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

Traditional Name

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

CAS Registry Number

33130-03-9

SMILES

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

InChI Identifier

InChI=1S/C12H14O5/c1-15-9-6-4-8(5-7-10(13)14)11(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b7-5+

InChI Key

ZYOPDNLIHHFGEC-FNORWQNLSA-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

Prostate (HMDB: HMDB0011721)

Source

Endogenous

Endogenous (HMDB: HMDB0011721)

Plant

Plant (HMDB: HMDB0011721)

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)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	2.23	ALOGPS
logP	1.66	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	-4.5	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	24.16 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]+	158.264	31661259
DarkChem	[M-H]-	159.423	31661259
DeepCCS	[M+H]+	154.06	30932474
DeepCCS	[M-H]-	151.702	30932474
DeepCCS	[M-2H]-	184.681	30932474
DeepCCS	[M+Na]+	160.153	30932474
AllCCS	[M+H]+	153.6	32859911
AllCCS	[M+H-H2O]+	149.8	32859911
AllCCS	[M+NH4]+	157.2	32859911
AllCCS	[M+Na]+	158.2	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.	5.22 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3259 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.33 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1762.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	291.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	145.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	412.1 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	430.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	132.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	976.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	360.5 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	1115.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	277.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	326.6 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	367.6 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	16.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trans-2, 3, 4-Trimethoxycinnamate	COC1=CC=C(\C=C\C(O)=O)C(OC)=C1OC	3578.4	Standard polar	33892256
Trans-2, 3, 4-Trimethoxycinnamate	COC1=CC=C(\C=C\C(O)=O)C(OC)=C1OC	1986.9	Standard non polar	33892256
Trans-2, 3, 4-Trimethoxycinnamate	COC1=CC=C(\C=C\C(O)=O)C(OC)=C1OC	2021.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Trans-2, 3, 4-Trimethoxycinnamate,1TMS,isomer #1	COC1=CC=C(/C=C/C(=O)O[Si](C)(C)C)C(OC)=C1OC	2064.5	Semi standard non polar	33892256
Trans-2, 3, 4-Trimethoxycinnamate,1TBDMS,isomer #1	COC1=CC=C(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)C(OC)=C1OC	2318.2	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 - Trans-2, 3, 4-Trimethoxycinnamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-0790000000-546566c77f735621458e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate GC-MS (1 TMS) - 70eV, Positive	splash10-00dm-5390000000-84739ec48a42b66e5594	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trans-2, 3, 4-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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 10V, Positive-QTOF	splash10-00di-0190000000-1e13429db4d85040c54d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 20V, Positive-QTOF	splash10-00dl-1960000000-4b218f0b564a1657e43f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 40V, Positive-QTOF	splash10-0729-4900000000-3cb11ab02839a3aabf06	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 10V, Negative-QTOF	splash10-000i-0190000000-f1990d4a97b412cc36b0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 20V, Negative-QTOF	splash10-00ku-0790000000-29bb631a9b0a887069fd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 40V, Negative-QTOF	splash10-03xs-1900000000-4fabb2bb92e441555d5b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 10V, Positive-QTOF	splash10-000i-0090000000-cc5b267c35e4cc81ce2d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 20V, Positive-QTOF	splash10-000f-0980000000-d08ea794055c7d924773	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 40V, Positive-QTOF	splash10-0a4i-3900000000-e096e3d21a4e3906168e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 10V, Negative-QTOF	splash10-000l-0590000000-26899881860df02e938a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 20V, Negative-QTOF	splash10-03fr-0900000000-515bec14a141b2c91d89	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-2, 3, 4-Trimethoxycinnamate 40V, Negative-QTOF	splash10-01t9-1900000000-e4f8a20c79574252d009	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Prostate

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

FDB028405

KNApSAcK ID

Not Available

Chemspider ID

642995

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

735841

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
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 Trans-2, 3, 4-Trimethoxycinnamate (HMDB0011721)

MOL for HMDB0011721 (Trans-2, 3, 4-Trimethoxycinnamate)

3D MOL for HMDB0011721 (Trans-2, 3, 4-Trimethoxycinnamate)

3D SDF for HMDB0011721 (Trans-2, 3, 4-Trimethoxycinnamate)

3D-SDF for HMDB0011721 (Trans-2, 3, 4-Trimethoxycinnamate)

PDB for HMDB0011721 (Trans-2, 3, 4-Trimethoxycinnamate)

3D PDB for HMDB0011721 (Trans-2, 3, 4-Trimethoxycinnamate)

SMILES for HMDB0011721 (Trans-2, 3, 4-Trimethoxycinnamate)

INCHI for HMDB0011721 (Trans-2, 3, 4-Trimethoxycinnamate)

Structure for HMDB0011721 (Trans-2, 3, 4-Trimethoxycinnamate)

3D Structure for HMDB0011721 (Trans-2, 3, 4-Trimethoxycinnamate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra