NP-MRD: Showing NP-Card for 3,4,5-Trimethoxycinnamic acid (NP0000110)

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Record Information

Version

2.0

Created at

2006-05-22 14:17:55 UTC

Updated at

2024-09-03 04:17:30 UTC

NP-MRD ID

NP0000110

Natural Product DOI

https://doi.org/10.57994/1063

Secondary Accession Numbers

None

Natural Product 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>
NP0000110

> <DATABASE_NAME>
NP-MRD

> <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

Synonyms

Value	Source
3,4,5-Trimethoxycinnamate	Generator
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	HMDB
3-(3,4,5-Trimethoxyphenyl)-2-propenoic acid	HMDB
3,4,5-Trimethoxycinnamic acid	MeSH

Chemical Formula

C₁₂H₁₄O₅

Average Mass

238.2366 Da

Monoisotopic Mass

238.08412 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-09	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-09	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-09	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, simulated)	v.dorna83@yahoo.com	Not Available	Not Available	2021-08-10	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Piper swartzianum	LOTUS Database	35616633
Piper tuberculatum	LOTUS Database	35616633
Polygala tenuifolia	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0002511

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1182681

References

General References

Showing NP-Card for 3,4,5-Trimethoxycinnamic acid (NP0000110)

MOL for NP0000110 (3,4,5-Trimethoxycinnamic acid)

3D MOL for NP0000110 (3,4,5-Trimethoxycinnamic acid)

3D SDF for NP0000110 (3,4,5-Trimethoxycinnamic acid)

3D-SDF for NP0000110 (3,4,5-Trimethoxycinnamic acid)

PDB for NP0000110 (3,4,5-Trimethoxycinnamic acid)

3D PDB for NP0000110 (3,4,5-Trimethoxycinnamic acid)

SMILES for NP0000110 (3,4,5-Trimethoxycinnamic acid)

INCHI for NP0000110 (3,4,5-Trimethoxycinnamic acid)

Structure for NP0000110 (3,4,5-Trimethoxycinnamic acid)

3D Structure for NP0000110 (3,4,5-Trimethoxycinnamic acid)