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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:30:26 UTC

Update Date

2022-03-07 02:54:10 UTC

HMDB ID

HMDB0034620

Secondary Accession Numbers

HMDB34620

Metabolite Identification

Common Name

cis-Coutaric acid

Description

cis-Coutaric acid, also known as cis-coutarate, belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. cis-Coutaric acid is found, on average, in the highest concentration within white wine. cis-Coutaric acid has also been detected, but not quantified in, a few different foods, such as alcoholic beverages, common grapes (Vitis vinifera), and fruits. This could make cis-coutaric acid a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on cis-Coutaric acid.

Structure

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

HMDB0034620
     RDKit          3D
cis-Coutaric acid
 33 33  0  0  0  0  0  0  0  0999 V2000
   -0.0071   -0.2043    0.3951 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3197   -0.1791   -0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807   -0.1999   -1.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7650   -0.2002   -2.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903   -0.1607   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6357    0.4020    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5910    0.2376    1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6815   -0.5392    1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6363   -0.7053    2.0473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8014   -1.1402   -0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8535   -0.9676   -1.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7492   -0.1188   -0.9420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5816   -0.0956    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5038   -1.2639    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3371   -1.4525    1.1277 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4347   -2.1639   -0.8265 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4061    1.1975    0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1645    1.2070   -1.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2679    1.3294    1.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5060    1.4278    1.1444 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7674    1.3489    2.5908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0690   -0.2185   -2.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2102   -0.2293   -3.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8565    1.1012    0.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4648    0.7240    2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5216   -0.2518    2.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6773   -1.7525   -0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9962   -1.4609   -2.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0113   -0.1282    1.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2549   -2.5837   -1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7285    2.0755    0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955    2.0111   -1.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719    1.4670    2.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
 11  5  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
M  END


  Mrv0541 05061307582D          

 21 21  0  0  0  0            999 V2000
   -0.7145    1.2375    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
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    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
    0.0000    2.4750    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
    0.7145    0.4125    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    0.0000    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    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    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
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    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
    0.7145   -1.2375    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
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  3  2  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 16 10  1  0  0  0  0
 17 12  2  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 20 13  1  0  0  0  0
 21  9  1  0  0  0  0
 21 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034620

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O8/c14-8-4-1-7(2-5-8)3-6-9(15)21-11(13(19)20)10(16)12(17)18/h1-6,10-11,14,16H,(H,17,18)(H,19,20)/b6-3-

> <INCHI_KEY>
INYJZRKTYXTZHP-UTCJRWHESA-N

> <FORMULA>
C13H12O8

> <MOLECULAR_WEIGHT>
296.2296

> <EXACT_MASS>
296.05321736

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
26.845325832771607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
0.9015255076666668

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.630014618327391

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.151380429466035

> <JCHEM_PKA_STRONGEST_BASIC>
-4.345612995541209

> <JCHEM_POLAR_SURFACE_AREA>
141.35999999999999

> <JCHEM_REFRACTIVITY>
67.76200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034620
     RDKit          3D
cis-Coutaric acid
 33 33  0  0  0  0  0  0  0  0999 V2000
   -0.0071   -0.2043    0.3951 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3197   -0.1791   -0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807   -0.1999   -1.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7650   -0.2002   -2.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903   -0.1607   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6357    0.4020    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5910    0.2376    1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6815   -0.5392    1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6363   -0.7053    2.0473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8014   -1.1402   -0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8535   -0.9676   -1.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7492   -0.1188   -0.9420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5816   -0.0956    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5038   -1.2639    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3371   -1.4525    1.1277 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4347   -2.1639   -0.8265 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4061    1.1975    0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1645    1.2070   -1.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2679    1.3294    1.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5060    1.4278    1.1444 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7674    1.3489    2.5908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0690   -0.2185   -2.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2102   -0.2293   -3.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8565    1.1012    0.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4648    0.7240    2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5216   -0.2518    2.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6773   -1.7525   -0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9962   -1.4609   -2.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0113   -0.1282    1.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2549   -2.5837   -1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7285    2.0755    0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955    2.0111   -1.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719    1.4670    2.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
 11  5  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  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      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   0.770   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   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334   0.770   0.000  0.00  0.00           O+0
CONECT    1    4    7                                                       
CONECT    2    5    7                                                       
CONECT    3    6    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    8                                                       
CONECT    6    3    9                                                       
CONECT    7    1    2    3                                                  
CONECT    8    4    5   14                                                  
CONECT    9    6   15   21                                                  
CONECT   10   11   12   16                                                  
CONECT   11   10   13   21                                                  
CONECT   12   10   17   18                                                  
CONECT   13   11   19   20                                                  
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17   12                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   13                                                            
CONECT   21    9   11                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0034620
HETATM    1  O1  UNL     1      -0.007  -0.204   0.395  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.320  -0.179  -0.795  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.481  -0.200  -1.984  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.765  -0.200  -2.034  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.690  -0.161  -0.952  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.636   0.402   0.275  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.591   0.238   1.280  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.682  -0.539   1.047  1.00  0.00           C  
HETATM    9  O2  UNL     1      -5.636  -0.705   2.047  1.00  0.00           O  
HETATM   10  C8  UNL     1      -4.801  -1.140  -0.187  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.853  -0.968  -1.156  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.749  -0.119  -0.942  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.582  -0.096   0.197  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.504  -1.264   0.209  1.00  0.00           C  
HETATM   15  O4  UNL     1       4.337  -1.453   1.128  1.00  0.00           O  
HETATM   16  O5  UNL     1       3.435  -2.164  -0.827  1.00  0.00           O  
HETATM   17  C12 UNL     1       3.406   1.198   0.103  1.00  0.00           C  
HETATM   18  O6  UNL     1       4.164   1.207  -1.050  1.00  0.00           O  
HETATM   19  C13 UNL     1       4.268   1.329   1.302  1.00  0.00           C  
HETATM   20  O7  UNL     1       5.506   1.428   1.144  1.00  0.00           O  
HETATM   21  O8  UNL     1       3.767   1.349   2.591  1.00  0.00           O  
HETATM   22  H1  UNL     1       0.069  -0.219  -2.988  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.210  -0.229  -3.100  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.857   1.101   0.507  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.465   0.724   2.236  1.00  0.00           H  
HETATM   26  H5  UNL     1      -5.522  -0.252   2.943  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.677  -1.753  -0.351  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.996  -1.461  -2.106  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.011  -0.128   1.137  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.255  -2.584  -1.266  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.729   2.075   0.085  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.995   2.011  -1.609  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.772   1.467   2.722  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   22
CONECT    4    5   23
CONECT    5    6    6   11
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9   10
CONECT    9   26
CONECT   10   11   11   27
CONECT   11   28
CONECT   12   13
CONECT   13   14   17   29
CONECT   14   15   15   16
CONECT   16   30
CONECT   17   18   19   31
CONECT   18   32
CONECT   19   20   20   21
CONECT   21   33
END

HMDB0034620
     RDKit          3D
cis-Coutaric acid
 33 33  0  0  0  0  0  0  0  0999 V2000
   -0.0071   -0.2043    0.3951 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3197   -0.1791   -0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807   -0.1999   -1.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7650   -0.2002   -2.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903   -0.1607   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6357    0.4020    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5910    0.2376    1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6815   -0.5392    1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6363   -0.7053    2.0473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8014   -1.1402   -0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8535   -0.9676   -1.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7492   -0.1188   -0.9420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5816   -0.0956    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5038   -1.2639    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3371   -1.4525    1.1277 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4347   -2.1639   -0.8265 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4061    1.1975    0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1645    1.2070   -1.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2679    1.3294    1.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5060    1.4278    1.1444 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7674    1.3489    2.5908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0690   -0.2185   -2.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2102   -0.2293   -3.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8565    1.1012    0.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4648    0.7240    2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5216   -0.2518    2.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6773   -1.7525   -0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9962   -1.4609   -2.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0113   -0.1282    1.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2549   -2.5837   -1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7285    2.0755    0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955    2.0111   -1.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719    1.4670    2.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
 11  5  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
cis-Coutarate	Generator
cis-P-Coumaroyltartaric acid	HMDB
2-Hydroxy-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioate	Generator

Chemical Formula

C₁₃H₁₂O₈

Average Molecular Weight

296.2296

Monoisotopic Molecular Weight

296.05321736

IUPAC Name

2-hydroxy-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

Traditional Name

2-hydroxy-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

CAS Registry Number

67920-37-0

SMILES

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

InChI Identifier

InChI=1S/C13H12O8/c14-8-4-1-7(2-5-8)3-6-9(15)21-11(13(19)20)10(16)12(17)18/h1-6,10-11,14,16H,(H,17,18)(H,19,20)/b6-3-

InChI Key

INYJZRKTYXTZHP-UTCJRWHESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
Tricarboxylic acid or derivatives
Styrene
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Sugar acid
Beta-hydroxy acid
Hydroxy acid
Monocyclic benzene moiety
Alpha-hydroxy acid
Monosaccharide
Fatty acyl
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034620)
Cytoplasm (HMDB: HMDB0034620)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034620)

Source

Exogenous

Food

Food (HMDB: HMDB0034620)

Beverage

Fermented beverage

White wine (FooDB: FOOD00917)

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Fruit

Berry

Common grape (FooDB: FOOD00204)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0034620)

Not Available

Nutrient (HMDB: HMDB0034620)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	101700 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.86 g/L	ALOGPS
logP	1.49	ALOGPS
logP	0.9	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	67.76 m³·mol⁻¹	ChemAxon
Polarizability	26.85 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
DeepCCS	[M+H]+	163.983	30932474
DeepCCS	[M-H]-	161.625	30932474
DeepCCS	[M-2H]-	194.511	30932474
DeepCCS	[M+Na]+	170.076	30932474
AllCCS	[M+H]+	164.9	32859911
AllCCS	[M+H-H2O]+	161.7	32859911
AllCCS	[M+NH4]+	167.9	32859911
AllCCS	[M+Na]+	168.8	32859911
AllCCS	[M-H]-	163.4	32859911
AllCCS	[M+Na-2H]-	163.4	32859911
AllCCS	[M+HCOO]-	163.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-Coutaric acid	OC(C(OC(=O)\C=C/C1=CC=C(O)C=C1)C(O)=O)C(O)=O	4914.6	Standard polar	33892256
cis-Coutaric acid	OC(C(OC(=O)\C=C/C1=CC=C(O)C=C1)C(O)=O)C(O)=O	2590.3	Standard non polar	33892256
cis-Coutaric acid	OC(C(OC(=O)\C=C/C1=CC=C(O)C=C1)C(O)=O)C(O)=O	2886.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-Coutaric acid,1TMS,isomer #1	C[Si](C)(C)OC(C(=O)O)C(OC(=O)/C=C\C1=CC=C(O)C=C1)C(=O)O	2800.3	Semi standard non polar	33892256
cis-Coutaric acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC(C(=O)O)C(O)C(=O)O)C=C1	2749.4	Semi standard non polar	33892256
cis-Coutaric acid,1TMS,isomer #3	C[Si](C)(C)OC(=O)C(OC(=O)/C=C\C1=CC=C(O)C=C1)C(O)C(=O)O	2776.5	Semi standard non polar	33892256
cis-Coutaric acid,1TMS,isomer #4	C[Si](C)(C)OC(=O)C(O)C(OC(=O)/C=C\C1=CC=C(O)C=C1)C(=O)O	2765.9	Semi standard non polar	33892256
cis-Coutaric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C(OC(=O)/C=C\C1=CC=C(O)C=C1)C(=O)O	2750.5	Semi standard non polar	33892256
cis-Coutaric acid,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC(C(=O)O)C(O[Si](C)(C)C)C(=O)O)C=C1	2775.1	Semi standard non polar	33892256
cis-Coutaric acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)C(OC(=O)/C=C\C1=CC=C(O)C=C1)C(O[Si](C)(C)C)C(=O)O	2760.3	Semi standard non polar	33892256
cis-Coutaric acid,2TMS,isomer #4	C[Si](C)(C)OC(=O)C(OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C=C1)C(O)C(=O)O	2740.0	Semi standard non polar	33892256
cis-Coutaric acid,2TMS,isomer #5	C[Si](C)(C)OC(=O)C(O)C(OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	2746.0	Semi standard non polar	33892256
cis-Coutaric acid,2TMS,isomer #6	C[Si](C)(C)OC(=O)C(O)C(OC(=O)/C=C\C1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C	2695.5	Semi standard non polar	33892256
cis-Coutaric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C(OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	2743.1	Semi standard non polar	33892256
cis-Coutaric acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(OC(=O)/C=C\C1=CC=C(O)C=C1)C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2705.1	Semi standard non polar	33892256
cis-Coutaric acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C=C1)C(O[Si](C)(C)C)C(=O)O	2738.3	Semi standard non polar	33892256
cis-Coutaric acid,3TMS,isomer #4	C[Si](C)(C)OC(=O)C(O)C(OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	2741.5	Semi standard non polar	33892256
cis-Coutaric acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C=C1)C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2750.2	Semi standard non polar	33892256
cis-Coutaric acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(C(=O)O)C(OC(=O)/C=C\C1=CC=C(O)C=C1)C(=O)O	3029.4	Semi standard non polar	33892256
cis-Coutaric acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC(C(=O)O)C(O)C(=O)O)C=C1	3039.1	Semi standard non polar	33892256
cis-Coutaric acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)/C=C\C1=CC=C(O)C=C1)C(O)C(=O)O	3018.1	Semi standard non polar	33892256
cis-Coutaric acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(O)C(OC(=O)/C=C\C1=CC=C(O)C=C1)C(=O)O	3007.2	Semi standard non polar	33892256
cis-Coutaric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C\C1=CC=C(O)C=C1)C(=O)O	3199.4	Semi standard non polar	33892256
cis-Coutaric acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C1	3262.0	Semi standard non polar	33892256
cis-Coutaric acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)/C=C\C1=CC=C(O)C=C1)C(O[Si](C)(C)C(C)(C)C)C(=O)O	3199.7	Semi standard non polar	33892256
cis-Coutaric acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(O)C(=O)O	3277.8	Semi standard non polar	33892256
cis-Coutaric acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C(O)C(OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	3281.3	Semi standard non polar	33892256
cis-Coutaric acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C(O)C(OC(=O)/C=C\C1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3177.8	Semi standard non polar	33892256
cis-Coutaric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	3480.2	Semi standard non polar	33892256
cis-Coutaric acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)/C=C\C1=CC=C(O)C=C1)C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3371.4	Semi standard non polar	33892256
cis-Coutaric acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(O[Si](C)(C)C(C)(C)C)C(=O)O	3482.1	Semi standard non polar	33892256
cis-Coutaric acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(O)C(OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3462.2	Semi standard non polar	33892256
cis-Coutaric acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3650.7	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 - cis-Coutaric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-4910000000-ba96d2f8de6be6c97efe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-Coutaric acid GC-MS (4 TMS) - 70eV, Positive	splash10-014i-6491260000-371f03ee0a7d99624a96	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-Coutaric 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Coutaric acid 10V, Positive-QTOF	splash10-002b-0790000000-783fd770de89781d273d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Coutaric acid 20V, Positive-QTOF	splash10-0032-2950000000-34cbeff6fa8a7110d0ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Coutaric acid 40V, Positive-QTOF	splash10-00oa-4900000000-aeb2dc4aefee4b50670d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Coutaric acid 10V, Negative-QTOF	splash10-0f6t-2690000000-b5c8d3a07aa9ed38ebf7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Coutaric acid 20V, Negative-QTOF	splash10-03ej-3940000000-a1799c7a99ba6feb7dd8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Coutaric acid 40V, Negative-QTOF	splash10-002b-3910000000-2e0c2fa4d35ecac5a1b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Coutaric acid 10V, Positive-QTOF	splash10-0002-0940000000-7987f1711c48bb602c0a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Coutaric acid 20V, Positive-QTOF	splash10-00kb-0900000000-630089dd29b945a3fb64	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Coutaric acid 40V, Positive-QTOF	splash10-014i-1900000000-aa7d4d40daa071395a92	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Coutaric acid 10V, Negative-QTOF	splash10-0019-9720000000-0a0c84406801b831e091	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Coutaric acid 20V, Negative-QTOF	splash10-00kr-7900000000-05ba688ac97301129cfc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Coutaric acid 40V, Negative-QTOF	splash10-014i-3900000000-8fc199380ced811553e2	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

495

FooDB ID

FDB013139

KNApSAcK ID

Not Available

Chemspider ID

35013748

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

69968525

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1844531

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 cis-Coutaric acid (HMDB0034620)

MOL for HMDB0034620 (cis-Coutaric acid)

3D MOL for HMDB0034620 (cis-Coutaric acid)

3D SDF for HMDB0034620 (cis-Coutaric acid)

3D-SDF for HMDB0034620 (cis-Coutaric acid)

PDB for HMDB0034620 (cis-Coutaric acid)

3D PDB for HMDB0034620 (cis-Coutaric acid)

SMILES for HMDB0034620 (cis-Coutaric acid)

INCHI for HMDB0034620 (cis-Coutaric acid)

Structure for HMDB0034620 (cis-Coutaric acid)

3D Structure for HMDB0034620 (cis-Coutaric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra