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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:55 UTC

Update Date

2022-03-07 02:53:32 UTC

HMDB ID

HMDB0032957

Secondary Accession Numbers

HMDB32957

Metabolite Identification

Common Name

2-O-Feruloyltartronic acid

Description

2-O-Feruloyltartronic acid 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. 2-O-Feruloyltartronic acid has been detected, but not quantified in, pulses. This could make 2-O-feruloyltartronic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-O-Feruloyltartronic acid.

Structure

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

HMDB0032957
     RDKit          3D
2-O-Feruloyltartronic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    3.6323    2.1245    1.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3373    1.1561    1.0127 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.1625    0.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198    0.0049    0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8485   -0.9852   -0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3950   -1.1311   -0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4822   -0.3456   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8967   -0.5453   -0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2953   -1.4806   -1.2098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8071    0.2916    0.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2073    0.1531   -0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8163    1.4107   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0658    2.3905   -0.7381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1651    1.5374   -0.7612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7617   -0.1110    1.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0423   -0.1785    2.3506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1196   -0.2907    1.4873 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7003   -1.8761   -1.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0512   -1.7300   -1.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6172   -0.7279   -0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9977   -0.6643   -0.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6595    1.7885    2.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5101    3.0163    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2650    2.5099    2.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7963    0.7220    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0090   -1.9310   -1.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1501    0.4620    0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4168   -0.7155   -0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7373    2.3059   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6204   -0.9123    0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599   -2.6548   -1.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7201   -2.4225   -1.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5761   -1.3336   -0.7931 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
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
 11 28  1  0
 14 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 21 33  1  0
M  END


  Mrv0541 05061306492D          

 21 21  0  0  0  0            999 V2000
   -5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    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
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 O   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
   -5.0013    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  7  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 15 10  2  0  0  0  0
 16 12  2  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19 13  1  0  0  0  0
 20  1  1  0  0  0  0
 20  9  1  0  0  0  0
 21 10  1  0  0  0  0
 21 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032957

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)OC(C(O)=O)C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O8/c1-20-9-6-7(2-4-8(9)14)3-5-10(15)21-11(12(16)17)13(18)19/h2-6,11,14H,1H3,(H,16,17)(H,18,19)/b5-3+

> <INCHI_KEY>
ZWXOJLRXYPVVQY-HWKANZROSA-N

> <FORMULA>
C13H12O8

> <MOLECULAR_WEIGHT>
296.2296

> <EXACT_MASS>
296.05321736

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
27.2849444462551

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propanedioic acid

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.5263784016666664

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.606564270866936

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1576734702954035

> <JCHEM_PKA_STRONGEST_BASIC>
-4.889288345883923

> <JCHEM_POLAR_SURFACE_AREA>
130.35999999999999

> <JCHEM_REFRACTIVITY>
68.33780000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032957
     RDKit          3D
2-O-Feruloyltartronic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    3.6323    2.1245    1.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3373    1.1561    1.0127 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.1625    0.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198    0.0049    0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8485   -0.9852   -0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3950   -1.1311   -0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4822   -0.3456   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8967   -0.5453   -0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2953   -1.4806   -1.2098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8071    0.2916    0.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2073    0.1531   -0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8163    1.4107   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0658    2.3905   -0.7381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1651    1.5374   -0.7612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7617   -0.1110    1.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0423   -0.1785    2.3506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1196   -0.2907    1.4873 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7003   -1.8761   -1.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0512   -1.7300   -1.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6172   -0.7279   -0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9977   -0.6643   -0.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6595    1.7885    2.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5101    3.0163    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2650    2.5099    2.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7963    0.7220    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0090   -1.9310   -1.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1501    0.4620    0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4168   -0.7155   -0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7373    2.3059   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6204   -0.9123    0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599   -2.6548   -1.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7201   -2.4225   -1.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5761   -1.3336   -0.7931 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
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
 11 28  1  0
 14 29  1  0
 17 30  1  0
 18 31  1  0
 19 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     -10.669  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  12.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002  12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -9.336  13.090   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -9.336  10.010   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    4    7                                                       
CONECT    3    5    7                                                       
CONECT    4    2    8                                                       
CONECT    5    3   10                                                       
CONECT    6    7    9                                                       
CONECT    7    2    3    6                                                  
CONECT    8    4    9   14                                                  
CONECT    9    6    8   20                                                  
CONECT   10    5   15   21                                                  
CONECT   11   12   13   21                                                  
CONECT   12   11   16   17                                                  
CONECT   13   11   18   19                                                  
CONECT   14    8                                                            
CONECT   15   10                                                            
CONECT   16   12                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   13                                                            
CONECT   20    1    9                                                       
CONECT   21   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0032957
HETATM    1  C1  UNL     1       3.632   2.125   1.721  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.337   1.156   1.013  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.789   0.162   0.242  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.420   0.005   0.076  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.849  -0.985  -0.692  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.395  -1.131  -0.853  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.482  -0.346  -0.289  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.897  -0.545  -0.489  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.295  -1.481  -1.210  1.00  0.00           O  
HETATM   10  O3  UNL     1      -2.807   0.292   0.113  1.00  0.00           O  
HETATM   11  C8  UNL     1      -4.207   0.153  -0.040  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.816   1.411  -0.530  1.00  0.00           C  
HETATM   13  O4  UNL     1      -4.066   2.391  -0.738  1.00  0.00           O  
HETATM   14  O5  UNL     1      -6.165   1.537  -0.761  1.00  0.00           O  
HETATM   15  C10 UNL     1      -4.762  -0.111   1.326  1.00  0.00           C  
HETATM   16  O6  UNL     1      -4.042  -0.178   2.351  1.00  0.00           O  
HETATM   17  O7  UNL     1      -6.120  -0.291   1.487  1.00  0.00           O  
HETATM   18  C11 UNL     1       2.700  -1.876  -1.337  1.00  0.00           C  
HETATM   19  C12 UNL     1       4.051  -1.730  -1.180  1.00  0.00           C  
HETATM   20  C13 UNL     1       4.617  -0.728  -0.402  1.00  0.00           C  
HETATM   21  O8  UNL     1       5.998  -0.664  -0.307  1.00  0.00           O  
HETATM   22  H1  UNL     1       2.659   1.789   2.107  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.510   3.016   1.039  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.265   2.510   2.570  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.796   0.722   0.597  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.009  -1.931  -1.471  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.150   0.462   0.333  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.417  -0.715  -0.704  1.00  0.00           H  
HETATM   29  H8  UNL     1      -6.737   2.306  -0.440  1.00  0.00           H  
HETATM   30  H9  UNL     1      -6.620  -0.912   0.882  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.260  -2.655  -1.941  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.720  -2.423  -1.680  1.00  0.00           H  
HETATM   33  H12 UNL     1       6.576  -1.334  -0.793  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   25
CONECT    5    6   18   18
CONECT    6    7    7   26
CONECT    7    8   27
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   15   28
CONECT   12   13   13   14
CONECT   14   29
CONECT   15   16   16   17
CONECT   17   30
CONECT   18   19   31
CONECT   19   20   20   32
CONECT   20   21
CONECT   21   33
END

HMDB0032957
     RDKit          3D
2-O-Feruloyltartronic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    3.6323    2.1245    1.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3373    1.1561    1.0127 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.1625    0.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198    0.0049    0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8485   -0.9852   -0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3950   -1.1311   -0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4822   -0.3456   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8967   -0.5453   -0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2953   -1.4806   -1.2098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8071    0.2916    0.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2073    0.1531   -0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8163    1.4107   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0658    2.3905   -0.7381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1651    1.5374   -0.7612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7617   -0.1110    1.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0423   -0.1785    2.3506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1196   -0.2907    1.4873 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7003   -1.8761   -1.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0512   -1.7300   -1.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6172   -0.7279   -0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9977   -0.6643   -0.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6595    1.7885    2.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5101    3.0163    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2650    2.5099    2.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7963    0.7220    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0090   -1.9310   -1.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1501    0.4620    0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4168   -0.7155   -0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7373    2.3059   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6204   -0.9123    0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599   -2.6548   -1.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7201   -2.4225   -1.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5761   -1.3336   -0.7931 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
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
 11 28  1  0
 14 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 21 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-O-Feruloyltartronate	Generator
2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propanedioate	HMDB

Chemical Formula

C₁₃H₁₂O₈

Average Molecular Weight

296.2296

Monoisotopic Molecular Weight

296.05321736

IUPAC Name

2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propanedioic acid

Traditional Name

2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propanedioic acid

CAS Registry Number

95519-25-8

SMILES

COC1=C(O)C=CC(\C=C\C(=O)OC(C(O)=O)C(O)=O)=C1

InChI Identifier

InChI=1S/C13H12O8/c1-20-9-6-7(2-4-8(9)14)3-5-10(15)21-11(12(16)17)13(18)19/h2-6,11,14H,1H3,(H,16,17)(H,18,19)/b5-3+

InChI Key

ZWXOJLRXYPVVQY-HWKANZROSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Methoxyphenol
Tricarboxylic acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Monosaccharide
1,3-dicarbonyl compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032957)
Cytoplasm (HMDB: HMDB0032957)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032957)

Source

Exogenous

Exogenous (HMDB: HMDB0032957)

Food

Food (HMDB: HMDB0032957)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0032957)
Fabaceae (HMDB: HMDB0032957)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032957)

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	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	1.63	ALOGPS
logP	1.53	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	2.16	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	68.34 m³·mol⁻¹	ChemAxon
Polarizability	27.28 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]+	171.632	30932474
DeepCCS	[M-H]-	169.274	30932474
DeepCCS	[M-2H]-	202.645	30932474
DeepCCS	[M+Na]+	178.789	30932474
AllCCS	[M+H]+	165.7	32859911
AllCCS	[M+H-H2O]+	162.3	32859911
AllCCS	[M+NH4]+	168.7	32859911
AllCCS	[M+Na]+	169.6	32859911
AllCCS	[M-H]-	163.7	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	163.7	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. Predicted by Afia on May 17, 2022.	4.31 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4621 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.36 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	64.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1469.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	254.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	100.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	69.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	394.6 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	325.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	295.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	830.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	355.4 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	1174.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	223.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	301.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	531.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	221.2 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	166.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-O-Feruloyltartronic acid	COC1=C(O)C=CC(\C=C\C(=O)OC(C(O)=O)C(O)=O)=C1	4658.5	Standard polar	33892256
2-O-Feruloyltartronic acid	COC1=C(O)C=CC(\C=C\C(=O)OC(C(O)=O)C(O)=O)=C1	2492.7	Standard non polar	33892256
2-O-Feruloyltartronic acid	COC1=C(O)C=CC(\C=C\C(=O)OC(C(O)=O)C(O)=O)=C1	2632.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-O-Feruloyltartronic acid,1TMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(=O)O)=CC=C1O[Si](C)(C)C	2708.9	Semi standard non polar	33892256
2-O-Feruloyltartronic acid,1TMS,isomer #2	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(=O)O[Si](C)(C)C)=CC=C1O	2661.2	Semi standard non polar	33892256
2-O-Feruloyltartronic acid,2TMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2678.1	Semi standard non polar	33892256
2-O-Feruloyltartronic acid,2TMS,isomer #2	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O	2609.4	Semi standard non polar	33892256
2-O-Feruloyltartronic acid,3TMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2672.4	Semi standard non polar	33892256
2-O-Feruloyltartronic acid,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	2985.6	Semi standard non polar	33892256
2-O-Feruloyltartronic acid,1TBDMS,isomer #2	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	2922.8	Semi standard non polar	33892256
2-O-Feruloyltartronic acid,2TBDMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3177.9	Semi standard non polar	33892256
2-O-Feruloyltartronic acid,2TBDMS,isomer #2	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	3112.9	Semi standard non polar	33892256
2-O-Feruloyltartronic acid,3TBDMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3371.2	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 - 2-O-Feruloyltartronic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004m-3910000000-4601be5f8030d0ee6ac6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-O-Feruloyltartronic acid GC-MS (3 TMS) - 70eV, Positive	splash10-007a-9030300000-32884f471e94498324c0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-O-Feruloyltartronic 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 - 2-O-Feruloyltartronic acid 10V, Positive-QTOF	splash10-002b-0590000000-e5e09fddc30a7251c858	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloyltartronic acid 20V, Positive-QTOF	splash10-00b9-0930000000-38aaa6b166542905ee7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloyltartronic acid 40V, Positive-QTOF	splash10-0umj-2900000000-73c145bb07ef14cf6656	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloyltartronic acid 10V, Negative-QTOF	splash10-0002-0390000000-f31db9976ff3b739efdb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloyltartronic acid 20V, Negative-QTOF	splash10-016s-2960000000-11bd0cfe6230d6fc7102	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloyltartronic acid 40V, Negative-QTOF	splash10-00fr-8930000000-0747acb4236396ee53ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloyltartronic acid 10V, Negative-QTOF	splash10-0k9b-0290000000-9c0ae3a8f221d2639cc2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloyltartronic acid 20V, Negative-QTOF	splash10-052r-2390000000-a7d5c14bbf258af8f2d5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloyltartronic acid 40V, Negative-QTOF	splash10-001i-1900000000-f39bf50be1918c811a73	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloyltartronic acid 10V, Positive-QTOF	splash10-004i-0950000000-ca5fae006f575b59a5fa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloyltartronic acid 20V, Positive-QTOF	splash10-0002-0900000000-7d2d6b557ec91e26884e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloyltartronic acid 40V, Positive-QTOF	splash10-0002-2900000000-23ea09e244220e3b5999	2021-09-24	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

Not Available

FooDB ID

FDB010943

KNApSAcK ID

Not Available

Chemspider ID

30776964

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751352

PDB ID

Not Available

ChEBI ID

174811

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 2-O-Feruloyltartronic acid (HMDB0032957)

MOL for HMDB0032957 (2-O-Feruloyltartronic acid)

3D MOL for HMDB0032957 (2-O-Feruloyltartronic acid)

3D SDF for HMDB0032957 (2-O-Feruloyltartronic acid)

3D-SDF for HMDB0032957 (2-O-Feruloyltartronic acid)

PDB for HMDB0032957 (2-O-Feruloyltartronic acid)

3D PDB for HMDB0032957 (2-O-Feruloyltartronic acid)

SMILES for HMDB0032957 (2-O-Feruloyltartronic acid)

INCHI for HMDB0032957 (2-O-Feruloyltartronic acid)

Structure for HMDB0032957 (2-O-Feruloyltartronic acid)

3D Structure for HMDB0032957 (2-O-Feruloyltartronic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra