MiMeDB: Showing metabocard for Fertaric acid (MMDBc0033641)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:57:05 UTC

Update Date

2022-08-31 22:37:20 UTC

Metabolite ID

MMDBc0033641

Metabolite Identification

Common Name

Fertaric acid

Description

Fertaric acid is a the ester of tartaric acid and the phenolic acid ferulic acid, a type of polyphenol. Polyphenol are secondary plant metabolites and components of grapes, wines and beers. They contribute to the sensory characteristics of wine. Yeast can influence the polyphenolic wine composition by adsorbing them throught its cell wall during wine making. [Caridi 2004]

Structure

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

HMDB0029199
     RDKit          3D
Fertaric acid
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.2304    1.0614    1.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4084   -0.1031    0.7854 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3732   -0.7274    0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0607   -0.2516    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267   -0.8630   -0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -0.4042   -0.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    0.6659    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0534    1.1283    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521    2.1425    0.8860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171    0.4401   -0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3699    0.9508   -0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7509    1.2074   -1.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9497    0.9069   -2.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9528    1.7731   -2.2069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2536   -0.1253    0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454   -0.4677    1.5003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5973    0.4311    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4245    0.7784   -0.4060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0442    0.6105    1.7920 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3709   -2.0096   -1.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376   -2.5164   -1.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6421   -1.8542   -0.6098 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9318   -2.3602   -0.6834 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7749    0.8460    2.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2394    1.5133    1.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069    1.7548    0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8993    0.6385    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482   -0.9047   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0383    1.2502    0.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4051    1.8400    0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9160    2.5707   -2.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2695   -1.0544   -0.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1649   -1.2891    1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4538    1.5022    2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691   -2.5026   -1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9178   -3.3966   -1.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1716   -3.1820   -1.2075 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  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 11 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
 23 37  1  0
M  END


  Mrv0541 02241223222D          

 23 23  0  0  0  0            999 V2000
   -2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033641

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=CC(\C=C\C(=O)OC(C(O)C(O)=O)C(O)=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O9/c1-22-9-6-7(2-4-8(9)15)3-5-10(16)23-12(14(20)21)11(17)13(18)19/h2-6,11-12,15,17H,1H3,(H,18,19)(H,20,21)/b5-3+

> <INCHI_KEY>
XIWXUSFCUBAMFH-HWKANZROSA-N

> <FORMULA>
C14H14O9

> <MOLECULAR_WEIGHT>
326.2556

> <EXACT_MASS>
326.063782046

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
29.88692138604489

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
0.7438542420000003

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.47823248663642

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.951276504214371

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3456129955412335

> <JCHEM_POLAR_SURFACE_AREA>
150.59

> <JCHEM_REFRACTIVITY>
74.2252

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fertaric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029199
     RDKit          3D
Fertaric acid
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.2304    1.0614    1.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4084   -0.1031    0.7854 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3732   -0.7274    0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0607   -0.2516    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267   -0.8630   -0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -0.4042   -0.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    0.6659    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0534    1.1283    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521    2.1425    0.8860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171    0.4401   -0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3699    0.9508   -0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7509    1.2074   -1.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9497    0.9069   -2.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9528    1.7731   -2.2069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2536   -0.1253    0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454   -0.4677    1.5003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5973    0.4311    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4245    0.7784   -0.4060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0442    0.6105    1.7920 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3709   -2.0096   -1.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376   -2.5164   -1.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6421   -1.8542   -0.6098 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9318   -2.3602   -0.6834 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7749    0.8460    2.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2394    1.5133    1.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069    1.7548    0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8993    0.6385    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482   -0.9047   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0383    1.2502    0.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4051    1.8400    0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9160    2.5707   -2.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2695   -1.0544   -0.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1649   -1.2891    1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4538    1.5022    2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691   -2.5026   -1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9178   -3.3966   -1.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1716   -3.1820   -1.2075 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  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 11 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
 23 37  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  O   UNK     0      -4.001  11.550   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   15   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0029199
HETATM    1  C1  UNL     1       5.230   1.061   1.563  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.408  -0.103   0.785  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.373  -0.727   0.122  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.061  -0.252   0.169  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.027  -0.863  -0.485  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.651  -0.404  -0.463  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.318   0.666   0.215  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.053   1.128   0.240  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.352   2.143   0.886  1.00  0.00           O  
HETATM   10  O3  UNL     1      -2.017   0.440  -0.453  1.00  0.00           O  
HETATM   11  C8  UNL     1      -3.370   0.951  -0.390  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.751   1.207  -1.784  1.00  0.00           C  
HETATM   13  O4  UNL     1      -2.950   0.907  -2.714  1.00  0.00           O  
HETATM   14  O5  UNL     1      -4.953   1.773  -2.207  1.00  0.00           O  
HETATM   15  C10 UNL     1      -4.254  -0.125   0.219  1.00  0.00           C  
HETATM   16  O6  UNL     1      -3.745  -0.468   1.500  1.00  0.00           O  
HETATM   17  C11 UNL     1      -5.597   0.431   0.469  1.00  0.00           C  
HETATM   18  O7  UNL     1      -6.424   0.778  -0.406  1.00  0.00           O  
HETATM   19  O8  UNL     1      -6.044   0.611   1.792  1.00  0.00           O  
HETATM   20  C12 UNL     1       2.371  -2.010  -1.214  1.00  0.00           C  
HETATM   21  C13 UNL     1       3.638  -2.516  -1.293  1.00  0.00           C  
HETATM   22  C14 UNL     1       4.642  -1.854  -0.610  1.00  0.00           C  
HETATM   23  O9  UNL     1       5.932  -2.360  -0.683  1.00  0.00           O  
HETATM   24  H1  UNL     1       4.775   0.846   2.554  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.239   1.513   1.701  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.607   1.755   0.953  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.899   0.639   0.758  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.148  -0.905  -0.989  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.038   1.250   0.781  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.405   1.840   0.226  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.916   2.571  -2.808  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.269  -1.054  -0.359  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.165  -1.289   1.823  1.00  0.00           H  
HETATM   34  H11 UNL     1      -6.454   1.502   2.043  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.569  -2.503  -1.735  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.918  -3.397  -1.850  1.00  0.00           H  
HETATM   37  H14 UNL     1       6.172  -3.182  -1.207  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   27
CONECT    5    6   20   20
CONECT    6    7    7   28
CONECT    7    8   29
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   15   30
CONECT   12   13   13   14
CONECT   14   31
CONECT   15   16   17   32
CONECT   16   33
CONECT   17   18   18   19
CONECT   19   34
CONECT   20   21   35
CONECT   21   22   22   36
CONECT   22   23
CONECT   23   37
END

HMDB0029199
     RDKit          3D
Fertaric acid
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.2304    1.0614    1.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4084   -0.1031    0.7854 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3732   -0.7274    0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0607   -0.2516    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267   -0.8630   -0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -0.4042   -0.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    0.6659    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0534    1.1283    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521    2.1425    0.8860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171    0.4401   -0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3699    0.9508   -0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7509    1.2074   -1.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9497    0.9069   -2.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9528    1.7731   -2.2069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2536   -0.1253    0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454   -0.4677    1.5003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5973    0.4311    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4245    0.7784   -0.4060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0442    0.6105    1.7920 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3709   -2.0096   -1.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376   -2.5164   -1.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6421   -1.8542   -0.6098 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9318   -2.3602   -0.6834 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7749    0.8460    2.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2394    1.5133    1.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069    1.7548    0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8993    0.6385    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482   -0.9047   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0383    1.2502    0.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4051    1.8400    0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9160    2.5707   -2.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2695   -1.0544   -0.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1649   -1.2891    1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4538    1.5022    2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691   -2.5026   -1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9178   -3.3966   -1.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1716   -3.1820   -1.2075 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  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 11 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
 23 37  1  0
M  END

Synonyms

Value	Source
Fertarate	Generator
2-Hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}butanedioate	HMDB
Fertaric acid	MeSH

Molecular Formula

C₁₄H₁₄O₉

Average Mass

326.2556

Monoisotopic Mass

326.063782046

IUPAC Name

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

Traditional Name

fertaric acid

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)OC(C(O)C(O)=O)C(O)=O)=CC=C1O

InChI Identifier

InChI=1S/C14H14O9/c1-22-9-6-7(2-4-8(9)15)3-5-10(16)23-12(14(20)21)11(17)13(18)19/h2-6,11-12,15,17H,1H3,(H,18,19)(H,20,21)/b5-3+

InChI Key

XIWXUSFCUBAMFH-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
Beta-hydroxy acid
Fatty acid ester
Sugar acid
Phenol
Alpha-hydroxy acid
Fatty acyl
Benzenoid
Hydroxy acid
Monocyclic benzene moiety
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Ether
Carboxylic acid derivative
Carboxylic acid
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.64 g/L	ALOGPS
logP	1.36	ALOGPS
logP	0.74	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	2.95	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	74.23 m³·mol⁻¹	ChemAxon
Polarizability	29.89 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9822000000-cb4901f7914e6caf5b61	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-002b-9131363000-ac326f583a3830e4fd72	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0936000000-df45e31840694c1d2b1b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-2931000000-d1a77c0c3104784ff180	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-005i-3900000000-663c5138128638f1738e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-3983000000-a2c5acc144c780e75984	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-005l-3950000000-9b4cc92a910ad49e86d1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-3920000000-48689ca2a662e37793bc	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-057i-0593000000-f0ac0be05076bb8d1f77	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-cc00cc03df657a19b0c8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-1900000000-06abf9c57bb9f9b40c59	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01tl-5891000000-98d13872aa3768032c04	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kbr-2920000000-ffa7904c5e9666e3bbe9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gzm-3900000000-31b118ca436a9e087af9	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0029199

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00055851

Chemspider ID

20058463

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fertaric acid

METLIN ID

Not Available

PubChem Compound

22298372

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ramirez-Gaona M, Marcu A, Pon A, Guo AC, Sajed T, Wishart NA, Karu N, Djoumbou Feunang Y, Arndt D, Wishart DS: YMDB 2.0: a significantly expanded version of the yeast metabolome database. Nucleic Acids Res. 2017 Jan 4;45(D1):D440-D445. doi: 10.1093/nar/gkw1058. Epub 2016 Nov 28. [PubMed:27899612 ]

Showing metabocard for Fertaric acid (MMDBc0033641)

MOL for #<Metabolite:0x00007fdae5cbf0a8>

3D MOL for #<Metabolite:0x00007fdae5cbf0a8>

3D SDF for #<Metabolite:0x00007fdae5cbf0a8>

3D-SDF for #<Metabolite:0x00007fdae5cbf0a8>

PDB for #<Metabolite:0x00007fdae5cbf0a8>

3D PDB for #<Metabolite:0x00007fdae5cbf0a8>

SMILES for #<Metabolite:0x00007fdae5cbf0a8>

INCHI for #<Metabolite:0x00007fdae5cbf0a8>

Structure for #<Metabolite:0x00007fdae5cbf0a8>

3D Structure for #<Metabolite:0x00007fdae5cbf0a8>