MiMeDB: Showing metabocard for Caftaric acid (MMDBc0033599)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:55:14 UTC

Update Date

2022-08-31 22:36:57 UTC

Metabolite ID

MMDBc0033599

Metabolite Identification

Common Name

Caftaric acid

Description

Caftaric acid is a the ester of tartaric acid and the phenolic acid caffeic 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

HMDB0013680
     RDKit          3D
Caftaric acid
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.3374    1.4406   -0.3602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339    0.2861   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023   -0.0413   -0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319    0.8832   -0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8649    0.6506    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4466   -0.5787    0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7959   -0.7880    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396    0.3023    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0009    0.0844    0.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1071    1.5678    0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9856    2.6156   -0.0672 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402    1.7233   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8327   -0.7406   -0.0976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2527   -0.5507   -0.2105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7816   -1.3164   -1.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0232   -2.1071   -2.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0842   -1.2825   -1.7764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9134   -0.9400    1.0972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3164   -0.1190    2.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3267   -0.5280    1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7001    0.5025    1.7302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3387   -1.1570    0.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8162   -1.0616    0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0631    1.8993   -0.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956   -1.4348    0.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2343   -1.7743    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6947    0.8106    0.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7627    3.5718   -0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    2.7028   -0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4176    0.5224   -0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5624   -2.0455   -2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8069   -2.0068    1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750    0.7868    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8912   -1.8777    0.8076 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  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 12  5  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  6
 17 31  1  0
 18 32  1  1
 19 33  1  0
 22 34  1  0
M  END


  Mrv0541 02241220552D          

 22 22  0  0  1  0            999 V2000
   -1.1674   -2.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1674   -3.6720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4530   -2.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2615   -2.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9760   -2.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905   -2.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049   -2.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194   -2.8470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049   -1.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194   -1.1970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905   -1.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9760   -1.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0253   -1.1970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3108   -1.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3108   -2.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -1.1970    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5964   -0.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8819   -1.6095    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8819   -2.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1674   -1.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4530   -1.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1674   -0.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19  1  1  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  5 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033599

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@H]([C@@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+/t10-,11-/m1/s1

> <INCHI_KEY>
SWGKAHCIOQPKFW-JTNORFRNSA-N

> <FORMULA>
C13H12O9

> <MOLECULAR_WEIGHT>
312.229

> <EXACT_MASS>
312.048131982

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
28.010055326288224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
0.5979601859999999

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.484001795143949

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9580286110976193

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3456129955412335

> <JCHEM_POLAR_SURFACE_AREA>
161.59

> <JCHEM_REFRACTIVITY>
69.74289999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
caftaric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013680
     RDKit          3D
Caftaric acid
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.3374    1.4406   -0.3602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339    0.2861   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023   -0.0413   -0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319    0.8832   -0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8649    0.6506    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4466   -0.5787    0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7959   -0.7880    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396    0.3023    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0009    0.0844    0.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1071    1.5678    0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9856    2.6156   -0.0672 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402    1.7233   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8327   -0.7406   -0.0976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2527   -0.5507   -0.2105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7816   -1.3164   -1.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0232   -2.1071   -2.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0842   -1.2825   -1.7764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9134   -0.9400    1.0972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3164   -0.1190    2.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3267   -0.5280    1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7001    0.5025    1.7302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3387   -1.1570    0.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8162   -1.0616    0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0631    1.8993   -0.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956   -1.4348    0.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2343   -1.7743    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6947    0.8106    0.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7627    3.5718   -0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    2.7028   -0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4176    0.5224   -0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5624   -2.0455   -2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8069   -2.0068    1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750    0.7868    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8912   -1.8777    0.8076 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  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 12  5  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  6
 17 31  1  0
 18 32  1  1
 19 33  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.179  -5.314   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.179  -6.854   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.846  -4.544   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.488  -5.314   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.822  -4.544   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.156  -5.314   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.489  -4.544   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.823  -5.314   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.489  -3.004   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.823  -2.234   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.156  -2.234   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.822  -3.004   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -7.514  -2.234   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.180  -3.004   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.180  -4.544   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.847  -2.234   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.847  -0.694   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.513  -3.004   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.513  -4.544   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.179  -2.234   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.846  -3.004   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.179  -0.694   0.000  0.00  0.00           O+0
CONECT    1   19    2    3                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    5                                                       
CONECT   13   14                                                            
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19    1   18                                                       
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0013680
HETATM    1  O1  UNL     1      -1.337   1.441  -0.360  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.934   0.286  -0.180  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.502  -0.041  -0.048  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.432   0.883  -0.115  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.865   0.651   0.005  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.447  -0.579   0.206  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.796  -0.788   0.317  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.640   0.302   0.222  1.00  0.00           C  
HETATM    9  O2  UNL     1       7.001   0.084   0.336  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.107   1.568   0.019  1.00  0.00           C  
HETATM   11  O3  UNL     1       5.986   2.616  -0.067  1.00  0.00           O  
HETATM   12  C9  UNL     1       3.740   1.723  -0.086  1.00  0.00           C  
HETATM   13  O4  UNL     1      -1.833  -0.741  -0.098  1.00  0.00           O  
HETATM   14  C10 UNL     1      -3.253  -0.551  -0.211  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.782  -1.316  -1.337  1.00  0.00           C  
HETATM   16  O5  UNL     1      -3.023  -2.107  -2.023  1.00  0.00           O  
HETATM   17  O6  UNL     1      -5.084  -1.282  -1.776  1.00  0.00           O  
HETATM   18  C12 UNL     1      -3.913  -0.940   1.097  1.00  0.00           C  
HETATM   19  O7  UNL     1      -3.316  -0.119   2.110  1.00  0.00           O  
HETATM   20  C13 UNL     1      -5.327  -0.528   1.068  1.00  0.00           C  
HETATM   21  O8  UNL     1      -5.700   0.503   1.730  1.00  0.00           O  
HETATM   22  O9  UNL     1      -6.339  -1.157   0.379  1.00  0.00           O  
HETATM   23  H1  UNL     1       0.816  -1.062   0.109  1.00  0.00           H  
HETATM   24  H2  UNL     1       1.063   1.899  -0.274  1.00  0.00           H  
HETATM   25  H3  UNL     1       2.796  -1.435   0.281  1.00  0.00           H  
HETATM   26  H4  UNL     1       5.234  -1.774   0.477  1.00  0.00           H  
HETATM   27  H5  UNL     1       7.695   0.811   0.281  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.763   3.572  -0.209  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.313   2.703  -0.244  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.418   0.522  -0.365  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.562  -2.046  -2.226  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.807  -2.007   1.343  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.675   0.787   1.909  1.00  0.00           H  
HETATM   34  H12 UNL     1      -6.891  -1.878   0.808  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   23
CONECT    4    5   24
CONECT    5    6    6   12
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   10
CONECT    9   27
CONECT   10   11   12   12
CONECT   11   28
CONECT   12   29
CONECT   13   14
CONECT   14   15   18   30
CONECT   15   16   16   17
CONECT   17   31
CONECT   18   19   20   32
CONECT   19   33
CONECT   20   21   21   22
CONECT   22   34
END

HMDB0013680
     RDKit          3D
Caftaric acid
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.3374    1.4406   -0.3602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339    0.2861   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023   -0.0413   -0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319    0.8832   -0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8649    0.6506    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4466   -0.5787    0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7959   -0.7880    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396    0.3023    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0009    0.0844    0.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1071    1.5678    0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9856    2.6156   -0.0672 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402    1.7233   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8327   -0.7406   -0.0976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2527   -0.5507   -0.2105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7816   -1.3164   -1.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0232   -2.1071   -2.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0842   -1.2825   -1.7764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9134   -0.9400    1.0972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3164   -0.1190    2.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3267   -0.5280    1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7001    0.5025    1.7302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3387   -1.1570    0.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8162   -1.0616    0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0631    1.8993   -0.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956   -1.4348    0.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2343   -1.7743    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6947    0.8106    0.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7627    3.5718   -0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    2.7028   -0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4176    0.5224   -0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5624   -2.0455   -2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8069   -2.0068    1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750    0.7868    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8912   -1.8777    0.8076 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  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 12  5  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  6
 17 31  1  0
 18 32  1  1
 19 33  1  0
 22 34  1  0
M  END

Synonyms

Value	Source
Caftarate	Generator
(2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioate	HMDB
Caftaric acid	MeSH
trans-Caffeoyl tartarate	Generator

Molecular Formula

C₁₃H₁₂O₉

Average Mass

312.229

Monoisotopic Mass

312.048131982

IUPAC Name

(2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

Traditional Name

caftaric acid

CAS Registry Number

Not Available

SMILES

O[C@H]([C@@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+/t10-,11-/m1/s1

InChI Key

SWGKAHCIOQPKFW-JTNORFRNSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Cinnamic acid ester
Coumaric acid or derivatives
Tricarboxylic acid or derivatives
Styrene
Catechol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Sugar acid
Fatty acid ester
Phenol
Beta-hydroxy acid
Fatty acyl
Benzenoid
Hydroxy acid
Alpha-hydroxy acid
Monosaccharide
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	0.82 g/L	ALOGPS
logP	1.68	ALOGPS
logP	0.6	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.96	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.59 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	69.74 m³·mol⁻¹	ChemAxon
Polarizability	28.01 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	splash10-0006-9840000000-cd512aa4b5b39796cfc9	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-0a4i-5126029000-1f161c82d9ceefc78534	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	splash10-03dj-0973000000-1a96d8a708695d13762e	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03gr-2940000000-a24c1bc2573e378ccd7e	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0540-4900000000-55b90a17ab1875f9bb88	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0409-3982000000-aabe941096f73c4a6cd1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02dr-3940000000-9757ec14c725e63e898e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03mi-3910000000-aec72816b3809d559efe	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dj-0962000000-19ce0e179f5b193f2f7a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0910000000-49fdfc79a0932b35006c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q1-0900000000-037e6f90dc36922bc658	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03fr-6921000000-0ee8740f8887a7ad0f3e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-5910000000-f8141e91f7902a965844	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0019-2900000000-e264a69a81737a39c54c	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

HMDB0013680

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Caftaric acid

METLIN ID

Not Available

PubChem Compound

6440397

PDB ID

Not Available

ChEBI ID

664875

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 Caftaric acid (MMDBc0033599)

MOL for #<Metabolite:0x00007fdb4d17df60>

3D MOL for #<Metabolite:0x00007fdb4d17df60>

3D SDF for #<Metabolite:0x00007fdb4d17df60>

3D-SDF for #<Metabolite:0x00007fdb4d17df60>

PDB for #<Metabolite:0x00007fdb4d17df60>

3D PDB for #<Metabolite:0x00007fdb4d17df60>

SMILES for #<Metabolite:0x00007fdb4d17df60>

INCHI for #<Metabolite:0x00007fdb4d17df60>

Structure for #<Metabolite:0x00007fdb4d17df60>

3D Structure for #<Metabolite:0x00007fdb4d17df60>