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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:28:29 UTC

Update Date

2022-03-07 02:56:46 UTC

HMDB ID

HMDB0040869

Secondary Accession Numbers

HMDB40869

Metabolite Identification

Common Name

2-O-Caffeoyltartronic acid

Description

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

Structure

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

HMDB0040869
     RDKit          3D
2-O-Caffeoyltartronic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -2.1067   -0.8770    1.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7798   -0.2857    0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3847   -0.0779    0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138   -0.5125    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0166   -0.3376    0.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9572   -0.8633    1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2807   -0.7400    1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6976   -0.0848   -0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0465    0.0367   -0.3135 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7865    0.4287   -0.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1067    1.0893   -2.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    0.2962   -0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892    0.1837   -0.3162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1681    0.0501   -0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8397   -0.7755   -1.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0689   -1.0073   -1.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0647   -1.2636   -2.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7527    1.3996   -0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9702    1.5454    0.2156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9816    2.5149   -0.2311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1669    0.4315   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3188   -1.0280    1.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407   -1.3699    2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0570   -1.1267    1.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3894    0.4886   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0515    1.2200   -2.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215    0.7103   -1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2882   -0.4933    0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6728   -2.1917   -2.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0790    2.6397    0.2301 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  2  0
 18 20  1  0
 12  5  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 17 29  1  0
 20 30  1  0
M  END

  Mrv0541 05061312122D          

 20 20  0  0  0  0            999 V2000
   -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
   -5.0013    5.3625    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
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 16 11  2  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 20  9  1  0  0  0  0
 20 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040869

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O8/c13-7-3-1-6(5-8(7)14)2-4-9(15)20-10(11(16)17)12(18)19/h1-5,10,13-14H,(H,16,17)(H,18,19)/b4-2+

> <INCHI_KEY>
URLZWXXTZHVFBD-DUXPYHPUSA-N

> <FORMULA>
C12H10O8

> <MOLECULAR_WEIGHT>
282.203

> <EXACT_MASS>
282.037567296

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
25.259354883767745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.3804843456666664

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.6184149728261605

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.161884543460566

> <JCHEM_PKA_STRONGEST_BASIC>
-6.2837637522027885

> <JCHEM_POLAR_SURFACE_AREA>
141.35999999999999

> <JCHEM_REFRACTIVITY>
63.85550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.73e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040869
     RDKit          3D
2-O-Caffeoyltartronic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -2.1067   -0.8770    1.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7798   -0.2857    0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3847   -0.0779    0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138   -0.5125    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0166   -0.3376    0.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9572   -0.8633    1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2807   -0.7400    1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6976   -0.0848   -0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0465    0.0367   -0.3135 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7865    0.4287   -0.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1067    1.0893   -2.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    0.2962   -0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892    0.1837   -0.3162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1681    0.0501   -0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8397   -0.7755   -1.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0689   -1.0073   -1.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0647   -1.2636   -2.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7527    1.3996   -0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9702    1.5454    0.2156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9816    2.5149   -0.2311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1669    0.4315   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3188   -1.0280    1.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407   -1.3699    2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0570   -1.1267    1.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3894    0.4886   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0515    1.2200   -2.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215    0.7103   -1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2882   -0.4933    0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6728   -2.1917   -2.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0790    2.6397    0.2301 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  2  0
 18 20  1  0
 12  5  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 17 29  1  0
 20 30  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      -5.335  12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002  12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -9.336  13.090   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -9.336  10.010   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      -2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    9                                                       
CONECT    5    6    8                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3    8   13                                                  
CONECT    8    5    7   14                                                  
CONECT    9    4   15   20                                                  
CONECT   10   11   12   20                                                  
CONECT   11   10   16   17                                                  
CONECT   12   10   18   19                                                  
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16   11                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   12                                                            
CONECT   20    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0040869
HETATM    1  O1  UNL     1      -2.107  -0.877   1.537  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.780  -0.286   0.483  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.385  -0.078   0.076  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.614  -0.513   0.814  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.017  -0.338   0.465  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.957  -0.863   1.366  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.281  -0.740   1.110  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.698  -0.085  -0.060  1.00  0.00           C  
HETATM    9  O2  UNL     1       6.046   0.037  -0.314  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.786   0.429  -0.940  1.00  0.00           C  
HETATM   11  O3  UNL     1       4.107   1.089  -2.116  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.429   0.296  -0.667  1.00  0.00           C  
HETATM   13  O4  UNL     1      -2.789   0.184  -0.316  1.00  0.00           O  
HETATM   14  C10 UNL     1      -4.168   0.050  -0.040  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.840  -0.776  -1.091  1.00  0.00           C  
HETATM   16  O5  UNL     1      -6.069  -1.007  -1.020  1.00  0.00           O  
HETATM   17  O6  UNL     1      -4.065  -1.264  -2.123  1.00  0.00           O  
HETATM   18  C12 UNL     1      -4.753   1.400  -0.012  1.00  0.00           C  
HETATM   19  O7  UNL     1      -5.970   1.545   0.216  1.00  0.00           O  
HETATM   20  O8  UNL     1      -3.982   2.515  -0.231  1.00  0.00           O  
HETATM   21  H1  UNL     1      -0.167   0.432  -0.830  1.00  0.00           H  
HETATM   22  H2  UNL     1       0.319  -1.028   1.733  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.641  -1.370   2.270  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.057  -1.127   1.770  1.00  0.00           H  
HETATM   25  H5  UNL     1       6.389   0.489  -1.122  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.051   1.220  -2.375  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.721   0.710  -1.378  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.288  -0.493   0.923  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.673  -2.192  -2.153  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.079   2.640   0.230  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   21
CONECT    4    5   22
CONECT    5    6    6   12
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9   10
CONECT    9   25
CONECT   10   11   12   12
CONECT   11   26
CONECT   12   27
CONECT   13   14
CONECT   14   15   18   28
CONECT   15   16   16   17
CONECT   17   29
CONECT   18   19   19   20
CONECT   20   30
END

HMDB0040869
     RDKit          3D
2-O-Caffeoyltartronic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -2.1067   -0.8770    1.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7798   -0.2857    0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3847   -0.0779    0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138   -0.5125    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0166   -0.3376    0.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9572   -0.8633    1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2807   -0.7400    1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6976   -0.0848   -0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0465    0.0367   -0.3135 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7865    0.4287   -0.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1067    1.0893   -2.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    0.2962   -0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892    0.1837   -0.3162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1681    0.0501   -0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8397   -0.7755   -1.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0689   -1.0073   -1.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0647   -1.2636   -2.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7527    1.3996   -0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9702    1.5454    0.2156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9816    2.5149   -0.2311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1669    0.4315   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3188   -1.0280    1.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407   -1.3699    2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0570   -1.1267    1.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3894    0.4886   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0515    1.2200   -2.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215    0.7103   -1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2882   -0.4933    0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6728   -2.1917   -2.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0790    2.6397    0.2301 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  2  0
 18 20  1  0
 12  5  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 17 29  1  0
 20 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-O-Caffeoyltartronate	Generator
2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanedioate	HMDB

Chemical Formula

C₁₂H₁₀O₈

Average Molecular Weight

282.203

Monoisotopic Molecular Weight

282.037567296

IUPAC Name

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

Traditional Name

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

CAS Registry Number

102606-75-7

SMILES

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

InChI Identifier

InChI=1S/C12H10O8/c13-7-3-1-6(5-8(7)14)2-4-9(15)20-10(11(16)17)12(18)19/h1-5,10,13-14H,(H,16,17)(H,18,19)/b4-2+

InChI Key

URLZWXXTZHVFBD-DUXPYHPUSA-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
Tricarboxylic acid or derivatives
Catechol
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
Fatty acyl
Benzenoid
1,3-dicarbonyl compound
Monocyclic benzene moiety
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040869)
Cytoplasm (HMDB: HMDB0040869)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040869)

Source

Exogenous

Exogenous (HMDB: HMDB0040869)

Food

Food (HMDB: HMDB0040869)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0040869)
Fabaceae (HMDB: HMDB0040869)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040869)

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	0.27 g/L	ALOGPS
logP	1.87	ALOGPS
logP	1.38	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	2.16	ChemAxon
pKa (Strongest Basic)	-6.3	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	6	ChemAxon
Refractivity	63.86 m³·mol⁻¹	ChemAxon
Polarizability	25.26 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]+	161.284	30932474
DeepCCS	[M-H]-	158.926	30932474
DeepCCS	[M-2H]-	191.812	30932474
DeepCCS	[M+Na]+	167.377	30932474
AllCCS	[M+H]+	160.8	32859911
AllCCS	[M+H-H2O]+	157.5	32859911
AllCCS	[M+NH4]+	164.0	32859911
AllCCS	[M+Na]+	164.9	32859911
AllCCS	[M-H]-	158.8	32859911
AllCCS	[M+Na-2H]-	158.7	32859911
AllCCS	[M+HCOO]-	158.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-O-Caffeoyltartronic acid	OC(=O)C(OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O	4582.2	Standard polar	33892256
2-O-Caffeoyltartronic acid	OC(=O)C(OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O	2507.7	Standard non polar	33892256
2-O-Caffeoyltartronic acid	OC(=O)C(OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O	2649.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-O-Caffeoyltartronic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O	2728.4	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC(/C=C/C(=O)OC(C(=O)O)C(=O)O)=CC=C1O	2675.2	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)OC(C(=O)O)C(=O)O)C=C1O	2698.2	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O	2654.9	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O	2645.8	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O[Si](C)(C)C	2642.3	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)OC(C(=O)O)C(=O)O)C=C1O[Si](C)(C)C	2691.2	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O	2674.4	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O[Si](C)(C)C	2637.0	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	2652.1	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	2689.6	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O	2990.2	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)OC(C(=O)O)C(=O)O)=CC=C1O	2944.7	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)OC(C(=O)O)C(=O)O)C=C1O	2963.2	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,2TBDMS,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(O)=C1)C(=O)O	3158.8	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O	3151.4	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C	3128.2	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)OC(C(=O)O)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C	3206.5	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,3TBDMS,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(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O	3403.1	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,3TBDMS,isomer #2	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(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C	3358.2	Semi standard non polar	33892256
2-O-Caffeoyltartronic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C	3360.8	Semi standard non polar	33892256
2-O-Caffeoyltartronic 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(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C	3573.0	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-Caffeoyltartronic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-1900000000-44670f5d323b6d37ea73	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-O-Caffeoyltartronic acid GC-MS (4 TMS) - 70eV, Positive	splash10-0aor-9756440000-6c1f723ff488815ebf68	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-O-Caffeoyltartronic 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-Caffeoyltartronic acid 10V, Positive-QTOF	splash10-0fz9-1890000000-2f5a16dd932bedb41604	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Caffeoyltartronic acid 20V, Positive-QTOF	splash10-0w90-1920000000-48e03f714c3560db2388	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Caffeoyltartronic acid 40V, Positive-QTOF	splash10-0uk9-4900000000-efa739682b8de65051ab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Caffeoyltartronic acid 10V, Negative-QTOF	splash10-001r-0290000000-4c9ca5cdb7eb091f2d32	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Caffeoyltartronic acid 20V, Negative-QTOF	splash10-02u0-3960000000-62857ccccc48b37340d7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Caffeoyltartronic acid 40V, Negative-QTOF	splash10-0h90-6910000000-92c0bebe5fb67cf7f468	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Caffeoyltartronic acid 10V, Positive-QTOF	splash10-03xr-0960000000-ae2a4cfb22ca9f47717f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Caffeoyltartronic acid 20V, Positive-QTOF	splash10-03ds-0900000000-744cfc4822fba668dec4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Caffeoyltartronic acid 40V, Positive-QTOF	splash10-00oa-2900000000-fa341de47f00fd6d247f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Caffeoyltartronic acid 10V, Negative-QTOF	splash10-01qi-1590000000-a6521a099e368b30a407	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Caffeoyltartronic acid 20V, Negative-QTOF	splash10-000l-1930000000-4f5882a47b70cef3a921	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Caffeoyltartronic acid 40V, Negative-QTOF	splash10-001r-1900000000-3bdc89ce44f10055571e	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

FDB020699

KNApSAcK ID

C00054038

Chemspider ID

30777514

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752962

PDB ID

Not Available

ChEBI ID

174677

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-Caffeoyltartronic acid (HMDB0040869)

MOL for HMDB0040869 (2-O-Caffeoyltartronic acid)

3D MOL for HMDB0040869 (2-O-Caffeoyltartronic acid)

3D SDF for HMDB0040869 (2-O-Caffeoyltartronic acid)

3D-SDF for HMDB0040869 (2-O-Caffeoyltartronic acid)

PDB for HMDB0040869 (2-O-Caffeoyltartronic acid)

3D PDB for HMDB0040869 (2-O-Caffeoyltartronic acid)

SMILES for HMDB0040869 (2-O-Caffeoyltartronic acid)

INCHI for HMDB0040869 (2-O-Caffeoyltartronic acid)

Structure for HMDB0040869 (2-O-Caffeoyltartronic acid)

3D Structure for HMDB0040869 (2-O-Caffeoyltartronic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra