Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:29:39 UTC

Update Date

2022-03-07 02:52:07 UTC

HMDB ID

HMDB0029318

Secondary Accession Numbers

HMDB29318

Metabolite Identification

Common Name

Caffeoylmalic acid

Description

Caffeoylmalic acid, also known as caffeoylmalate, 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. Caffeoylmalic acid has been detected, but not quantified in, several different foods, such as radishes (Raphanus sativus), teas (Camellia sinensis), green beans (Phaseolus vulgaris), green tea, and herbs and spices. This could make caffeoylmalic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Caffeoylmalic acid.

Structure

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

HMDB0029318
     RDKit          3D
Caffeoylmalic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    2.4013    0.6302    2.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5698    0.3754    2.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4078   -0.2942    3.1365 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467    0.7876    0.9388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5073   -0.1264   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0993   -0.1125   -0.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147   -1.2658    0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0448   -2.3184    0.4642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0644   -1.3177    0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7697   -0.2523   -0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2289   -0.1998   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0400   -1.2692    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4244   -1.1343    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0577    0.0318   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4424    0.1186   -0.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2300    1.1174   -0.6397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8230    2.2983   -0.9920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8616    0.9749   -0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    0.2478   -1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2369    0.3082   -1.6954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1485    0.5417   -2.5220 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4033   -0.3266    3.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1534    0.7844    0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7403    1.8442    0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8303   -1.1524    0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830   -2.2301    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1722    0.6391   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5792   -2.2063    0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0348   -2.0000    0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9603    0.9439   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7846    2.5165   -1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141    1.8201   -0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2628    0.2257   -3.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 18 11  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
M  END


  Mrv0541 02241219542D          

 21 21  0  0  0  0            999 V2000
   -0.7143    3.5077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143    2.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279    2.2702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294    1.4452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294    2.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1444    2.6827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143    2.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007    2.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007    1.4452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143    1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279    1.4452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143    0.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279   -1.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444   -2.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279   -2.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143   -2.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279   -3.5077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007   -2.6827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  2  0  0  0  0
 18 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029318

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O8/c14-8-3-1-7(5-9(8)15)2-4-12(18)21-10(13(19)20)6-11(16)17/h1-5,10,14-15H,6H2,(H,16,17)(H,19,20)/b4-2+

> <INCHI_KEY>
PMKQSEYPLQIEAY-DUXPYHPUSA-N

> <FORMULA>
C13H12O8

> <MOLECULAR_WEIGHT>
296.2296

> <EXACT_MASS>
296.05321736

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
26.853398909837985

> <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}butanedioic acid

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.3131186466666667

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.010506366272061

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.070120323000287

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283762288194251

> <JCHEM_POLAR_SURFACE_AREA>
141.36

> <JCHEM_REFRACTIVITY>
68.40470000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.32e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029318
     RDKit          3D
Caffeoylmalic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    2.4013    0.6302    2.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5698    0.3754    2.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4078   -0.2942    3.1365 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467    0.7876    0.9388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5073   -0.1264   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0993   -0.1125   -0.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147   -1.2658    0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0448   -2.3184    0.4642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0644   -1.3177    0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7697   -0.2523   -0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2289   -0.1998   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0400   -1.2692    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4244   -1.1343    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0577    0.0318   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4424    0.1186   -0.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2300    1.1174   -0.6397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8230    2.2983   -0.9920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8616    0.9749   -0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    0.2478   -1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2369    0.3082   -1.6954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1485    0.5417   -2.5220 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4033   -0.3266    3.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1534    0.7844    0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7403    1.8442    0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8303   -1.1524    0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830   -2.2301    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1722    0.6391   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5792   -2.2063    0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0348   -2.0000    0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9603    0.9439   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7846    2.5165   -1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141    1.8201   -0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2628    0.2257   -3.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 18 11  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  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      -1.333   6.548   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.333   5.008   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.665   4.238   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.668   2.698   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.668   4.238   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.003   5.008   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.333   5.008   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.001   4.238   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.001   2.698   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.333   1.928   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.665   2.698   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.333   0.388   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.665  -0.382   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.665  -1.922   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.003  -2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.003  -4.238   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.665  -5.008   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.333  -4.238   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.333  -2.695   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.665  -6.548   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.001  -5.008   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2                                                            
CONECT    4    5                                                            
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    2    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19   21                                                  
CONECT   19   14   18                                                       
CONECT   20   17                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0029318
HETATM    1  O1  UNL     1       2.401   0.630   2.646  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.570   0.375   2.278  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.408  -0.294   3.136  1.00  0.00           O  
HETATM    4  C2  UNL     1       4.047   0.788   0.939  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.507  -0.126  -0.148  1.00  0.00           C  
HETATM    6  O3  UNL     1       2.099  -0.112  -0.177  1.00  0.00           O  
HETATM    7  C4  UNL     1       1.415  -1.266   0.147  1.00  0.00           C  
HETATM    8  O4  UNL     1       2.045  -2.318   0.464  1.00  0.00           O  
HETATM    9  C5  UNL     1      -0.064  -1.318   0.137  1.00  0.00           C  
HETATM   10  C6  UNL     1      -0.770  -0.252  -0.185  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.229  -0.200  -0.225  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.040  -1.269   0.074  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.424  -1.134   0.013  1.00  0.00           C  
HETATM   14  C10 UNL     1      -5.058   0.032  -0.337  1.00  0.00           C  
HETATM   15  O5  UNL     1      -6.442   0.119  -0.383  1.00  0.00           O  
HETATM   16  C11 UNL     1      -4.230   1.117  -0.640  1.00  0.00           C  
HETATM   17  O6  UNL     1      -4.823   2.298  -0.992  1.00  0.00           O  
HETATM   18  C12 UNL     1      -2.862   0.975  -0.577  1.00  0.00           C  
HETATM   19  C13 UNL     1       4.003   0.248  -1.479  1.00  0.00           C  
HETATM   20  O7  UNL     1       5.237   0.308  -1.695  1.00  0.00           O  
HETATM   21  O8  UNL     1       3.148   0.542  -2.522  1.00  0.00           O  
HETATM   22  H1  UNL     1       5.403  -0.327   3.082  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.153   0.784   0.957  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.740   1.844   0.742  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.830  -1.152   0.153  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.583  -2.230   0.393  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.172   0.639  -0.434  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.579  -2.206   0.353  1.00  0.00           H  
HETATM   29  H8  UNL     1      -5.035  -2.000   0.255  1.00  0.00           H  
HETATM   30  H9  UNL     1      -6.960   0.944  -0.630  1.00  0.00           H  
HETATM   31  H10 UNL     1      -5.785   2.516  -1.070  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.214   1.820  -0.813  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.263   0.226  -3.465  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   22
CONECT    4    5   23   24
CONECT    5    6   19   25
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   10   26
CONECT   10   11   27
CONECT   11   12   12   18
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15   16
CONECT   15   30
CONECT   16   17   18   18
CONECT   17   31
CONECT   18   32
CONECT   19   20   20   21
CONECT   21   33
END

HMDB0029318
     RDKit          3D
Caffeoylmalic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    2.4013    0.6302    2.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5698    0.3754    2.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4078   -0.2942    3.1365 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467    0.7876    0.9388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5073   -0.1264   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0993   -0.1125   -0.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147   -1.2658    0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0448   -2.3184    0.4642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0644   -1.3177    0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7697   -0.2523   -0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2289   -0.1998   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0400   -1.2692    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4244   -1.1343    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0577    0.0318   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4424    0.1186   -0.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2300    1.1174   -0.6397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8230    2.2983   -0.9920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8616    0.9749   -0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    0.2478   -1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2369    0.3082   -1.6954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1485    0.5417   -2.5220 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4033   -0.3266    3.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1534    0.7844    0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7403    1.8442    0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8303   -1.1524    0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830   -2.2301    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1722    0.6391   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5792   -2.2063    0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0348   -2.0000    0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9603    0.9439   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7846    2.5165   -1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141    1.8201   -0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2628    0.2257   -3.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 18 11  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Caffeoylmalate	Generator
(S)-Phaselic acid	HMDB
Phaseolic acid?	HMDB
2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioate	Generator
Caffeoylmalic acid	MeSH
L-Malate caffeate	Generator
L-Malic acid caffeic acid	Generator

Chemical Formula

C₁₃H₁₂O₈

Average Molecular Weight

296.2296

Monoisotopic Molecular Weight

296.05321736

IUPAC Name

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

Traditional Name

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

CAS Registry Number

53755-04-7

SMILES

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

InChI Identifier

InChI=1S/C13H12O8/c14-8-3-1-7(5-9(8)15)2-4-12(18)21-10(13(19)20)6-11(16)17/h1-5,10,14-15H,6H2,(H,16,17)(H,19,20)/b4-2+

InChI Key

PMKQSEYPLQIEAY-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-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

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	0.33 g/L	ALOGPS
logP	1.87	ALOGPS
logP	1.31	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.07	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	7	ChemAxon
Refractivity	68.4 m³·mol⁻¹	ChemAxon
Polarizability	26.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	164.939	30932474
DeepCCS	[M-H]-	162.581	30932474
DeepCCS	[M-2H]-	195.467	30932474
DeepCCS	[M+Na]+	171.033	30932474
AllCCS	[M+H]+	164.3	32859911
AllCCS	[M+H-H2O]+	161.1	32859911
AllCCS	[M+NH4]+	167.3	32859911
AllCCS	[M+Na]+	168.1	32859911
AllCCS	[M-H]-	163.6	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	163.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Caffeoylmalic acid	OC(=O)CC(OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O	4821.4	Standard polar	33892256
Caffeoylmalic acid	OC(=O)CC(OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O	2576.9	Standard non polar	33892256
Caffeoylmalic acid	OC(=O)CC(OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O	2829.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Caffeoylmalic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC(OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O	2875.8	Semi standard non polar	33892256
Caffeoylmalic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)OC(CC(=O)O)C(=O)O)C=C1O	2791.3	Semi standard non polar	33892256
Caffeoylmalic acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC(/C=C/C(=O)OC(CC(=O)O)C(=O)O)=CC=C1O	2780.1	Semi standard non polar	33892256
Caffeoylmalic acid,1TMS,isomer #4	C[Si](C)(C)OC(=O)C(CC(=O)O)OC(=O)/C=C/C1=CC=C(O)C(O)=C1	2862.7	Semi standard non polar	33892256
Caffeoylmalic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O	2773.8	Semi standard non polar	33892256
Caffeoylmalic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CC(OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O	2767.5	Semi standard non polar	33892256
Caffeoylmalic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)CC(OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O[Si](C)(C)C	2788.7	Semi standard non polar	33892256
Caffeoylmalic acid,2TMS,isomer #4	C[Si](C)(C)OC(=O)C(CC(=O)O)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1	2757.9	Semi standard non polar	33892256
Caffeoylmalic acid,2TMS,isomer #5	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)OC(CC(=O)O)C(=O)O)C=C1O[Si](C)(C)C	2793.7	Semi standard non polar	33892256
Caffeoylmalic acid,2TMS,isomer #6	C[Si](C)(C)OC(=O)C(CC(=O)O)OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1	2761.1	Semi standard non polar	33892256
Caffeoylmalic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O	2797.2	Semi standard non polar	33892256
Caffeoylmalic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)CC(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O[Si](C)(C)C	2752.0	Semi standard non polar	33892256
Caffeoylmalic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)CC(OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	2767.2	Semi standard non polar	33892256
Caffeoylmalic acid,3TMS,isomer #4	C[Si](C)(C)OC(=O)C(CC(=O)O)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2776.4	Semi standard non polar	33892256
Caffeoylmalic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC(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	2826.3	Semi standard non polar	33892256
Caffeoylmalic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O	3131.6	Semi standard non polar	33892256
Caffeoylmalic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)OC(CC(=O)O)C(=O)O)C=C1O	3074.8	Semi standard non polar	33892256
Caffeoylmalic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)OC(CC(=O)O)C(=O)O)=CC=C1O	3069.4	Semi standard non polar	33892256
Caffeoylmalic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)O)OC(=O)/C=C/C1=CC=C(O)C(O)=C1	3137.6	Semi standard non polar	33892256
Caffeoylmalic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)C(=O)O	3304.1	Semi standard non polar	33892256
Caffeoylmalic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC(OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O	3292.3	Semi standard non polar	33892256
Caffeoylmalic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC(OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C	3294.2	Semi standard non polar	33892256
Caffeoylmalic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)O)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	3295.1	Semi standard non polar	33892256
Caffeoylmalic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)OC(CC(=O)O)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C	3313.1	Semi standard non polar	33892256
Caffeoylmalic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)O)OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	3295.5	Semi standard non polar	33892256
Caffeoylmalic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(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	3532.8	Semi standard non polar	33892256
Caffeoylmalic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC(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	3485.9	Semi standard non polar	33892256
Caffeoylmalic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC(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	3487.5	Semi standard non polar	33892256
Caffeoylmalic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)O)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	3526.4	Semi standard non polar	33892256
Caffeoylmalic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(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	3699.3	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 - Caffeoylmalic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-1910000000-74e3c09316c8d9fb3ea5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Caffeoylmalic acid GC-MS (4 TMS) - 70eV, Positive	splash10-0avi-4146190000-5a765f56e5efd99345a3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Caffeoylmalic 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 - Caffeoylmalic acid 10V, Positive-QTOF	splash10-0401-1790000000-ef531f4b3f8db4d508cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeoylmalic acid 20V, Positive-QTOF	splash10-03xr-3940000000-ff40fcbd1f957b9e680e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeoylmalic acid 40V, Positive-QTOF	splash10-00dr-7900000000-187b75c221f4f3c49fff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeoylmalic acid 10V, Negative-QTOF	splash10-0ftb-1970000000-6b43ca38ba19571e6a67	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeoylmalic acid 20V, Negative-QTOF	splash10-00bi-3920000000-98c6d2f5b48eb1a9ccc3	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeoylmalic acid 40V, Negative-QTOF	splash10-03g0-3900000000-60d5ea04840a20f30f6b	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeoylmalic acid 10V, Negative-QTOF	splash10-0a4i-0290000000-a44daa816456bebdbd8a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeoylmalic acid 20V, Negative-QTOF	splash10-000i-9540000000-6be49add441a49df34b9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeoylmalic acid 40V, Negative-QTOF	splash10-000i-3910000000-46381cd1c0d16863ebb5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeoylmalic acid 10V, Positive-QTOF	splash10-03di-0920000000-a4c71d6efa8a850a8ec6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeoylmalic acid 20V, Positive-QTOF	splash10-03di-0900000000-ecf10995634e427e58a9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeoylmalic acid 40V, Positive-QTOF	splash10-01p9-1900000000-ca91bf87f1f063f2269a	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

FDB000379

KNApSAcK ID

C00002765

Chemspider ID

4816367

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Caffeoylmalic acid

METLIN ID

Not Available

PubChem Compound

6124299

PDB ID

Not Available

ChEBI ID

493262

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 Caffeoylmalic acid (HMDB0029318)

MOL for HMDB0029318 (Caffeoylmalic acid)

3D MOL for HMDB0029318 (Caffeoylmalic acid)

3D SDF for HMDB0029318 (Caffeoylmalic acid)

3D-SDF for HMDB0029318 (Caffeoylmalic acid)

PDB for HMDB0029318 (Caffeoylmalic acid)

3D PDB for HMDB0029318 (Caffeoylmalic acid)

SMILES for HMDB0029318 (Caffeoylmalic acid)

INCHI for HMDB0029318 (Caffeoylmalic acid)

Structure for HMDB0029318 (Caffeoylmalic acid)

3D Structure for HMDB0029318 (Caffeoylmalic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra