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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 04:23:19 UTC

Update Date

2021-09-24 04:23:20 UTC

HMDB ID

HMDB0303755

Secondary Accession Numbers

None

Metabolite Identification

Common Name

D-Malic acid p-coumarate

Description

D-malic acid p-coumarate is a member of the class of compounds known as coumaric acid esters. Coumaric acid esters are aromatic compounds containing an ester derivative of coumaric acid. D-malic acid p-coumarate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). D-malic acid p-coumarate can be found in lentils, which makes D-malic acid p-coumarate a potential biomarker for the consumption of this food product.

Structure

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

HMDB0303755
     RDKit          3D
D-Malic acid p-coumarate
 32 32  0  0  0  0  0  0  0  0999 V2000
   -4.3345   -1.7097    2.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772   -1.3119    1.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8826   -2.1648    0.4782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1245    0.0085    0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3785    0.2880   -0.7322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9855    0.2613   -0.5173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -0.5286   -1.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7202   -1.2280   -2.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2711   -0.6133   -1.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9035    0.0822   -0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3295    0.0646    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693    0.8517    1.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2217    0.8740    1.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797    0.1006    0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4636    0.0874    0.8088 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6040   -0.6837   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2402   -0.6859   -0.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485    1.6509   -1.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501    1.8914   -1.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7480    2.5898   -1.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619   -2.9384    0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8380    0.7735    1.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2276    0.0223    0.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6680   -0.4086   -1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8562   -1.2551   -1.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746    0.7172    0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2206    1.4736    1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6413    1.4879    2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8338   -0.5798    1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2660   -1.3112   -1.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8553   -1.3108   -1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8941    3.5046   -1.0307 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  2  0
  5 18  1  0
 18 19  2  0
 18 20  1  0
 17 11  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 20 32  1  0
M  END


  Mrv0541 02241211062D          

 20 20  0  0  0  0            999 V2000
   -0.7897    1.7207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897    0.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750    0.4838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044   -0.3409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044    0.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2177    0.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9323    0.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9323   -0.3409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6470    0.8960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9216   -0.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1347   -1.7207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1245   -0.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4583   -1.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2555   -1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369   -1.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340   -1.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8498   -0.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2670   -0.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4686   -0.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6470   -0.4494    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  5  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  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
M  END
> <DATABASE_ID>
HMDB0303755

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O7/c14-9-4-1-8(2-5-9)3-6-12(17)20-10(13(18)19)7-11(15)16/h1-6,10,14H,7H2,(H,15,16)(H,18,19)/b6-3+

> <INCHI_KEY>
QVPHNABUSKBIMG-ZZXKWVIFSA-N

> <FORMULA>
C13H12O7

> <MOLECULAR_WEIGHT>
280.2302

> <EXACT_MASS>
280.058302738

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
25.894627309314814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.64

> <JCHEM_LOGP>
1.6166839683333332

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.123187788648176

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.328720778262075

> <JCHEM_PKA_STRONGEST_BASIC>
-5.954733338576973

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
66.42380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303755
     RDKit          3D
D-Malic acid p-coumarate
 32 32  0  0  0  0  0  0  0  0999 V2000
   -4.3345   -1.7097    2.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772   -1.3119    1.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8826   -2.1648    0.4782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1245    0.0085    0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3785    0.2880   -0.7322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9855    0.2613   -0.5173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -0.5286   -1.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7202   -1.2280   -2.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2711   -0.6133   -1.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9035    0.0822   -0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3295    0.0646    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693    0.8517    1.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2217    0.8740    1.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797    0.1006    0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4636    0.0874    0.8088 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6040   -0.6837   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2402   -0.6859   -0.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485    1.6509   -1.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501    1.8914   -1.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7480    2.5898   -1.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619   -2.9384    0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8380    0.7735    1.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2276    0.0223    0.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6680   -0.4086   -1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8562   -1.2551   -1.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746    0.7172    0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2206    1.4736    1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6413    1.4879    2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8338   -0.5798    1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2660   -1.3112   -1.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8553   -1.3108   -1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8941    3.5046   -1.0307 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  2  0
  5 18  1  0
 18 19  2  0
 18 20  1  0
 17 11  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 20 32  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      -1.474   3.212   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.474   1.673   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.140   0.903   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.808  -0.636   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.808   0.903   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.140   1.673   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.474   0.903   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.474  -0.636   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -6.808   1.673   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.720  -1.724   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.118  -3.212   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.232  -1.326   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.855  -2.414   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.344  -2.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.429  -3.112   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.917  -2.720   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.320  -1.234   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.232  -0.144   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.741  -0.541   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.808  -0.839   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2                                                            
CONECT    4    5   10                                                       
CONECT    5    2    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4   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                                                       
CONECT   19   14   18                                                       
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0303755
HETATM    1  O1  UNL     1      -4.334  -1.710   2.143  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.777  -1.312   1.064  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.883  -2.165   0.478  1.00  0.00           O  
HETATM    4  C2  UNL     1      -4.124   0.009   0.531  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.378   0.288  -0.732  1.00  0.00           C  
HETATM    6  O3  UNL     1      -1.985   0.261  -0.517  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.191  -0.529  -1.293  1.00  0.00           C  
HETATM    8  O4  UNL     1      -1.720  -1.228  -2.203  1.00  0.00           O  
HETATM    9  C5  UNL     1       0.271  -0.613  -1.127  1.00  0.00           C  
HETATM   10  C6  UNL     1       0.903   0.082  -0.203  1.00  0.00           C  
HETATM   11  C7  UNL     1       2.329   0.065   0.034  1.00  0.00           C  
HETATM   12  C8  UNL     1       2.869   0.852   1.049  1.00  0.00           C  
HETATM   13  C9  UNL     1       4.222   0.874   1.319  1.00  0.00           C  
HETATM   14  C10 UNL     1       5.080   0.101   0.574  1.00  0.00           C  
HETATM   15  O5  UNL     1       6.464   0.087   0.809  1.00  0.00           O  
HETATM   16  C11 UNL     1       4.604  -0.684  -0.426  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.240  -0.686  -0.675  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.749   1.651  -1.270  1.00  0.00           C  
HETATM   19  O6  UNL     1      -4.950   1.891  -1.531  1.00  0.00           O  
HETATM   20  O7  UNL     1      -2.748   2.590  -1.455  1.00  0.00           O  
HETATM   21  H1  UNL     1      -2.462  -2.938   0.961  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.838   0.774   1.296  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.228   0.022   0.367  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.668  -0.409  -1.544  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.856  -1.255  -1.769  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.275   0.717   0.422  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.221   1.474   1.656  1.00  0.00           H  
HETATM   28  H8  UNL     1       4.641   1.488   2.110  1.00  0.00           H  
HETATM   29  H9  UNL     1       6.834  -0.580   1.458  1.00  0.00           H  
HETATM   30  H10 UNL     1       5.266  -1.311  -1.037  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.855  -1.311  -1.473  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.894   3.505  -1.031  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   21
CONECT    4    5   22   23
CONECT    5    6   18   24
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   10   25
CONECT   10   11   26
CONECT   11   12   12   17
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15   16
CONECT   15   29
CONECT   16   17   17   30
CONECT   17   31
CONECT   18   19   19   20
CONECT   20   32
END

HMDB0303755
     RDKit          3D
D-Malic acid p-coumarate
 32 32  0  0  0  0  0  0  0  0999 V2000
   -4.3345   -1.7097    2.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772   -1.3119    1.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8826   -2.1648    0.4782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1245    0.0085    0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3785    0.2880   -0.7322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9855    0.2613   -0.5173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -0.5286   -1.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7202   -1.2280   -2.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2711   -0.6133   -1.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9035    0.0822   -0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3295    0.0646    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693    0.8517    1.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2217    0.8740    1.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797    0.1006    0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4636    0.0874    0.8088 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6040   -0.6837   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2402   -0.6859   -0.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485    1.6509   -1.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501    1.8914   -1.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7480    2.5898   -1.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619   -2.9384    0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8380    0.7735    1.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2276    0.0223    0.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6680   -0.4086   -1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8562   -1.2551   -1.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746    0.7172    0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2206    1.4736    1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6413    1.4879    2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8338   -0.5798    1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2660   -1.3112   -1.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8553   -1.3108   -1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8941    3.5046   -1.0307 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  2  0
  5 18  1  0
 18 19  2  0
 18 20  1  0
 17 11  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 20 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
D-Malate p-coumarate	Generator
D-Malic acid p-coumaric acid	Generator

Chemical Formula

C₁₃H₁₂O₇

Average Molecular Weight

280.2302

Monoisotopic Molecular Weight

280.058302738

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H12O7/c14-9-4-1-8(2-5-9)3-6-12(17)20-10(13(18)19)7-11(15)16/h1-6,10,14H,7H2,(H,15,16)(H,18,19)/b6-3+

InChI Key

QVPHNABUSKBIMG-ZZXKWVIFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
Tricarboxylic acid or derivatives
Styrene
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

Exogenous (HMDB: HMDB0303755)

Food

Pulse

Lentil

Lentils (FooDB: FOOD00098)

Fruit

Pome

Pear (FooDB: FOOD00152)

Process

Not Available

Role

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
logP	1.64	ALOGPS
logP	1.62	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	66.42 m³·mol⁻¹	ChemAxon
Polarizability	25.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	161.151	32859911
AllCCS	[M+H-H2O]+	157.829	32859911
AllCCS	[M+Na]+	165.115	32859911
AllCCS	[M+NH4]+	164.23	32859911
AllCCS	[M-H]-	161.342	32859911
AllCCS	[M+Na-2H]-	161.314	32859911
AllCCS	[M+HCOO]-	161.399	32859911
DeepCCS	[M+H]+	161.85	30932474
DeepCCS	[M-H]-	159.492	30932474
DeepCCS	[M-2H]-	192.377	30932474
DeepCCS	[M+Na]+	167.943	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.0059 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.09 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	513.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	315.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	65.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	50.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	343.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	281.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	797.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	693.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	53.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	816.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	193.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	259.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	839.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	457.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	557.8 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - D-Malic acid p-coumarate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-1910000000-f51de795cfcc769c3d8a	2017-07-27	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 - D-Malic acid p-coumarate 10V, Positive-QTOF	splash10-029t-1790000000-777019d30a0efd1135e0	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Malic acid p-coumarate 20V, Positive-QTOF	splash10-00kb-3930000000-b3932bc1ab93cf6c8921	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Malic acid p-coumarate 40V, Positive-QTOF	splash10-00y0-8900000000-c26233d18d51026a56bf	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Malic acid p-coumarate 10V, Negative-QTOF	splash10-02dr-1970000000-6953025efb4484e12100	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Malic acid p-coumarate 20V, Negative-QTOF	splash10-03y1-3920000000-167c6e4bad7336fee66a	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Malic acid p-coumarate 40V, Negative-QTOF	splash10-0292-3900000000-452879cbf86cb275d244	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Malic acid p-coumarate 10V, Positive-QTOF	splash10-0002-0940000000-f6bf022e8e2a23c83c61	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Malic acid p-coumarate 20V, Positive-QTOF	splash10-00kb-0910000000-f1ff15f7c335ef8ddd1f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Malic acid p-coumarate 40V, Positive-QTOF	splash10-014i-1900000000-83d80959617d7beed7ea	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Malic acid p-coumarate 10V, Negative-QTOF	splash10-00kr-0950000000-b500afe362f06b13b1d9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Malic acid p-coumarate 20V, Negative-QTOF	splash10-00kr-8910000000-006f3f39b70fee471b65	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Malic acid p-coumarate 40V, Negative-QTOF	splash10-014i-2900000000-f4775f326e591c4d9b52	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB020639

KNApSAcK ID

C00053636

Chemspider ID

22913548

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45359757

PDB ID

Not Available

ChEBI ID

139431

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

Not Available

Showing metabocard for D-Malic acid p-coumarate (HMDB0303755)

MOL for HMDB0303755 (D-Malic acid p-coumarate)

3D MOL for HMDB0303755 (D-Malic acid p-coumarate)

3D SDF for HMDB0303755 (D-Malic acid p-coumarate)

3D-SDF for HMDB0303755 (D-Malic acid p-coumarate)

PDB for HMDB0303755 (D-Malic acid p-coumarate)

3D PDB for HMDB0303755 (D-Malic acid p-coumarate)

SMILES for HMDB0303755 (D-Malic acid p-coumarate)

INCHI for HMDB0303755 (D-Malic acid p-coumarate)

Structure for HMDB0303755 (D-Malic acid p-coumarate)

3D Structure for HMDB0303755 (D-Malic acid p-coumarate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra