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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:07:58 UTC

Update Date

2022-03-07 02:56:38 UTC

HMDB ID

HMDB0040570

Secondary Accession Numbers

HMDB40570

Metabolite Identification

Common Name

2-O-p-Coumaroylhydroxycitric acid

Description

2-O-p-Coumaroylhydroxycitric acid belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. 2-O-p-Coumaroylhydroxycitric acid has been detected, but not quantified in, several different foods, such as breakfast cereal, cereals and cereal products, corns (Zea mays), and fats and oils. This could make 2-O-p-coumaroylhydroxycitric acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-O-p-Coumaroylhydroxycitric acid.

Structure

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

HMDB0040570
     RDKit          3D
2-O-p-Coumaroylhydroxycitric acid
 39 39  0  0  0  0  0  0  0  0999 V2000
    2.6751   -0.8299    2.9554 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304   -0.1887    2.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8791   -0.3534    2.6927 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725    0.7252    1.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2186   -0.0207   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5563   -0.4948   -0.1633 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617    0.9592   -1.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8477    1.4922   -1.2574 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9635    1.2591   -2.0446 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2921   -1.1979   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387   -0.8758   -0.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0183   -1.3651    0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3452   -2.2107    1.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4202   -0.9346    0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466   -0.0540   -0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199    0.4242   -0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5614    1.3581   -1.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8423    1.8424   -1.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8697    1.4124   -0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1625    1.8961   -0.7180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5398    0.4883    0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2416    0.0004    0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6332   -1.9506   -1.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7916   -2.3429   -1.6554 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6260   -2.2113   -2.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4416    0.4811    2.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8950    1.5723    1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1462    1.1399    1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6004   -1.2645    0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6485    0.6180   -2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5200   -1.8904    0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1207   -1.3491    1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1057    0.3377   -0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537    1.6981   -1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1048    2.5665   -2.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7922    1.3938   -1.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3259    0.1301    1.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0225   -0.7248    1.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2646   -1.5360   -2.9730 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
  5  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 10 23  1  0
 23 24  2  0
 23 25  1  0
 22 16  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 25 39  1  0
M  END

  Mrv0541 05061311572D          

 25 25  0  0  0  0            999 V2000
   -3.2529   -0.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727   -0.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8831    0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0394   -1.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6591   -0.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997    1.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696    0.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2425   -1.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299    5.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133    2.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9403    3.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5600    4.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0290   -2.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133    6.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1330    5.8896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3101    2.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237    3.3427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538    4.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902    2.9156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798    3.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767    4.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299    2.9156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  3  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 13 12  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  2  0  0  0  0
 18 10  1  0  0  0  0
 19 11  2  0  0  0  0
 20 13  2  0  0  0  0
 21 13  1  0  0  0  0
 22 14  2  0  0  0  0
 23 14  1  0  0  0  0
 24 15  1  0  0  0  0
 25 11  1  0  0  0  0
 25 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040570

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O10/c16-9-4-1-8(2-5-9)3-6-11(19)25-12(13(20)21)15(24,14(22)23)7-10(17)18/h1-6,12,16,24H,7H2,(H,17,18)(H,20,21)(H,22,23)/b6-3+

> <INCHI_KEY>
ZHUVVSHTKJAVQB-ZZXKWVIFSA-N

> <FORMULA>
C15H14O10

> <MOLECULAR_WEIGHT>
354.2657

> <EXACT_MASS>
354.058696668

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
31.730827462057682

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-1-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

> <ALOGPS_LOGP>
0.91

> <JCHEM_LOGP>
0.6924794836666667

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.392922950831496

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.038358703495942

> <JCHEM_PKA_STRONGEST_BASIC>
-4.58945451207645

> <JCHEM_POLAR_SURFACE_AREA>
178.65999999999997

> <JCHEM_REFRACTIVITY>
78.5107

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-1-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040570
     RDKit          3D
2-O-p-Coumaroylhydroxycitric acid
 39 39  0  0  0  0  0  0  0  0999 V2000
    2.6751   -0.8299    2.9554 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304   -0.1887    2.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8791   -0.3534    2.6927 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725    0.7252    1.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2186   -0.0207   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5563   -0.4948   -0.1633 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617    0.9592   -1.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8477    1.4922   -1.2574 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9635    1.2591   -2.0446 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2921   -1.1979   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387   -0.8758   -0.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0183   -1.3651    0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3452   -2.2107    1.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4202   -0.9346    0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466   -0.0540   -0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199    0.4242   -0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5614    1.3581   -1.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8423    1.8424   -1.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8697    1.4124   -0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1625    1.8961   -0.7180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5398    0.4883    0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2416    0.0004    0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6332   -1.9506   -1.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7916   -2.3429   -1.6554 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6260   -2.2113   -2.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4416    0.4811    2.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8950    1.5723    1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1462    1.1399    1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6004   -1.2645    0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6485    0.6180   -2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5200   -1.8904    0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1207   -1.3491    1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1057    0.3377   -0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537    1.6981   -1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1048    2.5665   -2.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7922    1.3938   -1.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3259    0.1301    1.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0225   -0.7248    1.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2646   -1.5360   -2.9730 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
  5  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 10 23  1  0
 23 24  2  0
 23 25  1  0
 22 16  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 25 39  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      -6.072  -0.799   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.496  -0.109   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.382   1.777   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.674  -2.287   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.097  -1.597   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.293   2.866   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   9.108   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.983   0.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.186  -2.686   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.602  10.595   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.691   4.353   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.489   7.329   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.823   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.912   8.019   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.787  -4.173   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.691  11.684   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.115  10.994   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.179   4.752   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -6.578   6.240   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.887   8.816   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.222   5.442   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.336   7.329   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.823   9.108   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -3.602   5.442   0.000  0.00  0.00           O+0
CONECT    1    4    8                                                       
CONECT    2    5    8                                                       
CONECT    3    6    8                                                       
CONECT    4    1    9                                                       
CONECT    5    2    9                                                       
CONECT    6    3   11                                                       
CONECT    7   10   15                                                       
CONECT    8    1    2    3                                                  
CONECT    9    4    5   16                                                  
CONECT   10    7   17   18                                                  
CONECT   11    6   19   25                                                  
CONECT   12   13   15   25                                                  
CONECT   13   12   20   21                                                  
CONECT   14   15   22   23                                                  
CONECT   15    7   12   14   24                                             
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   13                                                            
CONECT   21   13                                                            
CONECT   22   14                                                            
CONECT   23   14                                                            
CONECT   24   15                                                            
CONECT   25   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0040570
HETATM    1  O1  UNL     1       2.675  -0.830   2.955  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.530  -0.189   2.331  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.879  -0.353   2.693  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.172   0.725   1.238  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.219  -0.021  -0.071  1.00  0.00           C  
HETATM    6  O3  UNL     1       4.556  -0.495  -0.163  1.00  0.00           O  
HETATM    7  C4  UNL     1       2.962   0.959  -1.161  1.00  0.00           C  
HETATM    8  O4  UNL     1       1.848   1.492  -1.257  1.00  0.00           O  
HETATM    9  O5  UNL     1       3.963   1.259  -2.045  1.00  0.00           O  
HETATM   10  C5  UNL     1       2.292  -1.198  -0.157  1.00  0.00           C  
HETATM   11  O6  UNL     1       0.939  -0.876  -0.111  1.00  0.00           O  
HETATM   12  C6  UNL     1      -0.018  -1.365   0.751  1.00  0.00           C  
HETATM   13  O7  UNL     1       0.345  -2.211   1.605  1.00  0.00           O  
HETATM   14  C7  UNL     1      -1.420  -0.935   0.699  1.00  0.00           C  
HETATM   15  C8  UNL     1      -1.847  -0.054  -0.177  1.00  0.00           C  
HETATM   16  C9  UNL     1      -3.220   0.424  -0.292  1.00  0.00           C  
HETATM   17  C10 UNL     1      -3.561   1.358  -1.263  1.00  0.00           C  
HETATM   18  C11 UNL     1      -4.842   1.842  -1.409  1.00  0.00           C  
HETATM   19  C12 UNL     1      -5.870   1.412  -0.577  1.00  0.00           C  
HETATM   20  O8  UNL     1      -7.162   1.896  -0.718  1.00  0.00           O  
HETATM   21  C13 UNL     1      -5.540   0.488   0.386  1.00  0.00           C  
HETATM   22  C14 UNL     1      -4.242   0.000   0.530  1.00  0.00           C  
HETATM   23  C15 UNL     1       2.633  -1.951  -1.410  1.00  0.00           C  
HETATM   24  O9  UNL     1       3.792  -2.343  -1.655  1.00  0.00           O  
HETATM   25  O10 UNL     1       1.626  -2.211  -2.311  1.00  0.00           O  
HETATM   26  H1  UNL     1       5.442   0.481   2.918  1.00  0.00           H  
HETATM   27  H2  UNL     1       3.895   1.572   1.137  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.146   1.140   1.344  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.600  -1.265   0.452  1.00  0.00           H  
HETATM   30  H5  UNL     1       4.648   0.618  -2.396  1.00  0.00           H  
HETATM   31  H6  UNL     1       2.520  -1.890   0.679  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.121  -1.349   1.396  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.106   0.338  -0.862  1.00  0.00           H  
HETATM   34  H9  UNL     1      -2.754   1.698  -1.919  1.00  0.00           H  
HETATM   35  H10 UNL     1      -5.105   2.567  -2.163  1.00  0.00           H  
HETATM   36  H11 UNL     1      -7.792   1.394  -1.342  1.00  0.00           H  
HETATM   37  H12 UNL     1      -6.326   0.130   1.059  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.022  -0.725   1.299  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.265  -1.536  -2.973  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   26
CONECT    4    5   27   28
CONECT    5    6    7   10
CONECT    6   29
CONECT    7    8    8    9
CONECT    9   30
CONECT   10   11   23   31
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   32
CONECT   15   16   33
CONECT   16   17   17   22
CONECT   17   18   34
CONECT   18   19   19   35
CONECT   19   20   21
CONECT   20   36
CONECT   21   22   22   37
CONECT   22   38
CONECT   23   24   24   25
CONECT   25   39
END

HMDB0040570
     RDKit          3D
2-O-p-Coumaroylhydroxycitric acid
 39 39  0  0  0  0  0  0  0  0999 V2000
    2.6751   -0.8299    2.9554 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304   -0.1887    2.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8791   -0.3534    2.6927 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725    0.7252    1.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2186   -0.0207   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5563   -0.4948   -0.1633 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617    0.9592   -1.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8477    1.4922   -1.2574 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9635    1.2591   -2.0446 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2921   -1.1979   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387   -0.8758   -0.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0183   -1.3651    0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3452   -2.2107    1.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4202   -0.9346    0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466   -0.0540   -0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199    0.4242   -0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5614    1.3581   -1.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8423    1.8424   -1.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8697    1.4124   -0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1625    1.8961   -0.7180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5398    0.4883    0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2416    0.0004    0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6332   -1.9506   -1.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7916   -2.3429   -1.6554 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6260   -2.2113   -2.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4416    0.4811    2.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8950    1.5723    1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1462    1.1399    1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6004   -1.2645    0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6485    0.6180   -2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5200   -1.8904    0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1207   -1.3491    1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1057    0.3377   -0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537    1.6981   -1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1048    2.5665   -2.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7922    1.3938   -1.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3259    0.1301    1.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0225   -0.7248    1.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2646   -1.5360   -2.9730 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
  5  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 10 23  1  0
 23 24  2  0
 23 25  1  0
 22 16  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 25 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-O-p-Coumaroylhydroxycitrate	Generator
2-Hydroxy-1-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylate	HMDB

Chemical Formula

C₁₅H₁₄O₁₀

Average Molecular Weight

354.2657

Monoisotopic Molecular Weight

354.058696668

IUPAC Name

2-hydroxy-1-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

Traditional Name

2-hydroxy-1-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

CAS Registry Number

62345-85-1

SMILES

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

InChI Identifier

InChI=1S/C15H14O10/c16-9-4-1-8(2-5-9)3-6-11(19)25-12(13(20)21)15(24,14(22)23)7-10(17)18/h1-6,12,16,24H,7H2,(H,17,18)(H,20,21)(H,22,23)/b6-3+

InChI Key

ZHUVVSHTKJAVQB-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

Tetracarboxylic acid or derivatives
Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
Styrene
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Monocyclic benzene moiety
Alpha-hydroxy acid
Monosaccharide
Hydroxy acid
Benzenoid
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040570)
Cytoplasm (HMDB: HMDB0040570)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040570)

Source

Exogenous

Exogenous (HMDB: HMDB0040570)

Food

Food (HMDB: HMDB0040570)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Corn (FooDB: FOOD00205)

Cereals and cereal products (FooDB: FOOD00858)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0040570)
Poaceae (HMDB: HMDB0040570)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040570)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	155 °C	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	1.17 g/L	ALOGPS
logP	0.91	ALOGPS
logP	0.69	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.04	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	178.66 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	78.51 m³·mol⁻¹	ChemAxon
Polarizability	31.73 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]+	178.302	30932474
DeepCCS	[M-H]-	175.944	30932474
DeepCCS	[M-2H]-	210.087	30932474
DeepCCS	[M+Na]+	186.032	30932474
AllCCS	[M+H]+	176.0	32859911
AllCCS	[M+H-H2O]+	173.2	32859911
AllCCS	[M+NH4]+	178.5	32859911
AllCCS	[M+Na]+	179.2	32859911
AllCCS	[M-H]-	175.1	32859911
AllCCS	[M+Na-2H]-	175.1	32859911
AllCCS	[M+HCOO]-	175.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-O-p-Coumaroylhydroxycitric acid	OC(=O)CC(O)(C(OC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O)C(O)=O	5434.8	Standard polar	33892256
2-O-p-Coumaroylhydroxycitric acid	OC(=O)CC(O)(C(OC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O)C(O)=O	2665.5	Standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid	OC(=O)CC(O)(C(OC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O)C(O)=O	3280.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-O-p-Coumaroylhydroxycitric acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC(O)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	3106.8	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,1TMS,isomer #2	C[Si](C)(C)OC(CC(=O)O)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	3185.4	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O)C(=O)O)C=C1	3155.6	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,1TMS,isomer #4	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(O)(CC(=O)O)C(=O)O	3113.8	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,1TMS,isomer #5	C[Si](C)(C)OC(=O)C(O)(CC(=O)O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	3072.7	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC(O[Si](C)(C)C)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	3089.4	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TMS,isomer #10	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C	3022.5	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CC(O)(C(=O)O[Si](C)(C)C)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	3010.6	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)CC(O)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	3080.7	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TMS,isomer #4	C[Si](C)(C)OC(=O)CC(O)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C	3035.3	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TMS,isomer #5	C[Si](C)(C)OC(=O)C(CC(=O)O)(O[Si](C)(C)C)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	3078.9	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O)C=C1	3159.3	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TMS,isomer #7	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O	3111.1	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TMS,isomer #8	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(O)(CC(=O)O)C(=O)O	3076.2	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TMS,isomer #9	C[Si](C)(C)OC(=O)C(O)(CC(=O)O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	3057.7	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(O[Si](C)(C)C)(C(=O)O[Si](C)(C)C)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	3030.7	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TMS,isomer #10	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C	3012.2	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)CC(O[Si](C)(C)C)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	3071.7	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)CC(O[Si](C)(C)C)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C	3036.3	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TMS,isomer #4	C[Si](C)(C)OC(=O)CC(O)(C(=O)O[Si](C)(C)C)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	3018.0	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TMS,isomer #5	C[Si](C)(C)OC(=O)CC(O)(C(=O)O[Si](C)(C)C)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C	2966.1	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TMS,isomer #6	C[Si](C)(C)OC(=O)CC(O)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	3030.3	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TMS,isomer #7	C[Si](C)(C)OC(=O)C(CC(=O)O)(O[Si](C)(C)C)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	3066.1	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TMS,isomer #8	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	3041.5	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TMS,isomer #9	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O	3081.2	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC(O[Si](C)(C)C)(C(=O)O[Si](C)(C)C)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	3043.1	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)CC(O[Si](C)(C)C)(C(=O)O[Si](C)(C)C)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C	2992.3	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,4TMS,isomer #3	C[Si](C)(C)OC(=O)CC(O[Si](C)(C)C)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	3058.0	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,4TMS,isomer #4	C[Si](C)(C)OC(=O)CC(O)(C(=O)O[Si](C)(C)C)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	3029.1	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,4TMS,isomer #5	C[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	3046.8	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,5TMS,isomer #1	C[Si](C)(C)OC(=O)CC(O[Si](C)(C)C)(C(=O)O[Si](C)(C)C)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	3049.8	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(O)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	3396.1	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CC(=O)O)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	3414.2	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O)C(=O)O)C=C1	3432.1	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(O)(CC(=O)O)C(=O)O	3383.4	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C(O)(CC(=O)O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	3370.6	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	3564.7	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	3531.7	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC(O)(C(=O)O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	3529.1	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC(O)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	3628.5	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CC(O)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3538.6	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	3561.3	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C1	3624.8	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O	3571.7	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TBDMS,isomer #8	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=C1)C(O)(CC(=O)O)C(=O)O	3608.5	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC(=O)C(O)(CC(=O)O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	3618.8	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)(C(=O)O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	3685.6	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TBDMS,isomer #10	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=C1)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	3785.8	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	3816.8	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3690.6	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CC(O)(C(=O)O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	3804.8	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CC(O)(C(=O)O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3663.6	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)CC(O)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3795.3	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	3795.6	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3692.2	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,3TBDMS,isomer #9	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=C1)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O	3802.9	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)(C(=O)O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	3967.2	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)(C(=O)O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3812.0	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3968.6	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CC(O)(C(=O)O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3956.7	Semi standard non polar	33892256
2-O-p-Coumaroylhydroxycitric acid,4TBDMS,isomer #5	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=C1)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3949.3	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 - 2-O-p-Coumaroylhydroxycitric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-3901000000-01c91a9b2f6654c55566	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-O-p-Coumaroylhydroxycitric acid GC-MS (4 TMS) - 70eV, Positive	splash10-014l-5191021000-98f7c271502d0498e74c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-O-p-Coumaroylhydroxycitric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-O-p-Coumaroylhydroxycitric 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-p-Coumaroylhydroxycitric acid 10V, Positive-QTOF	splash10-052v-0549000000-b6d51736d0371fc05252	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-p-Coumaroylhydroxycitric acid 20V, Positive-QTOF	splash10-0a4i-7952000000-d04ed258aac03d606bb3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-p-Coumaroylhydroxycitric acid 40V, Positive-QTOF	splash10-0a4m-2900000000-9173f6449fdb0d2f0129	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-p-Coumaroylhydroxycitric acid 10V, Negative-QTOF	splash10-05o0-2965000000-fd079dd3e6401c3719b5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-p-Coumaroylhydroxycitric acid 20V, Negative-QTOF	splash10-0a5i-6793000000-87f9c6be007aead4c679	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-p-Coumaroylhydroxycitric acid 40V, Negative-QTOF	splash10-06tk-6930000000-beccf4c5b9887211f3d7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-p-Coumaroylhydroxycitric acid 10V, Negative-QTOF	splash10-0296-0090000000-158b1ec63bdc9e4745ba	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-p-Coumaroylhydroxycitric acid 20V, Negative-QTOF	splash10-03di-1940000000-7fd50dd66bba2e81fe44	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-p-Coumaroylhydroxycitric acid 40V, Negative-QTOF	splash10-000i-9400000000-3629dd807d6e2501d825	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-p-Coumaroylhydroxycitric acid 10V, Positive-QTOF	splash10-0a4u-1119000000-762d4e76facc692cda90	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-p-Coumaroylhydroxycitric acid 20V, Positive-QTOF	splash10-052b-2930000000-0d4f931e4b5ffa005a7a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-p-Coumaroylhydroxycitric acid 40V, Positive-QTOF	splash10-00kb-8900000000-16d9bb8a0cde5be7de93	2021-09-25	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

FDB020348

KNApSAcK ID

C00054231

Chemspider ID

35014963

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752858

PDB ID

Not Available

ChEBI ID

175529

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-p-Coumaroylhydroxycitric acid (HMDB0040570)

MOL for HMDB0040570 (2-O-p-Coumaroylhydroxycitric acid)

3D MOL for HMDB0040570 (2-O-p-Coumaroylhydroxycitric acid)

3D SDF for HMDB0040570 (2-O-p-Coumaroylhydroxycitric acid)

3D-SDF for HMDB0040570 (2-O-p-Coumaroylhydroxycitric acid)

PDB for HMDB0040570 (2-O-p-Coumaroylhydroxycitric acid)

3D PDB for HMDB0040570 (2-O-p-Coumaroylhydroxycitric acid)

SMILES for HMDB0040570 (2-O-p-Coumaroylhydroxycitric acid)

INCHI for HMDB0040570 (2-O-p-Coumaroylhydroxycitric acid)

Structure for HMDB0040570 (2-O-p-Coumaroylhydroxycitric acid)

3D Structure for HMDB0040570 (2-O-p-Coumaroylhydroxycitric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra