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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:10 UTC

Update Date

2022-03-07 02:52:42 UTC

HMDB ID

HMDB0030809

Secondary Accession Numbers

HMDB30809

Metabolite Identification

Common Name

(2R,3S)-Piscidic acid

Description

(2R,3S)-Piscidic acid, also known as (2R,3S)-piscidate, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid (2R,3S)-Piscidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (2R,3S)-Piscidic acid has been detected, but not quantified in, fruits and green vegetables. This could make (2R,3S)-piscidic acid a potential biomarker for the consumption of these foods.

Structure

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

HMDB0030809
     RDKit          3D
(2R,3S)-Piscidic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -2.3562   -0.4227   -2.5262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5835    0.3127   -1.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8032    0.9372   -1.4314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641    0.5123   -0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0121    1.3688    0.4962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1512   -0.7730    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6968   -1.6755   -0.8218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329   -0.4454    1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1669    0.1229    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612    1.4745    0.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5222    1.9816   -0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4923    1.1197   -0.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6520    1.6122   -1.2481 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250   -0.2242   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690   -0.7065    0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860   -1.3998    0.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415   -0.7579    1.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7798   -2.6634    0.6042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6802    0.5689   -1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419    0.9565   -0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9991    1.2977    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -2.4099   -0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2629   -1.4266    1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3804    0.1771    1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6001    2.1374    0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6890    3.0360   -0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3755    0.9979   -1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0894   -0.9248   -0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0451   -1.7646    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6820   -3.0192   -0.3471 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
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  6 16  1  0
 16 17  2  0
 16 18  1  0
 15  9  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 18 30  1  0
M  END


  Mrv0541 05061305312D          

 18 18  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  1  2  0  0  0  0
  6  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  9  8  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  2  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030809

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(C(O)=O)C(O)(CC1=CC=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O7/c12-7-3-1-6(2-4-7)5-11(18,10(16)17)8(13)9(14)15/h1-4,8,12-13,18H,5H2,(H,14,15)(H,16,17)

> <INCHI_KEY>
TUODPMGCCJSJRH-UHFFFAOYSA-N

> <FORMULA>
C11H12O7

> <MOLECULAR_WEIGHT>
256.2088

> <EXACT_MASS>
256.058302738

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
22.848586188648415

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dihydroxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
-0.043272956666666834

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.70034013433595

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2074587835648773

> <JCHEM_PKA_STRONGEST_BASIC>
-4.398660262447797

> <JCHEM_POLAR_SURFACE_AREA>
135.29000000000002

> <JCHEM_REFRACTIVITY>
57.5266

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydroxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030809
     RDKit          3D
(2R,3S)-Piscidic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -2.3562   -0.4227   -2.5262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5835    0.3127   -1.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8032    0.9372   -1.4314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641    0.5123   -0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0121    1.3688    0.4962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1512   -0.7730    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6968   -1.6755   -0.8218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329   -0.4454    1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1669    0.1229    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612    1.4745    0.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5222    1.9816   -0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4923    1.1197   -0.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6520    1.6122   -1.2481 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250   -0.2242   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690   -0.7065    0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860   -1.3998    0.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415   -0.7579    1.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7798   -2.6634    0.6042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6802    0.5689   -1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419    0.9565   -0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9991    1.2977    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -2.4099   -0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2629   -1.4266    1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3804    0.1771    1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6001    2.1374    0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6890    3.0360   -0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3755    0.9979   -1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0894   -0.9248   -0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0451   -1.7646    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6820   -3.0192   -0.3471 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
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  6 16  1  0
 16 17  2  0
 16 18  1  0
 15  9  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 18 30  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.897  -4.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667  -5.747   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.357  -4.414   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.437  -1.746   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    7                                                       
CONECT    5    6   11                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3    4   12                                                  
CONECT    8    9   11   13                                                  
CONECT    9    8   14   15                                                  
CONECT   10   11   16   17                                                  
CONECT   11    5    8   10   18                                             
CONECT   12    7                                                            
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0030809
HETATM    1  O1  UNL     1      -2.356  -0.423  -2.526  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.584   0.313  -1.544  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.803   0.937  -1.431  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.564   0.512  -0.519  1.00  0.00           C  
HETATM    5  O3  UNL     1      -2.012   1.369   0.496  1.00  0.00           O  
HETATM    6  C3  UNL     1      -1.151  -0.773   0.165  1.00  0.00           C  
HETATM    7  O4  UNL     1      -0.697  -1.676  -0.822  1.00  0.00           O  
HETATM    8  C4  UNL     1      -0.033  -0.445   1.110  1.00  0.00           C  
HETATM    9  C5  UNL     1       1.167   0.123   0.507  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.361   1.474   0.365  1.00  0.00           C  
HETATM   11  C7  UNL     1       2.522   1.982  -0.220  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.492   1.120  -0.664  1.00  0.00           C  
HETATM   13  O5  UNL     1       4.652   1.612  -1.248  1.00  0.00           O  
HETATM   14  C9  UNL     1       3.325  -0.224  -0.535  1.00  0.00           C  
HETATM   15  C10 UNL     1       2.169  -0.706   0.047  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.286  -1.400   0.888  1.00  0.00           C  
HETATM   17  O6  UNL     1      -2.841  -0.758   1.815  1.00  0.00           O  
HETATM   18  O7  UNL     1      -2.780  -2.663   0.604  1.00  0.00           O  
HETATM   19  H1  UNL     1      -4.680   0.569  -1.732  1.00  0.00           H  
HETATM   20  H2  UNL     1      -0.642   0.956  -0.959  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.999   1.298   0.578  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.260  -2.410  -0.343  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.263  -1.427   1.588  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.380   0.177   1.957  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.600   2.137   0.717  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.689   3.036  -0.338  1.00  0.00           H  
HETATM   27  H9  UNL     1       5.375   0.998  -1.580  1.00  0.00           H  
HETATM   28  H10 UNL     1       4.089  -0.925  -0.884  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.045  -1.765   0.144  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.682  -3.019  -0.347  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   19
CONECT    4    5    6   20
CONECT    5   21
CONECT    6    7    8   16
CONECT    7   22
CONECT    8    9   23   24
CONECT    9   10   10   15
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   13   14
CONECT   13   27
CONECT   14   15   15   28
CONECT   15   29
CONECT   16   17   17   18
CONECT   18   30
END

HMDB0030809
     RDKit          3D
(2R,3S)-Piscidic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -2.3562   -0.4227   -2.5262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5835    0.3127   -1.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8032    0.9372   -1.4314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641    0.5123   -0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0121    1.3688    0.4962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1512   -0.7730    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6968   -1.6755   -0.8218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329   -0.4454    1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1669    0.1229    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612    1.4745    0.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5222    1.9816   -0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4923    1.1197   -0.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6520    1.6122   -1.2481 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250   -0.2242   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690   -0.7065    0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860   -1.3998    0.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415   -0.7579    1.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7798   -2.6634    0.6042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6802    0.5689   -1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419    0.9565   -0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9991    1.2977    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -2.4099   -0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2629   -1.4266    1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3804    0.1771    1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6001    2.1374    0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6890    3.0360   -0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3755    0.9979   -1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0894   -0.9248   -0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0451   -1.7646    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6820   -3.0192   -0.3471 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
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  6 16  1  0
 16 17  2  0
 16 18  1  0
 15  9  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 18 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2R,3S)-Piscidate	Generator
2,3-Dihydroxy-2-[(4-hydroxyphenyl)methyl]butanedioate	Generator
Piscidic acid, (S-(r,s))-isomer	MeSH
Piscidic acid	MeSH
(p-Hydroxybenzyl)tartaric acid	MeSH

Chemical Formula

C₁₁H₁₂O₇

Average Molecular Weight

256.2088

Monoisotopic Molecular Weight

256.058302738

IUPAC Name

2,3-dihydroxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid

Traditional Name

2,3-dihydroxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid

CAS Registry Number

35388-57-9

SMILES

OC(C(O)=O)C(O)(CC1=CC=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C11H12O7/c12-7-3-1-6(2-4-7)5-11(18,10(16)17)8(13)9(14)15/h1-4,8,12-13,18H,5H2,(H,14,15)(H,16,17)

InChI Key

TUODPMGCCJSJRH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
Alpha-hydroxy acid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Hydroxy acid
Monosaccharide
Benzenoid
Tertiary alcohol
1,2-diol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Alcohol
Carbonyl group
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen 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: HMDB0030809)
Cytoplasm (HMDB: HMDB0030809)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030809)

Source

Endogenous

Endogenous (HMDB: HMDB0030809)

Plant

Plant (HMDB: HMDB0030809)

Exogenous

Food

Food (HMDB: HMDB0030809)

Fruit

Fruits (FooDB: FOOD00871)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0030809)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	186 - 187 °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	19.9 g/L	ALOGPS
logP	-0.02	ALOGPS
logP	-0.043	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	135.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	57.53 m³·mol⁻¹	ChemAxon
Polarizability	22.85 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
DarkChem	[M+H]+	158.485	31661259
DarkChem	[M-H]-	154.882	31661259
DeepCCS	[M+H]+	150.344	30932474
DeepCCS	[M-H]-	147.948	30932474
DeepCCS	[M-2H]-	180.956	30932474
DeepCCS	[M+Na]+	156.351	30932474
AllCCS	[M+H]+	156.3	32859911
AllCCS	[M+H-H2O]+	152.7	32859911
AllCCS	[M+NH4]+	159.6	32859911
AllCCS	[M+Na]+	160.6	32859911
AllCCS	[M-H]-	153.3	32859911
AllCCS	[M+Na-2H]-	153.4	32859911
AllCCS	[M+HCOO]-	153.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	2.3 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1804 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.06 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	289.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	585.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	260.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	69.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	58.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	273.4 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	264.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	821.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	610.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	108.0 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	802.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	195.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	536.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	329.2 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	399.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2R,3S)-Piscidic acid	OC(C(O)=O)C(O)(CC1=CC=C(O)C=C1)C(O)=O	3988.6	Standard polar	33892256
(2R,3S)-Piscidic acid	OC(C(O)=O)C(O)(CC1=CC=C(O)C=C1)C(O)=O	2064.6	Standard non polar	33892256
(2R,3S)-Piscidic acid	OC(C(O)=O)C(O)(CC1=CC=C(O)C=C1)C(O)=O	2395.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2R,3S)-Piscidic acid,1TMS,isomer #1	C[Si](C)(C)OC(C(=O)O)C(O)(CC1=CC=C(O)C=C1)C(=O)O	2380.0	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(O)C(O)(CC1=CC=C(O)C=C1)C(=O)O	2366.5	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,1TMS,isomer #3	C[Si](C)(C)OC(CC1=CC=C(O)C=C1)(C(=O)O)C(O)C(=O)O	2411.1	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,1TMS,isomer #4	C[Si](C)(C)OC1=CC=C(CC(O)(C(=O)O)C(O)C(=O)O)C=C1	2328.9	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,1TMS,isomer #5	C[Si](C)(C)OC(=O)C(O)(CC1=CC=C(O)C=C1)C(O)C(=O)O	2355.4	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C(O)(CC1=CC=C(O)C=C1)C(=O)O	2384.9	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TMS,isomer #10	C[Si](C)(C)OC(=O)C(O)(CC1=CC=C(O[Si](C)(C)C)C=C1)C(O)C(=O)O	2306.0	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TMS,isomer #2	C[Si](C)(C)OC(C(=O)O)C(CC1=CC=C(O)C=C1)(O[Si](C)(C)C)C(=O)O	2413.5	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(CC(O)(C(=O)O)C(O[Si](C)(C)C)C(=O)O)C=C1	2350.1	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TMS,isomer #4	C[Si](C)(C)OC(=O)C(O)(CC1=CC=C(O)C=C1)C(O[Si](C)(C)C)C(=O)O	2362.5	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TMS,isomer #5	C[Si](C)(C)OC(=O)C(O)C(CC1=CC=C(O)C=C1)(O[Si](C)(C)C)C(=O)O	2385.1	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TMS,isomer #6	C[Si](C)(C)OC(=O)C(O)C(O)(CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	2329.8	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TMS,isomer #7	C[Si](C)(C)OC(=O)C(O)C(O)(CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C	2338.6	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TMS,isomer #8	C[Si](C)(C)OC1=CC=C(CC(O[Si](C)(C)C)(C(=O)O)C(O)C(=O)O)C=C1	2361.9	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TMS,isomer #9	C[Si](C)(C)OC(=O)C(CC1=CC=C(O)C=C1)(O[Si](C)(C)C)C(O)C(=O)O	2362.2	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C(CC1=CC=C(O)C=C1)(O[Si](C)(C)C)C(=O)O	2366.6	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TMS,isomer #10	C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C=C1)(O[Si](C)(C)C)C(O)C(=O)O	2319.1	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C(O)(CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	2340.5	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C(O)(CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C	2309.3	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(CC(O[Si](C)(C)C)(C(=O)O)C(O[Si](C)(C)C)C(=O)O)C=C1	2334.5	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TMS,isomer #5	C[Si](C)(C)OC(=O)C(CC1=CC=C(O)C=C1)(O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)O	2328.0	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TMS,isomer #6	C[Si](C)(C)OC(=O)C(O)(CC1=CC=C(O[Si](C)(C)C)C=C1)C(O[Si](C)(C)C)C(=O)O	2321.9	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TMS,isomer #7	C[Si](C)(C)OC(=O)C(O)C(CC1=CC=C(O[Si](C)(C)C)C=C1)(O[Si](C)(C)C)C(=O)O	2337.7	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TMS,isomer #8	C[Si](C)(C)OC(=O)C(O)C(CC1=CC=C(O)C=C1)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2294.3	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TMS,isomer #9	C[Si](C)(C)OC(=O)C(O)C(O)(CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	2327.3	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C(CC1=CC=C(O[Si](C)(C)C)C=C1)(O[Si](C)(C)C)C(=O)O	2334.1	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C(CC1=CC=C(O)C=C1)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2280.4	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,4TMS,isomer #3	C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C(O)(CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	2347.4	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,4TMS,isomer #4	C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C=C1)(O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)O	2306.8	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,4TMS,isomer #5	C[Si](C)(C)OC(=O)C(O)C(CC1=CC=C(O[Si](C)(C)C)C=C1)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2339.9	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,5TMS,isomer #1	C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C(CC1=CC=C(O[Si](C)(C)C)C=C1)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2349.9	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(C(=O)O)C(O)(CC1=CC=C(O)C=C1)C(=O)O	2646.7	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(O)C(O)(CC1=CC=C(O)C=C1)C(=O)O	2629.6	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CC1=CC=C(O)C=C1)(C(=O)O)C(O)C(=O)O	2645.1	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(O)(C(=O)O)C(O)C(=O)O)C=C1	2618.0	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C(O)(CC1=CC=C(O)C=C1)C(O)C(=O)O	2637.7	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C(O)(CC1=CC=C(O)C=C1)C(=O)O	2850.7	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)C(O)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(O)C(=O)O	2864.1	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(C(=O)O)C(CC1=CC=C(O)C=C1)(O[Si](C)(C)C(C)(C)C)C(=O)O	2860.2	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(O)(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C1	2831.7	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(O)(CC1=CC=C(O)C=C1)C(O[Si](C)(C)C(C)(C)C)C(=O)O	2845.6	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C(O)C(CC1=CC=C(O)C=C1)(O[Si](C)(C)C(C)(C)C)C(=O)O	2845.8	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C(O)C(O)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	2865.1	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)C(O)C(O)(CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2863.5	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(O[Si](C)(C)C(C)(C)C)(C(=O)O)C(O)C(=O)O)C=C1	2820.5	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O)C=C1)(O[Si](C)(C)C(C)(C)C)C(O)C(=O)O	2851.4	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C(CC1=CC=C(O)C=C1)(O[Si](C)(C)C(C)(C)C)C(=O)O	3012.6	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)(O[Si](C)(C)C(C)(C)C)C(O)C(=O)O	3050.1	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C(O)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	3051.7	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C(O)(CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2998.9	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(O[Si](C)(C)C(C)(C)C)(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C1	3051.6	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O)C=C1)(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)O	2996.9	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C(O)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(O[Si](C)(C)C(C)(C)C)C(=O)O	3070.0	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)C(O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)(O[Si](C)(C)C(C)(C)C)C(=O)O	3091.6	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)C(O)C(CC1=CC=C(O)C=C1)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3003.0	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC(=O)C(O)C(O)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3107.6	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)(O[Si](C)(C)C(C)(C)C)C(=O)O	3262.2	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C(CC1=CC=C(O)C=C1)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3160.5	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C(O)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3258.1	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)O	3253.5	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C(O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3274.2	Semi standard non polar	33892256
(2R,3S)-Piscidic acid,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3419.9	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 - (2R,3S)-Piscidic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-3910000000-dbbe5789c0b1b6d6f467	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3S)-Piscidic acid GC-MS (5 TMS) - 70eV, Positive	splash10-0ufr-4313579000-ddf83901288e5955792e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3S)-Piscidic 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - (2R,3S)-Piscidic acid Linear Ion Trap , negative-QTOF	splash10-014i-0900000000-1c684a18b0005b9c6b2d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (2R,3S)-Piscidic acid Linear Ion Trap , positive-QTOF	splash10-01q1-0290000000-4ca6c46064b271a51f93	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3S)-Piscidic acid 10V, Positive-QTOF	splash10-0a4r-0890000000-7c840cdb703ae6acc44c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3S)-Piscidic acid 20V, Positive-QTOF	splash10-0a4i-2910000000-fee786245386365fe699	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3S)-Piscidic acid 40V, Positive-QTOF	splash10-0a6r-5900000000-8ef4873beb2c3d9b9eee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3S)-Piscidic acid 10V, Negative-QTOF	splash10-01si-1910000000-48baa647fbe2261648a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3S)-Piscidic acid 20V, Negative-QTOF	splash10-00a9-3900000000-33101c74eb066606d5b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3S)-Piscidic acid 40V, Negative-QTOF	splash10-06g0-7900000000-ab995222987db9b54fb3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3S)-Piscidic acid 10V, Negative-QTOF	splash10-03ec-2910000000-12386e4d30911c2d217d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3S)-Piscidic acid 20V, Negative-QTOF	splash10-0udi-4900000000-c889083798303d4ddfb8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3S)-Piscidic acid 40V, Negative-QTOF	splash10-06yc-5900000000-dfd18aa657895c100a86	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3S)-Piscidic acid 10V, Positive-QTOF	splash10-0a4i-0090000000-b8dddbe9603ac0e8d83b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3S)-Piscidic acid 20V, Positive-QTOF	splash10-0a4l-7900000000-00353a1b00c0c440ac64	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3S)-Piscidic acid 40V, Positive-QTOF	splash10-052f-9500000000-7016e395a598ec116282	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

FDB002762

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

120693

PDB ID

Not Available

ChEBI ID

Not Available

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.. .

Enzymes

Enzyme Details

1. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Reactions

(2R,3S)-Piscidic acid → 2-hydroxy-2-[(4-hydroxyphenyl)methyl]-3-(sulfooxy)butanedioic acid	details

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

(2R,3S)-Piscidic acid → 2-({4-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]phenyl}methyl)-2,3-dihydroxybutanedioic acid	details
(2R,3S)-Piscidic acid → 6-({3-carboxy-2,3-dihydroxy-2-[(4-hydroxyphenyl)methyl]propanoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
(2R,3S)-Piscidic acid → 6-({3-carboxy-2,3-dihydroxy-3-[(4-hydroxyphenyl)methyl]propanoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

3. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

(2R,3S)-Piscidic acid → 2,3-dihydroxy-2-{[4-(sulfooxy)phenyl]methyl}butanedioic acid	details

Showing metabocard for (2R,3S)-Piscidic acid (HMDB0030809)

MOL for HMDB0030809 ((2R,3S)-Piscidic acid)

3D MOL for HMDB0030809 ((2R,3S)-Piscidic acid)

3D SDF for HMDB0030809 ((2R,3S)-Piscidic acid)

3D-SDF for HMDB0030809 ((2R,3S)-Piscidic acid)

PDB for HMDB0030809 ((2R,3S)-Piscidic acid)

3D PDB for HMDB0030809 ((2R,3S)-Piscidic acid)

SMILES for HMDB0030809 ((2R,3S)-Piscidic acid)

INCHI for HMDB0030809 ((2R,3S)-Piscidic acid)

Structure for HMDB0030809 ((2R,3S)-Piscidic acid)

3D Structure for HMDB0030809 ((2R,3S)-Piscidic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions