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Showing metabocard for p-Hydroxyhippuric acid (HMDB0013678)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-04-03 14:10:30 UTC
Update Date2025-05-29 18:10:25 UTC
HMDB IDHMDB0013678
Secondary Accession Numbers
  • HMDB13678
Metabolite Identification
Common Namep-Hydroxyhippuric acid
Description4-Hydroxyhippuric acid, also known as 4-hydroxybenzoylglycine or 4-hydroxyhippate, belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine. 4-Hydroxyhippuric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 4-Hydroxyhippuric acid.
Structure
Data?1676999880
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0013678 (p-Hydroxyhippuric acid)


  Mrv1652310251917022D          

 14 14  0  0  0  0            999 V2000
    1.4289    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  8  2  0  0  0  0
 14  9  2  0  0  0  0
M  END
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3D MOL for HMDB0013678 (p-Hydroxyhippuric acid)

HMDB0013678
     RDKit          3D
4-Hydroxyhippuric acid
 23 23  0  0  0  0  0  0  0  0999 V2000
    2.7562   -0.8846    1.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -0.2641    0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8444   -0.5858    0.5914 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0020    0.7521   -0.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5479    0.8725   -0.2067 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7510   -0.2717   -0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2744   -1.3557   -0.7487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6831   -0.1957   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4020   -1.3897   -0.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7588   -1.3649   -0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4507   -0.1981    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8300   -0.2271    0.2390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7300    0.9719    0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3506    0.9865    0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4085   -0.5458   -0.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4535    1.7445   -0.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2125    0.3594   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1327    1.7866    0.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8785   -2.3317   -0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3302   -2.2999   -0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3388    0.6247    0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2826    1.8924    0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393    1.9242    0.0967 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  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14  8  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  9 19  1  0
 10 20  1  0
 12 21  1  0
 13 22  1  0
 14 23  1  0
M  END
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3D SDF for HMDB0013678 (p-Hydroxyhippuric acid)


  Mrv1652310251917022D          

 14 14  0  0  0  0            999 V2000
    1.4289    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  8  2  0  0  0  0
 14  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013678

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO4/c11-7-3-1-6(2-4-7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)

> <INCHI_KEY>
ZMHLUFWWWPBTIU-UHFFFAOYSA-N

> <FORMULA>
C9H9NO4

> <MOLECULAR_WEIGHT>
195.1721

> <EXACT_MASS>
195.053157781

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.539797993825562

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(4-hydroxyphenyl)formamido]acetic acid

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.2219801626666666

> <ALOGPS_LOGS>
-1.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.479619853992792

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.238573183597331

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1703331113622055

> <JCHEM_POLAR_SURFACE_AREA>
86.63

> <JCHEM_REFRACTIVITY>
48.0986

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4-hydroxyphenyl)formamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0013678 (p-Hydroxyhippuric acid)

HMDB0013678
     RDKit          3D
4-Hydroxyhippuric acid
 23 23  0  0  0  0  0  0  0  0999 V2000
    2.7562   -0.8846    1.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -0.2641    0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8444   -0.5858    0.5914 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0020    0.7521   -0.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5479    0.8725   -0.2067 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7510   -0.2717   -0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2744   -1.3557   -0.7487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6831   -0.1957   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4020   -1.3897   -0.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7588   -1.3649   -0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4507   -0.1981    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8300   -0.2271    0.2390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7300    0.9719    0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3506    0.9865    0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4085   -0.5458   -0.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4535    1.7445   -0.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2125    0.3594   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1327    1.7866    0.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8785   -2.3317   -0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3302   -2.2999   -0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3388    0.6247    0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2826    1.8924    0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393    1.9242    0.0967 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  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14  8  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  9 19  1  0
 10 20  1  0
 12 21  1  0
 13 22  1  0
 14 23  1  0
M  END
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PDB for HMDB0013678 (p-Hydroxyhippuric acid)

HEADER    PROTEIN                                 25-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-OCT-19         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.334   5.390   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       5.335   7.700   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   3.080   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    8   10                                                       
CONECT    6    1    2    9                                                  
CONECT    7    3    4   11                                                  
CONECT    8    5   12   13                                                  
CONECT    9    6   10   14                                                  
CONECT   10    5    9                                                       
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    8                                                            
CONECT   14    9                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for HMDB0013678 (p-Hydroxyhippuric acid)

COMPND    HMDB0013678
HETATM    1  O1  UNL     1       2.756  -0.885   1.371  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.492  -0.264   0.556  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.844  -0.586   0.591  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.002   0.752  -0.399  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.548   0.873  -0.207  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.751  -0.272  -0.412  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.274  -1.356  -0.749  1.00  0.00           O  
HETATM    8  C4  UNL     1      -0.683  -0.196  -0.233  1.00  0.00           C  
HETATM    9  C5  UNL     1      -1.402  -1.390  -0.327  1.00  0.00           C  
HETATM   10  C6  UNL     1      -2.759  -1.365  -0.168  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.451  -0.198   0.085  1.00  0.00           C  
HETATM   12  O4  UNL     1      -4.830  -0.227   0.239  1.00  0.00           O  
HETATM   13  C8  UNL     1      -2.730   0.972   0.175  1.00  0.00           C  
HETATM   14  C9  UNL     1      -1.351   0.986   0.018  1.00  0.00           C  
HETATM   15  H1  UNL     1       5.409  -0.546  -0.246  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.453   1.744  -0.236  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.212   0.359  -1.430  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.133   1.787   0.076  1.00  0.00           H  
HETATM   19  H5  UNL     1      -0.879  -2.332  -0.527  1.00  0.00           H  
HETATM   20  H6  UNL     1      -3.330  -2.300  -0.240  1.00  0.00           H  
HETATM   21  H7  UNL     1      -5.339   0.625   0.424  1.00  0.00           H  
HETATM   22  H8  UNL     1      -3.283   1.892   0.375  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.839   1.924   0.097  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5   16   17
CONECT    5    6   18
CONECT    6    7    7    8
CONECT    8    9    9   14
CONECT    9   10   19
CONECT   10   11   11   20
CONECT   11   12   13
CONECT   12   21
CONECT   13   14   14   22
CONECT   14   23
END
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SMILES for HMDB0013678 (p-Hydroxyhippuric acid)

OC(=O)CNC(=O)C1=CC=C(O)C=C1
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INCHI for HMDB0013678 (p-Hydroxyhippuric acid)

InChI=1S/C9H9NO4/c11-7-3-1-6(2-4-7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
4-HydroxybenzoylglycineChEBI
4-HydroxyhippateGenerator
4-Hydroxyhippic acidGenerator
2-[(4-Hydroxyphenyl)carbonylamino]acetic acidHMDB
2-[(4-Hydroxyphenyl)formamido]acetic acidHMDB
4-HydroxyhippurateHMDB
4-OH-Hippuric acidHMDB
p-Hydroxy-hippuric acidHMDB
[(4-Hydroxybenzoyl)amino]acetic acidHMDB
p-Hydroxyhippuric acidHMDB
p-HydroxyhippateHMDB
p-Hydroxyhippic acidHMDB
4'-HydroxyhippurateHMDB
4'-Hydroxyhippuric acidHMDB
4’-hydroxyhippurateHMDB
4’-hydroxyhippuric acidHMDB
N-(p-Hydroxybenzoyl)glycineHMDB
p-HydroxyhippurateHMDB
4-Hydroxyhippuric acidChEBI
2-[(4-Hydroxybenzoyl)amino]acetic acidHMDB
4'-Hydroxhippuric acidHMDB
Chemical FormulaC9H9NO4
Average Molecular Weight195.1721
Monoisotopic Molecular Weight195.053157781
IUPAC Name2-[(4-hydroxyphenyl)formamido]acetic acid
Traditional Name[(4-hydroxyphenyl)formamido]acetic acid
CAS Registry Number2482-25-9
SMILES
OC(=O)CNC(=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H9NO4/c11-7-3-1-6(2-4-7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)
InChI KeyZMHLUFWWWPBTIU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHippuric acids
Alternative Parents
Substituents
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.63 g/LALOGPS
logP0.44ALOGPS
logP0.22ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.1 m³·mol⁻¹ChemAxon
Polarizability18.54 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.44631661259
DarkChem[M-H]-142.58631661259
DeepCCS[M+H]+138.92830932474
DeepCCS[M-H]-136.53230932474
DeepCCS[M-2H]-171.73130932474
DeepCCS[M+Na]+146.24830932474
AllCCS[M+H]+141.832859911
AllCCS[M+H-H2O]+137.832859911
AllCCS[M+NH4]+145.632859911
AllCCS[M+Na]+146.732859911
AllCCS[M-H]-141.432859911
AllCCS[M+Na-2H]-142.032859911
AllCCS[M+HCOO]-142.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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. Predicted by Afia on May 17, 2022.2.6 minutes32390414
Predicted by Siyang on May 30, 20229.6124 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.03 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid163.9 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid935.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid267.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid82.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid166.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid64.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid260.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid301.2 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)421.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid609.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid237.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid917.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid202.9 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid225.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate554.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA263.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water243.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxyhippuric acidOC(=O)CNC(=O)C1=CC=C(O)C=C13281.9Standard polar33892256
4-Hydroxyhippuric acidOC(=O)CNC(=O)C1=CC=C(O)C=C12044.3Standard non polar33892256
4-Hydroxyhippuric acidOC(=O)CNC(=O)C1=CC=C(O)C=C12209.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxyhippuric acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CNC(=O)C1=CC=C(O)C=C12145.7Semi standard non polar33892256
4-Hydroxyhippuric acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(C(=O)NCC(=O)O)C=C12149.8Semi standard non polar33892256
4-Hydroxyhippuric acid,1TMS,isomer #3C[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=C(O)C=C12108.3Semi standard non polar33892256
4-Hydroxyhippuric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CNC(=O)C1=CC=C(O[Si](C)(C)C)C=C12258.9Semi standard non polar33892256
4-Hydroxyhippuric acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O)C=C1)[Si](C)(C)C2153.3Semi standard non polar33892256
4-Hydroxyhippuric acid,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(C(=O)N(CC(=O)O)[Si](C)(C)C)C=C12140.2Semi standard non polar33892256
4-Hydroxyhippuric acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C2147.5Semi standard non polar33892256
4-Hydroxyhippuric acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C2106.7Standard non polar33892256
4-Hydroxyhippuric acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C2233.8Standard polar33892256
4-Hydroxyhippuric acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=C(O)C=C12390.8Semi standard non polar33892256
4-Hydroxyhippuric acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)NCC(=O)O)C=C12427.6Semi standard non polar33892256
4-Hydroxyhippuric acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=C(O)C=C12385.1Semi standard non polar33892256
4-Hydroxyhippuric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12778.8Semi standard non polar33892256
4-Hydroxyhippuric acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C2653.3Semi standard non polar33892256
4-Hydroxyhippuric acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)C=C12687.1Semi standard non polar33892256
4-Hydroxyhippuric acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2885.4Semi standard non polar33892256
4-Hydroxyhippuric acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2739.4Standard non polar33892256
4-Hydroxyhippuric acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2595.3Standard polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.02 ± 0.01 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
BloodDetected and Quantified0.03 ± 0.02 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected and Quantified0.05 ± 0.03 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected and Quantified0.02 ± 0.01 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected and Quantified0.04 ± 0.03 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected and Quantified0.04 ± 0.02 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected and Quantified0.03 ± 0.02 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected and Quantified0.03 ± 0.03 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected and Quantified0.03 ± 0.02 uMAdult (>18 years old)Both
Normal
    • Quantitative comp...
 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected and Quantified0.369 (0.0461-1.0350) nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified1.691 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified1.742 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified1.793 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified4.0989 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0-30 umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Great Plains Labo...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.8 (1.4-6.0) umol/mmol creatinineAdult (>18 years old)BothNot Available details
UrineDetected and Quantified4.55 (3.40-7.47) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
UrineDetected and Quantified27.488 +/- 10.23 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified7.48(4.17-19.96) umol/mmol creatinineNewborn (0-30 days old)MaleNormal details
UrineDetected and Quantified7.42(4.69-18.33) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified4.2-19.59 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified0-14 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Great Plains Labo...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified93.846 +/- 33.846 uMAdult (>18 years old)Both
Uremia		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)		 details
UrineDetected and Quantified35.234 +/- 16.83 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified35.795 +/- 21.952 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029984
KNApSAcK IDC00052156
Chemspider ID133104
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151012
PDB IDNot Available
ChEBI ID71018
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029845
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jacobs DM, Spiesser L, Garnier M, de Roo N, van Dorsten F, Hollebrands B, van Velzen E, Draijer R, van Duynhoven J: SPE-NMR metabolite sub-profiling of urine. Anal Bioanal Chem. 2012 Nov;404(8):2349-61. doi: 10.1007/s00216-012-6339-2. Epub 2012 Aug 31. [PubMed:22932811 ]
  2. van Duynhoven J, Vaughan EE, Jacobs DM, Kemperman RA, van Velzen EJ, Gross G, Roger LC, Possemiers S, Smilde AK, Dore J, Westerhuis JA, Van de Wiele T: Metabolic fate of polyphenols in the human superorganism. Proc Natl Acad Sci U S A. 2011 Mar 15;108 Suppl 1:4531-8. doi: 10.1073/pnas.1000098107. Epub 2010 Jun 25. [PubMed:20615997 ]
  3. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]