Showing metabocard for Hippuric acid (MMDBc0000142)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:37:24 UTC
Update Date2024-10-17 07:13:12 UTC
Metabolite IDMMDBc0000142
Metabolite Identification
Common NameHippuric acid
DescriptionHippuric acid is an acyl glycine formed from the conjugation of benzoic acid with glycine. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine. Hippuric acid is a normal component of urine and is typically increased with increased consumption of phenolic compounds (tea, wine, fruit juices). These phenols are converted into benzoic acid which is then converted into hippuric acid and excreted in the urine. Hippuric acid is the most frequently used biomarker in the biological monitoring of occupational exposure to toluene. This product of solvent biotransformation may be also found in the urine of individuals who have not been exposed to the solvent. A smaller fraction of the absorbed toluene is oxidized into aromatic compounds including ortho-cresol, which is not found in the urine of nonexposed individuals in a significant amount. The concentration of hippuric acid in the urine of individuals exposed to a low toluene concentration does not differ from that of individuals not exposed to the solvent. This has led to the conclusion that hippuric acid should not be utilized in the biological monitoring of occupational exposure to low levels of toluene in the air. Protein-bound organic acids such as hippuric acid are markedly accumulated in uremic plasma and produce defective protein binding of drugs (PMID: 9120876 , 8734460 ). Hippuric acid has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Hippuric acid is also found to be associated with phenylketonuria, propionic acidemia, and tyrosinemia I, which are inborn errors of metabolism. Hippuric acid is an endogenous phenolic acid metabolite detected after the consumption of whole grain.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000562ee3c566e8>


  Mrv1652306131922522D          

 13 13  0  0  0  0            999 V2000
   -1.6292   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148    0.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -1.3275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9430   -0.0900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
  7 11  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000562ee3c566e8>

HMDB0000714
     RDKit          3D
Hippuric acid
 22 22  0  0  0  0  0  0  0  0999 V2000
    2.7052    0.6873   -1.8987 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684    0.3479   -0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7287    0.6257   -0.9146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8186   -0.3056    0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998   -0.5476    0.2218 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4280    0.4450    0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7880    1.6439   -0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9900    0.1450    0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9389    1.1659   -0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2776    0.9459   -0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7617   -0.3337   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8919   -1.3732    0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5230   -1.1236    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2322    0.9808   -0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3389   -1.2452    0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0095    0.3795    1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0836   -1.5392    0.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5621    2.1752   -0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9837    1.7690   -0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8315   -0.4795   -0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685   -2.3927    0.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8721   -1.9709    0.1942 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
 12 13  2  0
 13  8  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
 12 21  1  0
 13 22  1  0
M  END
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3D SDF for #<Metabolite:0x0000562ee3c566e8>


  Mrv1652306131922522D          

 13 13  0  0  0  0            999 V2000
   -1.6292   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148    0.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -1.3275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9430   -0.0900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
  7 11  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000142

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)

> <INCHI_KEY>
QIAFMBKCNZACKA-UHFFFAOYSA-N

> <FORMULA>
C9H9NO3

> <MOLECULAR_WEIGHT>
179.1727

> <EXACT_MASS>
179.058243159

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.573850113167715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(phenylformamido)acetic acid

> <ALOGPS_LOGP>
0.23

> <JCHEM_LOGP>
0.5255454843333334

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.086777361882415

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5912387558835803

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3083417398569668

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
46.117700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hippuric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x0000562ee3c566e8>

HMDB0000714
     RDKit          3D
Hippuric acid
 22 22  0  0  0  0  0  0  0  0999 V2000
    2.7052    0.6873   -1.8987 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684    0.3479   -0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7287    0.6257   -0.9146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8186   -0.3056    0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998   -0.5476    0.2218 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4280    0.4450    0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7880    1.6439   -0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9900    0.1450    0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9389    1.1659   -0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2776    0.9459   -0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7617   -0.3337   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8919   -1.3732    0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5230   -1.1236    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2322    0.9808   -0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3389   -1.2452    0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0095    0.3795    1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0836   -1.5392    0.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5621    2.1752   -0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9837    1.7690   -0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8315   -0.4795   -0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685   -2.3927    0.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8721   -1.9709    0.1942 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
 12 13  2  0
 13  8  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
 12 21  1  0
 13 22  1  0
M  END
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PDB for #<Metabolite:0x0000562ee3c566e8>

HEADER    PROTEIN                                 13-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUN-19         0                                  
HETATM    1  C   UNK     0      -3.041  -0.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.375  -0.168   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.709  -0.938   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.709  -2.478   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.375  -3.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.041  -2.478   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.708  -0.168   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.374  -0.938   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.960  -0.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.293  -0.938   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.708   1.372   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.293  -2.478   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.627  -0.168   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   12   13                                                  
CONECT   11    7                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for #<Metabolite:0x0000562ee3c566e8>

COMPND    HMDB0000714
HETATM    1  O1  UNL     1       2.705   0.687  -1.899  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.368   0.348  -0.886  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.729   0.626  -0.915  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.819  -0.306   0.295  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.400  -0.548   0.222  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.428   0.445   0.071  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.788   1.644  -0.008  1.00  0.00           O  
HETATM    8  C4  UNL     1      -0.990   0.145   0.003  1.00  0.00           C  
HETATM    9  C5  UNL     1      -1.939   1.166  -0.149  1.00  0.00           C  
HETATM   10  C6  UNL     1      -3.278   0.946  -0.219  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.762  -0.334  -0.140  1.00  0.00           C  
HETATM   12  C8  UNL     1      -2.892  -1.373   0.008  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.523  -1.124   0.077  1.00  0.00           C  
HETATM   14  H1  UNL     1       5.232   0.981  -0.106  1.00  0.00           H  
HETATM   15  H2  UNL     1       3.339  -1.245   0.551  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.009   0.379   1.171  1.00  0.00           H  
HETATM   17  H4  UNL     1       1.084  -1.539   0.286  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.562   2.175  -0.211  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.984   1.769  -0.337  1.00  0.00           H  
HETATM   20  H7  UNL     1      -4.831  -0.480  -0.199  1.00  0.00           H  
HETATM   21  H8  UNL     1      -3.268  -2.393   0.071  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.872  -1.971   0.194  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5   15   16
CONECT    5    6   17
CONECT    6    7    7    8
CONECT    8    9    9   13
CONECT    9   10   18
CONECT   10   11   11   19
CONECT   11   12   20
CONECT   12   13   13   21
CONECT   13   22
END
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SMILES for #<Metabolite:0x0000562ee3c566e8>

OC(=O)CNC(=O)C1=CC=CC=C1
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INCHI for #<Metabolite:0x0000562ee3c566e8>

InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)
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Synonyms
ValueSource
Benzamidoacetic acidChEBI
BenzamidoessigsaeureChEBI
Benzoylaminoacetic acidChEBI
BenzoylaminoessigsaeureChEBI
HippurateChEBI
HippursaeureChEBI
Phenylcarbonylaminoacetic acidChEBI
N-BenzoylglycineKegg
BenzamidoacetateGenerator
BenzoylaminoacetateGenerator
PhenylcarbonylaminoacetateGenerator
HippateGenerator
Hippic acidGenerator
(Benzoylamino)-acetateHMDB
(Benzoylamino)-acetic acidHMDB
2-BenzamidoacetateHMDB
2-Benzamidoacetic acidHMDB
BenzoylglycineHMDB
N-BenzoylglycinateHMDB
Hippuric acidHMDB
Molecular FormulaC9H9NO3
Average Mass179.1727
Monoisotopic Mass179.058243159
IUPAC Name2-(phenylformamido)acetic acid
Traditional Namehippuric acid
CAS Registry Number495-69-2
SMILES
OC(=O)CNC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)
InChI KeyQIAFMBKCNZACKA-UHFFFAOYSA-N