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Record Information
Version4.0
Creation Date2012-04-03 14:10:30 UTC
Update Date2017-09-27 08:27:24 UTC
HMDB IDHMDB0013678
Secondary Accession Numbers
  • HMDB13678
Metabolite Identification
Common Name4-Hydroxyhippuric acid
Description4-hydroxyhippuric acid is a microbial end-product derived from polyphenol metabolism by the microflora in the intestine (PMID: 22932811 ). It is derived from 4-hydroxybenzoic acid derivatives which may undergo glycination in the liver and kidney.
Structure
Thumb
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
N-(4-Hydroxybenzoyl)glycineHMDB
P-Hydroxy-hippuric acidHMDB
[(4-Hydroxybenzoyl)amino]acetic acidHMDB
P-Hydroxyhippuric acidMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as hippuric acids. These are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted 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
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.63 g/LALOGPS
logP0.44ALOGPS
logP0.22ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1900000000-07bd47210e1c18d19c78View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-8982000000-016ad8c26c264db9ef97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-0900000000-d252a86f47419d419bc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-a680ce571986b15d0d71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9600000000-39500903a2246ed4d7d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-f6ed56b2505b426ab18bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-0c2b762b727ebf3108f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9200000000-cfd75bbf2139a9e184edView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected and Quantified1.691 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified1.742 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified1.793 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified4.0989 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0-14 umol/mmol creatinineAdult (>18 years old)BothNormal
      • Great Plains Labo...
    details
    UrineDetected and Quantified0-30 umol/mmol creatinineChildren (1-13 years old)BothNormal
      • Great Plains Labo...
    details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified2.8 (1.4-6.0) umol/mmol creatinineAdult (>18 years old)BothNot Available details
    UrineDetected and Quantified27.488 +/- 10.23 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    UrineDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified35.234 +/- 16.83 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified35.795 +/- 21.952 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Gastroesophageal reflux disease
      • Mordechai, Hien, ...
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Hypertension (mild)
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Hypertension (mild)
    details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite ID926
    FoodDB IDNot Available
    KNApSAcK IDNot Available
    Chemspider ID133104
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound151012
    PDB IDNot Available
    ChEBI ID613375
    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 ]