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Record Information
Version3.6
Creation Date2012-04-03 14:10:30 UTC
Update Date2016-02-11 01:27:13 UTC
HMDB IDHMDB13678
Secondary Accession NumbersNone
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-Hydroxyhippuric acidChEBI
[(4-Hydroxyphenyl)formamido]acetateGenerator
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
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 KeyInChIKey=ZMHLUFWWWPBTIU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzamides
Direct ParentHippuric acids
Alternative Parents
Substituents
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Benzoic acid or derivatives
  • Benzoyl
  • Phenol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.1 m3·mol-1ChemAxon
Polarizability18.54 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
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 QuantifiedNot ApplicableAdult (>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 QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>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 QuantifiedNot ApplicableAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not QuantifiedNot ApplicableAdult (>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
NuGOwiki LinkHMDB13678
Metagene LinkHMDB13678
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. [22932811 ]