3-Hydroxyhippuric acid (CHEM021705)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:10:28 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021705
Identification
Common Name3-Hydroxyhippuric acid
ClassSmall Molecule
DescriptionAn N-acylglycine that is hippuric acid (N-benzoylglycine) substituted at position 3 on the phenyl ring by a hydroxy group.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-[(3-Hydroxyphenyl)formamido]acetic acidChEBI
3-HydroxybenzoylglycineChEBI
2-[(3-Hydroxyphenyl)formamido]acetateGenerator
3-HydroxyhippateGenerator
3-Hydroxyhippic acidGenerator
3-HydroxyhippurateHMDB
m-HydroxyhippurateHMDB
m-Hydroxyhippuric acidHMDB
N-m-HydroxylbenzoylglycineHMDB
3-Hydroxyhippuric acidChEBI
m-HydroxyhippateGenerator, HMDB
m-Hydroxyhippic acidGenerator, HMDB
2-[(3-Hydroxybenzoyl)amino]acetic acidHMDB
3'-Hydroxyhippuric acidHMDB
Chemical FormulaC9H9NO4
Average Molecular Mass195.172 g/mol
Monoisotopic Mass195.053 g/mol
CAS Registry Number1637-75-8
IUPAC Name2-[(3-hydroxyphenyl)formamido]acetic acid
Traditional Name3-hydroxyhippuric acid
SMILESOC(=O)CNC(=O)C1=CC(O)=CC=C1
InChI IdentifierInChI=1S/C9H9NO4/c11-7-3-1-2-6(4-7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)
InChI KeyXDOFWFNMYJRHEW-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 or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.91 g/LALOGPS
logP0.52ALOGPS
logP0.22ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.25ChemAxon
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
Polarizability18.51 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1900000000-49e4d27497eeeff45809Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-7982000000-7959bea2ab616ece8756Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udl-1900000000-dc85347d83766215a7b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9300000000-4d0f2ba79bccc743efd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-f1d71d9347520fec146cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-899450f53ef2c1cb3e4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-4900000000-0ce4cb09039d70fe8e8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9300000000-264f280344785775dc13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-caff5245d469f41c4da8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-8a379c794edd9eeb0a03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9300000000-74897c8ed9e9ff09d06bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-c7da1e28001d3b60249fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-cc2fe6c05438067b7defSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9100000000-a7e31e4050be2dac0876Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-7900000000-973fa316a4faa2fb85ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9200000000-feb5bed01fe869d8f260Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-134764e2910be589b6f9Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB07069
HMDB IDHMDB0006116
FooDB IDFDB023830
Phenol Explorer IDNot Available
KNApSAcK IDC00052143
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID396603
ChEBI ID70824
PubChem Compound ID450268
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=13295242
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22372405
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
4. Van Brussel, W.; Van Sumere, C. F. N-Acylamino acids and peptides. VI. A simple synthesis of N-acylglycines of the benzoyl and cinnamyl type. Bulletin des Societes Chimiques Belges (1978), 87(10), 791-7.
5. Rechner AR, Kuhnle G, Hu H, Roedig-Penman A, van den Braak MH, Moore KP, Rice-Evans CA: The metabolism of dietary polyphenols and the relevance to circulating levels of conjugated metabolites. Free Radic Res. 2002 Nov;36(11):1229-41.
6. Liebich HM, Forst C: Basic profiles of organic acids in urine. J Chromatogr. 1990 Jan 26;525(1):1-14.
7. Jaganath IB, Mullen W, Edwards CA, Crozier A: The relative contribution of the small and large intestine to the absorption and metabolism of rutin in man. Free Radic Res. 2006 Oct;40(10):1035-46.
8. Gonthier MP, Donovan JL, Texier O, Felgines C, Remesy C, Scalbert A: Metabolism of dietary procyanidins in rats. Free Radic Biol Med. 2003 Oct 15;35(8):837-44.
9. Gonthier MP, Rios LY, Verny M, Remesy C, Scalbert A: Novel liquid chromatography-electrospray ionization mass spectrometry method for the quantification in human urine of microbial aromatic acid metabolites derived from dietary polyphenols. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jun 15;789(2):247-55.
10. Xiong X, Liu D, Wang Y, Zeng T, Peng Y: Urinary 3-(3-Hydroxyphenyl)-3-hydroxypropionic Acid, 3-Hydroxyphenylacetic Acid, and 3-Hydroxyhippuric Acid Are Elevated in Children with Autism Spectrum Disorders. Biomed Res Int. 2016;2016:9485412. doi: 10.1155/2016/9485412. Epub 2016 Mar 30.
11. Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510