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Showing Compound 3-Hydroxyhippuric acid (FDB023830)

Record Information
Version1.0
Creation date2011-09-21 00:35:27 UTC
Update date2015-10-09 22:33:40 UTC
Primary IDFDB023830
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Hydroxyhippuric acid
Description3-Hydroxyhippuric acid is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. 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 3-Hydroxyhippuric acid is an organic acid found in normal human urine. 3-Hydroxyhippuric acid is a metabolite of rutin detected in urine after consumption of tomato juice (a source of rutin). 3-Hydroxyhippuric acid has its origin in dietary procyanidins (a major source of polyphenols consisting of elementary flavan-3-ol (epi)catechin units). 3-Hydroxyhippuric acid is a microbial aromatic acid metabolite derived from dietary polyphenols, found in normal human urine. (PMID: 12592675, 2338430, 17015248, 14556848, 12742116) [HMDB]
CAS Number1637-75-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H9NO4
IUPAC name2-[(3-hydroxyphenyl)formamido]acetic acid
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
Isomeric SMILESOC(=O)CNC(=O)C1=CC=CC(O)=C1
Average Molecular Weight195.1721
Monoisotopic Molecular Weight195.053157781
Classification
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
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    Predicted GC-MS3-Hydroxyhippuric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-1900000000-49e4d27497eeeff45809Spectrum
    Predicted GC-MS3-Hydroxyhippuric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-7982000000-7959bea2ab616ece8756Spectrum
    Predicted GC-MS3-Hydroxyhippuric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udl-1900000000-dc85347d83766215a7b72021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9300000000-4d0f2ba79bccc743efd02021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-f1d71d9347520fec146c2021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-899450f53ef2c1cb3e4b2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-4900000000-0ce4cb09039d70fe8e8b2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9300000000-264f280344785775dc132016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-caff5245d469f41c4da82016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-8a379c794edd9eeb0a032016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9300000000-74897c8ed9e9ff09d06b2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-c7da1e28001d3b60249f2021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-cc2fe6c05438067b7def2021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9100000000-a7e31e4050be2dac08762021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-7900000000-973fa316a4faa2fb85ec2021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9200000000-feb5bed01fe869d8f2602021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-134764e2910be589b6f92021-09-22View Spectrum
    NMRNot Available
    ChemSpider ID396603
    ChEMBL IDCHEMBL447627
    KEGG Compound IDNot Available
    Pubchem Compound ID450268
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID927
    DrugBank IDDB07069
    HMDB IDHMDB06116
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET ID3XH
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID927
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    Enzymes
    NameGene NameUniProt ID
    Glycine N-acyltransferaseGLYATQ6IB77
    Glycine N-acyltransferase-like protein 1GLYATL1Q969I3
    Glycine N-acyltransferase-like protein 2GLYATL2Q8WU03
    Glycine N-acyltransferase-like protein 3GLYATL3Q5SZD4
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference