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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-03-02 15:48:45 UTC
Update Date2020-02-26 21:35:44 UTC
HMDB IDHMDB0011723
Secondary Accession Numbers
  • HMDB11723
Metabolite Identification
Common Name2-Methylhippuric acid
Description2-Methylhippuric 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. 2-Methylhippuric acid is a metabolite of xylene which is an aromatic hydrocarbon widely used as a solvant. Its level can be measured in the urine of workers exposed to xylene (PMID: 8689499 ). 2-Methylhippuric acid is an endogenous phenolic acid metabolite detected after the consumption of whole grain.
Structure
Data?1582752944
Synonyms
ValueSource
N-(O-Toluoyl)glycineChEBI
O-Toluric acidChEBI
O-TolateGenerator
O-Tolic acidGenerator
2-MethylhippateGenerator
2-Methylhippic acidGenerator
N-(2-Methylbenzoyl)-glycineHMDB
N-(2-Methylbenzoyl)glycineHMDB
N-(Methylbenzoyl)-glycineHMDB
N-(Methylbenzoyl)glycineHMDB
N-(O-Toluoyl)-glycineHMDB
O-Methylhippuric acidHMDB
Ortho-methylhippuric acidHMDB
O-MethylhippateHMDB
O-Methylhippic acidHMDB
2-Methylhippuric acidChEBI
Chemical FormulaC10H11NO3
Average Molecular Weight193.1992
Monoisotopic Molecular Weight193.073893223
IUPAC Name2-[(2-methylphenyl)formamido]acetic acid
Traditional Namemethyl hippurate
CAS Registry Number42013-20-7
SMILES
CC1=C(C=CC=C1)C(=O)NCC(O)=O
InChI Identifier
InChI=1S/C10H11NO3/c1-7-4-2-3-5-8(7)10(14)11-6-9(12)13/h2-5H,6H2,1H3,(H,11,14)(H,12,13)
InChI KeyYOEBAVRJHRCKRE-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
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • O-toluamide
  • Toluamide
  • Benzoyl
  • Toluene
  • 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:

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 Solubility0.6 g/LALOGPS
logP0.66ALOGPS
logP1.04ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.16 m³·mol⁻¹ChemAxon
Polarizability19.48 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-8900000000-f3facdb25edf52b32bf5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-1921000000-99d8518c7ed8a7303750Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-2930000000-17087fd513ab1a3e48c8Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1911000000-d30157f1d23d841dd7faSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-3920000000-ffcf68f9d13b6ffa54c5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-8900000000-f3facdb25edf52b32bf5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-1921000000-99d8518c7ed8a7303750Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-2930000000-17087fd513ab1a3e48c8Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1911000000-d30157f1d23d841dd7faSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-3920000000-ffcf68f9d13b6ffa54c5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-7900000000-a0e6f767778cd1dac471Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9210000000-a706f78bdfa3ab6b4a0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2900000000-3a52e728af0927d90d61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0101-4900000000-be3581a92b3d98f72498Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-9200000000-ef2cb39cf678d6892d49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-848582a82498a747b60cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-d8c8ac579c87ff465eb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r6-9300000000-8f7a8b2f5617b2cda457Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified7.0 +/- 1.5 umol/mmol creatinineAdult (>18 years old)MaleNormal details
    UrineDetected and Quantified12.0 +/- 1.5 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FooDB IDFDB028406
    KNApSAcK IDNot Available
    Chemspider ID82742
    KEGG Compound ID C01586
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkMethylhippuric acid
    METLIN IDNot Available
    PubChem Compound91637
    PDB IDNot Available
    ChEBI ID68455
    Food Biomarker OntologyNot Available
    VMH IDCE2934
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Sakai T: [Studies on the evaluation of exposure to industrial chemicals]. Sangyo Eiseigaku Zasshi. 1996 May;38(3):119-37. [PubMed:8689499 ]
    2. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

    Enzymes

    General function:
    Involved in glycine N-acyltransferase activity
    Specific function:
    Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
    Gene Name:
    GLYAT
    Uniprot ID:
    Q6IB77
    Molecular weight:
    18506.33