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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-03-02 15:48:45 UTC
Update Date2017-12-07 02:32:19 UTC
HMDB IDHMDB0011723
Secondary Accession Numbers
  • HMDB11723
Metabolite Identification
Common Name2-Methylhippuric acid
DescriptionMethylhippuric 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. Methylhippuric acid is a metabolite of xylene which is an aromatic hydrocarbon widely used as a solvant. It's level can be measured in urine of workers exposed to xylene (PMID 8689499 ).
Structure
Thumb
Synonyms
ValueSource
N-(O-Toluoyl)glycineChEBI
O-Toluric acidChEBI
2-MethylhippateGenerator
2-Methylhippic acidGenerator
O-TolateGenerator
O-Tolic acidGenerator
N-(2-Methylbenzoyl)-glycineHMDB
N-(2-Methylbenzoyl)glycineHMDB
N-(Methylbenzoyl)-glycineHMDB
N-(Methylbenzoyl)glycineHMDB
N-(O-Toluoyl)-glycineHMDB
O-Methylhippuric acidHMDB
ortho-Methylhippuric acidMeSH
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=CC=CC=C1C(=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
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
  • 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:

  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 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-8900000000-f3facdb25edf52b32bf5View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-1921000000-99d8518c7ed8a7303750View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-2930000000-17087fd513ab1a3e48c8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1911000000-d30157f1d23d841dd7faView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-3920000000-ffcf68f9d13b6ffa54c5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-7900000000-a0e6f767778cd1dac471View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9210000000-a706f78bdfa3ab6b4a0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2900000000-3a52e728af0927d90d61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0101-4900000000-be3581a92b3d98f72498View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-9200000000-ef2cb39cf678d6892d49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-848582a82498a747b60cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-d8c8ac579c87ff465eb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r6-9300000000-8f7a8b2f5617b2cda457View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB028406
    KNApSAcK IDNot Available
    Chemspider ID82742
    KEGG Compound ID C01586
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound91637
    PDB IDNot Available
    ChEBI ID613303
    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 ]

    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