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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-03-02 15:48:45 UTC
Update Date2023-02-21 17:17:34 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?1676999854
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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker153.65230932474
[M-H]-Not Available153.652http://allccs.zhulab.cn/database/detail?ID=AllCCS00001916
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.03531661259
DarkChem[M-H]-137.48331661259
DeepCCS[M+H]+140.54530932474
DeepCCS[M-H]-137.15330932474
DeepCCS[M-2H]-174.21130932474
DeepCCS[M+Na]+149.74930932474
AllCCS[M+H]+141.832859911
AllCCS[M+H-H2O]+137.732859911
AllCCS[M+NH4]+145.632859911
AllCCS[M+Na]+146.732859911
AllCCS[M-H]-141.932859911
AllCCS[M+Na-2H]-142.532859911
AllCCS[M+HCOO]-143.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Methylhippuric acidCC1=C(C=CC=C1)C(=O)NCC(O)=O2851.2Standard polar33892256
2-Methylhippuric acidCC1=C(C=CC=C1)C(=O)NCC(O)=O1678.4Standard non polar33892256
2-Methylhippuric acidCC1=C(C=CC=C1)C(=O)NCC(O)=O1863.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Methylhippuric acid,1TMS,isomer #1CC1=CC=CC=C1C(=O)NCC(=O)O[Si](C)(C)C1885.5Semi standard non polar33892256
2-Methylhippuric acid,1TMS,isomer #2CC1=CC=CC=C1C(=O)N(CC(=O)O)[Si](C)(C)C1866.1Semi standard non polar33892256
2-Methylhippuric acid,2TMS,isomer #1CC1=CC=CC=C1C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1864.2Semi standard non polar33892256
2-Methylhippuric acid,2TMS,isomer #1CC1=CC=CC=C1C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1869.6Standard non polar33892256
2-Methylhippuric acid,2TMS,isomer #1CC1=CC=CC=C1C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C2123.1Standard polar33892256
2-Methylhippuric acid,1TBDMS,isomer #1CC1=CC=CC=C1C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C2128.3Semi standard non polar33892256
2-Methylhippuric acid,1TBDMS,isomer #2CC1=CC=CC=C1C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C2104.2Semi standard non polar33892256
2-Methylhippuric acid,2TBDMS,isomer #1CC1=CC=CC=C1C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2349.2Semi standard non polar33892256
2-Methylhippuric acid,2TBDMS,isomer #1CC1=CC=CC=C1C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2262.4Standard non polar33892256
2-Methylhippuric acid,2TBDMS,isomer #1CC1=CC=CC=C1C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2392.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Methylhippuric acid EI-B (Non-derivatized)splash10-014l-8900000000-f3facdb25edf52b32bf52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methylhippuric acid EI-B (Non-derivatized)splash10-014i-1921000000-99d8518c7ed8a73037502017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methylhippuric acid EI-B (Non-derivatized)splash10-014i-2930000000-17087fd513ab1a3e48c82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methylhippuric acid GC-EI-TOF (Non-derivatized)splash10-014i-1911000000-d30157f1d23d841dd7fa2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methylhippuric acid GC-EI-TOF (Non-derivatized)splash10-014i-3920000000-ffcf68f9d13b6ffa54c52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methylhippuric acid EI-B (Non-derivatized)splash10-014l-8900000000-f3facdb25edf52b32bf52018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methylhippuric acid EI-B (Non-derivatized)splash10-014i-1921000000-99d8518c7ed8a73037502018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methylhippuric acid EI-B (Non-derivatized)splash10-014i-2930000000-17087fd513ab1a3e48c82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methylhippuric acid GC-EI-TOF (Non-derivatized)splash10-014i-1911000000-d30157f1d23d841dd7fa2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methylhippuric acid GC-EI-TOF (Non-derivatized)splash10-014i-3920000000-ffcf68f9d13b6ffa54c52018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylhippuric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-7900000000-a0e6f767778cd1dac4712017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylhippuric acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9210000000-a706f78bdfa3ab6b4a0a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylhippuric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methylhippuric acid 40V, Negative-QTOFsplash10-0006-9200000000-964fdc6a530e3ced5e342021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methylhippuric acid 40V, Positive-QTOFsplash10-0006-9000000000-8b17a665175fbcba831b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methylhippuric acid 10V, Positive-QTOFsplash10-014i-0900000000-a9778b196de1304f34332021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methylhippuric acid 20V, Positive-QTOFsplash10-014l-6900000000-8af38895fa1d5760b92d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methylhippuric acid 10V, Negative-QTOFsplash10-0006-3900000000-a82d0267df099b7dfc4c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methylhippuric acid 20V, Negative-QTOFsplash10-0006-9200000000-1894a3131f12f0bc06302021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylhippuric acid 10V, Positive-QTOFsplash10-0006-2900000000-3a52e728af0927d90d612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylhippuric acid 20V, Positive-QTOFsplash10-0101-4900000000-be3581a92b3d98f724982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylhippuric acid 40V, Positive-QTOFsplash10-00b9-9200000000-ef2cb39cf678d6892d492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylhippuric acid 10V, Negative-QTOFsplash10-0006-0900000000-848582a82498a747b60c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylhippuric acid 20V, Negative-QTOFsplash10-0006-2900000000-d8c8ac579c87ff465eb92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylhippuric acid 40V, Negative-QTOFsplash10-00r6-9300000000-8f7a8b2f5617b2cda4572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylhippuric acid 10V, Negative-QTOFsplash10-0007-4900000000-ecfbd0d43eb964c793592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylhippuric acid 20V, Negative-QTOFsplash10-0006-9000000000-4946aff46366d89e59f02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylhippuric acid 40V, Negative-QTOFsplash10-0006-9000000000-5671d4c535a6553aaf0d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylhippuric acid 10V, Positive-QTOFsplash10-014l-4900000000-71d856c475306586b4902021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylhippuric acid 20V, Positive-QTOFsplash10-00kf-9700000000-e5cff62d21a3a704ee9c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylhippuric acid 40V, Positive-QTOFsplash10-0006-9000000000-a1e2bcbd969ecf85e4e52021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
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 IDC01586
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
MarkerDB IDNot Available
Good Scents IDNot Available
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