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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:15 UTC
HMDB IDHMDB0000859
Secondary Accession Numbers
  • HMDB00859
Metabolite Identification
Common NameMethyl hippurate
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. The amount of methylhippuric acid can be measured in urine of workers exposed to xylene (PMID 8689499 ).
Structure
Data?1676999715
Synonyms
ValueSource
Hippurate methyl esterChEBI
Hippuric acid methyl esterChEBI
N-Benzoyl-glycine methyl esterChEBI
N-Benzoylglycine methyl esterChEBI
Hippate methyl esterGenerator
Hippic acid methyl esterGenerator
Methyl hippuric acidGenerator
MethylhippateHMDB
Methylhippic acidHMDB
Methyl (benzoylamino)acetateHMDB
Methyl benzoylaminoacetateHMDB
Methyl benzoylglycinateHMDB
Methyl N-benzoylglycinateHMDB
Methyl hippurateHMDB
Chemical FormulaC10H11NO3
Average Molecular Weight193.1992
Monoisotopic Molecular Weight193.073893223
IUPAC Namemethyl 2-(phenylformamido)acetate
Traditional Namemethyl (phenylformamido)acetate
CAS Registry Number1205-08-9
SMILES
COC(=O)CNC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H11NO3/c1-14-9(12)7-11-10(13)8-5-3-2-4-6-8/h2-6H,7H2,1H3,(H,11,13)
InChI KeyXTKVNQKOTKPCKM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • N-acyl-alpha amino acid or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Methyl ester
  • Carboxylic acid ester
  • Carboximidic acid
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility17 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP0.96ALOGPS
logP0.67ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)14.93ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.89 m³·mol⁻¹ChemAxon
Polarizability19.67 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]+144.96131661259
DarkChem[M-H]-141.29931661259
AllCCS[M+H]+142.20232859911
AllCCS[M-H]-143.4432859911
DeepCCS[M+H]+140.34930932474
DeepCCS[M-H]-137.85430932474
DeepCCS[M-2H]-173.30330932474
DeepCCS[M+Na]+148.74630932474
AllCCS[M+H]+142.232859911
AllCCS[M+H-H2O]+138.132859911
AllCCS[M+NH4]+146.032859911
AllCCS[M+Na]+147.132859911
AllCCS[M-H]-143.432859911
AllCCS[M+Na-2H]-144.232859911
AllCCS[M+HCOO]-145.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methyl hippurateCOC(=O)CNC(=O)C1=CC=CC=C12464.0Standard polar33892256
Methyl hippurateCOC(=O)CNC(=O)C1=CC=CC=C11547.8Standard non polar33892256
Methyl hippurateCOC(=O)CNC(=O)C1=CC=CC=C11744.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methyl hippurate,1TMS,isomer #1COC(=O)CN(C(=O)C1=CC=CC=C1)[Si](C)(C)C1699.3Semi standard non polar33892256
Methyl hippurate,1TMS,isomer #1COC(=O)CN(C(=O)C1=CC=CC=C1)[Si](C)(C)C1720.5Standard non polar33892256
Methyl hippurate,1TMS,isomer #1COC(=O)CN(C(=O)C1=CC=CC=C1)[Si](C)(C)C2237.1Standard polar33892256
Methyl hippurate,1TBDMS,isomer #1COC(=O)CN(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C1929.0Semi standard non polar33892256
Methyl hippurate,1TBDMS,isomer #1COC(=O)CN(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C1935.4Standard non polar33892256
Methyl hippurate,1TBDMS,isomer #1COC(=O)CN(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2363.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methyl hippurate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0900000000-495f7967288f3bab63192017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl hippurate 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 - Methyl hippurate 20V, Negative-QTOFsplash10-014i-0900000000-0e07edbacaf6ec332bcf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate 10V, Negative-QTOFsplash10-03xr-0900000000-5ea337b26aefe7d992632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a4i-0900000000-e67faa45b3c1bdbbf33a2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a6r-6900000000-493c458dac8fe21c85932012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0ar0-9710000000-7e497b3b437d120014ad2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate LC-ESI-qTof , Positive-QTOFsplash10-0a4i-0902100000-a35144e3d3f28f6cdedf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate , positive-QTOFsplash10-0a4i-0902100000-a35144e3d3f28f6cdedf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate 30V, Positive-QTOFsplash10-004i-9200000000-8e560b4138252b1b70342021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate 10V, Positive-QTOFsplash10-0a6r-4900000000-ea4bbe340263c88307d22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate 10V, Positive-QTOFsplash10-0a4i-0900000000-9ef2ec7fd4e7489a70952021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate 20V, Positive-QTOFsplash10-0a4i-3900000000-8f0b80e955cf5a16443b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate 0V, Positive-QTOFsplash10-0a4l-0900000000-a211a9c162c4ea003d8c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate 30V, Positive-QTOFsplash10-004i-9200000000-7a892a4f5c40dc1684c72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate 0V, Positive-QTOFsplash10-0a4l-0900000000-b6759e156faed1af594b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate 10V, Positive-QTOFsplash10-0a4i-3900000000-ab63c11d1d6878a595512021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate 40V, Positive-QTOFsplash10-004i-9000000000-8665a5f35cccfcf4234a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hippurate 30V, Positive-QTOFsplash10-004i-9300000000-6d66150db10972f0e2462021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hippurate 10V, Negative-QTOFsplash10-0006-0900000000-2c603427f2601fe093b22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hippurate 20V, Negative-QTOFsplash10-006x-2900000000-c08b0b736ae0a886138e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hippurate 40V, Negative-QTOFsplash10-056u-9100000000-e9e3c2489aa41abc4b042017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hippurate 10V, Negative-QTOFsplash10-03di-1900000000-613f60966a740673aa732021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hippurate 20V, Negative-QTOFsplash10-004i-9200000000-4c1da2556764d8da36cc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hippurate 40V, Negative-QTOFsplash10-004i-9000000000-e8a8d127dd05bf7e49d32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hippurate 10V, Positive-QTOFsplash10-052f-0900000000-c8ba3b5500a0496394472017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hippurate 20V, Positive-QTOFsplash10-0a4i-2900000000-2f5f2219f261b10131ef2017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, 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 Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022285
KNApSAcK IDNot Available
Chemspider ID13907
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5822
PubChem Compound14566
PDB IDNot Available
ChEBI ID70869
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceRinderknecht, Heinrich; Niemann, Carl. Esterification of acylated a-amino acids. Journal of the American Chemical Society (1948), 70 2605-6.
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. Mizunuma K, Kawai T, Yasugi T, Horiguchi S, Iwami O, Ikeda M: In vitro hydrolysis of methyl acetate, a limitation in application of head-space gas-chromatography in biological monitoring of exposure. Toxicol Lett. 1992 Sep;62(2-3):247-53. [PubMed:1412510 ]
  3. Ernstgard L, Sjogren B, Warholm M, Johanson G: Sex differences in the toxicokinetics of inhaled solvent vaporsin humans 1. m-Xylene. Toxicol Appl Pharmacol. 2003 Dec 1;193(2):147-57. [PubMed:14644617 ]
  4. Yokoyama K, Araki S, Murata K, Nishikitani M, Nakaaki K, Yokota J, Ito A, Sakata E: Postural sway frequency analysis in workers exposed to n-hexane, xylene, and toluene: assessment of subclinical cerebellar dysfunction. Environ Res. 1997;74(2):110-5. [PubMed:9339223 ]
  5. Murata K, Araki S, Yokoyama K, Yamashita K, Okajima F, Nakaaki K: Changes in autonomic function as determined by ECG R-R interval variability in sandal, shoe and leather workers exposed to n-hexane, xylene and toluene. Neurotoxicology. 1994 Winter;15(4):867-75. [PubMed:7715857 ]
  6. (). Organic solvents in the working environment and exposure levels of workers in small-sized enterprises. Fukabori, S., Nakaaki, K., Hanaoka, Tomoyuki. Div. Work Environ. Occup. Dis., Inst. Sci. Labour, Kawasaki, Japan. Rodo Kagaku (1993), 69(5), 173-92. CODEN: ROKAAV ISSN: 0035-7774. Journal written in Japanese. CAN 119:42973 AN 1993:442973. .

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
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:
GLYATL1
Uniprot ID:
Q969I3
Molecular weight:
35100.895
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:
GLYATL2
Uniprot ID:
Q8WU03
Molecular weight:
34277.055
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:
GLYATL3
Uniprot ID:
Q5SZD4
Molecular weight:
32703.3