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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-11-30 15:52:24 UTC
Update Date2023-02-21 17:17:58 UTC
HMDB IDHMDB0013292
Secondary Accession Numbers
  • HMDB13292
Metabolite Identification
Common Namep-Methylhippuric acid
Descriptionp-Methylhippuric acid, also known as 4-methylhippate, 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. p-Methylhippuric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on p-Methylhippuric acid.
Structure
Data?1676999878
Synonyms
ValueSource
4-Methylhippuric acidChEBI
4-MethylhippateGenerator
4-Methylhippic acidGenerator
p-MethylhippateGenerator
p-Methylhippic acidGenerator
Para-methylhippuric acidMeSH
((4-Methylbenzoyl)amino)acetic acidHMDB
(4-Methyl-benzoylamino)-acetic acidHMDB
N-(4-Methylbenzoyl)glycineHMDB
N-(P-Toluoyl)-glycineHMDB
N-(P-Toluoyl)glycineHMDB
P-Toluric acidHMDB
Chemical FormulaC10H11NO3
Average Molecular Weight193.1992
Monoisotopic Molecular Weight193.073893223
IUPAC Name2-[(4-methylphenyl)formamido]acetic acid
Traditional Name[(4-methylphenyl)formamido]acetic acid
CAS Registry Number27115-50-0
SMILES
CC1=CC=C(C=C1)C(=O)NCC(O)=O
InChI Identifier
InChI=1S/C10H11NO3/c1-7-2-4-8(5-3-7)10(14)11-6-9(12)13/h2-5H,6H2,1H3,(H,11,14)(H,12,13)
InChI KeyNRSCPTLHWVWLLH-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
  • P-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 effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.52 g/LALOGPS
logP0.7ALOGPS
logP1.04ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.74ChemAxon
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
Polarizability19.77 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]+145.25731661259
DarkChem[M-H]-143.31131661259
DeepCCS[M+H]+142.50830932474
DeepCCS[M-H]-139.23130932474
DeepCCS[M-2H]-176.2230932474
DeepCCS[M+Na]+151.75830932474
AllCCS[M+H]+141.832859911
AllCCS[M+H-H2O]+137.732859911
AllCCS[M+NH4]+145.632859911
AllCCS[M+Na]+146.732859911
AllCCS[M-H]-143.232859911
AllCCS[M+Na-2H]-143.832859911
AllCCS[M+HCOO]-144.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
p-Methylhippuric acidCC1=CC=C(C=C1)C(=O)NCC(O)=O2787.8Standard polar33892256
p-Methylhippuric acidCC1=CC=C(C=C1)C(=O)NCC(O)=O1743.9Standard non polar33892256
p-Methylhippuric acidCC1=CC=C(C=C1)C(=O)NCC(O)=O1930.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
p-Methylhippuric acid,1TMS,isomer #1CC1=CC=C(C(=O)NCC(=O)O[Si](C)(C)C)C=C11955.0Semi standard non polar33892256
p-Methylhippuric acid,1TMS,isomer #2CC1=CC=C(C(=O)N(CC(=O)O)[Si](C)(C)C)C=C11920.2Semi standard non polar33892256
p-Methylhippuric acid,2TMS,isomer #1CC1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C=C11891.2Semi standard non polar33892256
p-Methylhippuric acid,2TMS,isomer #1CC1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C=C11920.9Standard non polar33892256
p-Methylhippuric acid,2TMS,isomer #1CC1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C=C12160.3Standard polar33892256
p-Methylhippuric acid,1TBDMS,isomer #1CC1=CC=C(C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)C=C12199.4Semi standard non polar33892256
p-Methylhippuric acid,1TBDMS,isomer #2CC1=CC=C(C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)C=C12165.2Semi standard non polar33892256
p-Methylhippuric acid,2TBDMS,isomer #1CC1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12383.4Semi standard non polar33892256
p-Methylhippuric acid,2TBDMS,isomer #1CC1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12318.7Standard non polar33892256
p-Methylhippuric acid,2TBDMS,isomer #1CC1=CC=C(C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12424.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - p-Methylhippuric acid EI-B (Non-derivatized)splash10-014i-5900000000-3993dac60df8a66d7eb92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Methylhippuric acid EI-B (Non-derivatized)splash10-014i-5900000000-3993dac60df8a66d7eb92018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Methylhippuric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-6900000000-b50d889b4e30980ba3ed2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Methylhippuric acid GC-MS (1 TMS) - 70eV, Positivesplash10-0g71-9510000000-2360f4755bd1eaeadfb32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Methylhippuric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Methylhippuric acid 10V, Positive-QTOFsplash10-00kf-1900000000-06ad39599696e1f523272017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Methylhippuric acid 20V, Positive-QTOFsplash10-014i-3900000000-07f81e34909c892b52082017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Methylhippuric acid 40V, Positive-QTOFsplash10-00mo-9200000000-e27d5101feb449b414762017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Methylhippuric acid 10V, Negative-QTOFsplash10-0006-0900000000-0cd9bf507120d68065832017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Methylhippuric acid 20V, Negative-QTOFsplash10-0006-2900000000-6d32875addcb79ef07262017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Methylhippuric acid 40V, Negative-QTOFsplash10-0596-9100000000-38c005a4d0e8087c21ee2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Methylhippuric acid 10V, Positive-QTOFsplash10-014i-1900000000-91f9539008e39dfbf87d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Methylhippuric acid 20V, Positive-QTOFsplash10-014l-6900000000-a5a1ad33d130a01c6ea92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Methylhippuric acid 40V, Positive-QTOFsplash10-0006-9000000000-78e2ac5905c874bf0a312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Methylhippuric acid 10V, Negative-QTOFsplash10-0007-2900000000-7746f2cdf62420aa6c0d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Methylhippuric acid 20V, Negative-QTOFsplash10-0006-9100000000-95602cc287d1239db4ec2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Methylhippuric acid 40V, Negative-QTOFsplash10-0006-9000000000-5671d4c535a6553aaf0d2021-09-23Wishart 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 LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029366
KNApSAcK IDNot Available
Chemspider ID87986
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylhippuric acid
METLIN IDNot Available
PubChem Compound97479
PDB IDNot Available
ChEBI ID68552
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Proctor JW: Rat sarcoma model supports both "soil seed" and "mechanical" theories of metastatic spread. Br J Cancer. 1976 Dec;34(6):651-4. [PubMed:1008992 ]