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Hippuric acid (FDB001819)

Record Information
Version1.0
Creation date2010-04-08 22:05:07 UTC
Update date2019-11-26 02:56:41 UTC
Primary IDFDB001819
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHippuric acid
DescriptionHippuric acid (Gr. hippos, horse, ouron, urine) is a carboxylic acid found in the urine of horses and other herbivores. Hippuric acid crystallizes in rhombic prisms which are readily soluble in hot water, melt at 187 °C and decompose at about 240 °C. High concentrations of hippuric acid can also indicate a toluene intoxication. When many aromatic compounds such as benzoic acid and toluene are taken internally, they are converted to hippuric acid by reaction with the amino acid, glycine.; Hippuric acid is an acyl glycine formed by the conjugation of benzoic aicd with glycine. 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. Hippuric acid is a normal component of urine and is typically increased with increased consumption of phenolic compounds (tea, wine, fruit juices). These phenols are converted to benzoic acid which is then converted to hippuric acid and excreted in the urine. Hippuric acid is the most frequently used biomarker in the biological monitoring of occupational exposure to toluene. This product of solvent biotransformation may be also found in the urine of individuals who have not been exposed to the solvent. A smaller fraction of the absorbed toluene is oxidized to aromatic compounds including ortho-cresol, which is not found significantly in the urine of nonexposed individuals. The concentration of hippuric acid in the urine of individuals exposed to a low toluene concentration does not differ from that of individuals not exposed to the solvent. This has led to the conclusion that hippuric acid should not be utilized in the biological monitoring of occupational exposure to low levels of toluene in the air.; Protein-bound organic acids such as hippuric acid are markedly accumulated in uremic plasma and produce defective protein binding of drugs. (PMID: 9120876, 8734460).
CAS Number495-69-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.18 g/LALOGPS
logP0.23ALOGPS
logP0.53ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.59ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.12 m³·mol⁻¹ChemAxon
Polarizability17.57 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H9NO3
IUPAC name2-(phenylformamido)acetic acid
InChI IdentifierInChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)
InChI KeyQIAFMBKCNZACKA-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CNC(=O)C1=CC=CC=C1
Average Molecular Weight179.1727
Monoisotopic Molecular Weight179.058243159
Classification
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
  • Benzoyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Biological role:

Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateNot Available
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting Point187-191 oC
    Boiling PointNot Available
    Experimental Water Solubility3.75 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
    Experimental logP0.31HANSCH,C ET AL. (1995)
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-5900000000-99084c1783177c8070112014-09-20View Spectrum
    GC-MSHippuric acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-2910000000-fac0a1c19c9209e1daf5Spectrum
    GC-MSHippuric acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-0930000000-6f50aaca6d403e269682Spectrum
    GC-MSHippuric acid, 1 TMS, GC-MS Spectrumsplash10-0a4i-5930000000-166d57ae498305a4eee9Spectrum
    GC-MSHippuric acid, 2 TMS, GC-MS Spectrumsplash10-0a4i-4920000000-358e012cae8853105371Spectrum
    GC-MSHippuric acid, non-derivatized, GC-MS Spectrumsplash10-0a6r-8900000000-01e7057139a995115ddbSpectrum
    GC-MSHippuric acid, non-derivatized, GC-MS Spectrumsplash10-0il0-9700000000-5eb7d5acc34cdb44f3e0Spectrum
    GC-MSHippuric acid, non-derivatized, GC-MS Spectrumsplash10-0a6r-6900000000-9bebc859a11a987fc2d4Spectrum
    GC-MSHippuric acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-2910000000-fac0a1c19c9209e1daf5Spectrum
    GC-MSHippuric acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-0930000000-6f50aaca6d403e269682Spectrum
    GC-MSHippuric acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-5930000000-166d57ae498305a4eee9Spectrum
    GC-MSHippuric acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-4920000000-358e012cae8853105371Spectrum
    GC-MSHippuric acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-2910000000-19b240c27664cf096501Spectrum
    GC-MSHippuric acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-0930000000-b1d771fba596fcbf4d44Spectrum
    Predicted GC-MSHippuric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-2900000000-3f2da6ec78f21732afeaSpectrum
    Predicted GC-MSHippuric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-9810000000-58ac2f50544c1db5247fSpectrum
    Predicted GC-MSHippuric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSHippuric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSHippuric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSHippuric acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0059-1900000000-412e9313d23685caab382012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-004i-9100000000-cc560a494407b3c33abb2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-004i-9200000000-103f81d635660cdb0aa02012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0a6r-8900000000-734176188abc8a1dd7662012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-0a6r-6900000000-9bebc859a11a987fc2d42012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-7f332f3c98391a2765472012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-003r-2900000000-a8b444dcb0522a2aab6d2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9200000000-fc8a26847a77460ed21a2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a6r-9000000000-9c160b377301023f1df22012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-7ac8420c577cebb0e8a92012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-7f332f3c98391a2765472017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-003r-2900000000-a8b444dcb0522a2aab6d2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9200000000-d20e52137daf3db2f6382017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a6r-9000000000-1beabd6a9820b379f52f2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-7ac8420c577cebb0e8a92017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0900000000-fae7f8c300bf6943f8d52017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-003r-0900000000-5d25dcc019489d8670732017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - , negativesplash10-003r-0900000000-ef98916bdf0fc86270832017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0900000000-cbfff04acbf0c95d7e302017-09-14View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-65954d58bf9851d84f752015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-730b49f058aae1303aba2015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9500000000-2707fadcc633cb9d989c2015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8040a946088ae227b41e2015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2900000000-48c46f688fb318e3a7ba2015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-4ded9b0d44ce0068065d2015-04-25View Spectrum
    NMR
    TypeDescriptionView
    1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider IDNot Available
    ChEMBL IDNot Available
    KEGG Compound IDC01586
    Pubchem Compound ID464
    Pubchem Substance IDNot Available
    ChEBI ID18089
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB00714
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDHIPPURIC-ACID
    BIGG IDNot Available
    KNApSAcK IDC00030483
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDHippuric acid
    Phenol-Explorer Metabolite ID929
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
    pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).