Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:05:07 UTC
Update date2018-05-28 23:06:16 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
Synonyms
SynonymSource
Benzamidoacetic acidChEBI
BenzamidoessigsaeureChEBI
Benzoylaminoacetic acidChEBI
BenzoylaminoessigsaeureChEBI
HippurateChEBI
HippursaeureChEBI
Phenylcarbonylaminoacetic acidChEBI
N-BenzoylglycineKegg
BenzamidoacetateGenerator
BenzoylaminoacetateGenerator
PhenylcarbonylaminoacetateGenerator
HippateGenerator
Hippic acidGenerator
(Benzoylamino)-acetateHMDB
(Benzoylamino)-acetic acidHMDB
2-BenzamidoacetateHMDB
2-Benzamidoacetic acidHMDB
BenzoylglycineHMDB
Hippuric acid, monosodium saltHMDB
Hippuric acid, (14)C-labeledHMDB
Hippuric acid, monoammonium saltHMDB
Hippuric acid, monopotassium saltHMDB
Ammonium hippurateHMDB
(benzoylamino)-acetatebiospider
(benzoylamino)-acetic acidbiospider
(benzoylamino)acetic acidbiospider
2-benzamido-acetic acidbiospider
532-93-4 (mono-ammonium salt)biospider
532-94-5 (mono-hydrochloride salt)biospider
583-10-8 (mono-potassium salt)biospider
Acetic acid, (benzoylamino)-biospider
Acetic acid,benzamide hippuric acidbiospider
Acido ippuricobiospider
Benzaminoacetic acidbiospider
Benzenecarboxamide, n-carboxymethyl-biospider
Benzoylglycinbiospider
Benzoylglycocollbiospider
Glycine, n-benzoyl-biospider
Hippuricum acidumbiospider
N-(phenylcarbonyl)glycinebiospider
N-benzoyl-glycinbiospider
N-benzoylglycinebiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-2910000000-fac0a1c19c9209e1daf5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0930000000-6f50aaca6d403e269682View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0a4i-5930000000-166d57ae498305a4eee9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4i-4920000000-358e012cae8853105371View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-8900000000-01e7057139a995115ddbView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0il0-9700000000-5eb7d5acc34cdb44f3e0View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-9bebc859a11a987fc2d4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-2910000000-fac0a1c19c9209e1daf5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0930000000-6f50aaca6d403e269682View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-5930000000-166d57ae498305a4eee9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-4920000000-358e012cae8853105371View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-2910000000-19b240c27664cf096501View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0930000000-b1d771fba596fcbf4d44View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2900000000-3f2da6ec78f21732afeaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9810000000-58ac2f50544c1db5247fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0059-1900000000-412e9313d23685caab38View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-004i-9100000000-cc560a494407b3c33abbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-004i-9200000000-103f81d635660cdb0aa0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0a6r-8900000000-734176188abc8a1dd766View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-0a6r-6900000000-9bebc859a11a987fc2d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-7f332f3c98391a276547View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-003r-2900000000-a8b444dcb0522a2aab6dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9200000000-fc8a26847a77460ed21aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a6r-9000000000-9c160b377301023f1df2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-7ac8420c577cebb0e8a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-7f332f3c98391a276547View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-003r-2900000000-a8b444dcb0522a2aab6dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9200000000-d20e52137daf3db2f638View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a6r-9000000000-1beabd6a9820b379f52fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-7ac8420c577cebb0e8a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0900000000-fae7f8c300bf6943f8d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-003r-0900000000-5d25dcc019489d867073View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-003r-0900000000-ef98916bdf0fc8627083View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0900000000-cbfff04acbf0c95d7e30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-65954d58bf9851d84f75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-730b49f058aae1303abaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9500000000-2707fadcc633cb9d989cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8040a946088ae227b41eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2900000000-48c46f688fb318e3a7baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-4ded9b0d44ce0068065dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-5900000000-99084c1783177c807011View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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).