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Record Information
Version1.0
Creation Date2016-09-30 22:35:21 UTC
Update Date2020-06-04 20:23:27 UTC
MCDB ID BMDB0000714
Secondary Accession Numbers
  • BMDB00714
Metabolite Identification
Common NameHippuric acid
DescriptionHippuric acid, also known as N-benzoylglycine or hippurate, 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. Hippuric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Hippuric acid is a potentially toxic compound. Hippuric acid has been found to be associated with several diseases known as uremia, ulcerative colitis, colorectal cancer, and eosinophilic esophagitis; also hippuric acid has been linked to the inborn metabolic disorders including tyrosinemia I.
Structure
Thumb
Synonyms
ValueSource
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
N-BenzoylglycinateHMDB
Chemical FormulaC9H9NO3
Average Molecular Weight179.1727
Monoisotopic Molecular Weight179.058243159
IUPAC Name2-(phenylformamido)acetic acid
Traditional Namehippuric acid
CAS Registry Number495-69-2
SMILES
OC(=O)CNC(=O)C1=CC=CC=C1
InChI Identifier
InChI=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
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
  • 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point187 - 191 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.75 mg/mLNot Available
LogP0.31HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
Detected and Quantified65 +/- 5 uM details
Detected and Quantified69 +/- 9 uM details
Detected and Quantified72 +/- 5 uM details
Detected and Quantified67 +/- 4 uM details
Detected and Quantified227 +/- 39 uM details
Detected and Quantified165 +/- 33 uM details
Detected and Quantified113 +/- 33 uM details
HMDB IDHMDB0000714
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001819
KNApSAcK IDC00030483
Chemspider ID451
KEGG Compound IDC01586
BioCyc IDCPD-425
BiGG IDNot Available
Wikipedia LinkHippuric_acid
METLIN ID1301
PubChem Compound464
PDB IDNot Available
ChEBI ID18089
References
Synthesis ReferenceIngersoll, A. W.; Barcock, S. H. Hippuric acid. Organic Syntheses (1932), XII 40-2.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
  2. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
  3. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
  4. Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
  5. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  6. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  7. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.