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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-17 16:37:33 UTC
NP-MRD IDNP0000139
Secondary Accession NumbersNone
Natural Product Identification
Common NameHippuric acid
DescriptionHippuric acid is an acyl glycine formed by the conjugation of benzoic acid 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 ). Hippuric acid is found to be associated with phenylketonuria, propionic acidemia, and tyrosinemia I, which are inborn errors of metabolism.
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 Mass179.1727 Da
Monoisotopic Mass179.05824 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-07-25View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-17View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-02-17View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Persea americanaKNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
Vaccinium macrocarponFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
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
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
Good Scents IDrw1592511
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. [PubMed:9625050 ]
  3. Angerer J, Kassebart V, Szadkowski D, Lehnert G: [Occupational chronic exposure to organic solvents. III. Gas-chromatographic determination of hippuric acid in serum (author's transl)]. Int Arch Arbeitsmed. 1975;34(3):199-207. [PubMed:1184200 ]
  4. Akira K, Hashimoto T: Hippuric acid test using 13C-labelling and NMR spectroscopy. Clin Chem Lab Med. 2001 Mar;39(3):215-7. [PubMed:11350017 ]
  5. Pelclova D, Cerna M, Pastorkova A, Vrbikova V, Prochazka B, Hurychova D, Dlaskova Z, Hornychova M: Study of the genotoxicity of toluene. Arch Environ Health. 2000 Jul-Aug;55(4):268-73. [PubMed:11005432 ]
  6. Rutner M, Fitzek J, Jahnel-Kracht H, Otto J, Krause W: [Therapy of rheumatic disease with a hydroxyethylsalicylate gel. Results of 2 clinical studies of effectiveness and bioavailability]. Fortschr Med. 1995 Mar 20;113(8):111-3. [PubMed:7759034 ]
  7. Bjorkman L, McLean C, Steen G: Organic acids in urine from human newborns. Clin Chem. 1976 Jan;22(1):49-52. [PubMed:1245060 ]
  8. Caldwell J, Moffatt JR, Smith RL: Post-mortem survival of hippuric acid formation in rat and human cadaver tissue samples. Xenobiotica. 1976 May;6(5):275-80. [PubMed:936647 ]
  9. Ukai H, Takada S, Inui S, Imai Y, Kawai T, Shimbo S, Ikeda M: Occupational exposure to solvent mixtures: effects on health and metabolism. Occup Environ Med. 1994 Aug;51(8):523-9. [PubMed:7951776 ]
  10. Sebekova K, Lajdova I, Spustova V, Opatrny K Jr: Comparison of creatinine, hippuric acid, 5-hydroxyindoleacetic acid, serotonin, and pseudouridine concentrations in blood withdrawn from vein and arteriovenous fistula of uremic patients on maintenance hemodialysis. Artif Organs. 1991 Oct;15(5):434-5. [PubMed:1741691 ]
  11. Pickert A, Bauerle A, Liebich HM: Determination of hippuric acid and furanic acid in serum of dialysis patients and control persons by high-performance liquid chromatography. J Chromatogr. 1989 Oct 27;495:95-104. [PubMed:2613830 ]
  12. Mulder TP, Rietveld AG, van Amelsvoort JM: Consumption of both black tea and green tea results in an increase in the excretion of hippuric acid into urine. Am J Clin Nutr. 2005 Jan;81(1 Suppl):256S-260S. [PubMed:15640488 ]
  13. Porter RD, Cathcart-Rake WF, Wan SH, Whittier FC, Grantham JJ: Secretory activity and aryl acid content of serum, urine, and cerebrospinal fluid in normal and uremic man. J Lab Clin Med. 1975 May;85(5):723-31. [PubMed:1168235 ]
  14. Lof A, Hansen SH, Naslund P, Steiner E, Wallen M, Hjelm EW: Relationship between uptake and elimination of toluene and debrisoquin hydroxylation polymorphism. Clin Pharmacol Ther. 1990 Mar;47(3):412-7. [PubMed:2311341 ]
  15. Kirshon B, Mari G, Moise KJ Jr: Indomethacin therapy in the treatment of symptomatic polyhydramnios. Obstet Gynecol. 1990 Feb;75(2):202-5. [PubMed:2405320 ]
  16. Beving H, Olsson U, Bemgard A, Kristensson J, Palmborg J, Sollenberg J: High-performance liquid chromatographic analysis of hippuric acid in human blood plasma. J Chromatogr. 1990 Oct 26;532(1):45-53. [PubMed:2079538 ]
  17. Niwa T: Organic acids and the uremic syndrome: protein metabolite hypothesis in the progression of chronic renal failure. Semin Nephrol. 1996 May;16(3):167-82. [PubMed:8734460 ]
  18. Amorim LC, Alvarez-Leite EM: Determination of o-cresol by gas chromatography and comparison with hippuric acid levels in urine samples of individuals exposed to toluene. J Toxicol Environ Health. 1997 Mar;50(4):401-7. [PubMed:9120876 ]
  19. Herrera-Van Oostdam AS, Castaneda-Delgado JE, Oropeza-Valdez JJ, Borrego JC, Monarrez-Espino J, Zheng J, Mandal R, Zhang L, Soto-Guzman E, Fernandez-Ruiz JC, Ochoa-Gonzalez F, Trejo Medinilla FM, Lopez JA, Wishart DS, Enciso-Moreno JA, Lopez-Hernandez Y: Immunometabolic signatures predict risk of progression to sepsis in COVID-19. PLoS One. 2021 Aug 30;16(8):e0256784. doi: 10.1371/journal.pone.0256784. eCollection 2021. [PubMed:34460840 ]