Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2022-02-17 16:37:33 UTC |
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NP-MRD ID | NP0000139 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Hippuric acid |
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Description | Hippuric 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. |
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Structure | 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) |
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Synonyms | Value | Source |
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Benzamidoacetic acid | ChEBI | Benzamidoessigsaeure | ChEBI | Benzoylaminoacetic acid | ChEBI | Benzoylaminoessigsaeure | ChEBI | Hippurate | ChEBI | Hippursaeure | ChEBI | Phenylcarbonylaminoacetic acid | ChEBI | N-Benzoylglycine | Kegg | Benzamidoacetate | Generator | Benzoylaminoacetate | Generator | Phenylcarbonylaminoacetate | Generator | Hippate | Generator | Hippic acid | Generator | (Benzoylamino)-acetate | HMDB | (Benzoylamino)-acetic acid | HMDB | 2-Benzamidoacetate | HMDB | 2-Benzamidoacetic acid | HMDB | Benzoylglycine | HMDB | N-Benzoylglycinate | HMDB |
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Chemical Formula | C9H9NO3 |
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Average Mass | 179.1727 Da |
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Monoisotopic Mass | 179.05824 Da |
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IUPAC Name | 2-(phenylformamido)acetic acid |
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Traditional Name | hippuric acid |
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CAS Registry Number | 495-69-2 |
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SMILES | OC(=O)CNC(=O)C1=CC=CC=C1 |
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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) |
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InChI Key | QIAFMBKCNZACKA-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-02-17 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, simulated) | v.dorna83@yahoo.com | Not Available | Not Available | 2021-07-25 | View Spectrum |
| Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzoic acids and derivatives |
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Direct Parent | Hippuric acids |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 187 - 191 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 3.75 mg/mL | Not Available | LogP | 0.31 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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Predicted Properties | |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- Bjorkman L, McLean C, Steen G: Organic acids in urine from human newborns. Clin Chem. 1976 Jan;22(1):49-52. [PubMed:1245060 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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