| Record Information |
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| Version | 2.0 |
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| Creation Date | 2014-08-29 05:47:53 UTC |
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| Update Date | 2014-12-24 20:26:40 UTC |
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| Accession Number | T3D4159 |
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| Identification |
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| Common Name | Hippuric acid |
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| Class | Small Molecule |
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| Description | Hippuric acid is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
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. (1, 2). |
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| Compound Type | - Amide
- Amine
- Ester
- Food Toxin
- Industrial/Workplace Toxin
- Metabolite
- Natural Compound
- Organic Compound
- Solvent
- Uremic Toxin
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| Chemical Structure | |
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| Synonyms | | Synonym | | (benzoylamino)-Acetate | | (benzoylamino)-Acetic acid | | 2-Benzamidoacetate | | 2-Benzamidoacetic acid | | Benzamidoacetate | | Benzamidoacetic acid | | Benzoylglycine | | Hippurate | | N-Benzoylglycine | | Phenylcarbonylaminoacetate | | Phenylcarbonylaminoacetic acid |
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| Chemical Formula | C9H9NO3 |
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| Average Molecular Mass | 179.173 g/mol |
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| Monoisotopic Mass | 179.058 g/mol |
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| CAS Registry Number | 495-69-2 |
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| IUPAC Name | 2-(phenylformamido)acetic acid |
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| Traditional Name | hippuric acid |
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| SMILES | OC(=O)CN=C(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 | InChIKey=QIAFMBKCNZACKA-UHFFFAOYSA-N |
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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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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Endogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 187 - 191°C | | Boiling Point | 240°C (decomposes) | | Solubility | 3.75 mg/mL | | LogP | 0.31 |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0a4i-2910000000-fac0a1c19c9209e1daf5 | 2014-06-16 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0a4i-0930000000-6f50aaca6d403e269682 | 2014-06-16 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-0a4i-5930000000-166d57ae498305a4eee9 | 2014-06-16 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0a4i-4920000000-358e012cae8853105371 | 2014-06-16 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a6r-8900000000-01e7057139a995115ddb | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0il0-9700000000-5eb7d5acc34cdb44f3e0 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a6r-6900000000-9bebc859a11a987fc2d4 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4i-2910000000-fac0a1c19c9209e1daf5 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4i-0930000000-6f50aaca6d403e269682 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0a4i-5930000000-166d57ae498305a4eee9 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0a4i-4920000000-358e012cae8853105371 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4i-2910000000-19b240c27664cf096501 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4i-0930000000-b1d771fba596fcbf4d44 | 2017-09-12 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-2900000000-3f2da6ec78f21732afea | 2017-07-27 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0ab9-9810000000-58ac2f50544c1db5247f | 2017-10-06 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0059-1900000000-412e9313d23685caab38 | 2012-07-24 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-004i-9100000000-cc560a494407b3c33abb | 2012-07-24 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-004i-9200000000-103f81d635660cdb0aa0 | 2012-07-24 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive | splash10-0a6r-8900000000-734176188abc8a1dd766 | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive | splash10-0a6r-6900000000-9bebc859a11a987fc2d4 | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0900000000-7f332f3c98391a276547 | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-003r-2900000000-a8b444dcb0522a2aab6d | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-9200000000-fc8a26847a77460ed21a | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0a6r-9000000000-9c160b377301023f1df2 | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a4i-9000000000-7ac8420c577cebb0e8a9 | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0900000000-7f332f3c98391a276547 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-003r-2900000000-a8b444dcb0522a2aab6d | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9200000000-d20e52137daf3db2f638 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a6r-9000000000-1beabd6a9820b379f52f | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9000000000-7ac8420c577cebb0e8a9 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-001i-0900000000-fae7f8c300bf6943f8d5 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-003r-0900000000-5d25dcc019489d867073 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-003r-0900000000-ef98916bdf0fc8627083 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0a4i-0900000000-cbfff04acbf0c95d7e30 | 2017-09-14 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-65954d58bf9851d84f75 | 2015-04-24 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0900000000-730b49f058aae1303aba | 2015-04-24 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-056r-9500000000-2707fadcc633cb9d989c | 2015-04-24 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-8040a946088ae227b41e | 2015-04-25 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-2900000000-48c46f688fb318e3a7ba | 2015-04-25 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9300000000-4ded9b0d44ce0068065d | 2015-04-25 | View Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-0a4i-5900000000-99084c1783177c807011 | 2014-09-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | Not Available | 2012-12-04 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Not Available | 2012-12-04 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental) | Not Available | 2014-09-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental) | Not Available | 2014-09-23 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | Not Available | 2021-10-10 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Not Available | 2012-12-05 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Endogenous, Ingestion, Dermal (contact) |
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| Mechanism of Toxicity | Uremic toxins such as hippuric acid are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (4). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (5). |
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| Metabolism | Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces. |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Naturally produced by the body (endogenous). |
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| Minimum Risk Level | Not Available |
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| Health Effects | Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. |
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| Symptoms | As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. |
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| Treatment | Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB00714 |
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| PubChem Compound ID | 464 |
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| ChEMBL ID | CHEMBL461 |
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| ChemSpider ID | 451 |
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| KEGG ID | C01586 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 18089 |
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| BioCyc ID | Not Available |
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| CTD ID | Not Available |
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| Stitch ID | Not Available |
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| PDB ID | Not Available |
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| ACToR ID | Not Available |
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| Wikipedia Link | Hippuric acid |
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| References |
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| Synthesis Reference | Ingersoll, A. W.; Barcock, S. H. Hippuric acid. Organic Syntheses (1932), XII 40-2. |
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| MSDS | Link |
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| General References | - 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. [9120876 ]
- 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. [8734460 ]
- Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [22626821 ]
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- Young GH, Wu VC: KLOTHO methylation is linked to uremic toxins and chronic kidney disease. Kidney Int. 2012 Apr;81(7):611-2. doi: 10.1038/ki.2011.461. [22419041 ]
- 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. [1184200 ]
- Akira K, Hashimoto T: Hippuric acid test using 13C-labelling and NMR spectroscopy. Clin Chem Lab Med. 2001 Mar;39(3):215-7. [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. [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. [7759034 ]
- Bjorkman L, McLean C, Steen G: Organic acids in urine from human newborns. Clin Chem. 1976 Jan;22(1):49-52. [1245060 ]
- 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. [9625050 ]
- 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. [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. [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. [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. [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. [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. [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. [2311341 ]
- Kirshon B, Mari G, Moise KJ Jr: Indomethacin therapy in the treatment of symptomatic polyhydramnios. Obstet Gynecol. 1990 Feb;75(2):202-5. [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. [2079538 ]
- 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. [19212411 ]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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