Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:07 UTC |
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Update date | 2019-11-26 02:56:41 UTC |
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Primary ID | FDB001819 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Hippuric acid |
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Description | Hippuric 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). |
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CAS Number | 495-69-2 |
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Structure | |
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Synonyms | Synonym | 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 | Hippuric acid | HMDB | (benzoylamino)-acetate | biospider | (benzoylamino)-acetic acid | biospider | (benzoylamino)acetic acid | biospider | 2-benzamido-acetic acid | biospider | 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 acid | biospider | Acido ippurico | biospider | Benzaminoacetic acid | biospider | Benzenecarboxamide, n-carboxymethyl- | biospider | Benzoylglycin | biospider | Benzoylglycocoll | biospider | Glycine, n-benzoyl- | biospider | Hippuricum acidum | biospider | N-(phenylcarbonyl)glycine | biospider | N-benzoyl-glycin | biospider | N-benzoylglycine | biospider |
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Predicted Properties | |
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Chemical Formula | C9H9NO3 |
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IUPAC name | 2-(phenylformamido)acetic acid |
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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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Isomeric SMILES | OC(=O)CNC(=O)C1=CC=CC=C1 |
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Average Molecular Weight | 179.1727 |
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Monoisotopic Molecular Weight | 179.058243159 |
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Classification |
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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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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Indirect biological role: Biological role: |
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Foods | Cocoa and cocoa products Grains: Nuts and legumes: Fruits and vegetables: Fats and oils: Beverages: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | 187-191 oC | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 3.75 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | 0.31 | HANSCH,C ET AL. (1995) |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0a4i-5900000000-99084c1783177c807011 | 2014-09-20 | View Spectrum | GC-MS | Hippuric acid, non-derivatized, GC-MS Spectrum | splash10-0a4i-2910000000-fac0a1c19c9209e1daf5 | Spectrum | GC-MS | Hippuric acid, non-derivatized, GC-MS Spectrum | splash10-0a4i-0930000000-6f50aaca6d403e269682 | Spectrum | GC-MS | Hippuric acid, 1 TMS, GC-MS Spectrum | splash10-0a4i-5930000000-166d57ae498305a4eee9 | Spectrum | GC-MS | Hippuric acid, 2 TMS, GC-MS Spectrum | splash10-0a4i-4920000000-358e012cae8853105371 | Spectrum | GC-MS | Hippuric acid, non-derivatized, GC-MS Spectrum | splash10-0a6r-8900000000-01e7057139a995115ddb | Spectrum | GC-MS | Hippuric acid, non-derivatized, GC-MS Spectrum | splash10-0il0-9700000000-5eb7d5acc34cdb44f3e0 | Spectrum | GC-MS | Hippuric acid, non-derivatized, GC-MS Spectrum | splash10-0a6r-6900000000-9bebc859a11a987fc2d4 | Spectrum | GC-MS | Hippuric acid, non-derivatized, GC-MS Spectrum | splash10-0a4i-2910000000-fac0a1c19c9209e1daf5 | Spectrum | GC-MS | Hippuric acid, non-derivatized, GC-MS Spectrum | splash10-0a4i-0930000000-6f50aaca6d403e269682 | Spectrum | GC-MS | Hippuric acid, non-derivatized, GC-MS Spectrum | splash10-0a4i-5930000000-166d57ae498305a4eee9 | Spectrum | GC-MS | Hippuric acid, non-derivatized, GC-MS Spectrum | splash10-0a4i-4920000000-358e012cae8853105371 | Spectrum | GC-MS | Hippuric acid, non-derivatized, GC-MS Spectrum | splash10-0a4i-2910000000-19b240c27664cf096501 | Spectrum | GC-MS | Hippuric acid, non-derivatized, GC-MS Spectrum | splash10-0a4i-0930000000-b1d771fba596fcbf4d44 | Spectrum | Predicted GC-MS | Hippuric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4i-2900000000-3f2da6ec78f21732afea | Spectrum | Predicted GC-MS | Hippuric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0ab9-9810000000-58ac2f50544c1db5247f | Spectrum | Predicted GC-MS | Hippuric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Hippuric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Hippuric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Hippuric acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0059-1900000000-412e9313d23685caab38 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-004i-9100000000-cc560a494407b3c33abb | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-004i-9200000000-103f81d635660cdb0aa0 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive | splash10-0a6r-8900000000-734176188abc8a1dd766 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive | splash10-0a6r-6900000000-9bebc859a11a987fc2d4 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0900000000-7f332f3c98391a276547 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-003r-2900000000-a8b444dcb0522a2aab6d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-9200000000-fc8a26847a77460ed21a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0a6r-9000000000-9c160b377301023f1df2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a4i-9000000000-7ac8420c577cebb0e8a9 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0900000000-7f332f3c98391a276547 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-003r-2900000000-a8b444dcb0522a2aab6d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9200000000-d20e52137daf3db2f638 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a6r-9000000000-1beabd6a9820b379f52f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9000000000-7ac8420c577cebb0e8a9 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-001i-0900000000-fae7f8c300bf6943f8d5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-003r-0900000000-5d25dcc019489d867073 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-003r-0900000000-ef98916bdf0fc8627083 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0a4i-0900000000-cbfff04acbf0c95d7e30 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-65954d58bf9851d84f75 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0900000000-730b49f058aae1303aba | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-056r-9500000000-2707fadcc633cb9d989c | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-8040a946088ae227b41e | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-2900000000-48c46f688fb318e3a7ba | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9300000000-4ded9b0d44ce0068065d | 2015-04-25 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C01586 |
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Pubchem Compound ID | 464 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 18089 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00714 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | HIPPURIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | C00030483 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Hippuric acid |
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Phenol-Explorer Metabolite ID | 929 |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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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).
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