| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:35:21 UTC |
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| Update Date | 2020-06-04 20:23:27 UTC |
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| BMDB ID | BMDB0000714 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Hippuric acid |
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| Description | Hippuric 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. |
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| Structure | |
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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 | | Hippuric acid | HMDB |
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| Chemical Formula | C9H9NO3 |
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| Average Molecular Weight | 179.1727 |
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| Monoisotopic Molecular Weight | 179.058243159 |
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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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| 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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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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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,C ET AL. (1995) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | |
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| Biospecimen Locations | - Blood
- Kidney
- Liver
- Mammary Gland
- Milk
- Placenta
- Prostate Tissue
- Semen
- Urine
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 112.76 +/- 33.00 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 65 +/- 5 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 69 +/- 9 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 72 +/- 5 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 67 +/- 4 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 227.93 +/- 38.90 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 165.93 +/- 32.77 uM | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Abnormal (male calves/vaccination biomarker) | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Mycobacterium avium subsp. paratuberculosis infection | | details | | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Fed barley-based concentrate diet and silage followed by pasture with concentrate diet | | details | | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Fed pasture vs barley-based concentrate | | details |
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| External Links |
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| HMDB ID | HMDB0000714 |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB001819 |
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| KNApSAcK ID | C00030483 |
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| Chemspider ID | 451 |
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| KEGG Compound ID | C01586 |
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| BioCyc ID | CPD-425 |
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| BiGG ID | Not Available |
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| Wikipedia Link | Hippuric_acid |
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| METLIN ID | 1301 |
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| PubChem Compound | 464 |
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| PDB ID | Not Available |
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| ChEBI ID | 18089 |
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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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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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.
- 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.
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