Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2020-11-24 22:22:09 UTC |
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NP-MRD ID | NP0001275 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 4-Hydroxyphenylpyruvic acid |
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Description | 4-Hydroxyphenylpyruvic acid (4-HPPA) is a keto acid that is involved in the tyrosine catabolism pathway. It is a product of the enzyme (R)-4-hydroxyphenyllactate dehydrogenase (EC 1.1.1.222) And is formed during tyrosine metabolism. The conversion from tyrosine to 4-HPPA is catalyzed by tyrosine aminotransferase. Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment. The enzyme 4-hydroxyphenylpyruvic acid dioxygenase (HPD) catalyzes the reaction that converts 4-hydroxyphenylpyruvic acid to homogentisic acid. A deficiency in the catalytic activity of HPD is known to lead to tyrosinemia type III, an autosomal recessive disorder characterized by elevated levels of blood tyrosine and massive excretion of tyrosine derivatives into urine. It has been shown that hawkinsinuria, an autosomal dominant disorder characterized by the excretion of 'hawkinsin,' may also be a result of HPD deficiency (PMID: 11073718 ). Moreover, 4-hydroxyphenylpyruvic acid is also found to be associated in phenylketonuria, which is also an inborn error of metabolism. There are two isomers of HPPA, specifically 4HPPA and 3HPPA, of which 4HPPA is the most common. |
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Structure | OC(=O)C(=O)CC1=CC=C(O)C=C1 InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13) |
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Synonyms | Value | Source |
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(4-Hydroxyphenyl)pyruvic acid | ChEBI | (p-Hydroxyphenyl)pyruvic acid | ChEBI | 3-(4-HYDROXY-phenyl)pyruvIC ACID | ChEBI | 3-(4-Hydroxyphenyl)pyruvic acid | ChEBI | 3-(p-Hydroxyphenyl)-2-oxopropanoic acid | ChEBI | 4-Hydroxy alpha-oxobenzenepropanoic acid | ChEBI | p-Hydroxyphenylpyruvic acid | ChEBI | 4-Hydroxyphenylpyruvate | Kegg | (4-Hydroxyphenyl)pyruvate | Generator | (p-Hydroxyphenyl)pyruvate | Generator | 3-(4-HYDROXY-phenyl)pyruvate | Generator | 3-(4-Hydroxyphenyl)pyruvate | Generator | 3-(p-Hydroxyphenyl)-2-oxopropanoate | Generator | 4-Hydroxy a-oxobenzenepropanoate | Generator | 4-Hydroxy a-oxobenzenepropanoic acid | Generator | 4-Hydroxy alpha-oxobenzenepropanoate | Generator | 4-Hydroxy α-oxobenzenepropanoate | Generator | 4-Hydroxy α-oxobenzenepropanoic acid | Generator | p-Hydroxyphenylpyruvate | Generator | (p-Hydroxyphenyl)-pyruvate | HMDB | (p-Hydroxyphenyl)-pyruvic acid | HMDB | 3-(4-Hydroxyphenyl)-2-oxo-propanoate | HMDB | 3-(4-Hydroxyphenyl)-2-oxo-propanoic acid | HMDB | 3-(4-Hydroxyphenyl)-2-oxopropionate | HMDB | 3-(4-Hydroxyphenyl)-2-oxopropionic acid | HMDB | 3-(p-Hydroxyphenyl)-2-oxopropionate | HMDB | 3-(p-Hydroxyphenyl)-2-oxopropionic acid | HMDB | 3-(p-Hydroxyphenyl)pyruvate | HMDB | 3-(p-Hydroxyphenyl)pyruvic acid | HMDB | 4-Hydroxy-a-oxobenzenepropanoate | HMDB | 4-Hydroxy-a-oxobenzenepropanoic acid | HMDB | 4-Hydroxy-alpha-oxobenzenepropanoate | HMDB | 4-Hydroxy-alpha-oxobenzenepropanoic acid | HMDB | 4HPPA | HMDB | HPPA | HMDB | Hydroxyphenylpyruvate | HMDB | Hydroxyphenylpyruvic acid | HMDB | p-Hydroxyphenylpyruvic | HMDB | Testacid | HMDB | 4-Hydroxyphenylpyruvic acid, ion | HMDB | 4-Hydroxyphenylpyruvic acid, sodium salt | HMDB | Para-hydroxyphenylpyruvic acid | HMDB |
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Chemical Formula | C9H8O4 |
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Average Mass | 180.1574 Da |
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Monoisotopic Mass | 180.04226 Da |
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IUPAC Name | 3-(4-hydroxyphenyl)-2-oxopropanoic acid |
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Traditional Name | 4-hydroxyphenylpyruvic acid |
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CAS Registry Number | 156-39-8 |
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SMILES | OC(=O)C(=O)CC1=CC=C(O)C=C1 |
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InChI Identifier | InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13) |
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InChI Key | KKADPXVIOXHVKN-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, 500 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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| Not Available | 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 phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. |
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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 | Phenylpyruvic acid derivatives |
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Direct Parent | Phenylpyruvic acid derivatives |
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Alternative Parents | |
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Substituents | - Phenylpyruvate
- 3-phenylpropanoic-acid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Alpha-keto acid
- Keto acid
- Alpha-hydroxy ketone
- Ketone
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- 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 | 219 - 220 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Tomoeda K, Awata H, Matsuura T, Matsuda I, Ploechl E, Milovac T, Boneh A, Scott CR, Danks DM, Endo F: Mutations in the 4-hydroxyphenylpyruvic acid dioxygenase gene are responsible for tyrosinemia type III and hawkinsinuria. Mol Genet Metab. 2000 Nov;71(3):506-10. [PubMed:11073718 ]
- 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 ]
- Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
- Endo F, Katoh H, Yamamoto S, Matsuda I: A murine model for type III tyrosinemia: lack of immunologically detectable 4-hydroxyphenylpyruvic acid dioxygenase enzyme protein in a novel mouse strain with hypertyrosinemia. Am J Hum Genet. 1991 Apr;48(4):704-9. [PubMed:2014797 ]
- Shoda J, Tanaka N, Osuga T, Matsuura K, Miyazaki H: Altered bile acid metabolism in liver disease: concurrent occurrence of C-1 and C-6 hydroxylated bile acid metabolites and their preferential excretion into urine. J Lipid Res. 1990 Feb;31(2):249-59. [PubMed:2324645 ]
- Wolff JA, Barshop B, Nyhan WL, Leslie J, Seegmiller JE, Gruber H, Garst M, Winter S, Michals K, Matalon R: Effects of ascorbic acid in alkaptonuria: alterations in benzoquinone acetic acid and an ontogenic effect in infancy. Pediatr Res. 1989 Aug;26(2):140-4. [PubMed:2771520 ]
- Deutsch JC: Determination of p-hydroxyphenylpyruvate, p-hydroxyphenyllactate and tyrosine in normal human plasma by gas chromatography-mass spectrometry isotope-dilution assay. J Chromatogr B Biomed Sci Appl. 1997 Mar 7;690(1-2):1-6. [PubMed:9106023 ]
- Muskiet FA, Fremouw-Ottevangers DC, Nagel GT, Wolthers BG, de Vries JA: Determination of 3-methoxy-4-hydroxyphenylpyruvic acid, 3,4-dihydroxyphenylethylene glycol, and 3,4-dihydroxyphenylmandelic acid in urine by mass fragmentography, with use of deuterium-labeled internal standards. Clin Chem. 1978 Nov;24(11):2001-8. [PubMed:709835 ]
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