| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 00:09:53 UTC |
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| Update date | 2019-11-26 03:21:01 UTC |
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| Primary ID | FDB022193 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | 4-Hydroxyphenylpyruvic acid |
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| Description | 4-Hydroxyphenylpyruvic acid (4-HPPA) is a keto acid. It is a product of the enzyme (R)-4-hydroxyphenyllactate dehydrogenase [EC 1.1.1.222] and is formed during tyrosine metabolism (KEGG). There are two isomers of HPPA, specifically 4HPPA and 3HPPA, of which 4HPPA is the most common. The enzyme 4-hydroxyphenylpyruvic acid dioxygenase (HPD) catalyzes the reaction of 4-hydroxyphenylpyruvic acid to homogentisic acid in the tyrosine catabolism pathway. 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). [HMDB] |
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| CAS Number | 156-39-8 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| 4-Hydroxyphenylpyruvate | Generator | | (p-hydroxyphenyl)-Pyruvate | hmdb | | (p-hydroxyphenyl)-Pyruvic acid | hmdb | | (p-Hydroxyphenyl)pyruvate | hmdb | | (p-Hydroxyphenyl)pyruvic acid | hmdb | | 3-(4-HYDROXY-phenyl)pyruvate | Generator | | 3-(4-HYDROXY-phenyl)pyruvIC ACID | ChEBI | | 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-(4-Hydroxyphenyl)pyruvate | hmdb | | 3-(4-Hydroxyphenyl)pyruvic acid | hmdb | | 3-(P-Hydroxyphenyl)-2-oxopropanoate | Generator | | 3-(P-Hydroxyphenyl)-2-oxopropanoic acid | ChEBI | | 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 | Generator | | 4-Hydroxy a-oxobenzenepropanoic acid | Generator | | 4-Hydroxy alpha-oxobenzenepropanoate | Generator | | 4-Hydroxy alpha-oxobenzenepropanoic acid | ChEBI | | 4-Hydroxy α-oxobenzenepropanoate | Generator | | 4-Hydroxy α-oxobenzenepropanoic acid | Generator | | 4-Hydroxy-a-oxobenzenepropanoate | hmdb | | 4-Hydroxy-a-oxobenzenepropanoic acid | hmdb | | 4-Hydroxy-alpha-oxobenzenepropanoate | hmdb | | 4-Hydroxy-alpha-oxobenzenepropanoic acid | hmdb | | 4-hydroxyphenylpyruvate | hmdb | | 4HPPA | hmdb | | Hydroxyphenylpyruvate | hmdb | | Hydroxyphenylpyruvic acid | hmdb | | P-Hydroxyphenylpyruvate | Generator | | p-hydroxyphenylpyruvic | hmdb | | P-Hydroxyphenylpyruvic acid | ChEBI | | Testacid | hmdb |
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| Predicted Properties | |
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| Chemical Formula | C9H8O4 |
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| IUPAC name | 3-hydroxy-2-oxo-3-phenylpropanoic acid |
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| InChI Identifier | InChI=1S/C9H8O4/c10-7(8(11)9(12)13)6-4-2-1-3-5-6/h1-5,7,10H,(H,12,13) |
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| InChI Key | ZHLWCBHWYUISFY-UHFFFAOYSA-N |
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| Isomeric SMILES | OC(C(=O)C(O)=O)C1=CC=CC=C1 |
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| Average Molecular Weight | 180.1574 |
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| Monoisotopic Molecular Weight | 180.042258744 |
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| Classification |
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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
- Beta-hydroxy acid
- Alpha-keto acid
- Acyloin
- Hydroxy acid
- Keto acid
- Monosaccharide
- Alpha-hydroxy ketone
- Ketone
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Hydrocarbon derivative
- Carbonyl group
- Alcohol
- Organooxygen compound
- Organic oxygen compound
- Organic oxide
- Aromatic alcohol
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Solid | |
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| Physical Description | Not Available | |
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| Mass Composition | Not Available | |
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| Melting Point | Not Available | |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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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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| Predicted GC-MS | 4-Hydroxyphenylpyruvic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4i-9600000000-37e5789e9e75e065483c | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-06si-0900000000-acf034eefde53804e4ac | 2015-09-15 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-0900000000-037a90063139ec62d81a | 2015-09-15 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9700000000-7c443a10a7af2fd25766 | 2015-09-15 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004r-0900000000-e34e03644f0b34007d85 | 2015-09-15 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0570-4900000000-32e0ef4141563f2be22c | 2015-09-15 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9200000000-fab36414b8e14847b9bd | 2015-09-15 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 954 |
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| ChEMBL ID | CHEMBL607712 |
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| KEGG Compound ID | C01179 |
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| Pubchem Compound ID | 979 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | DB07718 |
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| HMDB ID | HMDB00707 |
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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 | Not Available |
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| BIGG ID | 37006 |
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| KNApSAcK ID | Not Available |
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| HET ID | ENO |
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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 | Hydroxyphenylpyruvic acid |
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| Phenol-Explorer Metabolite ID | Not Available |
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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 | Not Available |
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| Enzymes | | Name | Gene Name | UniProt ID |
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| Tyrosine aminotransferase | TAT | P17735 | | Aspartate aminotransferase, cytoplasmic | GOT1 | P17174 | | Aspartate aminotransferase, mitochondrial | GOT2 | P00505 | | Macrophage migration inhibitory factor | MIF | P14174 |
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| Pathways | |
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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 | |
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