Record Information |
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Version | 1.0 |
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Created at | 2020-04-17 18:44:09 UTC |
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Updated at | 2020-12-07 19:11:07 UTC |
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CannabisDB ID | CDB004859 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | 4-Hydroxyphenylpyruvic acid |
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Description | 4-Hydroxyphenylpyruvic acid, also known as 4-hydroxy a-oxobenzenepropanoate or (p-hydroxyphenyl)pyruvate, 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. 4-Hydroxyphenylpyruvic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxyphenylpyruvic acid exists in all living species, ranging from bacteria to humans. Within humans, 4-hydroxyphenylpyruvic acid participates in a number of enzymatic reactions. In particular, 4-hydroxyphenylpyruvic acid and L-glutamic acid can be biosynthesized from L-tyrosine and oxoglutaric acid; which is catalyzed by the enzyme tyrosine aminotransferase. In addition, 4-hydroxyphenylpyruvic acid can be converted into homogentisic acid through its interaction with the enzyme 4-hydroxyphenylpyruvate dioxygenase. An oxo carboxylic acid that is pyruvic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. In humans, 4-hydroxyphenylpyruvic acid is involved in the metabolic disorder called tyrosinemia, transient, of the newborn. Outside of the human body, 4-Hydroxyphenylpyruvic acid has been detected, but not quantified in, several different foods, such as black chokeberries, limes, hazelnuts, pepper (c. baccatum), and dandelions. This could make 4-hydroxyphenylpyruvic acid a potential biomarker for the consumption of these foods. 4-Hydroxyphenylpyruvic acid is a potentially toxic compound. 4-Hydroxyphenylpyruvic acid, with regard to humans, has been found to be associated with several diseases such as deafness, onychodystrophy, osteodystrophy, mental retardation, and seizures syndrome, attachment loss, colorectal cancer, and periodontal probing depth; 4-hydroxyphenylpyruvic acid has also been linked to the inborn metabolic disorder phenylketonuria. 4-Hydroxyphenylpyruvic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | |
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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 Molecular Weight | 180.16 |
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Monoisotopic Molecular Weight | 180.0423 |
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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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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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Ontology |
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Physiological effect | Health effect: |
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Disposition | Source: Biological location: |
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Role | Industrial application: |
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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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Spectra |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0a59-5900000000-6c003e26816579df31ca | 2014-09-20 | View Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrum | splash10-002f-1920000000-75b07d9c09371340939f | Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, 3 TMS, GC-MS Spectrum | splash10-00xr-9340000000-087aad2497b3493d27c0 | Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, 1 MEOX; 2 TMS, GC-MS Spectrum | splash10-002o-5910000000-fd1e55c84c79bfeca559 | Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, 1 MEOX; 2 TMS, GC-MS Spectrum | splash10-002f-1941000000-2b4c87544657895fcaf6 | Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, 1 MEOX; 3 TMS, GC-MS Spectrum | splash10-014i-3492100000-483bdcea11d60fe4d306 | Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, 1 MEOX; 3 TMS, GC-MS Spectrum | splash10-014i-6791000000-ddc0a3b695cd1d0769f2 | Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrum | splash10-002f-1951000000-ecd071a64b26ca77684c | Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrum | splash10-002f-1920000000-75b07d9c09371340939f | Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrum | splash10-00xr-9340000000-087aad2497b3493d27c0 | Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrum | splash10-002o-5910000000-fd1e55c84c79bfeca559 | Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrum | splash10-002f-1941000000-2b4c87544657895fcaf6 | Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrum | splash10-014i-3492100000-483bdcea11d60fe4d306 | Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrum | splash10-014i-6791000000-ddc0a3b695cd1d0769f2 | Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrum | splash10-0006-2920000000-469469dfaad745fa78e8 | Spectrum | GC-MS | 4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrum | splash10-002o-2910000000-4f336335a2366e7dd6db | Spectrum | Predicted GC-MS | 4-Hydroxyphenylpyruvic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4i-6900000000-91bfe3ee54a36877251b | Spectrum | Predicted GC-MS | 4-Hydroxyphenylpyruvic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0adi-6961000000-670161f1542fda9ff1fe | Spectrum | Predicted GC-MS | 4-Hydroxyphenylpyruvic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 4-Hydroxyphenylpyruvic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 4-Hydroxyphenylpyruvic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 4-Hydroxyphenylpyruvic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 4-Hydroxyphenylpyruvic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 4-Hydroxyphenylpyruvic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 4-Hydroxyphenylpyruvic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 4-Hydroxyphenylpyruvic 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) | splash10-0a4i-0900000000-12033042c41b550bed42 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0a4i-0900000000-6e8a3701c6d254cc824d | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0560-1900000000-8082c68e259d24234d05 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0900000000-2416d7f64101b9473cbb | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0a4i-2900000000-b4c21b3d9751b9e56d67 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0005-9400000000-708e258e692a0abfbc92 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0002-9100000000-7d75e23ae6944c1e9c6d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-001m-9000000000-fb80dcbab23323a042af | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0900000000-2416d7f64101b9473cbb | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-2900000000-ad1f1fabdf6b1579fff7 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0005-9400000000-708e258e692a0abfbc92 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-9100000000-7d75e23ae6944c1e9c6d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-001m-9000000000-fb80dcbab23323a042af | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-001i-1900000000-76ae33b45e4348d50b07 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-02bf-7900000000-665940e67ad40f759048 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-053i-9800000000-0f708ba46e75f553e77c | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-00dl-5900000000-86f6d19bba9a914d22ee | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0159-0900000000-a1a6bf5b3a0ac3863c90 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-06ur-9700000000-18795e8a2dc93ca36a93 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-08gr-0900000000-be3cb913118057f499d1 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06rj-0900000000-6bebea0fda2ef3a2263b | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a6r-6900000000-ede11b81a97e891c66e3 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-2584f872c980915c1739 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01s9-1900000000-249c71cfa9cefe2a8020 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001l-3900000000-66991d861a91be9b9286 | 2015-04-25 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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Pathways |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | Tyrosine Metabolism | | | Phenylalanine and Tyrosine Metabolism | | | Phenylketonuria | | Not Available | Tyrosinemia Type 2 (or Richner-Hanhart syndrome) | | Not Available | Tyrosinemia Type 3 (TYRO3) | | Not Available |
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Protein Targets |
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Enzymes | |
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Transporters | Not Available |
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Metal Bindings | |
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Receptors | |
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Transcriptional Factors | Not Available |
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Concentrations Data |
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External Links |
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HMDB ID | HMDB0000707 |
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DrugBank ID | DB07718 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB030506 |
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KNApSAcK ID | C00007512 |
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Chemspider ID | 954 |
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KEGG Compound ID | C01179 |
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BioCyc ID | P-HYDROXY-PHENYLPYRUVATE |
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BiGG ID | 37006 |
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Wikipedia Link | 4-Hydroxyphenylpyruvic_acid |
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METLIN ID | 5675 |
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PubChem Compound | 979 |
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PDB ID | Not Available |
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ChEBI ID | 15999 |
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References |
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General References | Not Available |
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