Record Information |
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Version | 1.0 |
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Creation date | 2011-04-11 17:01:47 UTC |
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Update date | 2020-09-17 15:41:03 UTC |
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Primary ID | FDB021820 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Pyridoxal 5'-phosphate |
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Description | Pyridoxal 5'-phosphate, also known as PLP or codecarboxylase, belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively. Pyridoxal 5'-phosphate is a drug which is used for nutritional supplementation and for treating dietary shortage or imbalance. Pyridoxal 5'-phosphate is a strong basic compound (based on its pKa). Pyridoxal 5'-phosphate exists in all living species, ranging from bacteria to humans. In humans, pyridoxal 5'-phosphate is involved in glycine and serine metabolism. Outside of the human body, Pyridoxal 5'-phosphate is found, on average, in the highest concentration within milk (cow). Pyridoxal 5'-phosphate has also been detected, but not quantified in, several different foods, such as soursops, italian sweet red peppers, muscadine grapes, european plums, and blackcurrants. This could make pyridoxal 5'-phosphate a potential biomarker for the consumption of these foods. The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal. Pyridoxal 5'-phosphate is a potentially toxic compound. Pyridoxal 5'-phosphate, with regard to humans, has been found to be associated with several diseases such as epilepsy, early-onset, vitamin b6-dependent, odontohypophosphatasia, pyridoxamine 5-prime-phosphate oxidase deficiency, and hypophosphatasia; pyridoxal 5'-phosphate has also been linked to the inborn metabolic disorder celiac disease. |
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CAS Number | 54-47-7 |
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Structure | |
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Synonyms | Synonym | Source |
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3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde | ChEBI | 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate | ChEBI | Codecarboxylase | ChEBI | Phosphoric acid mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester | ChEBI | PLP | ChEBI | Pyridoxal 5'-(dihydrogen phosphate) | ChEBI | Pyridoxal 5-monophosphoric acid ester | ChEBI | Pyridoxal 5-phosphate | ChEBI | Pyridoxal phosphate | ChEBI | PYRIDOXAL-5'-phosphATE | ChEBI | 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphoric acid | Generator | Phosphate mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester | Generator | Pyridoxal 5'-(dihydrogen phosphoric acid) | Generator | Pyridoxal 5-monophosphate ester | Generator | Pyridoxal 5-phosphoric acid | Generator | Pyridoxal phosphoric acid | Generator | PYRIDOXAL-5'-phosphoric acid | Generator | Pyridoxal 5'-phosphoric acid | Generator | Apolon b6 | HMDB | Biosechs | HMDB | Coenzyme b6 | HMDB | Hairoxal | HMDB | Hexermin-p | HMDB | Hi-pyridoxin | HMDB | Hiadelon | HMDB | Himitan | HMDB | PAL-p | HMDB | Phosphopyridoxal | HMDB | Phosphopyridoxal coenzyme | HMDB | Pidopidon | HMDB | Piodel | HMDB | Pydoxal | HMDB | Pyridoxal p | HMDB | Pyridoxal-p | HMDB | Pyridoxyl phosphate | HMDB | Pyromijin | HMDB | Sechvitan | HMDB | Vitahexin-p | HMDB | Vitazechs | HMDB | Phosphate, pyridoxal | HMDB | Pyridoxal 5 phosphate | HMDB | 3-Hydroxy-2-methyl-5-[(onooxy)methyl]-4-pyridinecarboxaldehyde | ChEBI | 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-ate | ChEBI | 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-ic acid | Generator | Hexermin-P | HMDB | Opyridoxal | HMDB | Opyridoxal coenzyme | HMDB | Orate mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester | Generator | oric acid Mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester | ChEBI | PAL-P | HMDB | Pyridoxal 5-monoate ester | Generator | Pyridoxal 5-monoic acid ester | Generator | Pyridoxal 5-monooric acid ester | ChEBI | Pyridoxal 5-ate | ChEBI | Pyridoxal 5-ic acid | Generator | Pyridoxal 5'-(dihydrogen ate) | ChEBI | Pyridoxal 5'-(dihydrogen ic acid) | Generator | Pyridoxal 5'-ate | ChEBI | Pyridoxal 5'-ic acid | Generator | Pyridoxal ate | ChEBI | Pyridoxal ic acid | Generator | Pyridoxal P | HMDB | PYRIDOXAL-5'-ATE | ChEBI | PYRIDOXAL-5'-ic acid | Generator | Pyridoxal-P | HMDB | Pyridoxyl ate | HMDB | Vitahexin-P | HMDB |
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Predicted Properties | |
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Chemical Formula | C8H10NO6P |
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IUPAC name | [(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid |
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InChI Identifier | InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14) |
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InChI Key | NGVDGCNFYWLIFO-UHFFFAOYSA-N |
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Isomeric SMILES | CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O |
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Average Molecular Weight | 247.1419 |
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Monoisotopic Molecular Weight | 247.024573569 |
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Classification |
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Description | Belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyridines and derivatives |
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Sub Class | Pyridine carboxaldehydes |
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Direct Parent | Pyridoxals and derivatives |
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Alternative Parents | |
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Substituents | - Pyridoxal
- Aryl-aldehyde
- Monoalkyl phosphate
- Hydroxypyridine
- Methylpyridine
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Vinylogous acid
- Heteroaromatic compound
- Azacycle
- Organopnictogen compound
- Aldehyde
- Organic oxygen compound
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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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 | 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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GC-MS | Pyridoxal 5'-phosphate, 1 MEOX; 3 TMS, GC-MS Spectrum | splash10-0gb9-2690000000-c9bacb7e657461e28407 | Spectrum | GC-MS | Pyridoxal 5'-phosphate, non-derivatized, GC-MS Spectrum | splash10-0gb9-2690000000-c9bacb7e657461e28407 | Spectrum | GC-MS | Pyridoxal 5'-phosphate, non-derivatized, GC-MS Spectrum | splash10-004j-0910000000-0408f3957221fc9882cd | Spectrum | GC-MS | Pyridoxal 5'-phosphate, non-derivatized, GC-MS Spectrum | splash10-0gb9-1790000000-b01115fa8b4cfd3612c7 | Spectrum | Predicted GC-MS | Pyridoxal 5'-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0002-9520000000-bfd574b2e5355694902a | Spectrum | Predicted GC-MS | Pyridoxal 5'-phosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-006t-9152000000-26c9f631195663322986 | Spectrum | Predicted GC-MS | Pyridoxal 5'-phosphate, non-derivatized, 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, Positive (Annotated) | splash10-0f6t-0690000000-4aa57f3f28f0bdef9dcf | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0fxx-8900000000-ee972556340c61650528 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014l-9100000000-3cc29fb51820adecd59c | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0002-0090000000-9b86e80a9dd0de14ab59 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-03dj-9800000000-9313aa9cbf19bc6311c5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0002-9500000000-7ce120a58879e2214ce5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-004j-9200000000-7e6bd8c298613e59fb5d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-004i-9000000000-4c05178b1645bf01f3fa | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-3920000000-6c5e6106f5658d1d6c50 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-3920000000-f96097815e6922356131 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-002b-9000000000-2c4e243699a95e3a0f88 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-002b-9000000000-8aa111485891af9f0d02 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-0090000000-9b86e80a9dd0de14ab59 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03dj-9800000000-9313aa9cbf19bc6311c5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-9500000000-7ce120a58879e2214ce5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004j-9200000000-7e6bd8c298613e59fb5d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-4c05178b1645bf01f3fa | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-002b-9000000000-2c4e243699a95e3a0f88 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-002b-9000000000-8aa111485891af9f0d02 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f6t-1790000000-1dcb07cd1110c71f7005 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-ca6aab7f31a36863a417 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-9800000000-053802b9c0533d7943ea | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9080000000-12ca63d34d39d59f6b42 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-144099ec201adbbc4684 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-70a9559d65e78c488e7e | 2015-05-27 | 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 | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | 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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External Links |
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ChemSpider ID | 1022 |
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ChEMBL ID | CHEMBL82202 |
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KEGG Compound ID | C00018 |
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Pubchem Compound ID | 1051 |
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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 | DB00114 |
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HMDB ID | HMDB01491 |
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CRC / DFC (Dictionary of Food Compounds) ID | HDV11-W:HDV11-W |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 33526 |
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KNApSAcK ID | Not Available |
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HET ID | PLP |
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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 | Not Available |
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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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Aromatic-L-amino-acid decarboxylase | DDC | P20711 | Tyrosine aminotransferase | TAT | P17735 | Aspartate aminotransferase, cytoplasmic | GOT1 | P17174 | Aspartate aminotransferase, mitochondrial | GOT2 | P00505 | Branched-chain-amino-acid aminotransferase, cytosolic | BCAT1 | P54687 | Branched-chain-amino-acid aminotransferase, mitochondrial | BCAT2 | O15382 | 2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial | GCAT | O75600 | Alanine--glyoxylate aminotransferase 2, mitochondrial | AGXT2 | Q9BYV1 | Serine hydroxymethyltransferase, mitochondrial | SHMT2 | P34897 | Serine hydroxymethyltransferase, cytosolic | SHMT1 | P34896 | Glycine dehydrogenase [decarboxylating], mitochondrial | GLDC | P23378 | Kynurenine--oxoglutarate transaminase 3 | CCBL2 | Q6YP21 | Serine hydroxymethyltransferase | DKFZp686P09201 | Q5HYG8 | Ornithine aminotransferase, mitochondrial | OAT | P04181 | Histidine decarboxylase | HDC | P19113 | 4-aminobutyrate aminotransferase, mitochondrial | ABAT | P80404 | Alanine aminotransferase 1 | GPT | P24298 | Alanine aminotransferase 2 | GPT2 | Q8TD30 | Selenocysteine lyase | SCLY | Q96I15 | 5-phosphohydroxy-L-lysine phospho-lyase | AGXT2L2 | Q8IUZ5 | Molybdenum cofactor sulfurase | MOCOS | Q96EN8 | Serine palmitoyltransferase 1 | SPTLC1 | O15269 | Proline synthase co-transcribed bacterial homolog protein | PROSC | O94903 | Phosphoserine aminotransferase | PSAT1 | Q9Y617 | Glucose-6-phosphate 1-dehydrogenase | G6PD | P11413 | Glycogen phosphorylase, liver form | PYGL | P06737 | Glycogen phosphorylase, muscle form | PYGM | P11217 | Glycogen phosphorylase, brain form | PYGB | P11216 | Putative aspartate aminotransferase, cytoplasmic 2 | GOT1L1 | Q8NHS2 | Ornithine decarboxylase | ODC1 | P11926 | Cystathionine gamma-lyase | CTH | P32929 | Glutamate decarboxylase 2 | GAD2 | Q05329 | Glutamate decarboxylase 1 | GAD1 | Q99259 | Arginine decarboxylase | ADC | Q96A70 | O-phosphoseryl-tRNA(Sec) selenium transferase | SEPSECS | Q9HD40 | Sphingosine-1-phosphate lyase 1 | SGPL1 | O95470 | Cysteine sulfinic acid decarboxylase | CSAD | Q9Y600 | L-serine dehydratase/L-threonine deaminase | SDS | P20132 | Serine dehydratase-like | SDSL | Q96GA7 | Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | AADAT | Q8N5Z0 | Kynurenine--oxoglutarate transaminase 1 | CCBL1 | Q16773 | Formimidoyltransferase-cyclodeaminase | FTCD | O95954 | Ethanolamine-phosphate phospho-lyase | AGXT2L1 | Q8TBG4 | Serine racemase | SRR | Q9GZT4 | Phosphatidylserine decarboxylase proenzyme | PISD | Q9UG56 | Threonine synthase-like 1 | THNSL1 | Q8IYQ7 | Aspartate aminotransferase | GIG18 | Q2TU84 | Serine palmitoyltransferase 2 | SPTLC2 | O15270 | Serine palmitoyltransferase 3 | SPTLC3 | Q9NUV7 | Glutamate decarboxylase-like protein 1 | GADL1 | Q6ZQY3 | Pyridoxal-dependent decarboxylase domain-containing protein 1 | PDXDC1 | Q6P996 | Pyridoxal-dependent decarboxylase domain-containing protein 2 | PDXDC2 | Q6P474 | Threonine synthase-like 2 | THNSL2 | Q86YJ6 | Aminolevulinate, delta-, synthase 1, isoform CRA_a | ALAS1 | Q5JAM2 | Aminolevulinate, delta-, synthase 2 | ALAS2 | Q5JZF5 | P-selectin cytoplasmic tail-associated protein (PCAP) | pcap | Q96JQ3 | Glutamic acid decarboxylase | GAD65 | Q9UGI5 |
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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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