Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:46:42 UTC |
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Update Date | 2020-06-04 20:33:28 UTC |
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BMDB ID | BMDB0001491 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Pyridoxal 5'-phosphate |
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Description | Pyridoxal 5'-phosphate, also known as phosphopyridoxal or PLP, 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 exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Pyridoxal 5'-phosphate exists in all living species, ranging from bacteria to humans. In cattle, pyridoxal 5'-phosphate is involved in the metabolic pathway called the glycine and serine metabolism pathway. Pyridoxal 5'-phosphate is a potentially toxic compound. Pyridoxal 5'-phosphate has been found to be associated with several diseases known as rheumatoid arthritis, epilepsy, early-onset, vitamin b6-dependent, odontohypophosphatasia, and pyridoxamine 5-prime-phosphate oxidase deficiency; also pyridoxal 5'-phosphate has been linked to the inborn metabolic disorders including celiac disease. |
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Structure | |
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Synonyms | Value | 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 |
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Chemical Formula | C8H10NO6P |
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Average Molecular Weight | 247.1419 |
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Monoisotopic Molecular Weight | 247.024573569 |
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IUPAC Name | [(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid |
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Traditional Name | pyridoxal phosphate |
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CAS Registry Number | 54-47-7 |
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SMILES | CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O |
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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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Chemical Taxonomy |
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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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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 | 255 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 28 mg/mL | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS) | splash10-0gb9-2690000000-c9bacb7e657461e28407 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0gb9-2690000000-c9bacb7e657461e28407 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004j-0910000000-0408f3957221fc9882cd | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0gb9-1790000000-b01115fa8b4cfd3612c7 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9520000000-bfd574b2e5355694902a | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-006t-9152000000-26c9f631195663322986 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0f6t-0690000000-4aa57f3f28f0bdef9dcf | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0fxx-8900000000-ee972556340c61650528 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014l-9100000000-3cc29fb51820adecd59c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0002-0090000000-9b86e80a9dd0de14ab59 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-03dj-9800000000-9313aa9cbf19bc6311c5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0002-9500000000-7ce120a58879e2214ce5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-004j-9200000000-7e6bd8c298613e59fb5d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-004i-9000000000-4c05178b1645bf01f3fa | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-3920000000-6c5e6106f5658d1d6c50 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-3920000000-f96097815e6922356131 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-002b-9000000000-2c4e243699a95e3a0f88 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-002b-9000000000-8aa111485891af9f0d02 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-0090000000-9b86e80a9dd0de14ab59 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03dj-9800000000-9313aa9cbf19bc6311c5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-9500000000-7ce120a58879e2214ce5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004j-9200000000-7e6bd8c298613e59fb5d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-4c05178b1645bf01f3fa | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-002b-9000000000-2c4e243699a95e3a0f88 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-002b-9000000000-8aa111485891af9f0d02 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f6t-1790000000-1dcb07cd1110c71f7005 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-ca6aab7f31a36863a417 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-9800000000-053802b9c0533d7943ea | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9080000000-12ca63d34d39d59f6b42 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-144099ec201adbbc4684 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-70a9559d65e78c488e7e | View in MoNA |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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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) | Not Available | View in JSpectraViewer |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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