Identification Name Pyridoxal Accession Number DB00147 (NUTR00049) Type Small Molecule Groups Approved, Nutraceutical Description The 4-carboxyaldehyde form of vitamin B 6 which is converted to pyridoxal phosphate which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. [PubChem]
Structure Synonyms 2-methyl-3-hydroxy-4-formyl-5-hydroxymethylpyridine 3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxaldehyde 3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxaldehyde Piridoxal Pyridoxaldehyde
External IDs Not Available Product Ingredients Approved Prescription Products Not Available Approved Generic Prescription Products Not Available Approved Over the Counter Products Not Available Unapproved/Other Products Not Available International Brands Not Available Brand mixtures Not Available Categories UNII 3THM379K8A CAS number 66-72-8 Weight Average: 167.162 Chemical Formula C8 H9 NO3 InChI Key RADKZDMFGJYCBB-UHFFFAOYSA-N InChI InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3
IUPAC Name 3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde
SMILES CC1=NC=C(CO)C(C=O)=C1O
Pharmacology Indication Pyridoxal is one of the natural forms available of vitamin B6, therefore, it is used for nutritional supplementation and for treating dietary shortage or imbalances.
Structured Indications Not Available Pharmacodynamics Pyridoxal principally in the form of the coenzyme pyridoxal 5'-phosphate, is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA).
Mechanism of action Pyridoxal is the precursor to pyridoxal phosphate. Pyridoxal 5'-phosphate is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA).
Target Kind Pharmacological action Actions Organism UniProt ID Pyridoxal kinase Protein yes Not Available Human O00764 details
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Absorption Not Available Volume of distribution Not Available Protein binding Not Available Metabolism Not Available Route of elimination Not Available Half life Not Available Clearance Not Available Toxicity Oral LD50 Rat: 2150 mg/kg, Oral LD50 Mouse: 1800 mg/kg
Affected organisms Pathways Pathway Category SMPDB ID 3-Methylcrotonyl Coa Carboxylase Deficiency Type I Disease SMP00237 Hypophosphatasia Disease SMP00503 Valine, Leucine and Isoleucine Degradation Metabolic SMP00032 Beta-Ketothiolase Deficiency Disease SMP00173 3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency Disease SMP00138 3-hydroxyisobutyric acid dehydrogenase deficiency Disease SMP00521 3-hydroxyisobutyric aciduria Disease SMP00522 Vitamin B6 Metabolism Metabolic SMP00017 2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency Disease SMP00137 3-Methylglutaconic Aciduria Type I Disease SMP00139 3-Methylglutaconic Aciduria Type IV Disease SMP00141 Maple Syrup Urine Disease Disease SMP00199 Propionic Acidemia Disease SMP00236 3-Methylglutaconic Aciduria Type III Disease SMP00140 Methylmalonic Aciduria Disease SMP00200 Isovaleric Aciduria Disease SMP00238 Methylmalonate Semialdehyde Dehydrogenase Deficiency Disease SMP00384 Isobutyryl-coa dehydrogenase deficiency Disease SMP00523 Isovaleric acidemia Disease SMP00524
Pharmacogenomic Effects/ADRs Not Available Interactions Drug Interactions Not Available Food Interactions Not Available References Synthesis Reference Robert C. Siegel, "Synthesis of cross-links in the helical domain of collagen using pyridoxal 5-phosphate and copper or iron." U.S. Patent US4544638, issued June, 1981.
US4544638 General References Not Available External Links ATC Codes Not Available AHFS Codes Not Available PDB Entries FDA label Not Available MSDS Download (72.7 KB) Clinical Trials Clinical Trials Not Available Pharmacoeconomics Manufacturers Not Available Packagers Dosage forms Not Available Prices Unit description Cost Unit Pyridoxal-5-phosphate powder 18.24USD g
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Patents Not Available Properties State Solid Experimental Properties Property Value Source melting point (°C) 165 °C PhysProp water solubility 5E+005 mg/L COFFEN,DL (1978) logP 0 Not Available
Predicted Properties Predicted ADMET features Property Value Probability Human Intestinal Absorption + 0.9937 Blood Brain Barrier + 0.6605 Caco-2 permeable - 0.6034 P-glycoprotein substrate Non-substrate 0.6664 P-glycoprotein inhibitor I Non-inhibitor 0.9793 P-glycoprotein inhibitor II Non-inhibitor 0.9345 Renal organic cation transporter Non-inhibitor 0.8338 CYP450 2C9 substrate Non-substrate 0.7017 CYP450 2D6 substrate Non-substrate 0.8006 CYP450 3A4 substrate Non-substrate 0.7247 CYP450 1A2 substrate Non-inhibitor 0.7841 CYP450 2C9 inhibitor Non-inhibitor 0.9194 CYP450 2D6 inhibitor Non-inhibitor 0.9437 CYP450 2C19 inhibitor Non-inhibitor 0.8778 CYP450 3A4 inhibitor Non-inhibitor 0.8435 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7875 Ames test Non AMES toxic 0.801 Carcinogenicity Non-carcinogens 0.9323 Biodegradation Ready biodegradable 0.7562 Rat acute toxicity 1.4597 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.935 hERG inhibition (predictor II) Non-inhibitor 0.9528
ADMET data is predicted using
admetSAR , a free tool for evaluating chemical ADMET properties. (
23092397 )
Spectra Mass Spec (NIST) Not Available Spectra Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) splash10-00di-2690000000-5d018202be238b10582a View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) splash10-0aou-3974000000-8c963fdc714896ad343a View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) splash10-001j-0590000000-ed8a55680a0c9fa9cbaf View in MoNA GC-MS GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS) splash10-0a4i-5695000000-bd3bb22a5dd4a600cb6c View in MoNA GC-MS GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS) splash10-0aor-5895000000-e55e01ca30d17d2a8a72 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS Not Available GC-MS GC-MS Spectrum - GC-MS splash10-0a4i-5695000000-bd3bb22a5dd4a600cb6c View in MoNA GC-MS GC-MS Spectrum - GC-MS splash10-0aor-5895000000-e55e01ca30d17d2a8a72 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-0002-0900000000-4ce3f52baa36006ef4b2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-00kg-9500000000-658a96f6cda4a96de045 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-0gbc-9000000000-233fc8ab067b0dcd1f14 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative splash10-014i-0900000000-c49b207cafcf1c21302d View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative splash10-000i-0900000000-cad83f5f123a879fa0bb View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative splash10-0a4i-0900000000-4f12feae0e11a6d9016b View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative splash10-0a4i-2900000000-56fcdbb9b4363c84d2d0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative splash10-056r-9400000000-9700c9585f6c540bf007 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive splash10-0gb9-0900000000-e646a99b0c1521d1c8dd View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive splash10-0udi-0900000000-8fce1a7d8ceb3fced3ed View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive splash10-0udl-6900000000-e2fc0eaa17e57d0a2556 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive splash10-00kf-9200000000-0bda29931f8b6f2fcc77 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive splash10-014l-9000000000-469c127d1aef4f8a51d7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-0udi-2900000000-63ebef5a0818d6a1ccb8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative splash10-05n0-0900000000-f468a00d88bedc116485 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-014i-0900000000-c49b207cafcf1c21302d View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-000i-0900000000-bf0686eb8e3c28c30e85 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0a4i-0900000000-686848e0f222273e5089 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0a4i-2900000000-99577e7f4a39e47c5c42 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0uxr-0900000000-7f4ef736d1a810b2e8ab View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0udi-0900000000-9c4ead9423b52a47b2fe View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0udi-9500000000-aa6a11948622748c8469 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-014i-0900000000-dd6386614990770eaae5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-000i-0900000000-e9de9bab2598f0316525 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0abc-9300000000-f4bc767c42577b6a1d5f View in MoNA 1D NMR 1H NMR Spectrum Not Available 1D NMR 1H NMR Spectrum Not Available 1D NMR 13C NMR Spectrum Not Available 2D NMR [1H,13C] 2D NMR Spectrum Not Available
Taxonomy Description This compound belongs to the class of chemical entities known as pyridoxals and derivatives. These 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. Kingdom Chemical entities Super Class Organic compounds Class Organoheterocyclic compounds Sub Class Pyridines and derivatives Direct Parent Pyridoxals and derivatives Alternative Parents Methylpyridines / Hydroxypyridines / Aryl-aldehydes / Vinylogous acids / Heteroaromatic compounds / Azacyclic compounds / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Aromatic alcohols show 2 moreSubstituents Pyridoxal / Aryl-aldehyde / Hydroxypyridine / Methylpyridine / Vinylogous acid / Heteroaromatic compound / Azacycle / Hydrocarbon derivative / Aldehyde / Alcohol / Organic oxygen compound / Aromatic alcohol / Organic nitrogen compound / Primary alcohol / Organooxygen compound / Organonitrogen compound / Organopnictogen compound / Organic oxide / Aromatic heteromonocyclic compound show 9 moreMolecular Framework Aromatic heteromonocyclic compounds External Descriptors monohydroxypyridine, pyridinecarbaldehyde, methylpyridines, vitamin B6, hydroxymethylpyridine (CHEBI:17310 ) / Water-soluble vitamins (C00250 ) / a vitamin B6 (PYRIDOXAL ) 