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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyPyridoxal
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
Structure for DB00147 (Pyridoxal)
- 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
- Product Ingredients
Ingredient UNII CAS InChI Key Pyridoxal hydrochloride 1416KF0QBC 65-22-5 FCHXJFJNDJXENQ-UHFFFAOYSA-N - Categories
- UNII
- 3THM379K8A
- CAS number
- 66-72-8
- Weight
- Average: 167.162
Monoisotopic: 167.058243159 - Chemical Formula
- C8H9NO3
- 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.
- 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 Actions Organism APyridoxal kinase Not Available Human - 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
- Humans and other mammals
- Pathways
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
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
- Human Metabolome Database
- HMDB0001545
- KEGG Compound
- C00250
- PubChem Compound
- 1050
- PubChem Substance
- 46506282
- ChemSpider
- 1021
- BindingDB
- 50366979
- ChEBI
- 17310
- ChEMBL
- CHEMBL102970
- PharmGKB
- PA164749166
- HET
- PXL
- Wikipedia
- Pyridoxal
- PDB Entries
- 1td2 / 2ddw / 2z9w / 2z9x / 3fhx / 3mbh / 4c5l / 4c5n
- MSDS
- Download (72.7 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Medisca Inc.
- Dosage forms
- Not Available
- Prices
Unit description Cost Unit Pyridoxal-5-phosphate powder 18.24USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- 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
Property Value Source Water Solubility 11.7 mg/mL ALOGPS logP 0.02 ALOGPS logP 0.18 ChemAxon logS -1.2 ALOGPS pKa (Strongest Acidic) 7.97 ChemAxon pKa (Strongest Basic) 4.11 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 70.42 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 43.87 m3·mol-1 ChemAxon Polarizability 16.28 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- Description
- This compound belongs to the class of organic compounds 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
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Pyridine carboxaldehydes
- 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 show 2 more
- Substituents
- Pyridoxal / Aryl-aldehyde / Hydroxypyridine / Methylpyridine / Vinylogous acid / Heteroaromatic compound / Azacycle / Hydrocarbon derivative / Aldehyde / Alcohol show 9 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- monohydroxypyridine, pyridinecarbaldehyde, methylpyridines, vitamin B6, hydroxymethylpyridine (CHEBI:17310) / Water-soluble vitamins (C00250) / a vitamin B6 (PYRIDOXAL)
Targets
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Yes
- General Function
- Zinc ion binding
- Specific Function
- Required for synthesis of pyridoxal-5-phosphate from vitamin B6.
- Gene Name
- PDXK
- Uniprot ID
- O00764
- Uniprot Name
- Pyridoxal kinase
- Molecular Weight
- 35102.105 Da
References
- Tang L, Li MH, Cao P, Wang F, Chang WR, Bach S, Reinhardt J, Ferandin Y, Galons H, Wan Y, Gray N, Meijer L, Jiang T, Liang DC: Crystal structure of pyridoxal kinase in complex with roscovitine and derivatives. J Biol Chem. 2005 Sep 2;280(35):31220-9. Epub 2005 Jun 28. [PubMed:15985434]
- Adams JB, George F, Audhya T: Abnormally high plasma levels of vitamin B6 in children with autism not taking supplements compared to controls not taking supplements. J Altern Complement Med. 2006 Jan-Feb;12(1):59-63. [PubMed:16494569]
- Newman JA, Das SK, Sedelnikova SE, Rice DW: The crystal structure of an ADP complex of Bacillus subtilis pyridoxal kinase provides evidence for the parallel emergence of enzyme activity during evolution. J Mol Biol. 2006 Oct 20;363(2):520-30. Epub 2006 Aug 12. [PubMed:16978644]
Drug created on June 13, 2005 07:24 / Updated on August 02, 2018 07:58