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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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
PL
Pyridoxaldehyde
Vitamin B6 hydrochloride
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Dietary supplement
  • Micronutrient
  • Vitamins (Vitamin B Complex)
  • Vitamin B Complex
CAS number 65-22-5
Weight Average: 167.162
Monoisotopic: 167.058243159
Chemical Formula C8H9NO3
InChI Key InChIKey=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
Plain Text
IUPAC Name
3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde
SMILES
CC1=NC=C(CO)C(C=O)=C1O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Pyridoxals and Derivatives
Substructures
  • Pyridoxals and Derivatives
  • Hydroxy Compounds
  • Pyridines and Derivatives
  • Aldehydes
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Aromatic compounds
  • Imines
  • Phenols and Derivatives
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).
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 Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Pyridoxal-5-phosphate powder 18.24 USD 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 165 °C PhysProp
water solubility 5E+005 mg/L COFFEN,DL (1978)
logP 0 Not Available
Predicted Properties
Property Value Source
water solubility 1.17e+01 g/l 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 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 43.87 ChemAxon
polarizability 16.28 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C00250 Link_out
PubChem Compound 1050 Link_out
PubChem Substance 46506282 Link_out
ChemSpider 1021 Link_out
ChEBI 17310 Link_out
ChEMBL 17310 Link_out
PharmGKB PA164749166 Link_out
HET PXL Link_out
Wikipedia http://en.wikipedia.org/wiki/Pyridoxal Link_out
ATC Codes
  • A11HA06
  • C10AX07
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS show (72.7 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Pyridoxal kinase

Pharmacological action: yes

Required for synthesis of pyridoxal-5-phosphate from vitamin B6

Organism class: human
UniProt ID: O00764 Link_out
Gene: PDXK Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
  2. 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
  3. 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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19