You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NamePyridoxal
Accession NumberDB00147  (NUTR00049)
Typesmall molecule
Groupsapproved, 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
Synonyms
SynonymLanguageCode
PyridoxaldehydeNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number65-22-5
WeightAverage: 167.162
Monoisotopic: 167.058243159
Chemical FormulaC8H9NO3
InChI KeyRADKZDMFGJYCBB-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPyridines and Derivatives
SubclassPyridine Carboxaldehydes
Direct parentPyridoxals and Derivatives
Alternative parentsPolyols; Primary Alcohols; Enolates; Polyamines; Aldehydes
Substituentspolyol; polyamine; enolate; primary alcohol; organonitrogen compound; alcohol; aldehyde
Classification descriptionThis compound belongs to the 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, an hydroxyl group, a carbaldehyde group, and an hydroxymethyl group, respectively.
Pharmacology
IndicationPyridoxal is one of the natural forms available of vitamin B6, therefore, it is used for nutritional supplementation and for treating dietary shortage or imbalances.
PharmacodynamicsPyridoxal 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 actionPyridoxal 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).
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral LD50 Rat: 2150 mg/kg, Oral LD50 Mouse: 1800 mg/kg
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyDiseaseSMP00137
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyDiseaseSMP00138
3-hydroxyisobutyric aciduriaDiseaseSMP00522
3-Methylglutaconic Aciduria Type IVDiseaseSMP00141
3-Methylglutaconic Aciduria Type IDiseaseSMP00139
3-hydroxyisobutyric acid dehydrogenase deficiencyDiseaseSMP00521
3-Methylcrotonyl Coa Carboxylase Deficiency Type IDiseaseSMP00237
3-Methylglutaconic Aciduria Type IIIDiseaseSMP00140
Propionic AcidemiaDiseaseSMP00236
Isovaleric acidemiaDiseaseSMP00524
Methylmalonic AciduriaDiseaseSMP00200
Isovaleric AciduriaDiseaseSMP00238
Valine, Leucine and Isoleucine DegradationMetabolicSMP00032
Vitamin B6 MetabolismMetabolicSMP00017
Beta-Ketothiolase DeficiencyDiseaseSMP00173
Isobutyryl-coa dehydrogenase deficiencyDiseaseSMP00523
Methylmalonate Semialdehyde Dehydrogenase DeficiencyDiseaseSMP00384
Maple Syrup Urine DiseaseDiseaseSMP00199
HypophosphatasiaDiseaseSMP00503
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.9194
CYP450 2D6 substrate Non-inhibitor 0.9437
CYP450 2C19 substrate Non-inhibitor 0.8778
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Pyridoxal-5-phosphate powder18.24USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point165 °CPhysProp
water solubility5E+005 mg/LCOFFEN,DL (1978)
logP0Not Available
Predicted Properties
PropertyValueSource
water solubility1.17e+01 g/lALOGPS
logP0.02ALOGPS
logP0.18ChemAxon
logS-1.2ALOGPS
pKa (strongest acidic)7.97ChemAxon
pKa (strongest basic)4.11ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area70.42ChemAxon
rotatable bond count2ChemAxon
refractivity43.87ChemAxon
polarizability16.28ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
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 ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00250
PubChem Compound1050
PubChem Substance46506282
ChemSpider1021
ChEBI17310
ChEMBLCHEMBL102970
PharmGKBPA164749166
HETPXL
WikipediaPyridoxal
ATC CodesC10AX07
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(72.7 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Pyridoxal kinase

Kind: protein

Organism: Human

Pharmacological action: yes

Components

Name UniProt ID Details
Pyridoxal kinase O00764 Details

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
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08