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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
3-HYDROXY-5-(hydroxymethyl)-2-methylisonicotinaldehydeNot AvailableNot Available
PyridoxalNot AvailableNot Available
PyridoxaldehydeNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot 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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridine carboxaldehydes
Direct ParentPyridoxals and derivatives
Alternative Parents
Substituents
  • Pyridoxal
  • Methylpyridine
  • Hydroxypyridine
  • Aryl-aldehyde
  • Heteroaromatic compound
  • Vinylogous acid
  • Azacycle
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
Vitamin B6 MetabolismMetabolicSMP00017
HypophosphatasiaDiseaseSMP00503
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyDiseaseSMP00137
3-Methylglutaconic Aciduria Type IDiseaseSMP00139
Maple Syrup Urine DiseaseDiseaseSMP00199
Methylmalonic AciduriaDiseaseSMP00200
Isobutyryl-coa dehydrogenase deficiencyDiseaseSMP00523
Beta-Ketothiolase DeficiencyDiseaseSMP00173
3-Methylcrotonyl Coa Carboxylase Deficiency Type IDiseaseSMP00237
Isovaleric AciduriaDiseaseSMP00238
Propionic AcidemiaDiseaseSMP00236
3-Methylglutaconic Aciduria Type IIIDiseaseSMP00140
3-Methylglutaconic Aciduria Type IVDiseaseSMP00141
3-hydroxyisobutyric acid dehydrogenase deficiencyDiseaseSMP00521
Isovaleric acidemiaDiseaseSMP00524
Valine, Leucine and Isoleucine DegradationMetabolicSMP00032
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyDiseaseSMP00138
Methylmalonate Semialdehyde Dehydrogenase DeficiencyDiseaseSMP00384
3-hydroxyisobutyric aciduriaDiseaseSMP00522
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9937
Blood Brain Barrier+0.6605
Caco-2 permeable-0.6034
P-glycoprotein substrateNon-substrate0.6664
P-glycoprotein inhibitor INon-inhibitor0.9793
P-glycoprotein inhibitor IINon-inhibitor0.9345
Renal organic cation transporterNon-inhibitor0.8338
CYP450 2C9 substrateNon-substrate0.7017
CYP450 2D6 substrateNon-substrate0.8006
CYP450 3A4 substrateNon-substrate0.7247
CYP450 1A2 substrateNon-inhibitor0.7841
CYP450 2C9 substrateNon-inhibitor0.9194
CYP450 2D6 substrateNon-inhibitor0.9437
CYP450 2C19 substrateNon-inhibitor0.8778
CYP450 3A4 substrateNon-inhibitor0.8435
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7875
Ames testNon AMES toxic0.801
CarcinogenicityNon-carcinogens0.9323
BiodegradationReady biodegradable0.7562
Rat acute toxicity1.4597 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.935
hERG inhibition (predictor II)Non-inhibitor0.9528
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Pyridoxal-5-phosphate powder18.24USD g
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 Solubility11.7 mg/mLALOGPS
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 Area70.42 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.87 m3·mol-1ChemAxon
Polarizability16.28 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (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

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