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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
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 Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Pyridoxal hydrochloride
65-22-5
Thumb
  • InChI Key: FCHXJFJNDJXENQ-UHFFFAOYSA-N
  • Monoisotopic Mass: 203.0349209
  • Average Mass: 203.62
DBSALT001795
Categories
UNII3THM379K8A
CAS number66-72-8
WeightAverage: 167.162
Monoisotopic: 167.058243159
Chemical FormulaC8H9NO3
InChI KeyInChIKey=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
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).
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
3-Methylcrotonyl Coa Carboxylase Deficiency Type IDiseaseSMP00237
HypophosphatasiaDiseaseSMP00503
Valine, Leucine and Isoleucine DegradationMetabolicSMP00032
Beta-Ketothiolase DeficiencyDiseaseSMP00173
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyDiseaseSMP00138
3-hydroxyisobutyric acid dehydrogenase deficiencyDiseaseSMP00521
3-hydroxyisobutyric aciduriaDiseaseSMP00522
3-Methylglutaconic Aciduria Type IIIDiseaseSMP00140
Methylmalonic AciduriaDiseaseSMP00200
Isovaleric AciduriaDiseaseSMP00238
Methylmalonate Semialdehyde Dehydrogenase DeficiencyDiseaseSMP00384
Isobutyryl-coa dehydrogenase deficiencyDiseaseSMP00523
Isovaleric acidemiaDiseaseSMP00524
Vitamin B6 MetabolismMetabolicSMP00017
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyDiseaseSMP00137
3-Methylglutaconic Aciduria Type IDiseaseSMP00139
3-Methylglutaconic Aciduria Type IVDiseaseSMP00141
Maple Syrup Urine DiseaseDiseaseSMP00199
Propionic AcidemiaDiseaseSMP00236
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 inhibitorNon-inhibitor0.9194
CYP450 2D6 inhibitorNon-inhibitor0.9437
CYP450 2C19 inhibitorNon-inhibitor0.8778
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00di-2690000000-5d018202be238b10582aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0aou-3974000000-8c963fdc714896ad343aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-001j-0590000000-ed8a55680a0c9fa9cbafView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0a4i-5695000000-bd3bb22a5dd4a600cb6cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0aor-5895000000-e55e01ca30d17d2a8a72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-4ce3f52baa36006ef4b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kg-9500000000-658a96f6cda4a96de045View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0gbc-9000000000-233fc8ab067b0dcd1f14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-c49b207cafcf1c21302dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-0900000000-cad83f5f123a879fa0bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-0900000000-4f12feae0e11a6d9016bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-2900000000-56fcdbb9b4363c84d2d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-056r-9400000000-9700c9585f6c540bf007View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0gb9-0900000000-e646a99b0c1521d1c8ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-0900000000-8fce1a7d8ceb3fced3edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0udl-6900000000-e2fc0eaa17e57d0a2556View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00kf-9200000000-0bda29931f8b6f2fcc77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014l-9000000000-469c127d1aef4f8a51d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-2900000000-63ebef5a0818d6a1ccb8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-05n0-0900000000-f468a00d88bedc116485View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0900000000-7f4ef736d1a810b2e8abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-9c4ead9423b52a47b2feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9500000000-aa6a11948622748c8469View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-dd6386614990770eaae5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-e9de9bab2598f0316525View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9300000000-f4bc767c42577b6a1d5fView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot 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 ReferencesNot 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

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
Molecular Weight:
35102.105 Da
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:15985434 ]
  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:16494569 ]
  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:16978644 ]
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Drug created on June 13, 2005 07:24 / Updated on April 29, 2016 14:52