Pyridoxal

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
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
IngredientUNIICASInChI Key
Pyridoxal hydrochloride1416KF0QBC65-22-5FCHXJFJNDJXENQ-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.

Structured Indications
Not Available
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).

TargetActionsOrganism
APyridoxal kinaseNot AvailableHuman
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
PathwayCategory
3-Methylcrotonyl Coa Carboxylase Deficiency Type IDisease
HypophosphatasiaDisease
Valine, Leucine and Isoleucine DegradationMetabolic
Beta-Ketothiolase DeficiencyDisease
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyDisease
3-hydroxyisobutyric acid dehydrogenase deficiencyDisease
3-hydroxyisobutyric aciduriaDisease
3-Methylglutaconic Aciduria Type IIIDisease
Methylmalonic AciduriaDisease
Isovaleric AciduriaDisease
Methylmalonate Semialdehyde Dehydrogenase DeficiencyDisease
Isobutyryl-coa dehydrogenase deficiencyDisease
Isovaleric acidemiaDisease
Vitamin B6 MetabolismMetabolic
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyDisease
3-Methylglutaconic Aciduria Type IDisease
3-Methylglutaconic Aciduria Type IVDisease
Maple Syrup Urine DiseaseDisease
Propionic AcidemiaDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB01545
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

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
Not 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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)165 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00di-2690000000-5d018202be238b10582a
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0aou-3974000000-8c963fdc714896ad343a
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-001j-0590000000-ed8a55680a0c9fa9cbaf
GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)GC-MSsplash10-0a4i-5695000000-bd3bb22a5dd4a600cb6c
GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)GC-MSsplash10-0aor-5895000000-e55e01ca30d17d2a8a72
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-0a4i-5695000000-bd3bb22a5dd4a600cb6c
GC-MS Spectrum - GC-MSGC-MSsplash10-0aor-5895000000-e55e01ca30d17d2a8a72
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0002-0900000000-4ce3f52baa36006ef4b2
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00kg-9500000000-658a96f6cda4a96de045
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0gbc-9000000000-233fc8ab067b0dcd1f14
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-014i-0900000000-c49b207cafcf1c21302d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-000i-0900000000-cad83f5f123a879fa0bb
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0a4i-0900000000-4f12feae0e11a6d9016b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0a4i-2900000000-56fcdbb9b4363c84d2d0
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-056r-9400000000-9700c9585f6c540bf007
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0gb9-0900000000-e646a99b0c1521d1c8dd
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0udi-0900000000-8fce1a7d8ceb3fced3ed
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0udl-6900000000-e2fc0eaa17e57d0a2556
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-00kf-9200000000-0bda29931f8b6f2fcc77
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014l-9000000000-469c127d1aef4f8a51d7
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0udi-2900000000-63ebef5a0818d6a1ccb8
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-05n0-0900000000-f468a00d88bedc116485
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-0900000000-7f4ef736d1a810b2e8ab
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-9c4ead9423b52a47b2fe
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-9500000000-aa6a11948622748c8469
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-dd6386614990770eaae5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-e9de9bab2598f0316525
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0abc-9300000000-f4bc767c42577b6a1d5f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-c49b207cafcf1c21302d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-0900000000-bf0686eb8e3c28c30e85
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0900000000-686848e0f222273e5089
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-2900000000-99577e7f4a39e47c5c42
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-056r-9400000000-9700c9585f6c540bf007
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-05n0-0900000000-f468a00d88bedc116485
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0gb9-0900000000-e646a99b0c1521d1c8dd
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0900000000-efa3bb6939a773839fa4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udl-6900000000-706331d9857f352a1e31
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00kf-9200000000-1970844d04848cfd3635
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014l-9000000000-469c127d1aef4f8a51d7
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-2900000000-63ebef5a0818d6a1ccb8
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0900000000-c7fa3fe6b301c5f074e1
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

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
  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]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:33