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Identification
YMDB IDYMDB00392
NamePyridoxal
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPyridoxal, also known as pyridoxaldehyde, belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives 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. Pyridoxal is a strong basic compound (based on its pKa). Pyridoxal exists in all living species, ranging from bacteria to humans. Pyridoxal is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 3-Hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxaldehyde
  • Pyridoxal
  • Pyridoxaldehyde
  • 3-HYDROXY-5-(hydroxymethyl)-2-methylisonicotinaldehyde
CAS number66-72-8
WeightAverage: 167.162
Monoisotopic: 167.058243159
InChI KeyRADKZDMFGJYCBB-UHFFFAOYSA-N
InChIInChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3
IUPAC Name3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde
Traditional IUPAC Namepyridoxal
Chemical FormulaC8H9NO3
SMILES[H]OC1=C(N=C([H])C(=C1C([H])=O)C([H])([H])O[H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives 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
  • Aryl-aldehyde
  • Hydroxypyridine
  • Methylpyridine
  • Vinylogous acid
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Aldehyde
  • Alcohol
  • Organic oxygen compound
  • Aromatic alcohol
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point165 °C
Experimental Properties
PropertyValueReference
Water Solubility500 mg/mL [COFFEN,DL (1978)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility11.7 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 Area70.42 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.87 m³·mol⁻¹ChemAxon
Polarizability16.28 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Vitamin B6PW002488 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Vitamin B6 metabolismec00750 Map00750
SMPDB Reactions
Pyridoxal + Adenosine triphosphatePyridoxal 5'-phosphate + ADP
KEGG Reactions
Adenosine triphosphate + PyridoxalPyridoxal 5'-phosphate + hydron + ADP
water + oxygen + Ammonium + PyridoxalHydrogen peroxide + Pyridoxamine
Pyridoxine + oxygenHydrogen peroxide + Pyridoxal
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-2690000000-5d018202be238b10582aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0aou-3974000000-8c963fdc714896ad343aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001j-0590000000-ed8a55680a0c9fa9cbafJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0a4i-5695000000-bd3bb22a5dd4a600cb6cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0aor-5895000000-e55e01ca30d17d2a8a72JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-5695000000-bd3bb22a5dd4a600cb6cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0aor-5895000000-e55e01ca30d17d2a8a72JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1900000000-56d1f96c5ac868ce42a6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fs-6190000000-78d7f54ce0c5338f815fJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-4ce3f52baa36006ef4b2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kg-9500000000-658a96f6cda4a96de045JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0gbc-9000000000-233fc8ab067b0dcd1f14JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-c49b207cafcf1c21302dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-0900000000-cad83f5f123a879fa0bbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-0900000000-4f12feae0e11a6d9016bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-2900000000-56fcdbb9b4363c84d2d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-056r-9400000000-9700c9585f6c540bf007JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0gb9-0900000000-e646a99b0c1521d1c8ddJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-0900000000-8fce1a7d8ceb3fced3edJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0udl-6900000000-e2fc0eaa17e57d0a2556JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00kf-9200000000-0bda29931f8b6f2fcc77JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014l-9000000000-469c127d1aef4f8a51d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-2900000000-63ebef5a0818d6a1ccb8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-05n0-0900000000-f468a00d88bedc116485JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-c49b207cafcf1c21302dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-bf0686eb8e3c28c30e85JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-686848e0f222273e5089JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-2900000000-99577e7f4a39e47c5c42JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0900000000-7f4ef736d1a810b2e8abJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-9c4ead9423b52a47b2feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9500000000-aa6a11948622748c8469JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-dd6386614990770eaae5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-e9de9bab2598f0316525JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9300000000-f4bc767c42577b6a1d5fJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Fujimoto, Yasuo. Pyridoxal. Jpn. Tokkyo Koho (1971), 2 pp.
External Links:
ResourceLink
CHEBI ID17310
HMDB IDHMDB01545
Pubchem Compound ID1050
Kegg IDC00250
ChemSpider ID1021
FOODB IDFDB011169
WikipediaPyridoxal
BioCyc IDPYRIDOXAL

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the reduction of pyridoxal (PL) with NADPH and oxidation of pyridoxine (PN) with NADP(+)
Gene Name:
Not Available
Uniprot ID:
Q06494
Molecular weight:
38600.39844
Reactions
Pyridoxine + NADP(+) → pyridoxal + NADPH.
General function:
Involved in pyridoxamine-phosphate oxidase activity
Specific function:
Catalyzes the oxidation of either pyridoxine 5'- phosphate (PNP) or pyridoxamine 5'-phosphate (PMP) into pyridoxal 5'-phosphate (PLP)
Gene Name:
PDX3
Uniprot ID:
P38075
Molecular weight:
26908.0
Reactions
Pyridoxamine 5'-phosphate + H(2)O + O(2) → pyridoxal 5'-phosphate + NH(3) + H(2)O(2).
Pyridoxine 5'-phosphate + O(2) → pyridoxal 5'-phosphate + H(2)O(2).
General function:
Involved in pyridoxal kinase activity
Specific function:
Required for synthesis of pyridoxal-5-phosphate from vitamin B6. Important for bud site selection
Gene Name:
BUD16
Uniprot ID:
P39988
Molecular weight:
35558.89844
Reactions
ATP + pyridoxal → ADP + pyridoxal 5'-phosphate.
General function:
Involved in pyridoxal kinase activity
Specific function:
Required for synthesis of pyridoxal-5-phosphate from vitamin B6. Important for bud site selection
Gene Name:
BUD17
Uniprot ID:
P53727
Molecular weight:
35366.5
Reactions
ATP + pyridoxal → ADP + pyridoxal 5'-phosphate.