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Identification
YMDB IDYMDB00343
NameGlycolaldehyde
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGlycolaldehyde, also known as 2-hydroxyethanal or 2-OH-acetaldehyde, belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms. Glycolaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Glycolaldehyde exists in all living species, ranging from bacteria to humans. glycolaldehyde and 6-hydroxymethyl-7,8-dihydropterin can be biosynthesized from 7,8-dihydroneopterin; which is mediated by the enzyme folic acid synthesis. In yeast, glycolaldehyde is involved in the metabolic pathway called tetrahydrofolate biosynthesis pathway.
Structure
Thumb
Synonyms
  • 2-Hydroxyacetaldehyde
  • 2-Hydroxyethanal
  • 2-OH-acetaldehyde
  • 2-Oxoethanol
  • Diose
  • Glycolaldehyde
  • Glycolic aldehyde
  • Glycollaldehyde
  • Hydroxyacetaldehyde
  • Hydroxyethanal
  • Methylol formaldehyde
  • Methylolformaldehyde
  • Monomethylolformaldehyde
  • GLYCOALDEHYDE
CAS number141-46-8
WeightAverage: 60.052
Monoisotopic: 60.021129372
InChI KeyWGCNASOHLSPBMP-UHFFFAOYSA-N
InChIInChI=1S/C2H4O2/c3-1-2-4/h1,4H,2H2
IUPAC Name2-hydroxyacetaldehyde
Traditional IUPAC Nameglycolaldehyde
Chemical FormulaC2H4O2
SMILES[H]OC([H])([H])C([H])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentShort-chain aldehydes
Alternative Parents
Substituents
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point97 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility725 g/LALOGPS
logP-0.99ALOGPS
logP-1.2ChemAxon
logS1.08ALOGPS
pKa (Strongest Acidic)14.27ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity13.42 m³·mol⁻¹ChemAxon
Polarizability5.32 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
tetrahydrofolate biosynthesisPW002417 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Folate biosynthesisec00790 Map00790
Glyoxylate and dicarboxylate metabolismec00630 Map00630
Pentose and glucuronate interconversionsec00040 Map00040
Vitamin B6 metabolismec00750 Map00750
SMPDB Reactions
7,8-DihydroneopterinGlycolaldehyde + 2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol
KEGG Reactions
5-Aminoimidazole ribonucleotide + hydronGlycolaldehyde + phosphate + 4-amino-5-hydroxymethyl-2-methylpyrimidine
7,8-DihydroneopterinGlycolaldehyde + 2-amino-6-(hydroxymethyl)-7,8-dihydropteridin-4-ol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9000000000-c2f1922c3cfc298b56e6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0109-9200000000-6143e9afd72b9d7c5b6cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-00di-4900000000-49b53ff321501e621bffJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-00dl-9400000000-2bd428d561e19271ec88JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-00kf-9000000000-73ede536fea5e4ad63d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-4900000000-bb83469432ecea1f97faJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9400000000-ddfc724456c2aac5ea03JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-1eb34df93b3cd472f40dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-9aad7766f88c7ab6028bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-8dee0ff3027177f894d7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-f167702c9efe9cfcd0a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-666acd064bdf4b7e4e17JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-f129f99fe312906de2f3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-a4339f6764dcb3e35133JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-1d4ca7190bbdd61a3001JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-588ee6697087d4260422JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-6ffb9541e24882de3facJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-ee98b120aa7fd044da72JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-87bbaed151efac084591JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-87bbaed151efac084591JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-86c6c734f49f41d961f7JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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:Majerski, Piotr A.; Piskorz, Jan K.; Radlein, Desmond St. A. G. Production of glycolaldehyde by hydrous thermolysis of sugars. PCT Int. Appl. (2002), 41 pp.
External Links:
ResourceLink
CHEBI ID17071
HMDB IDHMDB03344
Pubchem Compound ID756
Kegg IDC00266
ChemSpider ID736
FOODB IDFDB030893
WikipediaGlycolaldehyde
BioCyc IDDIHYDROXYPHENYLGLYCOLALDEHYDE

Enzymes

General function:
Involved in dihydropteroate synthase activity
Specific function:
Catalyzes three sequential steps of tetrahydrofolate biosynthesis
Gene Name:
FOL1
Uniprot ID:
P53848
Molecular weight:
93119.10156
Reactions
2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine → 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine + glycolaldehyde.
ATP + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine → AMP + (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate.
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate + 4-aminobenzoate → diphosphate + dihydropteroate.