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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)14.23ChemAxon
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
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 IDFDB003297
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.