P. aeruginosa Metabolome Database: Glycolaldehyde (PAMDB000444)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000444

Identification

Name:

Glycolaldehyde

Description:

Glycolaldehyde (HOCH2-CH=O, IUPAC name 2-hydroxyethanal) is a type of diose (2-carbon monosaccharide). Glycolaldehyde is readily converted to acetyl coenzyme A. It has an aldehyde and a hydroxyl group. However, it is not actually a sugar, because there is only one hydroxyl group. Glycolaldehyde is formed from many sources, including the amino acid glycine and from purone catabolism. It can form by action of ketolase on fructose 1,6-bisphosphate in an alternate glycolysis pathway. This compound is transferred by thiamin pyrophosphate during the pentose phosphate shunt.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2-Hydroxyacetaldehyde
2-Hydroxyethanal
2-OH-acetaldehyde
2-Oxoethanol
Diose
Glycoaldehyde
Glycolaldehyde
Glycolic aldehyde
Glycollaldehyde
Hydroxyacetaldehyde
Hydroxyethanal
Methylol formaldehyde
Methylolformaldehyde
Monomethylolformaldehyde

Chemical Formula:

C₂H₄O₂

Average Molecular Weight:

60.052

Monoisotopic Molecular Weight:

60.021129372

InChI Key:

WGCNASOHLSPBMP-UHFFFAOYSA-N

InChI:

InChI=1S/C2H4O2/c3-1-2-4/h1,4H,2H2

CAS number:

141-46-8

IUPAC Name:

2-hydroxyacetaldehyde

Traditional IUPAC Name:

glycolaldehyde

SMILES:

OCC=O

Chemical Taxonomy

Taxonomy Description

This compound 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.

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbonyl compounds

Sub Class

Aldehydes

Direct Parent

Short-chain aldehydes

Alternative Parents

Substituents

Hydrocarbon derivative
Short-chain aldehyde
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glycolaldehydes (CHEBI:17071 )
a small molecule (GLYCOLALDEHYDE )

Physical Properties

State:

Solid

Charge:

Melting point:

97 °C

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	725.0 mg/mL	ALOGPS
logP	-0.99	ALOGPS
logP	-1.2	ChemAxon
logS	1.08	ALOGPS
pKa (Strongest Acidic)	14.23	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	13.42 m³·mol^-1	ChemAxon
Polarizability	5.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

FMNH + Isethionic acid + Oxygen > Flavin Mononucleotide + Glycolaldehyde + Hydrogen ion + Water + Sulfite
Glycolaldehyde + Water + NAD > Glycolic acid +2 Hydrogen ion + NADH
7,8-Dihydroneopterin <> 6-Hydroxymethyl dihydropterin + Glycolaldehyde
Ethylene glycol + NAD <> Glycolaldehyde + NADH + Hydrogen ion
D-Ribulose-1-phosphate <> Glycolaldehyde + Dihydroxyacetone phosphate
4-Hydroxy-L-threonine <> Glycolaldehyde + Glycine
Glycolaldehyde + NAD + Water > Glycolic acid + NADH
7,8-Dihydroneopterin + 7,8-Dihydroneopterin > Glycolaldehyde + 6-Hydroxymethyl dihydropterin

Pathways:

Folate biosynthesis pae00790
Glyoxylate and dicarboxylate metabolism pae00630
Metabolic pathways pae01100
Microbial metabolism in diverse environments pae01120
Pentose and glucuronate interconversions pae00040
Vitamin B6 metabolism pae00750

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-9aad7766f88c7ab6028b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9000000000-8dee0ff3027177f894d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-f167702c9efe9cfcd0a8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-666acd064bdf4b7e4e17	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-f129f99fe312906de2f3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-a4339f6764dcb3e35133	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-86c6c734f49f41d961f7	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available

References

References:

Choei H, Sasaki N, Takeuchi M, Yoshida T, Ukai W, Yamagishi S, Kikuchi S, Saito T: Glyceraldehyde-derived advanced glycation end products in Alzheimer's disease. Acta Neuropathol (Berl). 2004 Sep;108(3):189-93. Epub 2004 Jun 17. Pubmed: 15221334
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Takeuchi M, Yamagishi S: TAGE (toxic AGEs) hypothesis in various chronic diseases. Med Hypotheses. 2004;63(3):449-52. Pubmed: 15288366
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	17071
HMDB ID	HMDB03344
Pubchem Compound ID	756
Kegg ID	C00266
ChemSpider ID	736
Wikipedia	Glycolaldehyde
BioCyc ID	GLYCOLALDEHYDE
EcoCyc ID	GLYCOLALDEHYDE

Glycolaldehyde (PAMDB000444)

Structure for Glycolaldehyde (PAMDB000444)