You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2006-08-12 19:09:36 UTC
Update Date2017-09-27 08:24:21 UTC
HMDB IDHMDB0003344
Secondary Accession Numbers
  • HMDB02165
  • HMDB03344
Metabolite Identification
Common NameGlycolaldehyde
DescriptionGlycolaldehyde (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
Thumb
Synonyms
ValueSource
GLYCOALDEHYDEChEBI
Glycolic aldehydeChEBI
GlycollaldehydeChEBI
HydroxyacetaldehydeChEBI
Methylol formaldehydeChEBI
MonomethylolformaldehydeChEBI
2-HydroxyacetaldehydeHMDB
2-HydroxyethanalHMDB
2-OH-AcetaldehydeHMDB
2-OxoethanolHMDB
DioseHMDB
HydroxyethanalHMDB
MethylolformaldehydeHMDB
Chemical FormulaC2H4O2
Average Molecular Weight60.052
Monoisotopic Molecular Weight60.021129372
IUPAC Name2-hydroxyacetaldehyde
Traditional Nameglycolaldehyde
CAS Registry Number141-46-8
SMILES
OCC=O
InChI Identifier
InChI=1S/C2H4O2/c3-1-2-4/h1,4H,2H2
InChI KeyWGCNASOHLSPBMP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen 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
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point97 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-9aad7766f88c7ab6028bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-8dee0ff3027177f894d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-f167702c9efe9cfcd0a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-666acd064bdf4b7e4e17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-f129f99fe312906de2f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-a4339f6764dcb3e35133View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-86c6c734f49f41d961f7View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid LocationsNot Available
Tissue Location
  • Neuron
Pathways
NameSMPDB/PathwhizKEGG
HypophosphatasiaPw000479Pw000479 greyscalePw000479 simpleNot Available
Vitamin B6 MetabolismPw000053Pw000053 greyscalePw000053 simpleMap00750
Displaying all 2 entries
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003297
KNApSAcK IDC00007457
Chemspider ID736
KEGG Compound IDC00266
BioCyc IDDIHYDROXYPHENYLGLYCOLALDEHYDE
BiGG ID34446
Wikipedia LinkGlycolaldehyde
METLIN ID3205
PubChem Compound756
PDB IDNot Available
ChEBI ID17071
References
Synthesis ReferenceMajerski, 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)
General References
  1. 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. 2004 Sep;108(3):189-93. Epub 2004 Jun 17. [PubMed:15221334 ]
  2. Takeuchi M, Yamagishi S: TAGE (toxic AGEs) hypothesis in various chronic diseases. Med Hypotheses. 2004;63(3):449-52. [PubMed:15288366 ]

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Glycolaldehyde → (2-oxoethoxy)sulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Glycolaldehyde → 3,4,5-trihydroxy-6-(2-oxoethoxy)oxane-2-carboxylic aciddetails