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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 19:09:36 UTC
Update Date2020-04-08 18:56:11 UTC
HMDB IDHMDB0003344
Secondary Accession Numbers
  • HMDB0002165
  • 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
Data?1586372171
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
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
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point97 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility725 g/LALOGPS
logP10(-0.99) g/LALOGPS
logP10(-1.2) g/LChemAxon
logS10(1.08) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+108.19631661259
DarkChem[M-H]-100.24831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GlycolaldehydeOCC=O1268.5Standard polar33892256
GlycolaldehydeOCC=O520.6Standard non polar33892256
GlycolaldehydeOCC=O578.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glycolaldehyde,1TMS,isomer #1C[Si](C)(C)OCC=O836.5Semi standard non polar33892256
Glycolaldehyde,1TMS,isomer #2C[Si](C)(C)OC=CO867.2Semi standard non polar33892256
Glycolaldehyde,2TMS,isomer #1C[Si](C)(C)OC=CO[Si](C)(C)C992.7Semi standard non polar33892256
Glycolaldehyde,2TMS,isomer #1C[Si](C)(C)OC=CO[Si](C)(C)C920.6Standard non polar33892256
Glycolaldehyde,2TMS,isomer #1C[Si](C)(C)OC=CO[Si](C)(C)C1010.2Standard polar33892256
Glycolaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC=O1042.1Semi standard non polar33892256
Glycolaldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=CO1085.5Semi standard non polar33892256
Glycolaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CO[Si](C)(C)C(C)(C)C1420.8Semi standard non polar33892256
Glycolaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CO[Si](C)(C)C(C)(C)C1384.2Standard non polar33892256
Glycolaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CO[Si](C)(C)C(C)(C)C1321.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Glycolaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9000000000-c2f1922c3cfc298b56e62016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycolaldehyde GC-MS (1 TMS) - 70eV, Positivesplash10-0109-9200000000-6143e9afd72b9d7c5b6c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycolaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-86c6c734f49f41d961f72015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolaldehyde LC-ESI-QTOF 10V, positive-QTOFsplash10-00di-4900000000-49b53ff321501e621bff2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolaldehyde LC-ESI-QTOF 20V, positive-QTOFsplash10-00dl-9400000000-2bd428d561e19271ec882020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolaldehyde LC-ESI-QTOF 40V, positive-QTOFsplash10-00kf-9000000000-73ede536fea5e4ad63d02020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolaldehyde 10V, Positive-QTOFsplash10-00di-4900000000-bb83469432ecea1f97fa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolaldehyde 20V, Positive-QTOFsplash10-00dl-9400000000-ddfc724456c2aac5ea032021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolaldehyde 40V, Positive-QTOFsplash10-00kf-9000000000-1eb34df93b3cd472f40d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolaldehyde 10V, Positive-QTOFsplash10-03di-9000000000-9aad7766f88c7ab6028b2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolaldehyde 20V, Positive-QTOFsplash10-03di-9000000000-8dee0ff3027177f894d72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolaldehyde 40V, Positive-QTOFsplash10-0006-9000000000-f167702c9efe9cfcd0a82015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolaldehyde 10V, Negative-QTOFsplash10-0a4i-9000000000-666acd064bdf4b7e4e172015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolaldehyde 20V, Negative-QTOFsplash10-0a4i-9000000000-f129f99fe312906de2f32015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolaldehyde 40V, Negative-QTOFsplash10-052f-9000000000-a4339f6764dcb3e351332015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolaldehyde 10V, Negative-QTOFsplash10-0a4i-9000000000-1d4ca7190bbdd61a30012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolaldehyde 20V, Negative-QTOFsplash10-0a4i-9000000000-588ee6697087d42604222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolaldehyde 40V, Negative-QTOFsplash10-0006-9000000000-6ffb9541e24882de3fac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolaldehyde 10V, Positive-QTOFsplash10-0006-9000000000-ee98b120aa7fd044da722021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolaldehyde 20V, Positive-QTOFsplash10-0006-9000000000-87bbaed151efac0845912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolaldehyde 40V, Positive-QTOFsplash10-0006-9000000000-87bbaed151efac0845912021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen LocationsNot Available
Tissue Locations
  • Neuron
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030893
KNApSAcK IDC00007457
Chemspider ID736
KEGG Compound IDC00266
BioCyc IDGLYCOLALDEHYDE
BiGG ID34446
Wikipedia LinkGlycolaldehyde
METLIN ID3205
PubChem Compound756
PDB IDNot Available
ChEBI ID17071
Food Biomarker OntologyNot Available
VMH IDGCALD
MarkerDB IDNot Available
Good Scents IDNot Available
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