Record Information
Version2.0
Creation Date2012-05-31 13:03:52 -0600
Update Date2015-09-13 15:15:21 -0600
Secondary Accession Numbers
  • ECMDB01051
Identification
Name:D-Glyceraldehyde
Description:Glyceraldehyde is a triose monosaccharide with chemical formula C3H6O3. It is the simplest of all common aldoses. It is a sweet colorless crystalline solid that is an intermediate compound in carbohydrate metabolism. The word comes from combining glycerine and aldehyde, as glyceraldehyde is merely glycerine with one hydroxide changed to an aldehyde.
Structure
Thumb
Synonyms:
  • α,β-dihydroxypropionaldehyde
  • (+/-)-2,3-dihydroxy-Propanal
  • (+/-)-Glyceraldehyde
  • 2, 3-Dihydroxy-Propanal
  • 2,3-Dihydroxy-Propionaldehyde
  • 2,3-Dihydroxypropanal
  • 2,3-Dihydroxypropionaldehyde
  • A,b-Dihydroxypropionaldehyde
  • Alpha,beta-Dihydroxypropionaldehyde
  • D-(+)-Glyceraldehyde
  • D-2,3-Dihydroxypropanal
  • D-2,3-Dihydroxypropionaldehyde
  • D-Aldotriose
  • D-Glycerose
  • Delta-(+)-Glyceraldehyde
  • Delta-2,3-dihydroxypropanal
  • Delta-2,3-dihydroxypropionaldehyde
  • Delta-aldotriose
  • Delta-Glyceraldehyde
  • Delta-glycerose
  • Dihydroxypropionaldehyde
  • DL-GLYC
  • DL-Glyceraldehyde
  • DL-Glyceric aldehyde
  • DLG
  • Glyceraldehyde
  • Glyceric aldehyde
  • Glycerinaldehyde
  • Glycerinformal
  • Glycerose
  • α,β-Dihydroxypropionaldehyde
  • δ-(+)-Glyceraldehyde
  • δ-2,3-Dihydroxypropanal
  • δ-2,3-Dihydroxypropionaldehyde
  • δ-Aldotriose
  • δ-Glyceraldehyde
  • δ-Glycerose
Chemical Formula:C3H6O3
Weight:Average: 90.0779
Monoisotopic: 90.031694058
InChI Key:MNQZXJOMYWMBOU-UHFFFAOYSA-N
InChI:InChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2
CAS number:56-82-6
IUPAC Name:2,3-dihydroxypropanal
Traditional IUPAC Name:(+/-)-glyceraldehyde
SMILES:OCC(O)C=O
Chemical Taxonomy
ClassificationNot classified
Physical Properties
State:Solid
Charge:0
Melting point:145 °C
Experimental Properties:
PropertyValueSource
Water Solubility:29.2 mg/mlPhysProp
LogP:-1.014PhysProp
Predicted Properties
PropertyValueSource
Water Solubility814.0 mg/mLALOGPS
logP-1.6ALOGPS
logP-1.7ChemAxon
logS0.96ALOGPS
pKa (Strongest Acidic)12.8ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.46 m3·mol-1ChemAxon
Polarizability8.07 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udj-1900000000-66c3a7fb073f6c5c86a0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udi-1900000000-3fd8dc5205f5abb770caView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-03gl-9000000000-04537fb12b74f4857059View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0udi-0900000000-228dd3700017b511ddd9View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0w2a-0910000000-74411a9433752c08b424View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udj-1900000000-66c3a7fb073f6c5c86a0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-1900000000-3fd8dc5205f5abb770caView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0g4r-9730000000-bb9b8a35e01fa42c3f2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9000000000-25cf3a1adcc93448a673View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-c5b3efaddb77bd3470a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01ox-9000000000-ff6b63535e8104e1a60fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-9000000000-ca32a106d1461e63eea5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-af49bbc2fc7043fc3c04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9000000000-876e932a7b8564c247ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9000000000-9dc05bb3457ad5d98b3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-7749188cec001a162f6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-08daa6fe14473ac5bc2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-bb4eb4e9f59323f2cae5View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Beard KM, Shangari N, Wu B, O'Brien PJ: Metabolism, not autoxidation, plays a role in alpha-oxoaldehyde- and reducing sugar-induced erythrocyte GSH depletion: relevance for diabetes mellitus. Mol Cell Biochem. 2003 Oct;252(1-2):331-8. Pubmed: 14577607
  • 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
  • Fujita T, Funako T, Hayashi H: 8-Hydroxydaidzein, an aldose reductase inhibitor from okara fermented with Aspergillus sp. HK-388. Biosci Biotechnol Biochem. 2004 Jul;68(7):1588-90. Pubmed: 15277768
  • Gugliucci A: A practical method to study functional impairment of proteins by glycation and effects of inhibitors using current coagulation/fibrinolysis reagent kits. Clin Biochem. 2003 Mar;36(2):155-8. Pubmed: 12633766
  • Haraguchi H, Hayashi R, Ishizu T, Yagi A: A flavone from Manilkara indica as a specific inhibitor against aldose reductase in vitro. Planta Med. 2003 Sep;69(9):853-5. Pubmed: 14598214
  • Iwata H, Ukeda H, Maruyama T, Fujino T, Sawamura M: Effect of carbonyl compounds on red blood cells deformability. Biochem Biophys Res Commun. 2004 Aug 27;321(3):700-6. Pubmed: 15358163
  • Jonas AJ, Lin SN, Conley SB, Schneider JA, Williams JC, Caprioli RC: Urine glyceraldehyde excretion is elevated in the renal Fanconi syndrome. Kidney Int. 1989 Jan;35(1):99-104. Pubmed: 2709665
  • 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
  • Nagaraj RH, Oya-Ito T, Padayatti PS, Kumar R, Mehta S, West K, Levison B, Sun J, Crabb JW, Padival AK: Enhancement of chaperone function of alpha-crystallin by methylglyoxal modification. Biochemistry. 2003 Sep 16;42(36):10746-55. Pubmed: 12962499
  • Phillipou G, Seaborn CJ, Phillips PJ: Re-evaluation of the fructosamine reaction. Clin Chem. 1988 Aug;34(8):1561-4. Pubmed: 3402055
  • Takeuchi M, Yamagishi S: Alternative routes for the formation of glyceraldehyde-derived AGEs (TAGE) in vivo. Med Hypotheses. 2004;63(3):453-5. Pubmed: 15288367
  • Yamagishi S, Nakamura K, Inoue H, Kikuchi S, Takeuchi M: Serum or cerebrospinal fluid levels of glyceraldehyde-derived advanced glycation end products (AGEs) may be a promising biomarker for early detection of Alzheimer's disease. Med Hypotheses. 2005;64(6):1205-7. Pubmed: 15823718
  • Zakrzewska I, Prokopowicz J, Worowski K, Skrzydlewska E, Puchalski Z, Piotrowski Z: Low molecular organic inactivators in differentiating organ origin of alpha-amylase in humans. Part I. Mater Med Pol. 1989 Oct-Dec;21(4):274-6. Pubmed: 2518736
Synthesis Reference:Wan, Xin-Jun; Song, Ming-You; Wu, Rong; Chu, Dao-Bao. Synthesis of glyceraldehyde by indirect electrooxidation. Yingyong Huaxue (2003), 20(6), 578-581.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID5445
HMDB IDHMDB01051
Pubchem Compound ID751
Kegg IDC00577
ChemSpider ID731
WikipediaGlyceraldehyde
BioCyc IDGLYCERALD
EcoCyc IDGLYCERALD

Enzymes

General function:
Involved in catalytic activity
Specific function:
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate
Gene Name:
fbaB
Uniprot ID:
P0A991
Molecular weight:
38109
Reactions
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the aldol condensation of dihydroxyacetone phosphate (DHAP or glycerone-phosphate) with glyceraldehyde 3- phosphate (G3P) to form fructose 1,6-bisphosphate (FBP) in gluconeogenesis and the reverse reaction in glycolysis
Gene Name:
fbaA
Uniprot ID:
P0AB71
Molecular weight:
39147
Reactions
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate.
General function:
Involved in zinc ion binding
Specific function:
Has high formaldehyde dehydrogenase activity in the presence of glutathione and catalyzes the oxidation of normal alcohols in a reaction that is not GSH-dependent. In addition, hemithiolacetals other than those formed from GSH, including omega-thiol fatty acids, also are substrates
Gene Name:
frmA
Uniprot ID:
P25437
Molecular weight:
39359
Reactions
S-(hydroxymethyl)glutathione + NAD(P)(+) = S-formylglutathione + NAD(P)H.
An alcohol + NAD(+) = an aldehyde or ketone + NADH.

Transporters

General function:
Involved in transmembrane transport
Specific function:
Involved in the efflux of sugars. The physiological role may be the detoxification of non-metabolizable sugar analogs
Gene Name:
setC
Uniprot ID:
P31436
Molecular weight:
43493
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
Transporter of glycerol across the cytoplasmic membrane, with limited permeability to water and small uncharged compounds such as polyols
Gene Name:
glpF
Uniprot ID:
P0AER0
Molecular weight:
29780
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368