Tmic
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Record Information
Version2.0
Creation Date2014-10-02 19:00:21 UTC
Update Date2018-03-21 17:46:14 UTC
Accession NumberT3D4964
Identification
Common NameGlyceraldehyde
ClassSmall Molecule
DescriptionGlyceraldehyde is a triose monosaccharide with chemical formula C3H6O3. It is the simplest of all common aldoses. It is a sweet, colourless crystalline solid that is an intermediate compound in carbohydrate metabolism. The word "glyceraldehyde" comes from combining glycerine and aldehyde, as glyceraldehyde is merely glycerine with one hydroxide changed to an aldehyde. Glyceraldehyde is produced from the action of the enzyme glyceraldehyde dehydrogenase, which converts glycerol to glyceraldehyde using NADP as a cofactor. When present at sufficiently high levels, glyceraldehyde can be a cytotoxin and a mutagen. A cytotoxin is a compound that kills cells. A mutagen is a compound that causes mutations in DNA. Glyceraldehyde is a highly reactive compound that can modify and cross-link proteins. Glyceraldehyde-modified proteins appear to be cytotoxic, depress intracellular glutathione levels, and induce reactive oxygen species (ROS) production (PMID: 14981296). Glyceraldehyde has been shown to cause chromosome damage to human cells in culture and is mutagenic in the Ames bacterial test.
Compound Type
  • Animal Toxin
  • Metabolite
  • Natural Compound
Chemical Structure
Thumb
Synonyms
Synonym
(+/-)-2,3-dihydroxy-Propanal
(+/-)-Glyceraldehyde
2,3-Dihydroxypropanal
2,3-Dihydroxypropionaldehyde
alpha,beta-Dihydroxypropionaldehyde
D-(+)-Glyceraldehyde
D-2,3-Dihydroxypropanal
D-2,3-Dihydroxypropionaldehyde
D-Aldotriose
D-Glyceraldehyde
D-Glycerose
delta-(+)-Glyceraldehyde
delta-2,3-Dihydroxypropanal
delta-2,3-Dihydroxypropionaldehyde
delta-Aldotriose
delta-Glyceraldehyde
delta-Glycerose
Dihydroxypropionaldehyde
DL-Glyceraldehyde
Glyceric aldehyde
Glycerinaldehyde
Glycerinformal
Glycerose
Chemical FormulaC3H6O3
Average Molecular Mass90.078 g/mol
Monoisotopic Mass90.032 g/mol
CAS Registry Number56-82-6
IUPAC Name2,3-dihydroxypropanal
Traditional Name(+/-)-glyceraldehyde
SMILESOCC(O)C=O
InChI IdentifierInChI=1/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2
InChI KeyInChIKey=MNQZXJOMYWMBOU-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Monosaccharide
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • 1,2-diol
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Primary alcohol
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue Locations
  • Neuron
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point145 °C
Boiling PointNot Available
Solubility17 mg/mL
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility814 g/LALOGPS
logP-1.6ALOGPS
logP-1.7ChemAxon
logS0.96ALOGPS
pKa (Strongest Acidic)12.84ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.46 m³·mol⁻¹ChemAxon
Polarizability8.07 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udj-1900000000-66c3a7fb073f6c5c86a0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-1900000000-3fd8dc5205f5abb770caView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0900000000-228dd3700017b511ddd9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0w2a-0910000000-74411a9433752c08b424View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udj-1900000000-66c3a7fb073f6c5c86a0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1900000000-3fd8dc5205f5abb770caView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gl-9000000000-04537fb12b74f4857059View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0g4r-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 AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB01051
PubChem Compound ID751
ChEMBL IDNot Available
ChemSpider ID731
KEGG IDC02154
UniProt IDNot Available
OMIM ID
ChEBI ID5445
BioCyc IDGLYCERALD
CTD IDNot Available
Stitch IDNot Available
PDB ID3GR
ACToR IDNot Available
Wikipedia LinkGlyceraldehyde
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. 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. [12633766 ]
  2. 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. [14577607 ]
  3. 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. [15358163 ]
  4. 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. [2518736 ]
  5. Phillipou G, Seaborn CJ, Phillips PJ: Re-evaluation of the fructosamine reaction. Clin Chem. 1988 Aug;34(8):1561-4. [3402055 ]
  6. 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. [15277768 ]
  7. 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. [14598214 ]
  8. 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. [15823718 ]
  9. 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. [15221334 ]
  10. 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. [2709665 ]
  11. Takeuchi M, Yamagishi S: Alternative routes for the formation of glyceraldehyde-derived AGEs (TAGE) in vivo. Med Hypotheses. 2004;63(3):453-5. [15288367 ]
  12. 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. [12962499 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available