D-glyceraldehyde (YMDB00575)

Identification
YMDB IDYMDB00575
NameD-glyceraldehyde
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-glyceraldehyde, also known as D-aldotriose or D-glycerose, 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. D-glyceraldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). D-glyceraldehyde may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (r)-glyceraldehyde
  • 2,3-dihydroxypropanal
  • D-(+)-glyceraldehyde
  • D-2,3-dihydroxypropanal
  • D-2,3-dihydroxypropionaldehyde
  • D-aldotriose
  • D-Glyceraldehyde
  • D-glycerose
  • GLYCERALDEHYDE
  • Glyceraldehyde, D-
  • Propanal, 2,3-dihydroxy-, (R)-
  • Triose
CAS number453-17-8
WeightAverage: 90.0779
Monoisotopic: 90.031694058
InChI KeyMNQZXJOMYWMBOU-VKHMYHEASA-N
InChIInChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2/t3-/m0/s1
IUPAC Name(2R)-2,3-dihydroxypropanal
Traditional IUPAC Nametriose
Chemical FormulaC3H6O3
SMILES[H]C(=O)[C@H](O)CO
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
Physical Properties
StateSolid
Charge0
Melting point145 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility814 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.46 m³·mol⁻¹ChemAxon
Polarizability8.05 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Glycerol metabolismPW002407 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fructose and mannose metabolismec00051 Map00051
Glycerolipid metabolismec00561 Map00561
Pentose phosphate pathwayec00030 Map00030
SMPDB ReactionsNot Available
KEGG Reactions
D-glyceraldehyde + NADPH + hydron → NADP + Glycerol
D-fructose 1-phosphate ↔ D-glyceraldehyde + Dihydroxyacetone phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0uk9-3900000000-bf30db5c00007a2fa431JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0w90-2910000000-19f71d420e605faa1ca8JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gl-9000000000-04537fb12b74f4857059JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-7749188cec001a162f6bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-08daa6fe14473ac5bc2eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-bb4eb4e9f59323f2cae5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-af49bbc2fc7043fc3c04JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9000000000-876e932a7b8564c247ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9000000000-9dc05bb3457ad5d98b3bJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Ford, G., Ellis, E. M. (2002). "Characterization of Ypr1p from Saccharomyces cerevisiae as a 2-methylbutyraldehyde reductase." Yeast 19:1087-1096.12210903
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17378
HMDB IDNot Available
Pubchem Compound ID79014
Kegg IDC00577
ChemSpider ID71347
FOODB IDFDB030769
WikipediaGlyceraldehyde
BioCyc IDGLYCERALD

Enzymes

Protein Details
1. Fructose-bisphosphate aldolase
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:
FBA1
Uniprot ID:
P14540
Molecular weight:
39620.5
Reactions
D-fructose 1,6-bisphosphate → glycerone phosphate + D-glyceraldehyde 3-phosphate.
Protein Details
2. NADPH-dependent methylglyoxal reductase GRE2
General function:
Involved in catalytic activity
Specific function:
Catalyzes the irreversible reduction of the cytotoxic compound methylglyoxal (MG) to (R)-lactaldehyde as an alternative to detoxification of MG by glyoxalase I GLO1. MG is synthesized via a bypath of glycolysis from dihydroxyacetone phosphate and is believed to play a role in cell cycle regulation and stress adaptation
Gene Name:
GRE2
Uniprot ID:
Q12068
Molecular weight:
38169.19922
Reactions
Lactaldehyde + NADP(+) → methylglyoxal + NADPH.
3-methylbutanol + NAD(P)+ → 3-methylbutanal + NAD(P)H + H+
Protein Details
3. NADPH-dependent aldose reductase GRE3
General function:
Involved in oxidoreductase activity
Specific function:
Reduces the cytotoxic compound methylglyoxal (MG) to (R)-lactaldehyde similar to GRE2. MG is synthesized via a bypath of glycolysis from dihydroxyacetone phosphate and is believed to play a role in cell cycle regulation and stress adaptation. In pentose-fermenting yeasts, aldose reductase catalyzes the reduction of xylose into xylitol. The purified enzyme catalyzes this reaction, but the inability of S.cerevisiae to grow on xylose as sole carbon source indicates that the physiological function is more likely methylglyoxal reduction
Gene Name:
GRE3
Uniprot ID:
P38715
Molecular weight:
37118.5
Reactions
Alditol + NAD(P)(+) → aldose + NAD(P)H.
(R)-lactaldehyde + NADP(+) → methylglyoxal + NADPH.
Protein Details
4. Putative reductase 1
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
YPR1
Uniprot ID:
Q12458
Molecular weight:
34754.69922
Reactions