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Identification
YMDB IDYMDB00111
NameD-Lactaldehyde
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Lactaldehyde belongs to the class of organic compounds known as alpha-hydroxyaldehydes. These are organic compounds containing an aldehyde substituted with a hydroxyl group on the adjacent carbon. D-Lactaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Lactaldehyde exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • (2R)-2-hydroxypropanal
  • (R)-Lactaldehyde
  • D-2-hydroxypropionaldehyde
  • D-lactaldehyde
CAS number3946-09-6
WeightAverage: 74.0785
Monoisotopic: 74.036779436
InChI KeyBSABBBMNWQWLLU-GSVOUGTGSA-N
InChIInChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3/t3-/m1/s1
IUPAC Name(2R)-2-hydroxypropanal
Traditional IUPAC NameD-lactaldehyde
Chemical FormulaC3H6O2
SMILES[H]O[C@@]([H])(C([H])=O)C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha-hydroxyaldehydes. These are organic compounds containing an aldehyde substituted with a hydroxyl group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydroxyaldehydes
Alternative Parents
Substituents
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility658 g/LALOGPS
logP-1ALOGPS
logP-0.63ChemAxon
logS0.95ALOGPS
pKa (Strongest Acidic)14ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.91 m³·mol⁻¹ChemAxon
Polarizability7.19 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Nucleus
Organoleptic PropertiesNot Available
SMPDB Pathways
Pyruvate metabolismPW002447 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fructose and mannose metabolismec00051 Map00051
Pyruvate metabolismec00620 Map00620
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Inoue, Y., Watanabe, K., Shimosaka, M., Saikusa, T., Fukuda, Y., Murata, K., Kimura, A. (1985). "Metabolism of 2-oxoaldehydes in yeasts. Purification and characterization of lactaldehyde dehydrogenase from Saccharomyces cerevisiae." Eur J Biochem 153:243-247.3908097
Synthesis Reference:Lobell, Mario, Grout, David H. G. New insight into the pyruvate decarboxylase-catalyzed formation of lactaldehyde from H-D exchange experiments: a 'water proof' active site. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic C
External Links:
ResourceLink
CHEBI ID17167
HMDB IDHMDB06458
Pubchem Compound ID439350
Kegg IDC00937
ChemSpider ID388473
FOODB IDFDB023918
WikipediaLactaldehyde
BioCyc IDCPD-358

Enzymes

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.