D-Lactaldehyde (ECMDB06458) (M2MDB000673)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (4)XML
Proteins (121)
Record Information
Version2.0
Creation Date2012-05-31 14:08:30 -0600
Update Date2015-06-03 15:54:52 -0600
Secondary Accession Numbers
  • ECMDB06458
Identification
Name:D-Lactaldehyde
DescriptionD- and L-lactaldehyde are also good substrates for aldose reductase. The aldose reductase-catalyzed reduction of methylglyoxal produces 95% acetol, 5% D-lactaldehyde. (PMID: 1537826)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2R)-2-hydroxypropanal
  • (R)-Lactaldehyde
  • D-2-Hydroxy-propionaldehyde
  • D-2-Hydroxypropionaldehyde
  • D-Lactaldehyde
Chemical Formula:C3H6O2
Weight:Average: 74.0785
Monoisotopic: 74.036779436
InChI Key:BSABBBMNWQWLLU-GSVOUGTGSA-N
InChI:InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3/t3-/m1/s1
CAS number:3946-09-6
IUPAC Name:(2R)-2-hydroxypropanal
Traditional IUPAC Name:D-lactaldehyde
SMILES:C[C@@H](O)C=O
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
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Reactions:
Hydrogen ion + Pyruvaldehyde + NADH > D-Lactaldehyde + NAD
D-Lactaldehyde + NAD <> Pyruvaldehyde + NADH + Hydrogen ion
(R)-Propane-1,2-diol + NAD > D-Lactaldehyde + NADH
2-Dehydro-3-deoxy-L-rhamnonate > Pyruvic acid + D-Lactaldehyde
(R)-Propane-1,2-diol + (S)-Propane-1,2-diol + NAD <> D-Lactaldehyde + (S)-Lactaldehyde + NADH + Hydrogen ion
SMPDB Pathways:
Propanoate metabolismPW000940 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056v-9000000000-fe4416498788a968e467View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9300000000-12b08b93303d8cbf5c3aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-1aa2338222aff31e5e0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9000000000-c450e557b2fe7c5dc5a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-dceca37df952939d1084View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-cd6930d73efb436bc0ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-97d1b594dd3b1d9b08b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-90fa8913085480b29a8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-feb30b99fe1a3132abb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-9000000000-f5b28df550bdfcf22cc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052s-9000000000-db6ce3d247485bf9581bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-9000000000-518c4b32efb3532122eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9000000000-90bd5b8f63ecfac6a42aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-23a60e5f52ca732e0f56View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Hazen SL, Hsu FF, d'Avignon A, Heinecke JW: Human neutrophils employ myeloperoxidase to convert alpha-amino acids to a battery of reactive aldehydes: a pathway for aldehyde generation at sites of inflammation. Biochemistry. 1998 May 12;37(19):6864-73. Pubmed: 9578573
  • HUANG PC, MILLER ON: The metabolism of lactaldehyde. V. Metabolism of L-fucose. J Biol Chem. 1958 Mar;231(1):201-5. Pubmed: 13538961
  • 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
  • Vander Jagt, D. L., Robinson, B., Taylor, K. K., Hunsaker, L. A. (1992). "Reduction of trioses by NADPH-dependent aldo-keto reductases. Aldose reductase, methylglyoxal, and diabetic complications." J Biol Chem 267:4364-4369. Pubmed: 1537826
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17167
HMDB IDHMDB06458
Pubchem Compound ID439350
Kegg IDC00937
ChemSpider ID388473
WikipediaLactaldehyde
BioCyc IDCPD-358
EcoCyc IDCPD-358

Enzymes

Protein Details
1. Lactaldehyde reductase
General function:
Involved in oxidoreductase activity
Specific function:
(R)-propane-1,2-diol + NAD(+) = (R)- lactaldehyde + NADH
Gene Name:
fucO
Uniprot ID:
P0A9S1
Molecular weight:
40644
Reactions
(R)-propane-1,2-diol + NAD(+) = (R)-lactaldehyde + NADH.
(S)-propane-1,2-diol + NAD(+) = (S)-lactaldehyde + NADH.
Protein Details
2. Glycerol dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NAD-dependent oxidation of glycerol to dihydroxyacetone (glycerone). Allows microorganisms to utilize glycerol as a source of carbon under anaerobic conditions. In E.coli, an important role of gldA is also likely to regulate the intracellular level of dihydroxyacetone by catalyzing the reverse reaction, i.e. the conversion of dihydroxyacetone into glycerol. Possesses a broad substrate specificity, since it is also able to oxidize 1,2-propanediol and to reduce glycolaldehyde, methylglyoxal and hydroxyacetone into ethylene glycol, lactaldehyde and 1,2-propanediol, respectively
Gene Name:
gldA
Uniprot ID:
P0A9S5
Molecular weight:
38712
Reactions
Glycerol + NAD(+) = glycerone + NADH.
Protein Details
3. Glyoxylate/hydroxypyruvate reductase A
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Inactive towards 2-oxo-D-gluconate, 2-oxoglutarate, oxaloacetate and pyruvate. Only D- and L-glycerate are involved in the oxidative activity with NADP. Activity with NAD is very low
Gene Name:
ghrA
Uniprot ID:
P75913
Molecular weight:
35343
Reactions
Glycolate + NADP(+) = glyoxylate + NADPH.
D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H.
Protein Details
4. 2-keto-3-deoxy-L-rhamnonate aldolase
General function:
Involved in carbon-carbon lyase activity
Specific function:
Catalyzes the reversible retro-aldol cleavage of 2-keto- 3-deoxy-L-rhamnonate (KDR) to pyruvate and lactaldehyde. 2-keto-3- deoxy-L-mannonate, 2-keto-3-deoxy-L-lyxonate and 4-hydroxy-2- ketoheptane-1,7-dioate (HKHD) are also reasonably good substrates, although 2-keto-3-deoxy-L-rhamnonate is likely to be the physiological substrate
Gene Name:
rhmA
Uniprot ID:
P76469
Molecular weight:
28916
Reactions
2-dehydro-3-deoxy-L-rhamnonate = pyruvate + (R)-lactaldehyde.