Human Metabolome Database Version 3.5

Showing metabocard for D-Lactaldehyde (HMDB06458)

Record Information
Version 3.5
Creation Date 2007-05-23 03:54:11 -0600
Update Date 2013-05-29 13:43:46 -0600
HMDB ID HMDB06458
Secondary Accession Numbers
  • HMDB06949
Metabolite Identification
Common Name D-Lactaldehyde
Description D- 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 Link_out). D-lactaldehyde is an intermediate in the pyruvate metabolic pathway. Pyruvaldehyde is irreversibly produced from D-lactaldehyde via the enzyme glyoxylate reductase (NADP+, Swiss-Prot: Q5T945).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (2R)-2-hydroxypropanal
  2. (R)-Lactaldehyde
  3. D-2-Hydroxypropionaldehyde
  4. D-Lactaldehyde
Chemical Formula C3H6O2
Average Molecular Weight 74.0785
Monoisotopic Molecular Weight 74.036779436
IUPAC Name (2R)-2-hydroxypropanal
Traditional IUPAC Name (R)-lactaldehyde
CAS Registry Number 3946-09-6
SMILES C[C@@H](O)C=O
InChI Identifier InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3/t3-/m1/s1
InChI Key BSABBBMNWQWLLU-GSVOUGTGSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Alcohols and Polyols
Sub Class Secondary Alcohols
Other Descriptors
  • lactaldehyde(ChEBI)
Substituents
  • Aldehyde
Direct Parent Secondary Alcohols
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 658 g/L ALOGPS
LogP -1.04 ALOGPS
LogP -0.63 ChemAxon
LogS 0.95 ALOGPS
pKa (strongest acidic) 14 ChemAxon
pKa (strongest basic) -3.2 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 17.91 ChemAxon
Polarizability 7.19 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Pyruvate Metabolism SMP00060 map00620 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023918
KNApSAcK ID Not Available
Chemspider ID 388473 Link_out
KEGG Compound ID C00937 Link_out
BioCyc ID CPD-358 Link_out
BiGG ID 36414 Link_out
Wikipedia Link Lactaldehyde Link_out
NuGOwiki Link HMDB06458 Link_out
Metagene Link HMDB06458 Link_out
METLIN ID Not Available
PubChem Compound 439350 Link_out
PDB ID Not Available
ChEBI ID 17167 Link_out
References
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 Chemistry (1996), (13), 1577-1581; Kranz, Cyrill. Synthesis of Lactic Aldehyde. Chemicke Listy pro Vedu a Prumysl (1912), 5 323-7.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Vander Jagt DL, Robinson B, Taylor KK, Hunsaker LA: Reduction of trioses by NADPH-dependent aldo-keto reductases. Aldose reductase, methylglyoxal, and diabetic complications. J Biol Chem. 1992 Mar 5;267(7):4364-9. Pubmed: 1537826 Link_out
  2. 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 Link_out
  3. HUANG PC, MILLER ON: The metabolism of lactaldehyde. V. Metabolism of L-fucose. J Biol Chem. 1958 Mar;231(1):201-5. Pubmed: 13538961 Link_out

Enzymes
Name: Aldose reductase
Reactions: Not Available
Gene Name: AKR1B1
Uniprot ID: P15121 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glyoxylate reductase/hydroxypyruvate reductase
Reactions:
D-Lactaldehyde + NAD unknown Pyruvaldehyde + NADH + Hydrogen Ion details
Gene Name: GRHPR
Uniprot ID: Q9UBQ7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA