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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 09:54:11 UTC
Update Date2021-09-14 15:00:11 UTC
HMDB IDHMDB0006458
Secondary Accession Numbers
  • HMDB0006949
  • HMDB06458
  • HMDB06949
Metabolite Identification
Common NameD-Lactaldehyde
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 exists in all living species, ranging from bacteria to plants to humans. In humans, D-lactaldehyde is involved in the metabolic disorder called the leigh syndrome pathway. D-Lactaldehyde has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make D-lactaldehyde a potential biomarker for the consumption of these foods. D-Lactaldehyde is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on D-Lactaldehyde.
Structure
Data?1582752384
Synonyms
ValueSource
D-2-HydroxypropionaldehydeChEBI
(2R)-2-HydroxypropanalHMDB
(R)-LactaldehydeHMDB
Chemical FormulaC3H6O2
Average Molecular Weight74.0785
Monoisotopic Molecular Weight74.036779436
IUPAC Name(2R)-2-hydroxypropanal
Traditional NameD-lactaldehyde
CAS Registry Number3946-09-6
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 KeyBSABBBMNWQWLLU-GSVOUGTGSA-N
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
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility658 g/LALOGPS
logP10(-1) g/LALOGPS
logP10(-0.63) g/LChemAxon
logS10(0.95) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+112.72831661259
DarkChem[M-H]-108.66431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
D-LactaldehydeC[C@@H](O)C=O1196.8Standard polar33892256
D-LactaldehydeC[C@@H](O)C=O572.6Standard non polar33892256
D-LactaldehydeC[C@@H](O)C=O606.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Lactaldehyde,1TMS,isomer #1C[C@H](C=O)O[Si](C)(C)C829.4Semi standard non polar33892256
D-Lactaldehyde,1TMS,isomer #2CC(O)=CO[Si](C)(C)C926.3Semi standard non polar33892256
D-Lactaldehyde,2TMS,isomer #1CC(=CO[Si](C)(C)C)O[Si](C)(C)C1052.3Semi standard non polar33892256
D-Lactaldehyde,2TMS,isomer #1CC(=CO[Si](C)(C)C)O[Si](C)(C)C986.6Standard non polar33892256
D-Lactaldehyde,2TMS,isomer #1CC(=CO[Si](C)(C)C)O[Si](C)(C)C1016.7Standard polar33892256
D-Lactaldehyde,1TBDMS,isomer #1C[C@H](C=O)O[Si](C)(C)C(C)(C)C1062.2Semi standard non polar33892256
D-Lactaldehyde,1TBDMS,isomer #2CC(O)=CO[Si](C)(C)C(C)(C)C1149.3Semi standard non polar33892256
D-Lactaldehyde,2TBDMS,isomer #1CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1469.6Semi standard non polar33892256
D-Lactaldehyde,2TBDMS,isomer #1CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1442.1Standard non polar33892256
D-Lactaldehyde,2TBDMS,isomer #1CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1345.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - D-Lactaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-056v-9000000000-fe4416498788a968e4672016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Lactaldehyde GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9300000000-12b08b93303d8cbf5c3a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Lactaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Lactaldehyde 10V, Positive-QTOFsplash10-004i-9000000000-1aa2338222aff31e5e0f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Lactaldehyde 20V, Positive-QTOFsplash10-056r-9000000000-c450e557b2fe7c5dc5a12015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Lactaldehyde 40V, Positive-QTOFsplash10-0a6r-9000000000-dceca37df952939d10842015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Lactaldehyde 10V, Negative-QTOFsplash10-00di-9000000000-cd6930d73efb436bc0ff2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Lactaldehyde 20V, Negative-QTOFsplash10-00di-9000000000-97d1b594dd3b1d9b08b82015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Lactaldehyde 40V, Negative-QTOFsplash10-0a4i-9000000000-90fa8913085480b29a8a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Lactaldehyde 10V, Positive-QTOFsplash10-0a4i-9000000000-feb30b99fe1a3132abb82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Lactaldehyde 20V, Positive-QTOFsplash10-0a4j-9000000000-f5b28df550bdfcf22cc72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Lactaldehyde 40V, Positive-QTOFsplash10-052s-9000000000-db6ce3d247485bf9581b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Lactaldehyde 10V, Negative-QTOFsplash10-05fr-9000000000-518c4b32efb3532122ea2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Lactaldehyde 20V, Negative-QTOFsplash10-05fr-9000000000-90bd5b8f63ecfac6a42a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Lactaldehyde 40V, Negative-QTOFsplash10-0a4i-9000000000-23a60e5f52ca732e0f562021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023918
KNApSAcK IDNot Available
Chemspider ID388473
KEGG Compound IDC00937
BioCyc IDCPD-358
BiGG ID36414
Wikipedia LinkLactaldehyde
METLIN IDNot Available
PubChem Compound439350
PDB IDNot Available
ChEBI ID17167
Food Biomarker OntologyNot Available
VMH IDLALD_D
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLobell, 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 ]
  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 ]
  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 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular weight:
35853.125
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Enzyme with hydroxy-pyruvate reductase, glyoxylate reductase and D-glycerate dehydrogenase enzymatic activities. Reduces hydroxypyruvate to D-glycerate, glyoxylate to glycolate oxidizes D-glycerate to hydroxypyruvate.
Gene Name:
GRHPR
Uniprot ID:
Q9UBQ7
Molecular weight:
35667.875
Reactions
D-Lactaldehyde + NAD → Pyruvaldehyde + NADH + Hydrogen Iondetails