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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-23 09:54:11 UTC

Update Date

2021-09-14 15:00:11 UTC

HMDB ID

HMDB0006458

Secondary Accession Numbers

HMDB0006949
HMDB06458
HMDB06949

Metabolite Identification

Common Name

D-Lactaldehyde

Description

D-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
D-2-Hydroxypropionaldehyde	ChEBI
(2R)-2-Hydroxypropanal	HMDB
(R)-Lactaldehyde	HMDB

Chemical Formula

C₃H₆O₂

Average Molecular Weight

74.0785

Monoisotopic Molecular Weight

74.036779436

IUPAC Name

(2R)-2-hydroxypropanal

Traditional Name

D-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

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-hydroxyaldehydes

Alternative Parents

Substituents

Alpha-hydroxyaldehyde
Secondary alcohol
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

lactaldehyde (CHEBI:17167 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0006458)

Organelle

Mitochondrion (HMDB: HMDB0006458)

Source

Endogenous

Endogenous (HMDB: HMDB0006458)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Pyruvate Metabolism (PathBank: SMP0087394)
Pyruvate Metabolism (HMDB: HMDB0006458)

Disease pathway

Leigh Syndrome (PathBank: SMP0120726)
Primary Hyperoxaluria II, PH2 (PathBank: SMP0120841)
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency) (PathBank: SMP0120533)
Pyruvate Kinase Deficiency (PathBank: SMP0120623)
Pyruvate Dehydrogenase Complex Deficiency (PathBank: SMP0120531)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	658 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.63	ChemAxon
logS	0.95	ALOGPS
pKa (Strongest Acidic)	14	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	17.91 m³·mol⁻¹	ChemAxon
Polarizability	7.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	112.728	31661259
DarkChem	[M-H]-	108.664	31661259
DeepCCS	[M+H]+	118.459	30932474
DeepCCS	[M-H]-	116.381	30932474
DeepCCS	[M-2H]-	152.254	30932474
DeepCCS	[M+Na]+	126.821	30932474
AllCCS	[M+H]+	122.8	32859911
AllCCS	[M+H-H2O]+	118.3	32859911
AllCCS	[M+NH4]+	127.0	32859911
AllCCS	[M+Na]+	128.2	32859911
AllCCS	[M-H]-	129.8	32859911
AllCCS	[M+Na-2H]-	135.4	32859911
AllCCS	[M+HCOO]-	141.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.0 minutes	32390414
Predicted by Siyang on May 30, 2022	8.9297 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.34 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	162.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	858.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	359.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	95.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	251.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	67.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	269.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	334.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	200.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	606.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	129.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	825.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	230.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	279.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	576.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	298.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	231.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
D-Lactaldehyde	C[C@@H](O)C=O	1196.8	Standard polar	33892256
D-Lactaldehyde	C[C@@H](O)C=O	572.6	Standard non polar	33892256
D-Lactaldehyde	C[C@@H](O)C=O	606.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
D-Lactaldehyde,1TMS,isomer #1	C[C@H](C=O)O[Si](C)(C)C	829.4	Semi standard non polar	33892256
D-Lactaldehyde,1TMS,isomer #2	CC(O)=CO[Si](C)(C)C	926.3	Semi standard non polar	33892256
D-Lactaldehyde,2TMS,isomer #1	CC(=CO[Si](C)(C)C)O[Si](C)(C)C	1052.3	Semi standard non polar	33892256
D-Lactaldehyde,2TMS,isomer #1	CC(=CO[Si](C)(C)C)O[Si](C)(C)C	986.6	Standard non polar	33892256
D-Lactaldehyde,2TMS,isomer #1	CC(=CO[Si](C)(C)C)O[Si](C)(C)C	1016.7	Standard polar	33892256
D-Lactaldehyde,1TBDMS,isomer #1	C[C@H](C=O)O[Si](C)(C)C(C)(C)C	1062.2	Semi standard non polar	33892256
D-Lactaldehyde,1TBDMS,isomer #2	CC(O)=CO[Si](C)(C)C(C)(C)C	1149.3	Semi standard non polar	33892256
D-Lactaldehyde,2TBDMS,isomer #1	CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1469.6	Semi standard non polar	33892256
D-Lactaldehyde,2TBDMS,isomer #1	CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1442.1	Standard non polar	33892256
D-Lactaldehyde,2TBDMS,isomer #1	CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1345.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - D-Lactaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-056v-9000000000-fe4416498788a968e467	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Lactaldehyde GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9300000000-12b08b93303d8cbf5c3a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Lactaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Lactaldehyde 10V, Positive-QTOF	splash10-004i-9000000000-1aa2338222aff31e5e0f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Lactaldehyde 20V, Positive-QTOF	splash10-056r-9000000000-c450e557b2fe7c5dc5a1	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Lactaldehyde 40V, Positive-QTOF	splash10-0a6r-9000000000-dceca37df952939d1084	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Lactaldehyde 10V, Negative-QTOF	splash10-00di-9000000000-cd6930d73efb436bc0ff	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Lactaldehyde 20V, Negative-QTOF	splash10-00di-9000000000-97d1b594dd3b1d9b08b8	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Lactaldehyde 40V, Negative-QTOF	splash10-0a4i-9000000000-90fa8913085480b29a8a	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Lactaldehyde 10V, Positive-QTOF	splash10-0a4i-9000000000-feb30b99fe1a3132abb8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Lactaldehyde 20V, Positive-QTOF	splash10-0a4j-9000000000-f5b28df550bdfcf22cc7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Lactaldehyde 40V, Positive-QTOF	splash10-052s-9000000000-db6ce3d247485bf9581b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Lactaldehyde 10V, Negative-QTOF	splash10-05fr-9000000000-518c4b32efb3532122ea	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Lactaldehyde 20V, Negative-QTOF	splash10-05fr-9000000000-90bd5b8f63ecfac6a42a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Lactaldehyde 40V, Negative-QTOF	splash10-0a4i-9000000000-23a60e5f52ca732e0f56	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Pyruvate metabolism	Not Available
Leigh Syndrome		Not Available
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)		Not Available
Pyruvate Dehydrogenase Complex Deficiency		Not Available
Primary hyperoxaluria II, PH2		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023918

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

Not Available

PubChem Compound

439350

PDB ID

Not Available

ChEBI ID

17167

Food Biomarker Ontology

Not Available

VMH ID

LALD_D

MarkerDB ID

Not Available

Good Scents ID

Not Available

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

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 ]
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 ]

Enzymes

Enzyme Details

1. Aldose reductase

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

Enzyme Details

2. Glyoxylate reductase/hydroxypyruvate reductase

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 Ion	details

Showing metabocard for D-Lactaldehyde (HMDB0006458)

MOL for HMDB0006458 (D-Lactaldehyde)

3D MOL for HMDB0006458 (D-Lactaldehyde)

3D SDF for HMDB0006458 (D-Lactaldehyde)

3D-SDF for HMDB0006458 (D-Lactaldehyde)

PDB for HMDB0006458 (D-Lactaldehyde)

3D PDB for HMDB0006458 (D-Lactaldehyde)

SMILES for HMDB0006458 (D-Lactaldehyde)

INCHI for HMDB0006458 (D-Lactaldehyde)

Structure for HMDB0006458 (D-Lactaldehyde)

3D Structure for HMDB0006458 (D-Lactaldehyde)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions