MiMeDB: Showing metabocard for D-Lactaldehyde (MMDBc0032841)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 22:01:49 UTC

Update Date

2024-04-30 19:54:40 UTC

Metabolite ID

MMDBc0032841

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.

Structure

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

Synonyms

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

Molecular Formula

C₃H₆O₂

Average Mass

74.0785

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-056v-9000000000-fe4416498788a968e467	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9300000000-12b08b93303d8cbf5c3a	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-1aa2338222aff31e5e0f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-9000000000-c450e557b2fe7c5dc5a1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-dceca37df952939d1084	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-cd6930d73efb436bc0ff	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-97d1b594dd3b1d9b08b8	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-90fa8913085480b29a8a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-feb30b99fe1a3132abb8	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4j-9000000000-f5b28df550bdfcf22cc7	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052s-9000000000-db6ce3d247485bf9581b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-9000000000-518c4b32efb3532122ea	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-9000000000-90bd5b8f63ecfac6a42a	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-23a60e5f52ca732e0f56	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191761	Aldose reductase	Unknown	P15121	Homo sapiens
MMDBp0192058	Glyoxylate reductase/hydroxypyruvate reductase	Unknown	Q9UBQ7	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000275	Propylene glycol	Hydrogen Ion	Alcohol dehydrogenase 1a (class i), alpha polypeptide	Alcohol Dehydrogenase (D-1, 2-Propanediol)	VMH; KEGG	15987839 2296157
MMDBr0000277	D-Lactaldehyde	Hydrogen Ion	Alcohol dehydrogenase 1a (class i), alpha polypeptide	Alcohol Dehydrogenase (D-Lactaldehyde)	VMH	15987839 2296157
MMDBr0001538	Glutathione	Hydrogen Ion	Alcohol dehydrogenase 5 (class iii), chi polypeptide	D-Lactaldehyde:NAD+ Oxidoreductase (Glutathione-Formylating)	VMH; KEGG	30371894
MMDBr0001539	Hydrogen Ion	D-Lactaldehyde	Aldo-keto reductase family 7, member a2 (aflatoxin aldehyde reductase)	D-Lactaldehyde:NAD+ 1-Oxidoreductase	VMH	12071861 9823300
MMDBr0001541	Water	Hydrogen Ion	Not Available	Lactaldehyde Dehydrogenase	VMH; KEGG	30371894
MMDBr0001542	Water	Hydrogen Ion	Aldehyde dehydrogenase 18 family, member a1	Lactaldehyde Dehydrogenase, Mitochondrial	VMH	15987839 2296157 6487654
MMDBr0001976	Hydrogen Ion	Propylene glycol	Aldo-keto reductase family 7, member a2 (aflatoxin aldehyde reductase)	Propane-1, 2-Diol:NAD+ 1-Oxidoreductase	VMH	12071861 9823300
MMDBr0001977	Hydrogen Ion	Propylene glycol	Aldo-keto reductase family 1, member a1 (aldehyde reductase)	Propane-1, 2-Diol:NADP+ 1-Oxidoreductase	VMH	12071861 1537826 9823300
MMDBr0007885	Hydrogen Ion	Propylene glycol	Not Available	Lacaldehyde reductase (R-propane-1,2-diol forming), NADPH	VMH	30371894
MMDBr0010627	Hydrogen Ion	D-Lactaldehyde	Glyoxylate reductase/hydroxypyruvate reductase	Glyoxylate Reductase (NADP+)	VMH	30371894
MMDBr0010928	Hydrogen Ion	Propylene glycol	Not Available	Lacaldehyde reductase (R-propane-1,2-diol forming)	VMH	30371894
MMDBr0024756	Propylene glycol	Hydrogen Ion	Lactaldehyde reductase	Reduction	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	42	Human ; Human sputum; Human subgingival plaque; Human feces; Pig	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	13	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human	Metabolic reconstruction
Bacteria	Bacteroidetes	19	Human feces; Human stool	Metabolic reconstruction
Bacteria	Firmicutes	68	Human feces; Human ; Human saliva; Human stool	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	1	Human ; Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0006458

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

References

Synthesis Reference

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. doi: 10.1021/bi972449j. [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 ]

Showing metabocard for D-Lactaldehyde (MMDBc0032841)

MOL for #<Metabolite:0x0000564af37a6748>

3D MOL for #<Metabolite:0x0000564af37a6748>

3D SDF for #<Metabolite:0x0000564af37a6748>

3D-SDF for #<Metabolite:0x0000564af37a6748>

PDB for #<Metabolite:0x0000564af37a6748>

3D PDB for #<Metabolite:0x0000564af37a6748>

SMILES for #<Metabolite:0x0000564af37a6748>

INCHI for #<Metabolite:0x0000564af37a6748>

Structure for #<Metabolite:0x0000564af37a6748>

3D Structure for #<Metabolite:0x0000564af37a6748>