Hmdb loader

Showing metabocard for D-Lactaldehyde (HMDB0006458)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Show more...Show more...Show more...
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
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006458 (D-Lactaldehyde)

  Mrv0541 02231220392D          

  5  4  0  0  1  0            999 V2000
   12.6308  -11.8093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0598  -10.9843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3453  -12.2219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.3453  -13.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0598  -11.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  1  0  0  0
  2  5  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
M  END
Download

3D MOL for HMDB0006458 (D-Lactaldehyde)

HMDB0006458
     RDKit          3D
D-Lactaldehyde
 11 10  0  0  0  0  0  0  0  0999 V2000
   -1.1210   -0.3599   -0.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870    0.3454   -0.0428 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0496    1.2757    0.9844 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2467   -0.6460    0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4947   -1.5322   -0.5172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9693    0.1621    0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117   -1.4188   -0.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3275   -0.3559   -1.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4565    0.9363   -0.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2963    2.1915    0.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7987   -0.5983    1.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  6
  3 10  1  0
  4 11  1  0
M  END
Download

3D SDF for HMDB0006458 (D-Lactaldehyde)

  Mrv0541 02231220392D          

  5  4  0  0  1  0            999 V2000
   12.6308  -11.8093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0598  -10.9843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3453  -12.2219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.3453  -13.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0598  -11.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  1  0  0  0
  2  5  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006458

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C3H6O2

> <MOLECULAR_WEIGHT>
74.0785

> <EXACT_MASS>
74.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
7.186454740223683

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-hydroxypropanal

> <ALOGPS_LOGP>
-1.04

> <JCHEM_LOGP>
-0.6304457703333334

> <ALOGPS_LOGS>
0.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.000927735442815

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2307254345910668

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
17.9144

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.58e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
D-lactaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0006458 (D-Lactaldehyde)

HMDB0006458
     RDKit          3D
D-Lactaldehyde
 11 10  0  0  0  0  0  0  0  0999 V2000
   -1.1210   -0.3599   -0.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870    0.3454   -0.0428 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0496    1.2757    0.9844 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2467   -0.6460    0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4947   -1.5322   -0.5172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9693    0.1621    0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117   -1.4188   -0.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3275   -0.3559   -1.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4565    0.9363   -0.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2963    2.1915    0.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7987   -0.5983    1.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  6
  3 10  1  0
  4 11  1  0
M  END
Download

PDB for HMDB0006458 (D-Lactaldehyde)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      23.578 -22.044   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      26.245 -20.504   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      24.911 -22.814   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.911 -24.354   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.245 -22.044   0.000  0.00  0.00           C+0
CONECT    1    3                                                            
CONECT    2    5                                                            
CONECT    3    1    4    5                                                  
CONECT    4    3                                                            
CONECT    5    2    3                                                       
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
Download

3D PDB for HMDB0006458 (D-Lactaldehyde)

COMPND    HMDB0006458
HETATM    1  C1  UNL     1      -1.121  -0.360  -0.339  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.187   0.345  -0.043  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.050   1.276   0.984  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.247  -0.646   0.280  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.495  -1.532  -0.517  1.00  0.00           O  
HETATM    6  H1  UNL     1      -1.969   0.162   0.152  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.112  -1.419  -0.036  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.327  -0.356  -1.440  1.00  0.00           H  
HETATM    9  H4  UNL     1       0.457   0.936  -0.961  1.00  0.00           H  
HETATM   10  H5  UNL     1       0.296   2.191   0.718  1.00  0.00           H  
HETATM   11  H6  UNL     1       1.799  -0.598   1.200  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    4    9
CONECT    3   10
CONECT    4    5    5   11
END
Download

SMILES for HMDB0006458 (D-Lactaldehyde)

C[C@@H](O)C=O
Download

INCHI for HMDB0006458 (D-Lactaldehyde)

InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3/t3-/m1/s1
Download
View in JSmolView NMR AssignmentsView Stereo Labels
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 effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
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
Predicted Chromatographic Properties
Spectra
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

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 Iondetails