Np mrd loader

Showing NP-Card for (S)-Lactaldehyde (NP0062926)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-04-28 07:27:08 UTC
Updated at2022-04-28 07:27:08 UTC
NP-MRD IDNP0062926
Secondary Accession NumbersNone
Natural Product Identification
Common Name(S)-Lactaldehyde
DescriptionLactaldehyde, also known as 2-hydroxypropanal, 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. The molecule is chiral, its stereocenter being located on the second carbon atom. Lactaldehyde exists in several forms: In open-chain form and as cyclic hemiacetal; in solution and in crystal forms; as monomer and as dimer. Lactaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Lactaldehyde exists in all living species, ranging from bacteria to humans. Within humans, lactaldehyde participates in a number of enzymatic reactions. In particular, lactaldehyde can be converted into pyruvaldehyde; which is mediated by the enzyme aldose reductase. In addition, lactaldehyde can be biosynthesized from propylene glycol; which is catalyzed by the enzyme aldose reductase. Methylglyoxal is converted to D-lactaldehyde by glycerol dehydrogenase (gldA). Lactaldehyde is then oxidized to lactic acid by aldehyde dehydrogenase. In humans, lactaldehyde is involved in the metabolic disorder called the leigh syndrome pathway. Lactaldehyde is an intermediate in the methylglyoxal metabolic pathway. Lactaldehyde is a three-carbon atom species with a carbonyl group on the first carbon atom (making it an aldehyde), and a hydroxy group on the second carbon atom, making it a secondary alcohol. (S)-Lactaldehyde is found in Escherichia coli. (S)-Lactaldehyde was first documented in 1958 (PMID: 13502404). In crystal form, three conformers occur as hemiacetal dimers with a 1,4-dioxane ring skeleton:In equilibrium solution, negligibly small amounts of the monomer and at least one five-membered ring dimer exist (PMID: 6706932) (PMID: 6421801) (PMID: 14203169) (PMID: 14323585) (PMID: 6373710) (PMID: 6427403).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0062926 ((S)-Lactaldehyde)


  Mrv1652307191923412D          

  5  4  0  0  1  0            999 V2000
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
M  END
Download

3D MOL for NP0062926 ((S)-Lactaldehyde)

     RDKit          3D

 11 10  0  0  0  0  0  0  0  0999 V2000
   -0.6194   -1.0047    0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0707    0.4028    0.1603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6664    1.2857   -0.7071 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3832    0.3608   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1060   -0.3568    0.5527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7551   -1.4498    1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0777   -1.6635   -0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858   -1.0265   -0.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2672    0.7440    1.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4218    1.7429   -0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8194    0.9651   -0.8746 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  1
  3 10  1  0
  4 11  1  0
M  END
Download

3D SDF for NP0062926 ((S)-Lactaldehyde)


  Mrv1652307191923412D          

  5  4  0  0  1  0            999 V2000
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0062926

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3/t3-/m0/s1

> <INCHI_KEY>
BSABBBMNWQWLLU-VKHMYHEASA-N

> <FORMULA>
C3H6O2

> <MOLECULAR_WEIGHT>
74.0785

> <EXACT_MASS>
74.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
7.160243507150511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-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>
14.012447002485686

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2307254345910668

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
17.914400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.58e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-lactaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0062926 ((S)-Lactaldehyde)

Download
PDB for NP0062926 ((S)-Lactaldehyde)
HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END

Download
3D PDB for NP0062926 ((S)-Lactaldehyde)
Download
SMILES for NP0062926 ((S)-Lactaldehyde)
C[C@H](O)C=O
Download
INCHI for NP0062926 ((S)-Lactaldehyde)
InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3/t3-/m0/s1
Download
View in JSmol
Synonyms
ValueSource
L-2-HydroxypropionaldehydeChEBI
L-LactaldehydeChEBI
(+-)-2-HydroxypropanalHMDB
(2S)-2-HydroxypropanalHMDB
(S)-LactaldehydeHMDB
2-HydroxypropanalHMDB
2-HydroxypropionaldehydeHMDB
alpha-HydroxypropionaldehydeHMDB
HydroxypropionaldehydeHMDB
Chemical FormulaC3H6O2
Average Mass74.0785 Da
Monoisotopic Mass74.03678 Da
IUPAC Name(2S)-2-hydroxypropanal
Traditional NameL-lactaldehyde
CAS Registry NumberNot Available
SMILES
C[C@H](O)C=O
InChI Identifier
InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3/t3-/m0/s1
InChI KeyBSABBBMNWQWLLU-VKHMYHEASA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Escherichia coliBacteria
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1ALOGPS
logP-0.63ChemAxon
logS0.95ALOGPS
pKa (Strongest Acidic)14.01ChemAxon
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
Polarizability7.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003052  
DrugBank IDDB03776  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023101  
KNApSAcK IDC00019649  
Chemspider ID388368  
KEGG Compound IDC00424  
BioCyc IDNot Available
BiGG ID34941  
Wikipedia LinkLactaldehyde  
METLIN ID3214  
PubChem Compound439231  
PDB IDNot Available
ChEBI ID18041  
Good Scents IDNot Available
References
General References
  1. Casazza JP, Felver ME, Veech RL: The metabolism of acetone in rat. J Biol Chem. 1984 Jan 10;259(1):231-6. [PubMed:6706932  ] 
  2. Chen YM, Lin EC: Dual control of a common L-1,2-propanediol oxidoreductase by L-fucose and L-rhamnose in Escherichia coli. J Bacteriol. 1984 Mar;157(3):828-32. doi: 10.1128/jb.157.3.828-832.1984. [PubMed:6421801  ] 
  3. TING SM, SELLINGER OZ, MILLER ON: THE METABOLISM OF LACTALDEHYDE. VI. THE REDUCTION OF D- AND L-LACTALDEHYDE IN RAT LIVER. Biochim Biophys Acta. 1964 Aug 26;89:217-25. doi: 10.1016/0926-6569(64)90210-x. [PubMed:14203169  ] 
  4. TING SM, MILLER ON, SELLINGER OZ: THE METABOLISM OF LACTALDEHYDE. VII. THE OXIDATION OF D-LACTALDEHYDE IN RAT LIVER. Biochim Biophys Acta. 1965 Mar 8;97:407-15. doi: 10.1016/0304-4165(65)90151-0. [PubMed:14323585  ] 
  5. Akhy MT, Brown CM, Old DC: L-Rhamnose utilisation in Salmonella typhimurium. J Appl Bacteriol. 1984 Apr;56(2):269-74. doi: 10.1111/j.1365-2672.1984.tb01347.x. [PubMed:6373710  ] 
  6. Ros J, Aguilar J: Genetic and structural evidence for the presence of propanediol oxidoreductase isoenzymes in Escherichia coli. J Gen Microbiol. 1984 Mar;130(3):687-92. doi: 10.1099/00221287-130-3-687. [PubMed:6427403  ] 
  7. Di Costanzo L, Gomez GA, Christianson DW: Crystal structure of lactaldehyde dehydrogenase from Escherichia coli and inferences regarding substrate and cofactor specificity. J Mol Biol. 2007 Feb 16;366(2):481-93. doi: 10.1016/j.jmb.2006.11.023. Epub 2006  Nov 10. [PubMed:17173928  ] 
  8. Chen YM, Chakrabarti T, Lin EC: Constitutive activation of L-fucose genes by an unlinked mutation in Escherichia coli. J Bacteriol. 1984 Aug;159(2):725-9. doi: 10.1128/jb.159.2.725-729.1984. [PubMed:6378890  ] 
  9. SANDMAN RP, MILLER ON: Studies on the metabolism of lactaldehyde. I. Separation and determination of lactaldehyde and related 3-carbon compounds. J Biol Chem. 1958 Jan;230(1):353-9. [PubMed:13502404  ]