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Showing NP-Card for D-Lactaldehyde (NP0334758)

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Record Information
Version2.0
Created at2024-09-10 19:50:05 UTC
Updated at2024-09-10 19:50:05 UTC
NP-MRD IDNP0334758
Secondary Accession NumbersNone
Natural Product 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. The (R)-stereoisomer of lactaldehyde. D-Lactaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Lactaldehyde exists in all living species, ranging from bacteria to humans. D-lactaldehyde can be converted into pyruvaldehyde through its interaction with the enzyme glyoxylate reductase/hydroxypyruvate reductase. D-Lactaldehyde was first documented in 1992 (PMID: 1537826). In humans, D-lactaldehyde is involved in the metabolic disorder called the leigh syndrome pathway.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334758 (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
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3D MOL for NP0334758 (D-Lactaldehyde)

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3D SDF for NP0334758 (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>
NP0334758

> <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-/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

$$$$

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3D-SDF for NP0334758 (D-Lactaldehyde)
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PDB for NP0334758 (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

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3D PDB for NP0334758 (D-Lactaldehyde)
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SMILES for NP0334758 (D-Lactaldehyde)
C[C@@H](O)C=O
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INCHI for NP0334758 (D-Lactaldehyde)
InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3/t3-/m1/s1
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View in JSmol
Synonyms
ValueSource
D-2-HydroxypropionaldehydeChEBI
(2R)-2-HydroxypropanalHMDB
(R)-LactaldehydeHMDB
Chemical FormulaC3H6O2
Average Mass74.0785 Da
Monoisotopic Mass74.03678 Da
IUPAC Name(2R)-2-hydroxypropanal
Traditional NameD-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-/m1/s1
InChI KeyBSABBBMNWQWLLU-GSVOUGTGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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)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
HMDB IDHMDB0006458  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
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  ]