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Identification
YMDB IDYMDB00034
NameL-aspartic 4-semialdehyde
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-Aspartate-semialdehyde is involved in both the lysine biosynthesis I and homoserine biosynthesis pathways. In the lysine biosynthesis I pathway, L-aspartate-semialdehyde is produced from a reaction between L-aspartyl-4-phosphate and NADPH, with phosphate and NADP+ as byproducts. The reaction is catalyzed by aspartate-semialdehyde dehydrogenase. In the homoserine biosynthesis pathway, L-aspartate-semialdehyde is produced from a reaction between L-aspartyl-4-phosphate and NADPH, with phosphate and NADP+ as byproducts. The reaction is catalyzed by aspartate-semialdehyde dehydrogenase.
Structure
Thumb
Synonyms
  • (2S)-2-amino-4-oxobutanoic acid
  • Aspartate b-semialdehyde
  • Aspartate beta-semialdehyde
  • Aspartate β-semialdehyde
  • Aspartic acid b-semialdehyde
  • Aspartic acid beta-semialdehyde
  • Aspartic acid β-semialdehyde
  • L-Aspartate 4-semialdehyde
  • L-aspartate b-semialdehyde
  • L-aspartate-4-semialdehyde
  • L-Aspartic 4-semialdehyde
  • L-Aspartic acid-semialdehyde
CAS number15106-57-7
WeightAverage: 117.1033
Monoisotopic: 117.042593095
InChI KeyHOSWPDPVFBCLSY-VKHMYHEASA-N
InChIInChI=1S/C4H7NO3/c5-3(1-2-6)4(7)8/h2-3H,1,5H2,(H,7,8)/t3-/m0/s1
IUPAC Name(2S)-2-amino-4-oxobutanoic acid
Traditional IUPAC NameL-aspartic 4-semialdehyde
Chemical FormulaC4H7NO3
SMILES[H]C(=O)C[C@H](N)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Alpha-hydrogen aldehyde
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility225 g/LALOGPS
logP-2.7ALOGPS
logP-3.6ChemAxon
logS0.28ALOGPS
pKa (Strongest Acidic)1.95ChemAxon
pKa (Strongest Basic)8.98ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity25.61 m³·mol⁻¹ChemAxon
Polarizability10.51 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Cysteine MetabolismPW002383 ThumbThumb?image type=greyscaleThumb?image type=simple
Methionine metabolism and salvagePW002384 ThumbThumb?image type=greyscaleThumb?image type=simple
threonine metabolismPW002401 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
Cysteine and methionine metabolismec00270 Map00270
Glycine, serine and threonine metabolismec00260 Map00260
Lysine biosynthesisec00300 Map00300
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
SMPDB Reactions
NADPH + L-aspartic 4-semialdehyde + hydronL-Homoserine + NADP
4-Phospho-L-aspartic acid + hydron + NADPHphosphate + NADP + L-aspartic 4-semialdehyde
4-Phospho-L-aspartic acid + NADPH + hydronphosphate + NADP + L-aspartic 4-semialdehyde
L-aspartic 4-semialdehyde + hydron + NADPHNADP + L-Homoserine
KEGG Reactions
4-Phospho-L-aspartic acid + NADPH + hydronNADP + phosphate + L-aspartic 4-semialdehyde
NADH + L-aspartic 4-semialdehyde + hydronNAD + L-Homoserine
L-aspartic 4-semialdehyde + NADPH + hydronNADP + L-Homoserine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Jacques, S. L., Ejim, L. J., Wright, G. D. (2001). "Homoserine dehydrogenase from Saccharomyces cerevisiae: kinetic mechanism and stereochemistry of hydride transfer." Biochim Biophys Acta 1544:42-54.11341915
  • Thomas, D., Surdin-Kerjan, Y. (1989). "Structure of the HOM2 gene of Saccharomyces cerevisiae and regulation of its expression." Mol Gen Genet 217:149-154.2570346
  • Thomas, D., Barbey, R., Surdin-Kerjan, Y. (1993). "Evolutionary relationships between yeast and bacterial homoserine dehydrogenases." FEBS Lett 323:289-293.8500624
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18051
HMDB IDHMDB12249
Pubchem Compound ID439235
Kegg IDC00441
ChemSpider ID388372
FOODB IDFDB028891
Wikipedia IDNot Available
BioCyc IDL-ASPARTATE-SEMIALDEHYDE

Enzymes

General function:
Involved in aspartate-semialdehyde dehydrogenase activity
Specific function:
This enzyme catalyzes the second step in the common metabolic pathway to synthesize Thr and Met from Asp
Gene Name:
HOM2
Uniprot ID:
P13663
Molecular weight:
39543.30078
Reactions
L-aspartate 4-semialdehyde + phosphate + NADP(+) → L-4-aspartyl phosphate + NADPH.
General function:
Involved in amino acid binding
Specific function:
ATP + L-aspartate = ADP + 4-phospho-L- aspartate
Gene Name:
HOM3
Uniprot ID:
P10869
Molecular weight:
58109.19922
Reactions
ATP + L-aspartate → ADP + 4-phospho-L-aspartate.
General function:
Involved in oxidoreductase activity
Specific function:
L-homoserine + NAD(P)(+) = L-aspartate 4- semialdehyde + NAD(P)H
Gene Name:
HOM6
Uniprot ID:
P31116
Molecular weight:
38501.69922
Reactions
L-homoserine + NAD(P)(+) → L-aspartate 4-semialdehyde + NAD(P)H.