Record Information
Version2.0
Creation Date2012-05-31 14:21:18 -0600
Update Date2015-06-03 17:19:03 -0600
Secondary Accession Numbers
  • ECMDB12249
Identification
Name:L-Aspartate-semialdehyde
DescriptionL-Aspartate-semialdehyde is involved in both the lysine biosynthesis and homoserine biosynthesis pathways.
Structure
Thumb
Synonyms:
  • AspSA
  • L-aspartate β-semialdehyde
  • L-Aspartate 4-semialdehyde
  • L-aspartate b-semialdehyde
  • L-Aspartate beta-semialdehyde
  • L-Aspartate β-semialdehyde
  • L-Aspartate-4-semialdehyde
  • L-Aspartic 4-semialdehyde
  • L-Aspartic acid β-semialdehyde
  • L-Aspartic acid 4-semialdehyde
  • L-Aspartic acid b-semialdehyde
  • L-Aspartic acid beta-semialdehyde
  • L-Aspartic acid β-semialdehyde
  • L-Aspartic acid-4-semialdehyde
  • L-Aspartic acid-semialdehyde
Chemical Formula:C4H7NO3
Weight:Average: 117.1033
Monoisotopic: 117.042593095
InChI Key:HOSWPDPVFBCLSY-VKHMYHEASA-N
InChI:InChI=1S/C4H7NO3/c5-3(1-2-6)4(7)8/h2-3H,1,5H2,(H,7,8)/t3-/m0/s1
CAS number:15106-57-7
IUPAC Name:(2S)-2-amino-4-oxobutanoic acid
Traditional IUPAC Name:L-aspartic 4-semialdehyde
SMILES:N[C@@H](CC=O)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
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Reactions:
L-Homoserine + NADP <> L-Aspartate-semialdehyde + Hydrogen ion + NADPH
L-Aspartate-semialdehyde + Pyruvic acid > 2,3-Dihydrodipicolinic acid + Hydrogen ion +2 Water
L-Aspartate-semialdehyde + NADP + Phosphate <> L-Aspartyl-4-phosphate + Hydrogen ion + NADPH
L-Homoserine + NAD <> L-Aspartate-semialdehyde + NADH + Hydrogen ion
L-Aspartate-semialdehyde + Pyruvic acid <> 2,3-Dihydrodipicolinic acid +2 Water
Pyruvic acid + L-Aspartate-semialdehyde <> Hydrogen ion + Water + 2,3-Dihydrodipicolinic acid
NAD(P)<sup>+</sup> + L-Homoserine < NAD(P)H + L-Aspartate-semialdehyde + Hydrogen ion
L-Homoserine + NAD(P)(+) > L-Aspartate-semialdehyde + NAD(P)H
L-Aspartate-semialdehyde + Pyruvic acid > (S)-2,3-dihydrodipicolinate +2 Water
L-Aspartate-semialdehyde + Inorganic phosphate + NADP > L-4-aspartyl phosphate + NADPH
Pyruvic acid + L-Aspartate-semialdehyde <> (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate + Water
L-Aspartyl-4-phosphate + NADPH + Hydrogen ion + NADPH > Phosphate + NADP + L-Aspartate-semialdehyde
L-Aspartate-semialdehyde + Pyruvic acid > Hydrogen ion + Water + (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate
L-Aspartate-semialdehyde + Hydrogen ion + NADPH + NADPH > NADP + L-Homoserine + L-Homoserine
L-Aspartate-semialdehyde + Pyruvic acid >2 2,3-Dihydrodipicolinic acid + Hydrogen ion +2 Water
L-Aspartate-semialdehyde + NADP + Phosphate <> L-Aspartyl-4-phosphate + Hydrogen ion + NADPH
L-Aspartate-semialdehyde + Pyruvic acid >2 2,3-Dihydrodipicolinic acid + Hydrogen ion +2 Water
SMPDB Pathways:
Lysine biosynthesisPW000771 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: threonine biosynthesis from aspartatePW000976 ThumbThumb?image type=greyscaleThumb?image type=simple
methionine biosynthesisPW000814 ThumbThumb?image type=greyscaleThumb?image type=simple
threonine biosynthesisPW000817 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Arginine and proline metabolism ec00330
  • Cysteine and methionine metabolism ec00270
  • Glycine, serine and threonine metabolism ec00260
  • Lysine biosynthesis ec00300
  • Metabolic pathways eco01100
  • Microbial metabolism in diverse environments ec01120
  • Monobactam biosynthesis eco00261
  • Phenylalanine, tyrosine and tryptophan biosynthesis ec00400
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-fc95883465b06fe77fa1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9600000000-4dda3f4e4df10c3a920aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0v4i-9800000000-aa44dbab9da69646c984View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-58be73453302ce4f7f09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-e345870892ec8efb1abaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-6900000000-90fc00407b5ac2f29270View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-9200000000-ede87ec86d1914862dafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9000000000-e694b3a8f6038d7455c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-0b28596cb97f2d4d7a7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9000000000-7a12e06c4c34bc226441View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-988ff2b32628477425d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9200000000-c88e1a6c26d62b815d48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-f667b7d456d3acb3e0f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-ede149a9baa3d7f48cdbView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18051
HMDB IDHMDB12249
Pubchem Compound ID439235
Kegg IDC00441
ChemSpider ID388372
Wikipedia IDNot Available
BioCyc IDL-ASPARTATE-SEMIALDEHYDE
EcoCyc IDL-ASPARTATE-SEMIALDEHYDE

Enzymes

General function:
Involved in amino acid binding
Specific function:
L-homoserine + NAD(P)(+) = L-aspartate 4- semialdehyde + NAD(P)H
Gene Name:
thrA
Uniprot ID:
P00561
Molecular weight:
89119
Reactions
L-homoserine + NAD(P)(+) = L-aspartate 4-semialdehyde + NAD(P)H.
ATP + L-aspartate = ADP + 4-phospho-L-aspartate.
General function:
Involved in cellular amino acid biosynthetic process
Specific function:
L-homoserine + NAD(P)(+) = L-aspartate 4- semialdehyde + NAD(P)H
Gene Name:
metL
Uniprot ID:
P00562
Molecular weight:
88887
Reactions
L-homoserine + NAD(P)(+) = L-aspartate 4-semialdehyde + NAD(P)H.
ATP + L-aspartate = ADP + 4-phospho-L-aspartate.
General function:
Involved in catalytic activity
Specific function:
L-aspartate 4-semialdehyde + pyruvate = dihydrodipicolinate + 2 H(2)O
Gene Name:
dapA
Uniprot ID:
P0A6L2
Molecular weight:
31270
Reactions
L-aspartate 4-semialdehyde + pyruvate = dihydrodipicolinate + 2 H(2)O.
General function:
Involved in aspartate-semialdehyde dehydrogenase activity
Specific function:
L-aspartate 4-semialdehyde + phosphate + NADP(+) = L-4-aspartyl phosphate + NADPH
Gene Name:
asd
Uniprot ID:
P0A9Q9
Molecular weight:
40018
Reactions
L-aspartate 4-semialdehyde + phosphate + NADP(+) = L-4-aspartyl phosphate + NADPH.
General function:
Involved in catalytic activity
Specific function:
Specific function unknown
Gene Name:
yjhH
Uniprot ID:
P39359
Molecular weight:
32721
General function:
Involved in catalytic activity
Specific function:
Unknown Function
Gene Name:
yagE
Uniprot ID:
P75682
Molecular weight:
33316