L-Aspartate-semialdehyde (PAMDB000833)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000833
Identification
Name: L-Aspartate-semialdehyde
Description:L-Aspartate-semialdehyde is involved in both the lysine biosynthesis and homoserine biosynthesis pathways.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 117.1033
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent D-alpha-amino acids
Alternative Parents
Substituents
  • D-alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Alpha-hydrogen aldehyde
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aldehyde
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility225.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity25.61 m3·mol-1ChemAxon
Polarizability10.51 Å3ChemAxon
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 + 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
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
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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
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

Protein Details
• Dihydrodipicolinate synthase
General function:
Involved in catalytic activity
Specific function:
L-aspartate 4-semialdehyde + pyruvate = dihydrodipicolinate + 2 H(2)O
Gene Name:
dapA
Locus Tag:
PA1010
Molecular weight:
31.4 kDa
Reactions
L-aspartate 4-semialdehyde + pyruvate = dihydrodipicolinate + 2 H(2)O.
Protein Details
• Aspartate-semialdehyde dehydrogenase
General function:
Involved in aspartate-semialdehyde dehydrogenase activity
Specific function:
L-aspartate 4-semialdehyde + phosphate + NADP(+) = L-4-aspartyl phosphate + NADPH
Gene Name:
asd
Locus Tag:
PA3117
Molecular weight:
40.5 kDa
Reactions
L-aspartate 4-semialdehyde + phosphate + NADP(+) = L-4-aspartyl phosphate + NADPH.