(S)-4-Amino-5-oxopentanoate (ECMDB20017) (M2MDB000866)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (759)
Record Information
Version2.0
Creation Date2012-05-31 14:23:05 -0600
Update Date2015-06-03 17:19:08 -0600
Secondary Accession Numbers
  • ECMDB20017
Identification
Name:(S)-4-Amino-5-oxopentanoate
Description(s)-4-amino-5-oxopentanoate is a member of the chemical class known as Gamma Amino Acids and Derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (S)-4-amino-5-oxopentanoate
  • (S)-4-amino-5-oxopentanoic acid
  • GluSA
  • L-Glutamate 1-semialdehyde
  • L-Glutamic acid 1-semialdehyde
Chemical Formula:C5H9NO3
Weight:Average: 131.1299
Monoisotopic: 131.058243159
InChI Key:MPUUQNGXJSEWTF-BYPYZUCNSA-N
InChI:InChI=1S/C5H9NO3/c6-4(3-7)1-2-5(8)9/h3-4H,1-2,6H2,(H,8,9)/t4-/m0/s1
CAS number:Not Available
IUPAC Name:(4S)-4-amino-5-oxopentanoic acid
Traditional IUPAC Name:glutamate-1-semialdehyde
SMILES:[H][C@](N)(CCC(O)=O)C=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma amino acids and derivatives
Alternative Parents
Substituents
  • Gamma amino acid or derivatives
  • Amino fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Aldehyde
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility143 g/LALOGPS
logP-2.9ALOGPS
logP-3.4ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)4.03ChemAxon
pKa (Strongest Basic)8.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.36 m³·mol⁻¹ChemAxon
Polarizability12.44 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
(S)-4-Amino-5-oxopentanoate <> 5-Aminolevulinic acid
L-Glutamyl-tRNA(Glu) + Hydrogen ion + NADPH > (S)-4-Amino-5-oxopentanoate + NADP + tRNA (Glu)
5-Aminolevulinic acid <> (S)-4-Amino-5-oxopentanoate
L-Glutamyl-tRNA(Glu) + NADPH + Hydrogen ion + tRNA(Glu) <> (S)-4-Amino-5-oxopentanoate + tRNA(Glu) + NADP + L-Glutamyl-tRNA(Glu)
(S)-4-Amino-5-oxopentanoate > 5-Aminolevulinic acid
(S)-4-Amino-5-oxopentanoate + NADP + tRNA(Glu) > L-glutamyl-tRNA(Glu) + NADPH
8 L-glutamyl-tRNA(Glu) + 8 NADPH + 8 NADPH >8 tRNA(Glu) +8 NADP +8 (S)-4-Amino-5-oxopentanoate
8 (S)-4-Amino-5-oxopentanoate >8 5-Aminolevulinic acid
(S)-4-Amino-5-oxopentanoate <>5 5-Aminolevulinic acid
5 5-Aminolevulinic acid <> (S)-4-Amino-5-oxopentanoate
L-Glutamyl-tRNA(Glu) + NADPH + Hydrogen ion + tRNA(Glu) <> (S)-4-Amino-5-oxopentanoate + NADP
(S)-4-Amino-5-oxopentanoate <>5 5-Aminolevulinic acid
SMPDB Pathways:
Porphyrin metabolismPW000936 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4900000000-8f9c0b818ce14db9d246View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ds-9400000000-3c1b8a4b2955039932cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-d66d20622e0abf092fc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-d708646f1d954c770d58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-8900000000-b9f27c52e5a45f61e019View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-433906be96d34e7c825eView in MoNA
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
1D NMR1H 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15757
HMDB IDNot Available
Pubchem Compound ID742
Kegg IDC03741
ChemSpider ID114525
Wikipedia IDNot Available
BioCyc IDGLUTAMATE-1-SEMIALDEHYDE
EcoCyc IDGLUTAMATE-1-SEMIALDEHYDE
Ligand ExpoGLU_LSN3_DHE2

Enzymes

Protein Details
1. Glutamyl-tRNA reductase
General function:
Involved in glutamyl-tRNA reductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of glutamyl- tRNA(Glu) to glutamate 1-semialdehyde (GSA). In the absence of NADPH, exhibits substrate esterase activity, leading to the release of glutamate from tRNA
Gene Name:
hemA
Uniprot ID:
P0A6X1
Molecular weight:
46306
Reactions
L-glutamate 1-semialdehyde + NADP(+) + tRNA(Glu) = L-glutamyl-tRNA(Glu) + NADPH.
Protein Details
2. Glutamate-1-semialdehyde 2,1-aminomutase
General function:
Involved in glutamate-1-semialdehyde 2,1-aminomutase activity
Specific function:
(S)-4-amino-5-oxopentanoate = 5- aminolevulinate
Gene Name:
hemL
Uniprot ID:
P23893
Molecular weight:
45366
Reactions
(S)-4-amino-5-oxopentanoate = 5-aminolevulinate.