Record Information
Version2.0
Creation Date2012-05-31 13:49:31 -0600
Update Date2015-06-03 15:53:55 -0600
Secondary Accession Numbers
  • ECMDB01305
Identification
Name:L-Glutamic-gamma-semialdehyde
DescriptionGlutamic gamma-semialdehyde is the metabolic precursor for proline biosynthesis. The conversion from L-Glutamate, an ATP- and NADPH-dependent reaction, is catalyzed by the enzyme Delta-1-pyrroline-5-carboxylate synthetase (P5CS) (OMIM 138250). L-Glutamic-gamma-semialdehyde can also be converted to or be formed from the amino acids L-ornithine (EC 2.6.1.13) and L-proline (EC 1.5.99.8 and EC 1.5.1.2). It is also one of the few metabolites that can be a precursor to other metabolites of both the urea cycle and the citric acid cycle (BioCyc)
Structure
Thumb
Synonyms:
  • Glutamate-semialdehyde
  • Glutamic γ-semialdehyde
  • Glutamic acid-semialdehyde
  • Glutamic g-semialdehyde
  • Glutamic gamma-semialdehyde
  • Glutamic γ-semialdehyde
  • L-Glutamate 5-semialdehyde
  • L-Glutamate g-semialdehyde
  • L-Glutamate gamma-semialdehyde
  • L-Glutamate γ-semialdehyde
  • L-Glutamate-5-semialdehyde
  • L-Glutamic acid 5-semialdehyde
  • L-Glutamic acid g-semialdehyde
  • L-Glutamic acid gamma-semialdehyde
  • L-Glutamic acid γ-semialdehyde
  • L-Glutamic acid-5-semialdehyde
  • L-Glutamic-g-semialdehyde
  • L-Glutamic-gamma-semialdehyde
  • L-Glutamic-γ-semialdehyde
Chemical Formula:C5H9NO3
Weight:Average: 131.1299
Monoisotopic: 131.058243159
InChI Key:KABXUUFDPUOJMW-BYPYZUCNSA-N
InChI:InChI=1S/C5H9NO3/c6-4(5(8)9)2-1-3-7/h3-4H,1-2,6H2,(H,8,9)/t4-/m0/s1
CAS number:496-92-4
IUPAC Name:(2S)-2-amino-5-oxopentanoic acid
Traditional IUPAC Name:4-carboxy-4-aminobutanal
SMILES:N[C@@H](CCC=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 Solubility144 g/LALOGPS
logP-2.6ALOGPS
logP-3.4ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)2.12ChemAxon
pKa (Strongest Basic)9.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.36 m³·mol⁻¹ChemAxon
Polarizability12.56 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
proline metabolismPW000794 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 (Non-derivatized) - 70eV, Positivesplash10-059l-9000000000-c907c5e28c6d3b047532View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-9200000000-b09702360bf061bd64dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02a9-9700000000-ffc8c81a881bac7a0ca7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9100000000-7061d8b19402303b61afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-fa50d608bfaec666722dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-485c1c464e6d065cb4acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-7900000000-cd2ef70374a324d28ee0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-8685f6b3a1d6936c24c3View 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 ID17232
HMDB IDHMDB02104
Pubchem Compound ID193305
Kegg IDC01165
ChemSpider ID167744
Wikipedia IDNot Available
BioCyc IDL-GLUTAMATE_GAMMA-SEMIALDEHYDE
EcoCyc IDL-GLUTAMATE_GAMMA-SEMIALDEHYDE
Ligand ExpoILG

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH dependent reduction of L-gamma- glutamyl 5-phosphate into L-glutamate 5-semialdehyde and phosphate. The product spontaneously undergoes cyclization to form 1-pyrroline-5-carboxylate
Gene Name:
proA
Uniprot ID:
P07004
Molecular weight:
44630
Reactions
L-glutamate 5-semialdehyde + phosphate + NADP(+) = L-glutamyl 5-phosphate + NADPH.
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes proline to glutamate for use as a carbon and nitrogen source and also function as a transcriptional repressor of the put operon
Gene Name:
putA
Uniprot ID:
P09546
Molecular weight:
143814
Reactions
L-proline + acceptor = (S)-1-pyrroline-5-carboxylate + reduced acceptor.
(S)-1-pyrroline-5-carboxylate + NAD(P)(+) + 2 H(2)O = L-glutamate + NAD(P)H.
General function:
Involved in zinc ion binding
Specific function:
Displays a broad specificity and can also deacylate substrates such as acetylarginine, acetylhistidine or acetylglutamate semialdehyde
Gene Name:
argE
Uniprot ID:
P23908
Molecular weight:
42347
Reactions
N(2)-acetyl-L-ornithine + H(2)O = acetate + L-ornithine.