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l-Glutamic-gamma-semialdehyde (YMDB00918)

Identification
YMDB IDYMDB00918
Namel-Glutamic-gamma-semialdehyde
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-Glutamic gamma-semialdehyde, also known as L-glutamate 5-semialdehyde or 5-oxo-L-norvaline, 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. L-Glutamic gamma-semialdehyde is a very strong basic compound (based on its pKa). L-Glutamic gamma-semialdehyde exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • glutamate-semialdehyde
  • glutamic gamma-semialdehyde
  • L-glutamate 5-semialdehyde
  • L-glutamate gamma-semialdehyde
  • L-glutamate-5-semialdehyde
  • L-Glutamic-gamma-semialdehyde
  • 5-oxo-L-Norvaline
  • L-Glutamic acid 5-semialdehyde
  • L-Glutamate g-semialdehyde
  • L-Glutamate γ-semialdehyde
  • L-Glutamic acid g-semialdehyde
  • L-Glutamic acid gamma-semialdehyde
  • L-Glutamic acid γ-semialdehyde
  • L-Glutamic g-semialdehyde
  • L-Glutamic γ-semialdehyde
  • L-Glutamate-gamma-semialdehyde
  • gamma-Glutamyl semialdehyde
  • Glutamate gamma-semialdehyde
  • Glutamic acid gamma-semialdehyde
  • Glutamic acid gamma-semialdehyde, (L)-isomer
CAS number496-92-4
WeightAverage: 131.1299
Monoisotopic: 131.058243159
InChI KeyKABXUUFDPUOJMW-BYPYZUCNSA-N
InChIInChI=1S/C5H9NO3/c6-4(5(8)9)2-1-3-7/h3-4H,1-2,6H2,(H,8,9)/t4-/m0/s1
IUPAC Name(2S)-2-amino-5-oxopentanoic acid
Traditional IUPAC Name4-carboxy-4-aminobutanal
Chemical FormulaC5H9NO3
SMILES[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C([H])([H])C([H])=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 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
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Glutamate MetabolismPW002376 ThumbThumb?image type=greyscaleThumb?image type=simple
Proline MetabolismPW002365 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
SMPDB Reactions
L-Glutamic acid 5-phosphate + hydron + NADPH → l-Glutamic-gamma-semialdehyde + NADP + phosphate
l-Glutamic-gamma-semialdehyde + NAD + water → hydron + NADH + L-Glutamic acid
Ornithine + Oxoglutaric acid ↔ L-Glutamic acid + l-Glutamic-gamma-semialdehyde
KEGG Reactions
NADP + water + l-Glutamic-gamma-semialdehyde → L-Glutamic acid + NADPH + hydron
L-Glutamic acid 5-phosphate + NADPH + hydron → NADP + phosphate + l-Glutamic-gamma-semialdehyde
NADH + L-Glutamic acid 5-phosphate + hydron → NAD + phosphate + l-Glutamic-gamma-semialdehyde
l-Glutamic-gamma-semialdehyde ↔ 1-Pyrroline-5-carboxylic acid + water + hydron
Oxoglutaric acid + Ornithine → L-Glutamic acid + l-Glutamic-gamma-semialdehyde
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
  • Takagi, H., Takaoka, M., Kawaguchi, A., Kubo, Y. (2005). "Effect of L-proline on sake brewing and ethanol stress in Saccharomyces cerevisiae." Appl Environ Microbiol 71:8656-8662.16332860
  • Brandriss, M. C., Magasanik, B. (1979). "Genetics and physiology of proline utilization in Saccharomyces cerevisiae: enzyme induction by proline." J Bacteriol 140:498-503.387737
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17232
HMDB IDHMDB02104
Pubchem Compound ID193305
Kegg IDC01165
ChemSpider ID167744
FOODB IDFDB022847
Wikipedia IDNot Available
BioCyc IDL-GLUTAMATE_GAMMA-SEMIALDEHYDE

Enzymes

Protein Details
1. Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
(S)-1-pyrroline-5-carboxylate + NAD(P)(+) + 2 H(2)O = L-glutamate + NAD(P)H
Gene Name:
PUT2
Uniprot ID:
P07275
Molecular weight:
64434.60156
Reactions
(S)-1-pyrroline-5-carboxylate + NAD(P)(+) + 2 H(2)O → L-glutamate + NAD(P)H.
Protein Details
2. Gamma-glutamyl phosphate reductase
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:
PRO2
Uniprot ID:
P54885
Molecular weight:
49740.0
Reactions
L-glutamate 5-semialdehyde + phosphate + NADP(+) → L-glutamyl 5-phosphate + NADPH.
Protein Details
3. Ornithine aminotransferase
General function:
Involved in transaminase activity
Specific function:
L-ornithine + a 2-oxo acid = L-glutamate 5- semialdehyde + an L-amino acid
Gene Name:
CAR2
Uniprot ID:
P07991
Molecular weight:
46085.60156
Reactions
L-ornithine + a 2-oxo acid → L-glutamate 5-semialdehyde + an L-amino acid.