l-Glutamic-gamma-semialdehyde (YMDB00918)

Identification

YMDB ID

YMDB00918

Name

l-Glutamic-gamma-semialdehyde

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

L-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

MOL SDF PDB SMILES InChI

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 number

496-92-4

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

IUPAC Name

(2S)-2-amino-5-oxopentanoic acid

Traditional IUPAC Name

4-carboxy-4-aminobutanal

Chemical Formula

C₅H₉NO₃

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-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 Framework

Aliphatic acyclic compounds

External Descriptors

glutamic semialdehyde (CHEBI:17232 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	144 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.4	ChemAxon
logS	0.04	ALOGPS
pKa (Strongest Acidic)	2.12	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	30.36 m³·mol⁻¹	ChemAxon
Polarizability	12.56 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

mitochondrion
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Glutamate Metabolism	PW002376
Proline Metabolism	PW002365

KEGG Pathways

Arginine and proline metabolism

ec00330

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

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-059l-9000000000-c907c5e28c6d3b047532	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-000i-9200000000-b09702360bf061bd64db	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02a9-9700000000-ffc8c81a881bac7a0ca7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-9100000000-7061d8b19402303b61af	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-fa50d608bfaec666722d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-485c1c464e6d065cb4ac	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-7900000000-cd2ef70374a324d28ee0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-8685f6b3a1d6936c24c3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-30a10f2c9d729eb39f1f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03e9-6900000000-22f02534479a7a01c5bf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-cb0e34b8ef2d18870f9b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9200000000-69607aaecb41dd2d014a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014u-9000000000-d6928830fd6c484b658f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-915ef2dc6a2dda8f2ee6	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	17232
HMDB ID	HMDB02104
Pubchem Compound ID	193305
Kegg ID	C01165
ChemSpider ID	167744
FOODB ID	FDB030963
Wikipedia ID	Not Available
BioCyc ID	L-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.

Structure for #<Compound:0xa29c7f8c>

Enzymes

Reactions

Reactions

Reactions