L-aspartic 4-semialdehyde (YMDB00034)

Identification

YMDB ID

YMDB00034

Name

L-aspartic 4-semialdehyde

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

L-Aspartate-semialdehyde is involved in both the lysine biosynthesis I and homoserine biosynthesis pathways. In the lysine biosynthesis I pathway, L-aspartate-semialdehyde is produced from a reaction between L-aspartyl-4-phosphate and NADPH, with phosphate and NADP+ as byproducts. The reaction is catalyzed by aspartate-semialdehyde dehydrogenase. In the homoserine biosynthesis pathway, L-aspartate-semialdehyde is produced from a reaction between L-aspartyl-4-phosphate and NADPH, with phosphate and NADP+ as byproducts. The reaction is catalyzed by aspartate-semialdehyde dehydrogenase.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(2S)-2-amino-4-oxobutanoic acid
Aspartate b-semialdehyde
Aspartate beta-semialdehyde
Aspartate β-semialdehyde
Aspartic acid b-semialdehyde
Aspartic acid beta-semialdehyde
Aspartic acid β-semialdehyde
L-Aspartate 4-semialdehyde
L-aspartate b-semialdehyde
L-aspartate-4-semialdehyde
L-Aspartic 4-semialdehyde
L-Aspartic acid-semialdehyde
(S)-2-Amino-4-oxobutanoic acid
3-Formylalanine
Aspartic beta-semialdehyde
L-Aspartic acid beta-semialdehyde
L-Aspartic beta-semialdehyde
(S)-2-Amino-4-oxobutanoate
Aspartic b-semialdehyde
Aspartic β-semialdehyde
L-Aspartate beta-semialdehyde
L-Aspartate β-semialdehyde
L-Aspartic acid b-semialdehyde
L-Aspartic acid β-semialdehyde
L-Aspartic b-semialdehyde
L-Aspartic β-semialdehyde
2-Amino-4-oxobutanoic acid
2-Amino-adipic semialdehyde
Aspartic-beta-semialdehyde
Aspartic-β-semialdehyde
beta-Aspartaldehydic acid
beta-Aspartic semialdehyde
β-Aspartaldehydic acid
β-Aspartic semialdehyde

CAS number

15106-57-7

Weight

Average: 117.1033
Monoisotopic: 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

IUPAC Name

(2S)-2-amino-4-oxobutanoic acid

Traditional IUPAC Name

L-aspartic 4-semialdehyde

Chemical Formula

C₄H₇NO₃

SMILES

[H]C(=O)C[C@H](N)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.

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

amino-acid betaine (CHEBI:537519 )

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	225 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-3.6	ChemAxon
logS	0.28	ALOGPS
pKa (Strongest Acidic)	1.95	ChemAxon
pKa (Strongest Basic)	8.98	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	3	ChemAxon
Refractivity	25.61 m³·mol⁻¹	ChemAxon
Polarizability	10.51 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

cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Cysteine Metabolism	PW002383
Methionine metabolism and salvage	PW002384
threonine metabolism	PW002401

KEGG Pathways

Arginine and proline metabolism	ec00330
Cysteine and methionine metabolism	ec00270
Glycine, serine and threonine metabolism	ec00260
Lysine biosynthesis	ec00300
Phenylalanine, tyrosine and tryptophan biosynthesis	ec00400

SMPDB Reactions

NADPH + L-aspartic 4-semialdehyde + hydron → L-Homoserine + NADP

4-Phospho-L-aspartic acid + hydron + NADPH → phosphate + NADP + L-aspartic 4-semialdehyde

4-Phospho-L-aspartic acid + NADPH + hydron → phosphate + NADP + L-aspartic 4-semialdehyde

L-aspartic 4-semialdehyde + hydron + NADPH → NADP + L-Homoserine

KEGG Reactions

4-Phospho-L-aspartic acid + NADPH + hydron → NADP + phosphate + L-aspartic 4-semialdehyde

NADH + L-aspartic 4-semialdehyde + hydron → NAD + L-Homoserine

L-aspartic 4-semialdehyde + NADPH + hydron → NADP + L-Homoserine

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	splash10-006x-9000000000-fc95883465b06fe77fa1	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9600000000-4dda3f4e4df10c3a920a	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	splash10-0v4i-9800000000-aa44dbab9da69646c984	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-58be73453302ce4f7f09	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-e345870892ec8efb1aba	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-6900000000-90fc00407b5ac2f29270	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ba-9200000000-ede87ec86d1914862daf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9000000000-e694b3a8f6038d7455c1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-0b28596cb97f2d4d7a7d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-7a12e06c4c34bc226441	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-988ff2b32628477425d6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9200000000-c88e1a6c26d62b815d48	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-f667b7d456d3acb3e0f4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-ede149a9baa3d7f48cdb	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
1D NMR	13C 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
Jacques, S. L., Ejim, L. J., Wright, G. D. (2001). "Homoserine dehydrogenase from Saccharomyces cerevisiae: kinetic mechanism and stereochemistry of hydride transfer." Biochim Biophys Acta 1544:42-54.11341915
Thomas, D., Surdin-Kerjan, Y. (1989). "Structure of the HOM2 gene of Saccharomyces cerevisiae and regulation of its expression." Mol Gen Genet 217:149-154.2570346
Thomas, D., Barbey, R., Surdin-Kerjan, Y. (1993). "Evolutionary relationships between yeast and bacterial homoserine dehydrogenases." FEBS Lett 323:289-293.8500624

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	18051
HMDB ID	HMDB12249
Pubchem Compound ID	439235
Kegg ID	C00441
ChemSpider ID	388372
FOODB ID	FDB028891
Wikipedia ID	Not Available
BioCyc ID	L-ASPARTATE-SEMIALDEHYDE

Enzymes

Protein Details

1. Aspartate-semialdehyde dehydrogenase

General function:: Involved in aspartate-semialdehyde dehydrogenase activity
Specific function:: This enzyme catalyzes the second step in the common metabolic pathway to synthesize Thr and Met from Asp
Gene Name:: HOM2
Uniprot ID:: P13663
Molecular weight:: 39543.30078

Reactions

L-aspartate 4-semialdehyde + phosphate + NADP(+) → L-4-aspartyl phosphate + NADPH.

Protein Details

2. Aspartokinase

General function:: Involved in amino acid binding
Specific function:: ATP + L-aspartate = ADP + 4-phospho-L- aspartate
Gene Name:: HOM3
Uniprot ID:: P10869
Molecular weight:: 58109.19922

Reactions

ATP + L-aspartate → ADP + 4-phospho-L-aspartate.

Protein Details

3. Homoserine dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: L-homoserine + NAD(P)(+) = L-aspartate 4- semialdehyde + NAD(P)H
Gene Name:: HOM6
Uniprot ID:: P31116
Molecular weight:: 38501.69922

Reactions

L-homoserine + NAD(P)(+) → L-aspartate 4-semialdehyde + NAD(P)H.

Structure for #<Compound:0xad5e1d2c>

Enzymes

Reactions

Reactions

Reactions